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Browse Annapolis Boat Rentals

4.9(Average of 510 reviews in this area)

All Annapolis Listings

Page 1 of 2 (39 listings)
2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island
Powerboats in Annapolis · 8 guests

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

4.9
Best of 2023
$225hour
41' Lagoon Catamaran in Maryland
Sailing in Annapolis · 12 guests

41' Lagoon Catamaran in Maryland

5.0
Superowner
Best of 2023
$390hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland
Sailing in Annapolis · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland

5.0
Superowner
Best of 2023
$138-$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
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
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
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.8
$165hour
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

New
$425hour
Charter this 42ft Sailboat, for up 6 persons to enjoy the middle Chesapeake Bay
Sailing in Mayo · 6 guests

Charter this 42ft Sailboat, for up 6 persons to enjoy the middle Chesapeake Bay

5.0
$175hour
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
Events in Annapolis · 8 guests

Luxury SeaRay Yacht with Captain | Explore the 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
Relax in the Sun in Edgewater and Annapolis
Powerboats in Edgewater · 10 guests

Relax in the Sun in Edgewater and Annapolis

New
$200hour
Fully Crewed Annapolis Sailing Cruises
Sailing in Annapolis · 6 guests

Fully Crewed Annapolis Sailing Cruises

New
$175person
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
43ft Cruiser Express Yacht for Daily Charter
Events in Selby-on-the-Bay · 8 guests

43ft Cruiser Express Yacht for Daily Charter

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
Come take a cruise on the Annapolis Jet Boat
Powerboats in Annapolis · 11 guests

Come take a cruise on the Annapolis Jet Boat

New
$500hour
Cruise on the Shannon Brendan
Fishing in Annapolis · 6 guests

Cruise on the Shannon Brendan

New
$350hour
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

New
$400hour
Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland
Events in North Beach · 8 guests

Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland

5.0
$400hour
Robbins Chesapeake 40' Fishing Charters in Maryland
Fishing in Annapolis · 6 guests

Robbins Chesapeake 40' Fishing Charters in Maryland

5.0
$125-$150hour
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500-$750hour

Annapolis Reviews

  1. DK

    Deanna

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

    Our group had the most amazing early evening trip! We went swimming, stopped for drinks and had the best day of summer so far! DuShawn and Carla took great care of us and cruising the bay at 4 pm was so peaceful, relaxing and the perfect temperature! It would be hard to top the fun we had especially crashing a 50th birthday party at the Rumor Reel! We all can’t wait to go out with DuShawn again!!

  2. SM

    Shabnam

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

    Dushaune was an incredibly wonderful and amazing captain! He has a fun, warm, welcoming personality! He was very easy to communicate with, and he answered all my questions in-depth! The whole boating tour experience was perfect - from start to finish! He is extremely knowledgeable about the history of the surrounding landmarks! My friends and I cannot stop raving about the boating experiences; we will hands down go back to Dushaune’s boating tour!! 5/5 stars for everything! :)

  3. LaToya

    LaToya

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

    This experience was amazing, we had a great time, Shaune was a great captain, we talked, laughed and even learned a few things. I would definitely recommend Shaune to all of my friends and family if they would like to rent a boat. Definitely looking forward to next time.

  4. Keri

    Keri

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

    Wow! What an experience we had on the water with Captain Dushaune. The boat was very nice and he was very knowledgeable about the area. Will definitely book with him again and might make it an annual kick off to summer! Thanks again Captain for a wonderful trip!

  5. MS

    Mylee

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

    If you want an awesome experience or have a unique request, Dushaune is your guy! He did an absolutely wonderful job for us. For our Indian wedding, we wanted to use a boat for the Groom's entrance into the wedding. This was a complicated ask, especially since the marina next door to our hotel was having a boat show and no one could assist us there. Dushaune walked us through how we could make it work by using a nearby dock on the other side of the hotel. He was always available before the big day to talk to us and his communication was top notch. On the day of, he was on time (even early) and it worked out perfectly. All the guests thought it was an epic way to enter. Dushaune was also very flexible throughout, letting us bring a photographer and videographer on the boat. He also has a giant bluetooth speaker which is awesome to use. HIGHLY RECOMMEND using Dushaune, he is an awesome person to work with and his boat is super nice.

  6. Jodi

    Jodi

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

    Cursing on the River on a Thursday evening was everything! We surprised my daughter for her Birthday and it amazing! We had a dance party! We sang together! We embraced watching the sun go down changing colors and being so breathtaking, my goodness there is nothing like the light of the moon on the water. The sun set to the East and the moon showed up to the west, Aaa-ma-zing! Captain was a gracious host, dropped the anchor so we could chill and chat, this guy is great and I would recommend him 100 times over!!! My daughter LOVED her Birthday surprise on the River!