yacht rental annapolis

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The Best Boat Rentals in Annapolis

Browse, book, and get out onto the water with local captains and boat owners., our favorite boat rentals in annapolis.

5 (628 reviews)

• Boat Rentals

the United States

Private Yacht Charter: On 40ft Regal Commodore

Experience the Serenity of Sailing SV Magic

2022 Sea Ray SDX Boat with Captain Included!

50ft Catamaran Charter with Water Toys - Annapolis, MD

Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine

2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

38' Hunter 376 Cruising Monohull in Annapolis, Maryland

Catamaran in Maryland

Pristine Hooligan Departs from a Private Pier with a Captain and Fuel INCLUDED

31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

Suggested Searches

Types of boats popular in annapolis.

From mid-size to mega yachts, these luxury boats are great for groups and celebrations

₽4,770-₽159,860

Set sail with these traditional wind-powered boats

₽13,060-₽159,860

Explore local waters with a boat rental dedicated to sightseeing and exploration

₽13,510-₽40,530

Perfect for casual cruising, sandbar stops, swimming, and parties

₽5,850-₽36,030

All the comforts of home out on the water, for multi-day boat trips

₽8,560-₽13,510

Fishing Boats

Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts

₽8,560-₽31,520

• Fishing Charters

Let a captain do the driving while you do the fishing

Who says you need a motor to have fun on the water?

₽38,280-₽40,530

Top Boat Rental Locations Near Annapolis

Washington , District of Columbia

109 listings

Baltimore , Maryland

44 listings

Most Popular Yacht Rentals in Annapolis

Discover the Spirit of the Chesapeake Bay with our Nautical-Themed Photography

43ft Cruiser Express Yacht for Daily Charter

50ft Catamaran Charter with Water Toys in St. Michaels, MD

Charter 44' Orana Cruising Catamaran In Deale, Maryland

Most popular sailboat rentals in annapolis.

Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

Experience the Charm of St. Michaels Aboard the 41ft S/Y Selina II Sl - 2 Hours

Most popular boat tours in annapolis.

Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!

Catalina 425 Sailing Yacht in Rock Hall, Maryland

Relaxing Excitement of the Chesapeake Bay and tributaries on our Ocean Yacht

Recent reviews in annapolis.

Enjoy a Day on the Bay and Cruise the South River

Alan was great from the start! Very communicative and accommodating. Booking process was smooth. Our ride was super relaxing as we all felt safe with Alan as our captain! He took great photos of us to capture the memories! 10/10 recommend! Thanks Alan ✨

Our sailing trip exceeded our expectations! Captain Alberto is a complete treasure: he shared his sailing knowledge and involved us in the sail as much as we wanted - The boat was clean and comfortable with space to enjoy the trip both above and below deck. We only had 2 in our party, but 6 people would absolutely be comfortable given the space. We hope to book a trip with Capt. Alberto again!

I found Captain Alberto and his first mate lovely wife were the ultimate hosts and storytellers. What I didn't expect, was to get impromptu sailing lessons. It was a beautiful day on the Chesapeake and I would highly recommend this to anyone who wants to truly appreciate the beauty and magnificence and physics of sailing

We had a wonderful time at Captain McCoy’s boat. The boat is gorgeous, impeccably clean, and very spacious. The Captain played great music (we didn’t bring our own playlist). He found a great spot for our group to take a swim. It was a perfect balance of cruising and swimming and a perfect 2 hr cruise

BOOK WITH CAPTAIN ALBERTO!! I mean this was the BEST thing experience I had all summer. He accommodated our needs, let us have fun, and taught us soo much during the process. Captain Alberto just had the best hospitality that I’ve seen in a long time. As a first-time boat goer, he made me feel so comfortable and welcomed! I will definitely be back and will rebook with captain Alberto. I mf you are looking through boat options and stumble on this, this is your sign to book with him!

Here’s what I have for a review for our incredible day on the Bay. Feel free to add or make Our experience with Captain Alberto was nothing short of amazing. From start to finish, he was incredibly kind, extremely knowledgeable, and highly professional. We not only enjoyed breathtaking views of the Chesapeake Bay, but we also had the opportunity to learn a great deal about the physics of sailing—thanks to Captain Alberto's expertise. One of the highlights of our trip was when Captain Alberto allowed us to take turns at the helm. It was an exhilarating experience to steer the boat under his guidance, making us feel like true sailors. His patience and clear instructions made it easy for us to confidently handle the boat, adding a personal and interactive element to the voyage that we greatly appreciated. The weather couldn’t have been more perfect, with clear skies and gentle winds that made for a serene and enjoyable trip. The views were extraordinary, offering us a stunning panorama of the Bay that we'll never forget. But what truly made this experience exceptional was Captain Alberto himself. His warm personality and deep understanding of sailing were the phenomenal icing on the proverbial cake. We highly recommend sailing with Captain Alberto. Whether you're a seasoned sailor or a complete novice, you're guaranteed to have an unforgettable experience!

