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    All listings in Chesapeake Bay

    Incredible sailboat rentals in Chesapeake Bay, United States.

    5.0
    (403 Reviews)

    Page 1 of 2 • 33 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    38-ft Hunter 376 Sailing Adventure in Annapolis
    Sailing in Annapolis · 6 guests

    38-ft Hunter 376 Sailing Adventure in Annapolis

    5.0
    Superowner
    $138+/hour
    Instant Book
    SEARAY SLX400 | $800hr | 13 People
    Events in Washington · 13 guests

    SEARAY SLX400 | $800hr | 13 People

    5.0
    Superowner
    Best of 2025
    $800/hour
    Instant Book
    50ft Catamaran Charter with Water Toys - Annapolis, MD
    Sailing in Annapolis · 12 guests

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    5.0
    $325/hour
    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
    $150/hour
    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
    $125/hour
    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+/hour
    Take your Sailing Dream on Chesapeake Bay. Rates reduced to for that dream!!
    Sailing in Mayo · 6 guests

    Take your Sailing Dream on Chesapeake Bay. Rates reduced to for that dream!!

    5.0
    $150+/hour
    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+/hour
    Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia
    Sailing in Kilmarnock · 4 guests

    Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia

    5.0
    $15+/hour
    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

    4.6
    $275+/night
    Charter 44' Orana Cruising Catamaran In Deale, Maryland
    Sailing in Deale · 10 guests

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    5.0
    $250+/hour
    JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!
    Sailing in Annapolis · 12 guests

    JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!

    5.0
    $250+/hour
    SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
    Sailing in Annapolis · 12 guests

    SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

    5.0
    $400+/hour
    Melges 24 - One Design Racing Experience
    Sailing in Hampton · 5 guests

    Melges 24 - One Design Racing Experience

    5.0
    Superowner
    $100/hour
    Instant Book
    Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!
    Powerboats in Washington · 6 guests

    Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!

    5.0
    $185/hour
    Charter 42' Lagoon Catamaran in Annapolis, MD
    Sailing in Edgewater · 12 guests

    Charter 42' Lagoon Catamaran in Annapolis, MD

    5.0
    $425/hour
    New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
    Sailing in Annapolis · 13 guests

    New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

    5.0
    $1,100/hour
    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
    $325/hour
    43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
    Sailing in Rock Hall · 6 guests

    43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

    5.0
    $150+/hour
    SLOWDOWN - DUFOUR 430
    Sailing in Annapolis · 12 guests

    SLOWDOWN - DUFOUR 430

    New
    $250+/hour
    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
    $725/day
    DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!
    Sailing in Annapolis · 10 guests

    DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

    New
    $232+/hour
    Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour
    Sailing in Saint Michaels · 6 guests

    Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour

    New
    $350/hour
    Sailing Adventures on the Choptank River
    Sailing in Cambridge · 6 guests

    Sailing Adventures on the Choptank River

    New
    $100/hour

    Sailing Reviews in Chesapeake Bay

    1. Kasie

      Kasie

      38-ft Hunter 376 Sailing Adventure in Annapolis

      Wonderful Captain and wonderful boat! Plenty of shade above and below deck if the August heat becomes too much. We did the three hour tour, and it was a great half day length. We received a tour of downtown Annapolis and then Captain Alberto opened up the sails and we went on a beautiful ride down the river. It was fun and unique - even for those who have motor boat experience. Sailing is quintessential Annapolis and Captain Alberto was a great host.

    2. Bobby

      Bobby

      38-ft Hunter 376 Sailing Adventure in Annapolis

      We went out for an afternoon sail with Capt Alberto and had an amazing time. We were blessed with a beautiful sunny day with perfect wind. Capt Alberto shared interesting stories and taught us a good bit about sailing along the way. Highly recommend!

    3. ES

      Emil

      Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

      Capt. Joe gave us a wonderful afternoon! He is friendly, knowledgable, and fun! The boat is perfect for cruising around the Bay. Lots of space to lay out and clean facilities downstairs. An excellent value!

    4. LP

      Laura

      38-ft Hunter 376 Sailing Adventure in Annapolis

      Captain Alberto and his wife are absolute jewels! We sailed with them a couple of years ago and were excited to have this time with them today. They are friendly, professional and just such a joy to be around. Will be seeing them again soon, for sure!

    5. AE

      Amer

      38-ft Hunter 376 Sailing Adventure in Annapolis

      Great, fun, safe sailing trip with Captain Alberto. Very knowledgeable and entertaining. Very welcoming and kept it safe. Excellent and safe trip idea for families. Highly recommended.

    6. SS

      Stephen

      38-ft Hunter 376 Sailing Adventure in Annapolis

      Captain Alberto and Grace were absolutely amazing. We had a wonderful evening and sunset sail. The boat and sail were only topped by meeting Alberto and Grace. Simply wonderful people.

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