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Getmyboat Logo
    04/27/2024  ± 1 day
    All listings in Chesapeake Bay

    Incredible sailboat rentals in Chesapeake Bay, United States.

    5.0
    (413 Reviews)

    Page 1 of 2 • 28 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River
    Powerboats in Fort Washington · 6 guests

    2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

    5.0
    $150-$190hour
    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
    Chesapeake Bay Sailing Charter - 33' Cape Dory sailing from Kilmarnock, Virginia
    Sailing in Kilmarnock · 6 guests

    Chesapeake Bay Sailing Charter - 33' Cape Dory sailing from Kilmarnock, Virginia

    5.0
    $73-$112hour
    Experience the Serenity of Sailing SV Magic
    Sailing in Mayo · 6 guests

    Experience the Serenity of Sailing SV Magic

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

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    New
    $425hour
    Let's Go Sail in Gloucester Point, Virginia
    Sailing in Gloucester Point · 6 guests

    Let's Go Sail in Gloucester Point, Virginia

    5.0
    Superowner
    $117-$125hour
    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
    Sailing in Gloucester Point · 6 guests

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    5.0
    Superowner
    $125hour
    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
    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
    Charter 42' Lagoon Catamaran in Annapolis, MD
    Sailing in Edgewater · 12 guests

    Charter 42' Lagoon Catamaran in Annapolis, MD

    5.0
    $425hour
    Melges 24 - One Design Racing Experience Or Charter
    Sailing in Hampton · 8 guests

    Melges 24 - One Design Racing Experience Or Charter

    5.0
    Superowner
    $200hour
    Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail
    Sailing in Saint Michaels · 6 guests

    Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

    5.0
    $325hour
    Catalina 425 Sailing Yacht in Rock Hall, Maryland
    Sailing in Rock Hall · 6 guests

    Catalina 425 Sailing Yacht in Rock Hall, Maryland

    5.0
    $160hour
    Fully Crewed Annapolis Sailing Cruises
    Sailing in Annapolis · 6 guests

    Fully Crewed Annapolis Sailing Cruises

    New
    $175person
    $400 M-Th | $600 F-Su | 13 ppl | Luxury Yacht SLX 400
    Events in Washington · 13 guests

    $400 M-Th | $600 F-Su | 13 ppl | Luxury Yacht SLX 400

    New
    Superowner
    $400hour
    Instant Book
    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
    Experience the Charm of St. Michaels Aboard the 41ft S/Y Selina II Sl - 2 Hours
    Sailing in Saint Michaels · 6 guests

    Experience the Charm of St. Michaels Aboard the 41ft S/Y Selina II Sl - 2 Hours

    New
    $350hour
    Fish On! Rent Your 38ft Dawson Sportfish in Norfolk, VA
    Sailing in Norfolk · 6 guests

    Fish On! Rent Your 38ft Dawson Sportfish in Norfolk, VA

    New
    $725day
    Sail the Sea on the Pintita
    Sailing in Annapolis · 20 guests

    Sail the Sea on the Pintita

    New
    $500-$750hour
    Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours
    Sailing in Saint Michaels · 6 guests

    Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

    New
    $400hour

    Sailing Reviews in Chesapeake Bay

    1. DB

      Dan

      38' Hunter 376 Cruising Monohull in Annapolis, Maryland

      Capt Alberto and Grace were wonderful hosts. They were very flexible regarding the weather, great teachers of sailing, and were very hospitable and welcoming with their boat. We had an amazing time. Capt Alberto truly loves the sea.

    2. bb

      brent

      41' Lagoon Catamaran in Maryland

      Captain J was excellent. So nice and accommodating to our requests. It is our second time with him and will book with him again next time we want to have a great day on the water

    3. KC

      Kevin

      Charter 42' Lagoon Catamaran in Annapolis, MD

      Adam Yearwood is a fantastic captain! His boat is beautiful and he is well organized. We did a team outing sailing around the Chesapeake and had an awesome time - I highly recommend working with Adam!

    4. Apolinar

      Apolinar

      41' Lagoon Catamaran in Maryland

      Overall, it was very worth it.

    5. ac

      akhil

      Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

      Great trip, knowledgeable crew - was very accommodating with my family.

    6. JD

      Josiah

      2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

      Didn't believe we still have such wonderful people. Captain Dash and his co-captain are amongst the very best. Good service, friendly, timely, and most importantly, people Centered. My wife, kids, and I enjoyed riding with this team and we will always wish to ride with them.

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