Top Boat Rental Locations in the United States

Miami , Florida

934 listings

Miami Beach , Florida

441 listings

Tampa , Florida

448 listings

Los Angeles , California

409 listings

Chicago , Illinois

279 listings

Hollywood , Florida

273 listings

How To Book on Getmyboat

Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.

Inquire & Book

Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.

Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!

Dive into Our Journal

August 01, 2023

10 Boating Adventures of a Lifetime

Read Article

November 23, 2022

Eco-Friendly Tips for Boating Sustainably

October 03, 2022

Getmyboat's Guides to the World of Boating

April 14, 2022

The Best Meals & Snacks for a Boat Day

December 11, 2020

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December 29, 2019

How to Rent a Boat with Getmyboat

Frequently asked questions.

Renting a sailboat for a day in Annapolis starts at $350 a day for an Oceanis Cruising Monohull and goes up to $2,100 a day for a Lagoon Cruising Catamaran.

Renting a boat in Annapolis starts at $100 for a sailboat and goes up to $1,600 for a motor yacht rental .

No, you do not need a license to rent a boat or sail in Annapolis. With Getmyboat, you can rent a boat with a licensed captain to enjoy your time on the water. If you want to captain the boat yourself, you must, at the very least, have a Boating Safety Certificate. Be aware that owners will have a checkout process to test your competency with their boat, so if you question your ability, even if you have your boating safety certificate, it is best to go out with a captain.

While boating season can vary a bit depending on the weather, it usually starts near the tail end of April and ends in September.

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Elite Charters of Annapolis

Luxury yacht charter experiences.

Unique and Unforgettable Memories Await in Annapolis and on the Chesapeake Bay

Why Choose Elite Charters of Annapolis

Exclusive Yacht Charter Experiences

Let us host your next special occasion, cocktail cruise, relaxing weekend, or wedding cruise aboard one of our luxury yachts.  

Located in the heart of Annapolis, our professionally crewed charter yachts are easily accessible and create stunning and memorable experiences on the Chesapeake Bay. 

Our yachts are equipped with state-of-the-art amenities, including air conditioning, comfortable seating, and entertainment systems.

Professional Captains and Crew

Our crew members are experienced and knowledgeable about the Chesapeake Bay. They will ensure that you have a safe and memorable experience on your charter.

Muse - 87' Warren Yacht

• This sleek 87 ft sport yacht is available in Annapolis and the Chesapeake Bay.
• Invite up to 12 guests for half or full-day private yacht charters.
• She boasts beautiful teak decks, dual salons, and a spacious aft entertainment area.
• With a 5 ft draft, Muse can navigate secluded coves and anchorages.
• A 27-knot cruise speed ensures fast travel and exploration of multiple destinations.
• Overnight guest accommodations for six plus crew.

Shredder - 54' Eastbay

• Built by Grand Banks, the 54 ft Shredder is the quintessential Downeast-style cruiser.
• Accommodates up to 12 guests for half or full-day private yacht charters.
• Ideal for multi-day or week-long luxury Chesapeake Bay cruises for a couple in the spacious master stateroom.
• Perfect for day excursions to quaint Chesapeake Bay towns, romantic dinners, and water activities.

Firefly - 68' Azimut

• The Italian-designed and built Firefly turns heads with its sleek lines and lavish leather interiors.
• With a 6 ft draft, Firefly can access secluded Chesapeake Bay coves and shallow rivers.
• Features two spacious staterooms, making it an ideal overnight retreat for two couples or accommodating up to 12 guests on a day charter.
• Suitable for various experiences, from an elegant sunset cruise to a week-long excursion along the Chesapeake Bay, Annapolis, and Baltimore.
• Firefly ensures your private yacht charter is marked by style, comfort, and luxury.

Photo Gallery

The stunning yacht Muse at her winter home in Miami

Reserve Your Charter Today!

Get in touch.

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326 1st Street, Suite 403, Annapolis, MD 21403

Mike Esposito / [email protected] 239-227-7879

Copyright © 2024 Elite Charters of Annapolis - All Rights Reserved.

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Classic Sail Charters

Private sailing charters in maryland, choose your location, annapolis, md.

May - October

Learn More »

• Most Popular!

Sunset Sail - Licentia

Come join us for an unforgettable cruise on one of our world-class sailing yachts and enjoy the beautiful sunsets in Chesapeake bay!

• Hour Glass 2.5 Hours
• Users Up to 6 Passengers

Your Dream Adventure Awaits

Catering to clients seeking a unique, private sailing adventure for up to six passengers, we offer world-class sailing yachts, decades of experience, and 5-star service to ensure that your charter is truly memorable. All our charters are for private parties, so you can have it your way. is required. 

Charters Feature

Sunset Cruises

Daily Sails

Weekend Cruises

Milestone Celebrations

Marriage Proposals

Family Adventures

Check-out what our Guests say about us! ★★★★★

Capt. Nate & Payton were great! We did an engagement shoot on the boat and they were unbelievably helpful. They were extremely accommodating to the photographer and worked to position the boat perfectly as the sun was setting. Siena is a beautiful boat and the west river is idyllic. Can't recommend enough.

