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    All listings in Chesapeake Bay

    Incredible tours in Chesapeake Bay, United States.

    5.0
    (269 Reviews)

    Page 2 of 2 • 47 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    27' Godfrey Tritoon Pontoon Boat - Perfect for Cruising and Entertaining
    Powerboats in Annapolis · 12 guests

    27' Godfrey Tritoon Pontoon Boat - Perfect for Cruising and Entertaining

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

    2022 Catspace 38 Sailing Catamaran in Chesapeake Bay

    New
    $334+/hour
    Big Thrills, Big Water, Big Fun — Introducing the 24′ Hurricane Sundeck
    Powerboats in Annapolis · 12 guests

    Big Thrills, Big Water, Big Fun — Introducing the 24′ Hurricane Sundeck

    New
    $175+/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
    Adventure for 8 Monterey 322 Cruiser with Water Activities $300/hr
    Events in Washington · 8 guests

    Adventure for 8 Monterey 322 Cruiser with Water Activities $300/hr

    New
    $300/hour
    DC Private Sea Ray Sundancer Yacht for Celebrations & Sunset Cruises
    Events in Washington · 11 guests

    DC Private Sea Ray Sundancer Yacht for Celebrations & Sunset Cruises

    New
    $295/hour
    Relax along the Potomac on Crush! 55’ Luxury 4-Deck Yacht
    Events in Washington · 12 guests

    Relax along the Potomac on Crush! 55’ Luxury 4-Deck Yacht

    New
    $597/hour
    Luxury Lagoon 42 Catamaran for 12 in Annapolis
    Sailing in Annapolis · 12 guests

    Luxury Lagoon 42 Catamaran for 12 in Annapolis

    New
    $335+/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
    23ft Parker Center Console | Seats 6 | Edgewater, Maryland
    Powerboats in Annapolis · 6 guests

    23ft Parker Center Console | Seats 6 | Edgewater, Maryland

    New
    $125+/hour
    Meridian 541 Sedan Motor Yacht Ideal For Chesapeake Bay Cruising
    Events in Annapolis · 12 guests

    Meridian 541 Sedan Motor Yacht Ideal For Chesapeake Bay Cruising

    New
    $1,280/hour
    32' Yacht with a hard hitting sound system!
    Powerboats in Washington · 12 guests

    32' Yacht with a hard hitting sound system!

    New
    $300/hour
    Exclusive Charter at the National Harbor with Sea Ray 330 Sundancer Yacht
    Events in Oxon Hill · 9 guests

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

    New
    $250/hour
    Charter a Regal 400 Commodore Express Cruiser in Hampton for Up to 6 Guests
    Powerboats in Hampton · 6 guests

    Charter a Regal 400 Commodore Express Cruiser in Hampton for Up to 6 Guests

    New
    $250/hour
    Supercharged Yamaha FX Cruiser Jet Ski Rentals Near National Harbor - 1-3 Riders
    Water Sports in Oxon Hill · 3 guests

    Supercharged Yamaha FX Cruiser Jet Ski Rentals Near National Harbor - 1-3 Riders

    New
    $100/hour
    Sea-Doo GTX 170 -- your fun, powerful, fast, smooth ride
    Water Sports in California · 3 guests

    Sea-Doo GTX 170 -- your fun, powerful, fast, smooth ride

    New
    $110/hour
    90 Minute Scenic Back Bay Luxury Party Cruise
    Powerboats in Wildwood · 6 guests

    90 Minute Scenic Back Bay Luxury Party Cruise

    New
    $175/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
    Great for water sports "tubing/ski" and cruising the bay for romantic outings!
    Powerboats in Virginia Beach · 7 guests

    Great for water sports "tubing/ski" and cruising the bay for romantic outings!

    New
    $200/hour
    68ft Viking Princess Flybridge Motor Yacht in Washington, DC
    Events in Washington · 20 guests

    68ft Viking Princess Flybridge Motor Yacht in Washington, DC

    New
    $800/hour
    50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD
    Sailing in Annapolis · 12 guests

    50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD

    5.0
    Snoozed - Active 02 Jul 2026

    Top Destinations Nearby

    Tours Reviews in Chesapeake Bay

    1. ML

      Martha

      50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD

      We intentionally booked a late afternoon cruise around the Chesapeake so we would return around sunset to get great views and photos. Kristal was super responsive in preparing us and Captain Wayne and his 'first mate' Mish were super helpful with capturing the perfect photos. We would definitely book again!

    2. Jordan

      Jordan

      50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD

      Captain Deren and the crew were amazing — they made my birthday so special. They were super accommodating the entire day for everyone! They were even kind enough to put up some birthday decorations for our group. I’m definitely going to be booking with Captain Deren again!

    3. DW

      Dominique

      50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD

      Amazing experience! Amazing, professional crew! It was very easy to book from the beginning. We had an amazing time! Group of 12.

    4. JM

      Josephine

      50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD

      I will charter the boat over, and over again because of their warm hospitality. I will recommend them to everyone

    5. TH

      Tina

      50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD

      Excellent trip for our department outing!!! Boat and crew were fantastic, great time was had by all!

    6. Angela

      Angela

      50ft Leopard Catamaran Charter with Water Toys - Annapolis, MD

      Amazing! Fun! Professional, Great value for the money paid. One of the best ever! Coming back soon.

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