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Browse Annapolis Boat Rentals

4.9(Average of 511 reviews in this area)
Learn more about boating in Annapolis
Page 1 of 2 (37 listings)
46' Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 8 guests

46' Catamaran Charter with Water Toys - Annapolis, MD

5.0
$213hour
2016 Regal 31' CruiseThe Inner Harbor, Annapolis, Hart Miller Island, discount weekday pricing
Powerboats in Annapolis · 8 guests

2016 Regal 31' CruiseThe Inner Harbor, Annapolis, Hart Miller Island, discount weekday pricing

4.9
Best of 2022
$225hour
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.7
$165hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
Sailing in Annapolis · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

5.0
Superowner
Best of 2022
$138-150hour
41' Lagoon Catamaran in Maryland, United States
Sailing in Annapolis · 12 guests

41' Lagoon Catamaran in Maryland, United States

5.0
Superowner
Best of 2022
$320hour
31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD
Powerboats in Selby-on-the-Bay · 12 guests

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

5.0
$250hour
2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland
Powerboats in Severna Park · 4 guests

2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

5.0
$120hour
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0
Superowner
$150hour
Charter this 42ft Sailboat in Edgewater, Maryland for up to 6 persons MAXIMUM.  Take a sail on beautiful Chesapeake Bay or take some Beginner or Advanced sailing lessons on a big boat.
Sailing in Mayo · 6 guests

Charter this 42ft Sailboat in Edgewater, Maryland for up to 6 persons MAXIMUM. Take a sail on beautiful Chesapeake Bay or take some Beginner or Advanced sailing lessons on a big boat.

5.0
$175-200hour
Luxury yacht with Captain for 8 passengers to your Annapolis waterways
Events in Annapolis · 8 guests

Luxury yacht with Captain for 8 passengers to your Annapolis waterways

5.0
$250hour
Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
Powerboats in Annapolis · 6 guests

Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

4.8
$95-150hour
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Sailing in Rock Hall · 4 guests

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

4.5
$275-375night
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$2,600day
43ft Cruiser Express Yacht for Daily Charter on Chesapeake Bay, Annapolis, Rhodes River or South River
Events in Selby-on-the-Bay · 8 guests

43ft Cruiser Express Yacht for Daily Charter on Chesapeake Bay, Annapolis, Rhodes River or South River

5.0
$400hour
Maxum 30ft Yacht! Escape for a day on the Chesapeake
Events in Selby-on-the-Bay · 6 guests

Maxum 30ft Yacht! Escape for a day on the Chesapeake

New
$365hour
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500-750hour
Cruise the Chesapeake Bay on a beautiful 34ft Maxum Yacht
Powerboats in Deale · 6 guests

Cruise the Chesapeake Bay on a beautiful 34ft Maxum Yacht

5.0
$250hour
Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!
Sailing in Annapolis · 4 guests

Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!

5.0
$150hour
Robbins Chesapeake 40' Fishing Charters in Maryland
Fishing in Annapolis · 6 guests

Robbins Chesapeake 40' Fishing Charters in Maryland

5.0
$125-150hour
Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland
Powerboats in North Beach · 8 guests

Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland

5.0
$400hour
Cruise on the Shannon Brendan
Powerboats in Annapolis · 6 guests

Cruise on the Shannon Brendan

New
$350hour
30ft Bowrider! Enjoy a day on the water around the Chesapeake Bay in Maryland!
Powerboats in Annapolis · 8 guests

30ft Bowrider! Enjoy a day on the water around the Chesapeake Bay in Maryland!

3.7
$170hour
Catalina 425 Sailing Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Catalina 425 Sailing Yacht in Rock Hall, Maryland

5.0
$150hour
Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland
Sailing in Saint Michaels · 6 guests

Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

5.0
$250-350hour

Annapolis Boat Rentals

Annapolis is a great place for boat rentals. The city is a big boating hub, with hundreds of stunning motor yachts, sailboats, and more. As the sailing capital of the United States, it stays true to its name with beautiful wooden schooners and sailboats cruising in and out of the many ports around Annapolis. A visit to this city isn’t complete without time spent on a boat exploring the beauty of Chesapeake Bay. Rent a motor yacht or sailboat charter while in Annapolis and spend hours cruising and touring. A boat charter can take you to all the great highlights, seeing the skyline from the perspective of the water.

How much does it cost to rent a sailboat for a day in Annapolis?

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.

How much does it cost to rent a boat for a week in Annapolis?

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

Can you sail in Annapolis without a License?

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.

When does the boating season start in Annapolis?

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

Annapolis Reviews

  1. MS
    Monique
    46' Catamaran Charter with Water Toys - Annapolis, MD

    Deren & Kristal were excellent hosts! We had a lovely day sailing the Chesapeake. They were very communicative and timely with their responses and were flexible with our parties needs and wants. What an excellent experience! Would highly recommend their boat.

  2. TS
    Tom
    Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

    This is a solid boat that I will rent again when in Annapolis. The engine and navigation display are brand new and made for a smooth ride for my family of 4. The boat could comfortably fit 6 adults, so we had lots of room. Controls were simple and handling easy. Great way to see the Academy from the water. When I asked my wife and sons what their highlight of our DC vacation was, they all said "the boat ride"! William the owner was right on time for pickup and drop off, and even gave us a great crabcake restaurant recommendation!

  3. LR
    Loretta
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    What a gorgeous day on the water aboard Sol Searcher! Captain Joe was an awesome host for our day! Peaceful, serene and exactly what we were hoping for to bring the summer to a close. What a lovely world we have to enjoy when we step away from the hustle of life and take the opportunity to take in all that it has to offer. Thank you Capt’n Joe for a wonderful sailing experience. Until we meet again, Loretta and Greg

  4. WC
    Whitney
    Experience the Serenity of Sailing SV Magic

    We had an awesome trip with Josh. He was very flexible with timing and knowledgeable about sailing. We were able to take our engagement photos on Josh’s boat with his help and input on lighting/backgrounds. It was a wonderful experience we will never forget!

  5. BM
    Bernadette
    31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

    Capt Michael is amazing. His boat is beautiful and well maintained. He is friendly, professional and knows how to Captain. He was very flexible and understanding when we had a change of plans and dropped off some of our crew at another location. We highly recommend him for your fun day out on the bay and we will be booking him again!

  6. JW
    Julie
    46' Catamaran Charter with Water Toys - Annapolis, MD

    Incredible! Deren and Krystal made our experience phenomenal. From start to finish they were fun and professional. The boat is a stunner! We felt like royalty. My son celebrated his 8th birthday in style with all the toys and had a blast. We will be using them again next year.

Boating Guide - Annapolis

Annapolis Boat Rentals

Annapolis is a great place for boat rentals. The city is a big boating hub, with hundreds of stunning motor yachts, sailboats, and more. As the sailing capital of the United States, it stays true to its name with beautiful wooden schooners and sailboats cruising in and out of the many ports around Annapolis. A visit to this city isn’t complete without time spent on a boat exploring the beauty of Chesapeake Bay. Rent a motor yacht or sailboat charter while in Annapolis and spend hours cruising and touring. A boat charter can take you to all the great highlights, seeing the skyline from the perspective of the water.

GetMyBoat has 37 listings for boating experiences in Annapolis with 511 reviews.

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