Captain Tony was great host and helped us have a fantastic experience. He even taught my husband some sailing skills, which allowed me to relax, have some snacks and drinks. Boat was clean and very well maintained. He has a strong commitment to saftey and is very knowledgable about sailing. Highly encourage others to book a trip with him.

My fiancé and I are both from New England and grew up by the water, so we knew we wanted a nautical setting for our engagement photos. We had a fabulous time with Classic Sail Charters on the beautiful Siena! Captain was so helpful in offering to angle the boat this way and that for better light and even raising or collapsing sails. We'll definitely be back!

My husband I along with our two grown children (in their 30's), had a wonderful day with decent wind in July sailing at times to 15 knots! Captain Tony was accommodating and friendly. He had a variety of snacks and beverages on board and encouraged participation in sailing the boat as well as relaxing in the sun or shade! We will definitely do this again and we're thinking of also offering this as a gift to my parents who also love to sail.

This past Friday, we joined Capt. Tony aboard the Licentia for an afternoon sailing the Bay. We had a great afternoon sailing and motoring (we lost the wind) around the Bay and through the Annapolis Harbor. Capt. Tony is very knowledgeable, friendly, and helpful. He has loads of sailing experience and all enjoyed his sea stories. Would we go again? Absolutely - planning a trip for next May.

Four of us sailed with Captain Tony on 2 different trips - one afternoon and one morning. Both days were fantastic and relaxing and lovely. The 2nd trip we lost the wind eventually so motored around the Bay and Annapolis and Tony gave us some history and stories. He is delightful and skilled and we had a terrific time. We will definitely plan another trip one of these day.

• Chesapeake Bay Itineraries
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Chesapeake Bay

• Virgin Islands
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Celebrate or relax in style on a private yacht charter

Charter a luxury catamaran yacht for a few hours, days or weeks.

Enjoy the scenic views, sailing yacht charter amenities and the adventure that lays ahead for you and your guests. Our experienced captains provide local knowledge and nautical skills to ensure a safe and fun experience for everyone. We can’t wait to have you aboard!

Destinations

Charters available in these beautiful destinations

Key West, FL

The Abacos, Bahamas

U.S., British & Spanish Virgin Islands

St. Vincent & The Grenadines

Make your special occasion a one of a kind experience.

Our mission at Sail Away Catamarans is to provide you and your party a one of a kind experience. Chartering a private yacht is a fun and decadent way to celebrate birthdays, weddings, anniversaries and retirements. Or get the gang together for a family trip, bachelorette party, or a corporate event. Our experienced charter agents are standing by to help make your event a memorable one.

Book Today and Set Sail

Select a Yacht or Itinerary

Search for the yacht or find an itinerary that best fits your event.

Submit Request

" Book Now " to submit your preferences and make your payment. You will receive a confirmation number & email.

We Will Review

One of our specialists will call and review your booking with you as your date nears. Let’s go sailing!

"Can not recommend Sail Away Catamarans enough! I was planning a bachelorette party with 12 girls and they could not have been more accommodating. They were very responsive, reasonably priced and the day of went off without a hitch! ...the boat was just beautiful! All the girls had wonderful things to say and a great time!

Our Most Popular Itineraries

Sunset cruise on the bay, so maryland: crab feast + sail, overnight in annapolis or saint michaels, custom itinerary, book your sailing charter now.

Darling Charters Annapolis

Welcome aboard darling, a classic lobster yacht built on martha’s vineyard.

Perfect for those early risers, or for when you have an action packed day and want to fit it all in.

Harbor Cruise

This cruise will make you feel like a local and discover all that Annapolis has to offer from the water.

Sit back and enjoy this cruise around the harbor, and watch as Annapolis lights up with the setting sun.

Special Event

We are pleased to speak with you to design a unique day on the water.  We think we are the ultimate way to arrive at your special event or wedding , spectator boat for a regatta, or celebrate that special occasion with your friends, family or clients. Contact us to find out how we can bring that added classic elegance to your next event.

Blog Posts ‍

What to bring, what to wear , refreshments, cancellation policy, departure & arrival, terms and conditions, the fine print, testimonials.

“The prettiest boat in Annapolis"

"Wonderful captain, conversation, sights, boat & charcuterie board! ‍ I would do it again!

“ l loved being out on the water on a beautiful August afternoon. It was the perfect way to entertain three of my close friends. We enjoyed Champagne, sunshine and a guided tour of Annapolis area creeks and the Chesapeake Bay. We all agreed that our time on the picnic boat was greatly enhanced because of our captain Alexandra"

About the Boat

Darling is a 1973 Wasque 32 (pronounced “Way-squee”) named after Wasque point on Martha’s Vineyard.  She is a much loved classic and one of only 50 built by Martha’s Vineyard Boatworks.     Based on the lobster boat hulls of Maine, she was designed to be a fishing boat for the often challenging waters around the Vineyard and Buzzards Bay. As result she is a seaworthy vessel, cruising smoothly on the near full length keel. Darling had a major refit in the early 2000s that included the hard top and a new engine, and has continued to be upgraded to keep her in great shape. She is a very sea worthy design and also provides a wonderful open cockpit - the perfect setting for your next cruise.

