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    Browse Annapolis Boat Rentals

    4.9
    (519 Reviews)
    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated

    Most Popular Sailboats in Annapolis

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    • Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD
      Sailing in Rock Hall · 4 guests

      Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

      5.0
      $150hour
    • 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
    • 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
    • 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
    • Fully Crewed Annapolis Sailing Cruises
      Sailing in Annapolis · 6 guests

      Fully Crewed Annapolis Sailing Cruises

      New
      $175person
    • 34ft Sailing Yacht in Annapolis, Maryland
      Sailing in Annapolis · 4 guests

      34ft Sailing Yacht in Annapolis, Maryland

      New
      $250hour
    • The Licensed Captain of this 42ft Sailboat, provides charters on Chesapeake Bay.
      Sailing in Mayo · 6 guests

      The Licensed Captain of this 42ft Sailboat, provides charters on Chesapeake Bay.

      5.0
      $175hour
    • 41' Lagoon Catamaran in Maryland
      Sailing in Annapolis · 12 guests

      41' Lagoon Catamaran in Maryland

      5.0
      Superowner
      Best of 2023
      $390hour

    All Annapolis Listings

    Page 1 of 2 • 40 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
    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
    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
    The Licensed Captain of this 42ft Sailboat, provides charters on Chesapeake Bay.
    Sailing in Mayo · 6 guests

    The Licensed Captain of this 42ft Sailboat, provides charters on 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
    Experience the Serenity of Sailing SV Magic
    Sailing in Mayo · 6 guests

    Experience the Serenity of Sailing SV Magic

    4.8
    $165hour
    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
    Sea Doo Switch - Sea Cruiser Pontoon in Pasadena MD
    Powerboats in Riviera Beach · 11 guests

    Sea Doo Switch - Sea Cruiser Pontoon in Pasadena MD

    New
    $150hour
    50ft Catamaran Charter with Water Toys - Annapolis, MD
    Sailing in Annapolis · 12 guests

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    New
    $400hour
    Relax in Edgewater and Annapolis
    Powerboats in Edgewater · 10 guests

    Relax 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
    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
    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
    Robbins Chesapeake 40' Fishing Charters in Maryland
    Fishing in Annapolis · 6 guests

    Robbins Chesapeake 40' Fishing Charters in Maryland

    5.0
    $125-$150hour
    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
    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-$349hour
    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
    Snoozed - Active 02 Jan 2025

    Top Destinations Nearby

    Annapolis Reviews

    1. Noelle

      Noelle

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      My group and I had an amazing time! If you’re looking to have a great experience make sure to book with Captain McCoy. The boat was very clean. Getting on board was simple and finding the dock was easy. Also enjoyed stopping in the middle of our trip to just enjoy the weather and laying out on the front of the boat. I’d definitely book again!

    2. LW

      Lianna

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      Captain McCoy was wonderful! Very accommodating and communicative. Our group had a great time!

    3. KC

      Kevin

      41' Lagoon Catamaran in Maryland

      Captain Jess was fantastic! Great experience!

    4. 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!!

    5. 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! :)

    6. 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.

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