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All listings in Chesapeake Bay

Incredible tours in Chesapeake Bay, United States.

Page 1 of 122 listings

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
$220+/hour
Private Yacht Charter: On 40ft Regal Commodore
Events in Selby-on-the-Bay · 10 guests

Private Yacht Charter: On 40ft Regal Commodore

5.0
$350/hour
Instant Book
Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
Sailing in Mayo · 6 guests

Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.

5.0
$175+/hour
Sunset Boat Rides in Va Beach
Powerboats in Virginia Beach · 6 guests

Sunset Boat Rides in Va Beach

5.0
$225/hour
36' Carver Yacht on the Washington, DC waterfront
Events in Washington · 8 guests

36' Carver Yacht on the Washington, DC waterfront

5.0
$300/hour
2022 Avalon Tritoon!
Powerboats in Virginia Beach · 10 guests

2022 Avalon Tritoon!

5.0
$199/hour
"Pursuit of Hoppiness" Hospitality at Sea!
Tours in Stone Harbor · 6 guests

"Pursuit of Hoppiness" Hospitality at Sea!

5.0
$129+/hour
Party Cruises & Fishing Trips in Virginia Beach
Fishing in Norfolk · 6 guests

Party Cruises & Fishing Trips in Virginia Beach

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

Enjoy your magical moments with a VIP experience

New
Superowner
Best of 2025
$425/day
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
Cruise the Potomac On a Rinker 310
Tours in Washington · 6 guests

Cruise the Potomac On a Rinker 310

5.0
$250/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
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
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
 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
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
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
90 Minute Scenic Back Bay Luxury Party Cruise
Powerboats in Wildwood · 6 guests

90 Minute Scenic Back Bay Luxury Party Cruise

New
$175/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
Instant Book
 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
Still Crazy II - Cruise the Chesapeake in luxury! (Captain Included)
Powerboats in Pasadena · 10 guests

Still Crazy II - Cruise the Chesapeake in luxury! (Captain Included)

New
Snoozed - Active 02 Aug 2025

Tours Reviews in Chesapeake Bay

  1. IS

    Isaac

    36' Carver Yacht on the Washington, DC waterfront

    Captain Everett made every part of this charter great for the guests. We had literally the best view of the 4th of July fireworks from anywhere in Washington D.C., and Everett made sure our safety during a busy night on the water was a top priority. Thank you, Everett!

  2. SV

    Steph

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

    Troy was great and the boat was amazing! Troy was super nice, easy going, and flexible to how we spent the day. Very experienced at navigating a busy Potomac on a holiday weekend, felt safe the whole time! The tables were super nice to have to lay out all our snacks for the day. We had so much fun, highly recommend!!

  3. SM

    Selamawit

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

    The trip with Captain Troy was great! It was a delayed Father’s Day trip and he was able to accommodate with the rescheduling. We had a great time and glad he reminded us that we could go up on the deck to get some pictures. We had a memorable time and will be coming back!

  4. GG

    Gbo

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

    Capt Troy is really a nice person he and his wife went the extra mile to plan a special surprise for my wife. They very welcoming. I will recommend them for anyone that wants to plan a surprise or special occasion to go with him.

  5. MH

    Michael

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

    Can't wait to book again my next outing with my group. Amazing time and energy. If you looking to relax, rejuvenate, restart, book with Troy.

  6. KM

    Kentez

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

    Captain Troy was awesome! It was easy to find the dock. He is friendly and helpful. Definitely will book again!