Founded by two lifelong sailors, we wanted to share our love of the water with you and provide the ultimate way to experience Annapolis! ‍ When we found Darling it was love at first sight - book your cruise today to find out why!

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Departure date

Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $, 24 annapolis boat rentals: private yacht charters md.

Annapolis, MD

boating guide

In addition to the best offers we have for boat and yacht charters in Annapolis, MD, see also options available for rent in these nearby locations:

• 25 boat rentals in Annapolis, MD
• 25 boat rentals in Parole, MD
• 25 boat rentals in Highland Beach, MD
• 25 boat rentals in Arnold, MD
• 25 boat rentals in MD
• 25 boat rentals in Edgewater, MD
• 25 boat rentals in Riva, MD
• 25 boat rentals in Severna Park, MD
• 12 boat rentals in Stevensville, MD
• 25 boat rentals in Shady Side, MD

Rent a Boat Charter in Annapolis, Maryland with Sailo!

Looking for a boat rental Annapolis, MD? Let's start choosing the right private yacht rental in Annapolis, MD - the charming capital of Maryland — is quintessentially maritime. Home of the US Naval Academy, this amazing town preserves the authentic Colonial atmosphere: cobblestone streets, original lamp posts and brick row houses. Sailing is ingrained in Annapolis — a boat rental comes naturally if you choose to spend a few days around here.

How to rent a boat in Annapolis, Maryland?

Check out our extensive inventory and pick the yacht rental in Annapolis, MD that suits your plans for having fun on the water. Whether you are into watersports, looking for a relaxed cruise, or to go for a fishing trip, this famous boating destination has something for every taste. If you’re around for the 4th of July, you’ll get the chance to enjoy the amazing fireworks right from your boat!

A boat rental to Chesapeake bay is the perfect choice for a romantic sunset cruise to enjoy the scenic skyline, or a visit to the historic Kent island. There are many things to do by boat in “America’s Sailing Capital”. Browse, pick your Annapolis, MD boat rental and get ready for a memorable nautical adventure! We also invite you to check our top boat selections in other locations in Maryland: Pasadena boat charters and Solomons Island boat rentals .

Sailo concierge team is here to help you rent the perfect private boat charter in Annapolis to go sailing in Maryland. To ask for more details or request special arrangements on your private yacht rental in Annapolis, MD, please send a direct message to the boat representative, or reach out to us on live chat.

Annapolis, MD could be the ideal yachting playground for you

Boating in Annapolis is a thrilling experience and one best savoured with your own private yacht charter. Choose your perfect boat rental in Annapolis and step aboard with your family or friends for a spectacular day on the water. Escape the crowds and enjoy some of the most beautiful scenery in Maryland from the deck of your own yacht charter.

Top private boat rentals in Annapolis, MD

Want to rent a boat in Annapolis, MD? You’ll find 9 boats waiting for you to take them on an adventure here on Sailo. Choose from our sailboat rentals in Annapolis, MD . Another great choice is a catamaran rental in Annapolis, MD . Fans of luxury motor yachts will be spoiled for choice with our multiple motor yacht charters in Annapolis . Maryland is an excellent place to enjoy a party, so discover our party boat rentals in Annapolis, MD for 13+ guests in Annapolis and see for yourself.

How to find a boat charter in Annapolis, Maryland?

Choosing the perfect Sailo boat for you in Annapolis, MD is easy and quick thanks to our advanced filters! First we recommend filtering by date and trip duration. Whether you look for a 2, 4 hrs or a full day boat rental in Annapolis, MD, the group size is very important, as well as the type of boat you want for your adventure in the waters of Maryland. Use the price filter to see only options according to your budget and click on the 'Crew' button to choose if you want a Annapolis boat charter with a captain or you want to drive it yourself (option Bareboat). Once a Annapolis yacht charter catches your eye, click on it to see the boat page with more photos and a detailed description. Check the reviews and send a direct message to the boat owner to ask more details!

How much does it cost to rent a yacht charter in Annapolis, MD for a day?

Annapolis boat rentals prices vary significantly. You can find great budget friendly private yacht rentals in Annapolis, MD starting from $250 for a daily trip. Luxury or party yacht rentals for the day can cost up to $6500 where service fees and mandatory extras are not included. Your budget per day will vary depending on whether you are renting the boat in Annapolis with captain and/or crew, fuel cost, special requests for pick-up and drop-off or other special arrangements you may want to make with the owner.

Can I pay in installments for my Sailo Annapolis boat rental?

A lot of our boat owners allow payment in installments, particularly for the weekly yacht charters in Annapolis, MD. First installment is always charged at the time the booking is confirmed. To find out if a boat has an installment plan, reach out to the boat representative and ask details via 'Message Owner' before you submit the booking or check out the Payment Schedule at top of the booking page.

