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    All listings in Chesapeake Bay

    Awesome motor yacht charters in Chesapeake Bay, United States.

    5.0
    (997 Reviews)

    Page 4 of 4 • 94 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht
    Events in Annapolis · 6 guests

    Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht

    New
    $300/hour
    Enjoy the best views of Annapolis, MD aboard the Island Princess
    Events in Annapolis · 128 guests

    Enjoy the best views of Annapolis, MD aboard the Island Princess

    New
    $600+/hour
    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
    $400/hour
    Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape
    Sailing in Annapolis · 13 guests

    Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape

    New
    $350+/hour
    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
    Exclusive Charter at the National Harbor with Sea Ray 330 Sundancer Yacht
    Events in Oxon Hill · 10 guests

    Exclusive Charter at the National Harbor with Sea Ray 330 Sundancer Yacht

    New
    $220/hour
    46′ CARMEN | Take Everybody With You! | Captain Included
    Events in Annapolis · 30 guests

    46′ CARMEN | Take Everybody With You! | Captain Included

    New
    $670+/hour
    50′ VIKING - Your Chartered Experience Awaits!
    Events in Annapolis · 12 guests

    50′ VIKING - Your Chartered Experience Awaits!

    New
    $841+/hour
    35' Monterey Luxury Sports Yacht | Entertainment Galore for up to 12 People!
    Events in Washington · 12 guests

    35' Monterey Luxury Sports Yacht | Entertainment Galore for up to 12 People!

    New
    $350/hour
    "Stress Free" Four Winns Vista 348
    Events in Virginia · 8 guests

    "Stress Free" Four Winns Vista 348

    New
    $599/hour
    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
    $350/hour
    44ft ''Four Winds'' Yacht for Fishing/Cruising/Sightseeing in Hampton, Virginia
    Events in Hampton · 19 guests

    44ft ''Four Winds'' Yacht for Fishing/Cruising/Sightseeing in Hampton, Virginia

    4.0
    $275/hour
    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
    $400/hour
    31ft Cruiser Yacht Charter – Private Luxury on the Potomac!
    Powerboats in Washington · 10 guests

    31ft Cruiser Yacht Charter – Private Luxury on the Potomac!

    New
    $275/hour
    Instant Book
    Escape the Ordinary: Discover the Beauty and History of the Potomac!
    Events in Washington · 6 guests

    Escape the Ordinary: Discover the Beauty and History of the Potomac!

    New
    $350+/hour
    Beautiful 35ft Regal Cruiser with Swim pad
    Events in Washington · 12 guests

    Beautiful 35ft Regal Cruiser with Swim pad

    New
    $325+/hour
    WASHINGTON, DC! CRUISE THE POTOMAC IN 5 STAR EXCELLENCE!!
    Events in Washington · 12 guests

    WASHINGTON, DC! CRUISE THE POTOMAC IN 5 STAR EXCELLENCE!!

    New
    $499/hour
    Cruise DC and turn heads aboard the vintage 1985 Chris Craft, American Pie
    Powerboats in Washington · 6 guests

    Cruise DC and turn heads aboard the vintage 1985 Chris Craft, American Pie

    New
    $300/hour
    Sea Ray Sundancer 55' Tours on the Potomac River
    Events in Woodbridge · 6 guests

    Sea Ray Sundancer 55' Tours on the Potomac River

    New
    $600/hour
    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
    Snoozed - Active 02 Aug 2025
    STARZ -Lagoon 42 Catamaran in Chesapeake Bay
    Sailing in Annapolis · 13 guests

    STARZ -Lagoon 42 Catamaran in Chesapeake Bay

    5.0
    Snoozed - Active 02 Oct 2025
    Sea Ray 36ft Motor Yacht Rental in Washington, District of Columbia
    Events in Washington · 10 guests

    Sea Ray 36ft Motor Yacht Rental in Washington, District of Columbia

    New
    Snoozed - Active 02 Aug 2025

    Motor Yacht Reviews in Chesapeake Bay

    1. ET

      Eris

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      This is everything you could want. Great boat and captain. McCoy has everything you need for a great trip. Plenty of space onboard for all your food and drink and all the toys you could want for a fun day on the water. We count thank him enough fro a such great experience and a great price! We will be booking again for sure!

    2. WW

      Walter

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      Overall, we had a good experience. We ran into some mechanical issues with the boat and had to cut our trip short. Captain McCoy offered to give me a partial refund and was very apologetic. Things happen sometimes, and we were not upset. We will come back.

    3. martine

      martine

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      Our Trip with McCoy was great! He was very accommodating and knew the good swimming spots. Boat came with floaties and was very nice and clean.

    4. PM

      Pam

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      Great communication, very helpful with questions. On time and the boat was very clean . Had a great time !

    5. MR

      Matt

      STARZ -Lagoon 42 Catamaran in Chesapeake Bay

      Great experience and our family and friends had a wonderful time. Clean boat and fun crew to help us celebrate a special occasion. Highly recommend!

    6. MT

      Marija

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      We had a wonderful time at Captain McCoy’s boat. The boat is gorgeous, impeccably clean, and very spacious. The Captain played great music (we didn’t bring our own playlist). He found a great spot for our group to take a swim. It was a perfect balance of cruising and swimming and a perfect 2 hr cruise

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