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All listings in Chesapeake Bay

Incredible tours in Chesapeake Bay, United States.

5.0

(85 Reviews)

Page 1 of 1 • 15 listings

Powerboats in Annapolis · 4 guests

2023 12ft Highfield Tender

5.0

$63+/hour

Events in Washington · 6 guests

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

5.0

$220+/hour

Events in Selby-on-the-Bay · 10 guests

Private Yacht Charter: On 40ft Regal Commodore

5.0

$300/hour

Sailing in Mayo · 6 guests

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

5.0

$175/hour

Powerboats in Virginia Beach · 10 guests

2022 Avalon Tritoon!

5.0

$199/hour

Events in Washington · 10 guests

Enjoy your magical moments with a VIP experience

New

Superowner

Best of 2025

$425/day

Fishing in Norfolk · 6 guests

Party Cruises & Fishing Trips in Virginia Beach

5.0

$170+/hour

Instant Book

Events in Washington · 8 guests

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

New

$300/hour

Instant Book

Events in Washington · 8 guests

36' Carver Yacht on the Washington, DC waterfront

New

$300/hour

Sailing in Annapolis · 13 guests

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

New

$350+/hour

Events in Washington · 12 guests

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

New

$499/hour

Tours in Washington · 6 guests

Cruise the Potomac On a Rinker 310

New

$250/hour

Water Sports in Oxon Hill · 3 guests

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

New

$100/hour

Powerboats in Dewey Beach · 12 guests

2021 tri-toon Godfrey w/ 200 HP Yamaha and nice Soundsystem

5.0

Snoozed - Active 17 May 2025

Powerboats in Pasadena · 10 guests

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

New

Snoozed - Active 02 Jul 2025

Tours Reviews in Chesapeake Bay

Oneshia

Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.
Our sail with Captain Troy was phenomenal! He was an absolute gentleman—attentive, fun, and made us feel completely at ease. The boat was spotless, and we felt safe and well cared for the entire time. We had an incredible experience and are already looking forward to sailing with him again!
Luqman

Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.
Captain Troy made our boat trip unforgettable! He was professional, knowledgeable, and ensured we were comfortable and safe the whole time. With great stories and a fun attitude, he made the experience relaxed and enjoyable. Highly recommend booking with Captain Troy for a fantastic day on the water!
J
Jorge Alcazar

2023 12ft Highfield Tender
Alan made the extra effort to ensure the boat was ready on arrival and made return very simple. The boat fit exactly we will always recommend reach out to the best. He has proven support over and over !
HH
Hadiya

Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.
We had the most amazing time celebrating my birthday with Captain Troy. He is accommodating, kind, and very responsive, making the entire planning process seamless and stress-free. Captain created the best environment for us to be able to have fun and enjoy our charter. Will absolutely recommend and will book again!
Blaise

Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.
From punctuality to everything good 10/10
JK
Jagpreet

Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.
This was our first time on a yacht and we loved every bit of it. Captain Troy took care of our special requests as well and was a wonderful host. He gave clear instructions, showed us amazing view spots and clicked beautiful pictures for us as well! All in all we loved celebrating at Captain Troy’s yacht and suggest you do the same 😍