Responsible boating guidelines

• Take your rubbish home
• Use eco-friendly sunblock
• Avoid single use plastic

Popular locations to rent a boat in Maryland

• boat rental St Michaels, MD
• boat rental Cambridge, MD
• boat rental Baltimore, MD
• FAQ and Policies
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• Discover Boating
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• British Virgin Islands
• La Paz, Mexico
• Cabo San Lucas, Mexico
• Key Largo, FL
• St. Vincent and Grenadines

Rent a boat in Annapolis. MD

18 boats available for bareboat or crewed charter

Yachts from professional fleet operators in Annapolis. MD

Free cancellation of reservation without obligations within 4 days

Yacht types available in Annapolis. MD

Catamaran charter

Sailboat charter

Power boat charter

Most affordable boats for rent in annapolis. md list of boats sorted by the price per week. starting with the most affordable boats from ₽322,380 per week (like sun odyssey 389 - 2018) going to more premium yachts available in annapolis. md from ₽1,206,090 per week..

Sun Odyssey 389 (2018)

Sun Odyssey 440 - 3 cab. (2018)

Dufour 430 - 3 cab. (2021)

Jeanneau NC 33 (2018)

Jeanneau 53 - 3 cab. (2018)

Dufour 530 - 4 cab. (2021)

Jeanneau 58 (2017)

Fountaine Pajot Astrea 42 - 3 + 1 cab. (2024)

Fountaine Pajot Isla 40 - 3 cab. (2022)

Fountaine Pajot Astrea 42 - 3 + 1 cab. (2021)

Most popular sailboat rentals in annapolis. md, popular catamarans charters in annapolis. md.

Fountaine Pajot Aura 51 (2024)

Fountaine Pajot Saona 47 (Quintet) - 3 + 1 cab. (2019)

Fountaine Pajot Saona 47 - 5 cab. (2024)

Lagoon 50 - 6 + 1 cab. (2022)

Fountaine Pajot Elba 45 (2022)

Fountaine Pajot Tanna 47 Maestro - 3 cab. (2025)

Fountaine Pajot Aura 51 (2023)

Annapolis. md yacht charter options, bareboat charter, crewed yachts, skippered boats, cost of boat rental in annapolis. md.

The prices for yacht charters in Annapolis. MD are closely tied to the weather and sailing conditions throughout the year. They tend to be at their lowest in January, corresponding to the low season, and reach their peak in July when demand is high and sailing conditions are optimal.

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New Model Charter Yachts In Annapolis, MD

Waypoints Annapolis offers a variety of new model sailing monohulls, catamarans, and powerboats for multi-day charters on the Chesapeake Bay. Our team prides itself in providing an elevated charter experience for each of our guests aboard our meticulously maintained yachts equipped with all of the comforts of home. Come charter with us and discover the Waypoints difference.

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Casa Bay Rentals

Unique overnight lodging experience in annapolis, md, chillin' time overnight accommodations.

Enjoy a relaxing getaway on a wonderfully unique stay in Annapolis aboard Chillin’ Time, a 41-foot Carver yacht.

• Tags Ages 25+
• Hour Glass 2-28 Nights

About Casa Bay Rentals

Casa Bay Rentals was formed in 2022 with the mission of adding a unique short-term lodging opportunity to the Maritime Republic of Eastport, in the historic Annapolis area. Casa Bay rentals believes that if you’re going to visit one of the boating capitols of the world you should stay aboard a luxury boat where you can enjoy the true feeling of Annapolis and the water from the comfort of a yacht, and at a very affordable cost.

Find the best Annapolis, MD Boat Rentals and Yacht Charters Near You

• Boat Rentals
• Maryland Boat Rentals

Top Annapolis, MD Boat Rentals and Yacht Charters

Glen Burnie, MD

Tahoe T16: Your Ticket to Fun on the Water!

Stevensville, MD

Fun and Sporty 20' Sea Hunt 207 Triton

Annapolis, MD

46' Catamaran Charter with Water Toys - Annapolis, MD

20' Regal Great for cruising & relaxing

Edgewater, MD

Excellent Chesapeake sailing onboard Windsnap

Chaparral 256 SSX

"Equinox" - Center of the Sun - Lippincott 30'

Grasonville, MD

Fun 27' Bow Rider. Great for Water Tubing!

Amazing boating experience on the Chesapeake Bay

25' Coronado Clara B in Arnold, MD!

Sailing Vessel (S/V) DreamCatcher

Chester, MD

Bayliner VR6 at Kent Narrows!

Luxurious 51’ Flybridge Yacht,

Custom Sailing Charters - 44’ Catamaran

Stable, comfortable & fast - sleeps 8 w/4 baths!

20ft Fishing/Crabbing/Pleasure Craft

Stratos walkaround fishing boat

Sailing Charter - Sunset Cruises, Learn to Sail, and Family Fun Time!

How to rent a boat in annapolis, find the perfect boat.

Enter your desired location and date to explore our fleet of boat, Annapolis, MD, United Statess.

Select a captain

Choose to drive yourself or select a USCG licensed captain.

Book with ease

Connect with your boat owner and complete your booking online.

Enjoy your day on the water with friends and family!

Why Boatsetter?

As the global leader in peer-to-peer boat rentals, Boatsetter offers an easy, safe and accessible way to experience on-the-water adventure. With boat rentals in 600+ locations, finding a boat is easy and with the option to tap into the largest network of USCG licensed captains, boating experience is not required.

