Browse Annapolis Boat Rentals

Average of 313 reviews in this area.
1 - 18 of 35 listings
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
hour$150
Potomac RiverCruising Monohull
Super Owner6 guests

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

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
hour$150
Chesapeake BayCruising Monohull
Super Owner6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

41' Lagoon Cruising Catamaran in Maryland, United States
day$1,849
Potomac RiverCruising Catamaran
12 guests

41' Lagoon Cruising Catamaran in Maryland, United States

Charter the 60' Sea Spirit Motor Yacht in Annapolis, Maryland
day$2,100
Potomac RiverMotor Yacht
85 guests

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

34' Hunter Cruising Monohull In Rock Hall, Maryland United States
night$220
Chesapeake BayCruising Monohull
4 guests

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

Charter 44' Orana Cruising Catamaran In Deale, Maryland
day$2,400
Potomac RiverCruising Catamaran
10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

Beneteau 41ft Sailing Charter in Annapolis, Maryland
hour$180
Potomac RiverCruising Monohull
8 guests

Beneteau 41ft Sailing Charter in Annapolis, Maryland

Rent this 300 Sea Ray Cuddy Cabin Cruiser in Edgewater, MD
hour$200
Potomac RiverCuddy Cabin/Walk Around
6 guests

Rent this 300 Sea Ray Cuddy Cabin Cruiser in Edgewater, MD

2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland
hour$120
Potomac RiverPower
4 guests

2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

Awesome Savannah SS21 Center Console Fishing in Chester
hour$130
Chesapeake BayCenter Console
10 guests

Awesome Savannah SS21 Center Console Fishing in Chester

21' Center Console Cruises in Chesapeake Bay, Annapolis MD
hour$130
Potomac RiverCenter Console
10 guests

21' Center Console Cruises in Chesapeake Bay, Annapolis MD

Annapolis Sailing on a 34' Beneteau Sloop!
hour$150
Potomac RiverSail
6 guests

Annapolis Sailing on a 34' Beneteau Sloop!

Sail the Bay with Hunter 380 Sailing Yacht from Edgewater, Maryland
hour$175
Potomac RiverCruising Monohull
6 guests

Sail the Bay with Hunter 380 Sailing Yacht from Edgewater, Maryland

Blue Angels Annapolis on Ghost Rider
day$490
Potomac RiverRIB
6 guests

Blue Angels Annapolis on Ghost Rider

35 results

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.

Annapolis Boat Rental FAQs

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 that includes a licensed captain so that you can enjoy your time on the water. If you want to captain the boat yourself you will need to 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.

GetMyBoat customer reviews for boat rentals in Annapolis.

  1. DS
    Dan
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Capt Alberto and his wife Grace are amazing hosts and people! This was our families first trip on the Getty oat site and we’re happy to choose this one. The boat was in pristine condition and even though there wasn’t much wind the day we went out, the Capt searched and found some! The kids were able to steer and learn about sailing. All in all a perfect morning and would definitely recommend to anyone!

  2. FT
    FREDERICK
    Get away for a day or weekend! Charter 44' Catalina Sailboat!

    John was exceptional he made our first experience memorable and wonderful and paid attention to the little details!! we celebrated our 20th anniversary here and he made it extra special . we will definitely be back for more celebration!!!

  3. AM
    Amy
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Captain Alberto was such an amazing host and captain! He and his wife were wonderful hosts, and made our trip even more amazing. We had such a great time and can not wait to go back again for another "girls weekend" or with our family and friends. We will be recommending Captain Alberto to everyone we know!

  4. EG
    Emmanuel
    2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

    Booked the boat last minute for my girlfriends surprise birthday weekend and Sunmi was very flexible with the location and time. If you’re looking for a sentimental experience, please book him. If I had more than 5 stars, I’d give it to him. Thanks Sunmi!!!

  5. AH
    Angela
    Charter this 42ft Hunter Passage Sailboat in Edgewater, Maryland and sail on the beautiful Chesapeake Bay

    Captain Bill was absolutely marvelous!! The trip was amazing!! My guest and I chartered a three hour venture and had the wonderful adventure! We celebrated my cousin’s birthday and everyone was elated to ride with such a great captain! He went above and beyond to make sure we had a joyous occasion! His personality was second to none!! I extremely recommend you charter him for your next boat ride!! You will not be disappointed!!

  6. JL
    Jonathan
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Capt. Alberto and Grace were fantastic hosts to our foursome. Alberto was knowledgeable and seasoned, and gave great advice to us aspiring sailors about buying our first boat. We’ve made great nautical friends in Alberto and Grace!