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    All listings in Chesapeake Bay

    Incredible tours in Chesapeake Bay, United States.

    5.0
    (229 Reviews)

    Page 1 of 2 • 41 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.
    Events in Washington · 6 guests

    Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.

    5.0
    Superowner
    Best of 2026
    $270+/hour
    $300hr | National Harbor| 10 Guests | 35Ft Searay
    Events in Oxon Hill · 8 guests

    $300hr | National Harbor| 10 Guests | 35Ft Searay

    New
    Superowner
    $300/hour
    The Play Station-23 Foot Pontoon With Lights, Bluetooth, Charging Ports, Cooler
    Powerboats in Fort Washington · 10 guests

    The Play Station-23 Foot Pontoon With Lights, Bluetooth, Charging Ports, Cooler

    4.9
    Superowner
    Best of 2026
    $225/hour
    High Demand
    Spacious Luxury Carver 37' in Washington D.C.
    Events in Washington · 13 guests

    Spacious Luxury Carver 37' in Washington D.C.

    4.7
    $200+/hour
    Limited Availability
    Private Yacht Charter: On 40ft Regal Commodore
    Events in Selby-on-the-Bay · 10 guests

    Private Yacht Charter: On 40ft Regal Commodore

    5.0
    $400/hour
    38' Dawson Sportfish Motor Yacht Charter in Norfolk, Virginia
    Fishing in Norfolk · 6 guests

    38' Dawson Sportfish Motor Yacht Charter in Norfolk, Virginia

    5.0
    $175/hour
    High Demand
    DMV’s 12 passenger Luxury Party Yacht Silverton Convertible
    Events in Washington · 12 guests

    DMV’s 12 passenger Luxury Party Yacht Silverton Convertible

    5.0
    $399/hour
    2022 Avalon Tritoon!
    Powerboats in Virginia Beach · 10 guests

    2022 Avalon Tritoon!

    5.0
    $199/hour
    Sunset Boat Rides in Va Beach
    Powerboats in Virginia Beach · 6 guests

    Sunset Boat Rides in Va Beach

    5.0
    $225/hour
    Hospitality at sea with Crownline 252 EX Deck Boat In Stone Harbor
    Powerboats in Stone Harbor · 6 guests

    Hospitality at sea with Crownline 252 EX Deck Boat In Stone Harbor

    5.0
    $129+/hour
    Cruise the Chesapeake on a Classic 46’ Deadrise – Up to 30 Guests
    Powerboats in Edgewater · 20 guests

    Cruise the Chesapeake on a Classic 46’ Deadrise – Up to 30 Guests

    5.0
    $600/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

    5.0
    $325/hour
    Enjoy the best views of Annapolis, MD aboard this beautiful Lydia dinner yacht
    Events in Annapolis · 128 guests

    Enjoy the best views of Annapolis, MD aboard this beautiful Lydia dinner yacht

    5.0
    $480+/hour
    Luxury Bentley Pontoon with Captain - DC Cruises, Parties & Events!
    Powerboats in Washington · 12 guests

    Luxury Bentley Pontoon with Captain - DC Cruises, Parties & Events!

    New
    $150/hour
    Best Bachelorette party on the water in Dewey Beach!
    Tours in Dewey Beach · 18 guests

    Best Bachelorette party on the water in Dewey Beach!

    New
    $500/hour
    26′ Bennington Pontoon | Adventure Awaits | Seats 12
    Powerboats in Annapolis · 12 guests

    26′ Bennington Pontoon | Adventure Awaits | Seats 12

    5.0
    $194+/hour
    Party Cruises & Fishing Trips in Virginia Beach
    Events in Norfolk · 6 guests

    Party Cruises & Fishing Trips in Virginia Beach

    5.0
    $170+/hour
    Enjoy your magical moments with a VIP experience
    Events in Washington · 10 guests

    Enjoy your magical moments with a VIP experience

    New
    Superowner
    $425/day
    14 People | $700hr | Mt Vernon- Ft Washington- Occoquan Sailing
    Events in Washington · 13 guests

    14 People | $700hr | Mt Vernon- Ft Washington- Occoquan Sailing

    New
    Superowner
    $700/hour
    Take your Sailing Dream on Chesapeake Bay.
    Sailing in Mayo · 6 guests

    Take your Sailing Dream on Chesapeake Bay.

    New
    $175+/hour
    2022 Catspace 38 Sailing Catamaran in Chesapeake Bay
    Sailing in Annapolis · 12 guests

    2022 Catspace 38 Sailing Catamaran in Chesapeake Bay

    New
    $334+/hour
    25' Crownline 255 SS from Cape May - 6 Guest Charter
    Powerboats in Stone Harbor · 6 guests

    25' Crownline 255 SS from Cape May - 6 Guest Charter

    New
    $129+/hour
    Luxury 2022 Excess 11 Catamaran for 12 in Annapolis
    Sailing in Annapolis · 12 guests

    Luxury 2022 Excess 11 Catamaran for 12 in Annapolis

    New
    $335+/hour
    A Romantic Vintage 1954 Wooden Boat Escape in the Heart of Washington, D.C.
    Powerboats in Arlington · 2 guests

    A Romantic Vintage 1954 Wooden Boat Escape in the Heart of Washington, D.C.

    New
    $150/hour

    Top Destinations Nearby

    Tours Reviews in Chesapeake Bay

    1. AF

      Anna

      The Play Station-23 Foot Pontoon With Lights, Bluetooth, Charging Ports, Cooler

      My experience booking Captain Troy was amazing! He had great communication throughout the entire booking process leading up to the day. He made sure to ask my vision for the experience beforehand. His boat is absolutely beautiful and very clean and he was a pleasure to be around. I will definitely book with him again in the future.

    2. SH

      Shalis

      Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.

      Troy was fantastic, super friendly, professional, and made sure we had an amazing time. He really helped make the experience memorable. Highly recommend!

    3. hm

      hanna

      Cruise the Chesapeake on a Classic 46’ Deadrise – Up to 30 Guests

      Amazing communication and very fun boat. I recommend everyone to book with her!!

    4. MS

      Mars

      The Play Station-23 Foot Pontoon With Lights, Bluetooth, Charging Ports, Cooler

      I booked Troy for my Birthday Trip and we had an amazing time. Troy is an amazing person and boat captain and we had a lot of fun!!!

    5. CR

      Carmen

      The Play Station-23 Foot Pontoon With Lights, Bluetooth, Charging Ports, Cooler

      The group had a wonderful time on your boat. Very accommodating. Everyone had positive feedback. 10/10 recommend. Thank you!

    6. CA

      Chris

      Sunset Boat Rides in Va Beach

      The best of the best if you're looking for the perfect sunset cruise.

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