Get out on the water worry-free, knowing our insurance covers every boating trip

Choosing the right boat rental platform is essential to your peace of mind while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

Got questions?

Frequently asked questions

What makes Boatsetter different from other boat rental platforms?

What makes Boatsetter different is peace of mind. Boatsetter is the first and only boat rental marketplace to offer insurance on every peer-to-peer boat rental. We know choosing the right boat rental platform is essential to your experience while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

How to rent a boat on Boatsetter?

At Boatsetter, our mission is to make getting out on the water as easy as possible. With our intuitive booking system, you can rent a boat as soon as today. -First, you must determine your budget and the type of boat you want to rent. -Next, decide where you would like to boat and the kind of boat you would like to spend the day on. -Finally, determine if you will be needing a boat captain and reach out to the boat owner. That’s it! You’re officially on your way to a fantastic day out on the water.

How much does it cost to rent a boat?

The cost to rent a boat depends on whether you are renting for a half-day or a full day, the boat features and the boat size can impact your boat rental price. Rental prices can range from $200 to $1,000 plus depending on the boat rental itself and the length of time of the rental.

How many people can fit on the boat rental?

The number of people who can fit on boat rental largely depends on the boat’s size and how many life jackets are on board. Currently the coast guard allows a maximum of 10-12 people on a Boatsetter boat rental.

How much does it cost to rent a yacht?

The cost of renting a yacht depends on the boat’s size and the amount of time you’ll use the yacht. The onboard amenities and luxurious accommodations also dictate the price. You can contact our yacht specialists for a custom quote by visiting https://www.boatsetter.com/luxury-yacht-charters .

How old do you have to be to rent a boat?

You must be 18 years old to rent a captained boat and 25 years old if you would like to rent a bareboat charter.

Do I need a boating license to rent a boat?

Boating license requirements vary from state to state. As a renter, you are responsible for understanding local state requirements.

Can you rent a yacht for the day?

Boatsetter allows you to rent a yacht for the day. Single-day yacht rentals are available for a select number of yachts. To chat with a yacht specialist please visit https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the week?

Boatsetter allows its customers to rent a yacht for the week. Renting a yacht for a week gives you more access to the wide range of yachts available on our platform. You can either book a rental directly through the site or connect with one of our charter specialists to plan your trip here: https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the month?

Booking a month-long yacht rental is a detailed and hands-off process when working with our team of yacht charter specialists. We tailor each yacht charter to our client's specific wants and needs. Our luxury yacht charter specialists can be reached at (954) 715-4114 or by visiting https://www.boatsetter.com/luxury-yacht-charters .

How to rent a private yacht?

Renting a private yacht is a very detailed experience that caters to your exact needs while onboard one of our luxury yachts. To plan your private yacht rentals experience please visit https://www.boatsetter.com/luxury-yacht-charters .

How much does it cost to rent a pontoon boat?

The cost of renting a pontoon boat depends on the size, location, and rental time of the boat. Prices can range anywhere from $200 for a half-day rental or just under a $1,000 for longer rentals.

How much does it cost to charter a yacht?

The cost to charter a yacht varies depending on the boat size and the length of the charter. Prices typically range from less than $1,000 to $5,000 plus if you’re wanting to charter the yacht overnight.

How much does it cost to rent a boat for the day?

The cost of renting a boat for the day on average ranges from $200 to $1200. The cost to rent a boat varies depending on the size of the boat and the length of time that you will be using the boat.

How does the boat insurance work?

Boat insurance typically covers loss caused by things such as fire, sinking, storms, and collisions. The extent of the coverage varies depending on the policy.

Do I need my own insurance to rent a boat?

You do not need boat insurance when renting with Boatsetter. Coverage is provided under the Peer-to-Peer Boat Rental Policy, which is underwritten by GEICO Marine Insurance Company. The policy was written from the ground up as a stand-alone recreational boat rental insurance policy covering the period of time that the boat is being rented and is available for all non-commercially insured boats.

Does Boatsetter screen renters?

Yes. We use a system called Cognito to ensure that payment information matches the renter's identity. We also require renters taking out a captained boat to be at least 18 years old and on a bareboat to be at least 25 years old.

Is listing my boat on Boatsetter free?

Yes! Listing a boat is completely free. We only take a commission when your boat is rented. We only make money when you do!

What if I'm not comfortable having a renter drive my boat?

If you are not comfortable having a renter drive your boat, we have an expansive network of licensed and experienced captains. Once your boat is listed, you can filter through our network of captains and favorite captains in your area that you would like to operate your boat.

Top destinations for boat rentals, Annapolis, MD, United States

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Annapolis’ Most Popular Experiences

Given its history, you will soon begin to understand why Annapolis is the perfect place to sail. Here are a few of the things you can get up to by the water. Join the fun at the Sailing Races In the summer months, all of the action can be found at the weekly Wednesday sailing race. You can either spectate from the side or follow the action from aboard your Annapolis boat rental. Get down to the Boat Shows In the spring and fall months, you can check out the U.S.’s oldest boat shows. Spectators flock in their tens of thousands to check out what’s been shown. Take a wander around and think about what type of Annapolis boat rental you’ll be taking out the next morning. Make Sure you Pack your Rod Fishing is a must when out on the water in Annapolis. You’re bound to fill your bags with the likes of Redfish, black drum, spotted seatrout, as well as both smallmouth and largemouth bass.

