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Browse Annapolis Boat Rentals

4.9(Average of 479 reviews in this area)
Learn more about boating in Annapolis

All Annapolis Listings

Page 1 of 2 (42 listings)
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
Beneteau 41ft Sailing Charter in Annapolis, Maryland
Sailing in Annapolis · 8 guests

Beneteau 41ft Sailing Charter in Annapolis, Maryland

5.0
$245hour
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
41' Lagoon Cruising Catamaran in Maryland, United States
Sailing in Annapolis · 12 guests

41' Lagoon Cruising Catamaran in Maryland, United States

5.0
Superowner
Best of 2022
$349hour
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
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
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
Charter the 60' Sea Spirit Motor Yacht in Annapolis, Maryland
Events in Annapolis · 65 guests

Charter the 60' Sea Spirit Motor Yacht in Annapolis, Maryland

4.9
$3,600day
Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
Powerboats in Annapolis · 6 guests

Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

4.8
$150hour
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
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
Like new 2021 Bayliner Element e18 Bowrider on the Magothy River
Powerboats in Severna Park · 8 guests

Like new 2021 Bayliner Element e18 Bowrider on the Magothy River

5.0
$125hour
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
31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD
Powerboats in Selby-on-the-Bay · 14 guests

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

5.0
$225hour
Rent this 300 Sea Ray Cuddy Cabin Cruiser in Washington, DC
Powerboats in Selby-on-the-Bay · 6 guests

Rent this 300 Sea Ray Cuddy Cabin Cruiser in Washington, DC

5.0
$160-200hour
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
Seawind 1260 Cruising Catamaran Rental in Annapolis, MD
Sailing in Edgewater · 12 guests

Seawind 1260 Cruising Catamaran Rental in Annapolis, MD

5.0
$425hour
Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland
Events in Stevensville · 6 guests

Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland

New
$550hour
Robbins Chesapeake 40' Fishing Charters in Maryland
Fishing in Annapolis · 6 guests

Robbins Chesapeake 40' Fishing Charters in Maryland

5.0
$125-150hour
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
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
41ft Luxury Yacht for Charter on the Chesapeake Bay
Events in North Beach · 10 guests

41ft Luxury Yacht for Charter on the Chesapeake Bay

4.0
$600hour
''3 BuOYS'' Regal 38 SAV Motor Yacht Rental in Arnold, Maryland
Events in Arnold · 10 guests

''3 BuOYS'' Regal 38 SAV Motor Yacht Rental in Arnold, Maryland

5.0
Superowner
$575hour

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. Alex
    Alex
    41' Lagoon Cruising Catamaran in Maryland, United States

    Jess was an amazing captain with a gorgeous boat. We had a group of ten women and Jess was so friendly but also gave us our privacy. He offered to take us swimming, but we opted to ride along the bay instead. While it’s an expensive excursion, it’s worth every penny and I will definitely reach out to jess again in the future. I highly recommend!!

  2. bb
    brent
    31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

    From the very start of our day, Michael was very accommodating to all our desires and tailored the day to make it absolutely fabulous. Would 100% recommend him to everyone and plan to use him again next year. Great Experience!!!!!

  3. Melody
    Melody
    Beneteau 41ft Sailing Charter in Annapolis, Maryland

    Best day! Captain Gus is who you want to take you out on the bay. He is engaging but also gives you space to hang with your group. His boat had toe accommodations that made our day perfect. Thanks so much for a wonderful afternoon!

  4. Laura
    Laura
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Capt Alberto was great. Clean well-maintained boat. Easy parking and access. Fun relaxed day for the family. Got to drive, and relax. Highly recommend and working on rebooking now.

  5. MI
    Maria
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Beautiful experience in the Annapolis bay. Alberto is a fantastic captain and teacher! He let us get involved in the sailing and gave us great conversation! Will definitely repeat!

  6. KW
    Kevin
    2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

    Great time on the water. Sunmi was super flexible and accommodating with our last minute plans. Boat was great. Would recommend.

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 42 listings for boating experiences in Annapolis with 479 reviews.

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