Annapolis’ Best Bodies of Water

Enjoy the Severn River

The Severn River is a quiet body of water that makes for the ultimate place to unwind on your Annapolis boat rental. It’s home to a restored oyster reef which gives it an abundance of marine life, so have your rod at the ready.

Loop Around Kent Island

You’ll see Kent Island directly opposite the shoreline at Annapolis. Take your Annapolis boat rental around for a casual loop of the island and take in its sights. Given its size, it’s likely to be the first destination on your mind.

Sail Down South River

South River offers a pleasant place to explore in Annapolis. Its tranquil waters create a relaxing and peaceful aura whereby you can only hear your boat skim across the water. Once you reach this body of water, all of your worries will pass away.

Top boat rental reviews in Annapolis, MD

Bayliner VR6 at...

We had a fabulous time! We will definitely rent this boat again!!

46' Catamaran...

We rented this boat for my sister's bachelorette party and had the BEST time! Seriously it was the highlight of the...

Will was great to work with. Very responsive with communication. I really liked the size and layout of the boat. The...

This boat owner was hospitable and efficient. The boat was clean. He put my four guests at ease . He explained the...

My group had the best time with Windsong Charters. Everything was exactly as described and we had a wonderful day....

We had a wonderful day on the Bay with Tyler as our guide. He knew the best spots to go to hang out, tube and...

Wonderful boat, captain was very flexible with allowing additional passengers on board, would definitely recommend...

The boat was super spacious and filled with an array of water toys that were a crowd favorite at my sister’s...

Fun and Sporty...

Sailing Charter -...

Audrey and Garrett were fun, friendly, knowledgable, and accommodating. Perfect first sailing experience. Highly...

"Equinox" -...

Great time on the water, appreciate your facilitating

Boat rentals in Annapolis, MD

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Annapolis Yacht Charters

Captain and Bareboat, Cruising or Fishing

Daily through weekly rates

1505 Shipsview Road

Annapolis, MD 21409

[email protected]

410-353-8242

Yacht Rentals Near You

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Annapolis Yacht Rentals

Yacht charters at annapolis.

America’s Sailing Capital!

Annapolis is the state capital of Maryland, and, is also one of the oldest cities in the US. dating back to the 1600’s, full of authentic architecture, and, is home to the famous US naval academy. This historic city is also in the heart of the Chesapeake Bay. This gigantic estuary is fed by hundreds of rivers. The combination of salt and fresh water nurture an amazing amount of wild life and sea food, so be sure to east as many crabs, oysters, and local fish as you can!

Winters, early spring and fall are cool, while summers are warm and humid. The best time to visit for warm weather is from May until early October, with on average 205 Sunny days a year

Quick Facts

Why hire a yacht in annapolis.

Charter a boat in Annapolis

Why hire a yacht in Annapolis? That is because this is considered the sailing capital of the United States. This is because of the beautiful waters of Chespeake bay. You need to rent a boat in Annapolis to experience this. Charter a boat in Annapolis and sail your rental yacht in Chesapeake bay, visit authentic fishing, and sail into scenic rivers full of wildlife. An Annapolis rental yacht is also so relaxing! When you rent a yacht in Annapolis, you will see a natural coastline of bays, rivers, and islands , rich in history and nature. Your Annapolis boat rental can also take you to nearby historic villages and destinations. These include villages like Saint, Michales, Oxford, and Kent Island., Onboat has curated a collection of select Annapolis charter yachts for you to choose from. A boat rental in Annapolis is how this city was really meant to be celebrated. Also, inquire about party boats in Annapolis when you are having an event!

Call (844) 500-2628 to book a private Annapolis charter boat today.

How to rent a yacht in Annapolis?

How much does it cost to rent a yacht in annapolis, what yacht charter is popular in annapolis, what to do before you board a charter boat in annapolis, while aboard.

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410-956-9729

South River Boat Rentals

Welcome to south river boat rentals, boat rentals and charters on the chesapeake bay, family, social & corporate outings.

30+ Years Serving Chesapeake Bay Boaters

We had a FANTASTIC time on the Bennington boat. Our Captain Max was a blast! He found multiple spots for us to hang out in the water, and even drove us around tubing! 10/10 recommend for your Annapolis boat rental!

WATER SPORTS AND MORE

We offer water sports – tubing, skiing, wakeboarding, and kneeboarding.

Water Sports on the Chesapeake Bay bring all of your family and friends together.  Whether you enjoy water skiing, wakeboarding, tubing, or knee boarding, we have the water sports for you on the Chesapeake Bay.

Our Rental Fleet

19' Hurricane (S)

1/2 day: $550 | full day: $900, 6 max / wt limit: 1410 lbs.

21' Kencraft

6 max / wt limit: 1250 lbs.

26' Bennington Pontoon

1/2 day: $800 | full day: $1400, 12 max/wt limit 2200 lbs..

26' Chaparral Sunesta

10 max/wt limit 2600 lbs..

26' Crest Tritoon

12 max/ wt limit 2400 lbs..

26' Everglades

1/2 day: $950 | full day: $1700, 10 max including our captain.

SEE PRICING DETAILS

30 max passengers / includes captain.

50' LRC Trawler

12 max passengers / includes captain.

Our Customers Love Us!

 Just Google "South River Boat Rentals" to see all the positive reviews we have earned throughout the years. Customer service and ensuring you have an excellent day on the water is our top priority.

We used South River boat rentals this past weekend for a bachelorette party and had the absolute best time. Special thanks to Captain Chris and the rest of the crew who were all kind, courteous, and informative. Definitely will be returning! - Gabby Cooper

Amazing day on the pontoon boat with our extended family. Graham was a WONDERFUL captain and host. He took us to a quiet area to swim, dragged all 4 kids in the tube, and slowed the boat so we could look at wildlife up close. Worth every penny! Highly recommend requesting Graham as your captain. - Meredith Bove

Thank you for a memorable experience. Would recommend this place to everyone. Can’t wait to make another reservation in the future. A big thank you to Nancy for your amazing customer service and friendly personality!! - Nicole Wilkinson

Thank you for an amazing time. We rented the 26' Chaparral for a day of cruising and tubing. We could not be more grateful. The boat ran perfectly and the staff was king, courteous and accommodating. We will return! - Garrick Muench

Had a great experience with them. I even had to reschedule for a later date and they were able to accommodate! Would definitely recommend the 50' Trawler! - Kourtney Ramseur

Such an amazing company to work with!!! From scheduling, to weather related rescheduling, the captain, and the overall boat condition and experience - I cannot say enough good things about South River Boat Rentals! Definitely will return! - Tara Klimovitz

The boat was ready and waiting for us; the service was good from booking to returning the boat. South River made it an easy and enjoyable experience. - Judy Graham

So much fun renting a boat for the day. Our Captain Wayne was awesome and took us wherever we wanted to go. He gave suggestions based on weather/water conditions/our ideas of what we wanted to do. It was really a great day! - Sarah Edwards

Outstanding Labor Day out on the water thanks to South River Boat Rentals! Best prices in the area, great vessel, easy to use, a lot of fun for our family! - Mark Fratto

The staff was awesome and super hospitable. They walked us through everything and made sure we felt comfortable on the boat. Boat was in great condition too! - Dylan Stoskus

We had a wonderful experience with South River Boat Rental! The boat was in perfect condition, very clean, and the staff was a pleasure to work with. Would highly recommend! - Liz Gillette

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Start with A Free Quote For Your Next Adventure. You can also book online by going here: Book Online

For questions, information and details about your rental/charter please call: 410-956-9729.

Private Yacht Charters & Weddings

The perfect venue for any occasion; providing dynamic events with an ever-changing backdrop.

Weddings on the Bay

Chartering a boat is a refreshing alternative for your wedding celebrations! From ceremonies and receptions to engagement parties, rehearsal dinners, and beyond, our luxury yachts make a stunning venue.

Corporate Outings

Take your company event to the water! Treat your employees, entertain clients, celebrate the holidays, host networking events … The possibilities are endless. Corporate yacht charters are flexible and offer a unique, one-of-a-kind experience.

Social Events

The perfect venue for any occasion! From birthday parties and family reunions to anniversaries and milestones, chartering a yacht is a refreshing way to celebrate. Treat your guests to the best waterfront venue in Annapolis and Baltimore.

Yacht Charters on the Bay

Our diverse fleet of yachts is available for private rental for up to 200 passengers.

Catherine Marie

Harbor Queen

Annapolitan II

Celebrate in Style

From the original proposal to the actual event, Watermark offers professional, polished service down to the most precise detail, so you and your guests can sit back, relax, and enjoy!

Yacht Venues for Social Events

Take your next event to the water. Contact us to see how we can make your birthday, reunion, or just for fun event a truly memorable experience. Our event specialists will assist you throughout the entire process to ensure your event is a resounding success!

Unique Business Events & Corporate Entertainment

Add a unique experience to your corporate event and ask us for a full day on the bay trip to St. Michaels, a lighthouse cruise with a live narrator, or cruise with Francis Scott Key. Whether it is cocktails and hors d'oeuvres or a full crab feast on the top deck, a private yacht charter will become your most popular event.

Breathtaking Wedding Venues

Watermark specializes in rehearsal dinners, welcome cruises, bachelor/bachelorette parties, wedding receptions/ceremonies, and other wedding related events. Simply choose your dream waterfront wedding venue from our entire fleet of pristine vessels. Watermark is home to all things weddings in Annapolis, Baltimore, and the Eastern Shore.

Guest Journeys

Celebrating unforgettable journeys for 50 years!

Steve and Kim

Keith and Galina

Sunset Cruise

Eileen and Chuck

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Sailing Season is Here. Join Us for a Sail!

Welcome Aboard!

Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II , for a true sailing experience in Annapolis, Maryland.

Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us!

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Make your sailing experience a memorable one! Sail away with us!