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Chesapeake Bay, US Boat Rentals & Yacht Charters

Page 3 of 10 • 227 listings

Let's Go Sail in Gloucester Point, Virginia
Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

4.9
Superowner
$117+/hour
Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine
Events in Edgewater · 10 guests

Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine

5.0
$500/hour
Luxe Party Boat Washington D.C.
Powerboats in Washington · 12 guests

Luxe Party Boat Washington D.C.

5.0
Superowner
$275/hour
Chaparral 350 Signature Motor Yacht Rental in Washington, District of Columbia
Events in Washington · 9 guests

Chaparral 350 Signature Motor Yacht Rental in Washington, District of Columbia

5.0
$300/hour
Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay
Sailing in Mayo · 6 guests

Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

5.0
$150+/hour
$285 HR | 10 Guests | Sea Ray Boat
Events in Washington · 10 guests

$285 HR | 10 Guests | Sea Ray Boat

5.0
Superowner
$285/hour
$350hr|11 Guests | Water Toys
Events in Washington · 11 guests

$350hr|11 Guests | Water Toys

5.0
Superowner
$350/hour
Your Aquatic Escape: Bayliner 180 | Fast, Fun & Ready to Cruise!
Powerboats in Arlington · 6 guests

Your Aquatic Escape: Bayliner 180 | Fast, Fun & Ready to Cruise!

5.0
$100+/hour
$1000hr | 14 Guests | Chesapeake Bay
Events in Edgewater · 13 guests

$1000hr | 14 Guests | Chesapeake Bay

New
Superowner
$1,000/hour
Sanpan 2500 RE Pontoon in Washington, Living room comfort on the water!
Powerboats in Washington · 10 guests

Sanpan 2500 RE Pontoon in Washington, Living room comfort on the water!

5.0
$200/hour
 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
Enjoy your magical moments with a VIP experience
Events in Washington · 10 guests

Enjoy your magical moments with a VIP experience

5.0
Superowner
$425/day
$300 per hour | 8 Guests | Water Activity + Grill BBQ |
Events in Washington · 8 guests

$300 per hour | 8 Guests | Water Activity + Grill BBQ |

5.0
Superowner
$300/hour
41' Meridian Sedan Yacht for Charter in Washington, D.C.
Events in Washington · 13 guests

41' Meridian Sedan Yacht for Charter in Washington, D.C.

5.0
$300+/hour
$350hr | 9 Guests | Sport Regal Boat
Events in Washington · 9 guests

$350hr | 9 Guests | Sport Regal Boat

5.0
Superowner
$350/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
$400/hour
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.6
$275+/night
$450 HR | 7 Guests | Luxury Italian Vibe
Events in Washington · 10 guests

$450 HR | 7 Guests | Luxury Italian Vibe

New
Superowner
$450/hour
$300hr | 8 Guests | Sport Boat
Events in Washington · 8 guests

$300hr | 8 Guests | Sport Boat

5.0
Superowner
$285/hour
$250 hr | 6 Guests | Small Boat
Powerboats in Washington · 8 guests

$250 hr | 6 Guests | Small Boat

5.0
Superowner
$250/hour
$150hr |6 Guests | Bayliner Small boat
Events in Washington · 6 guests

$150hr |6 Guests | Bayliner Small boat

5.0
Superowner
$175/hour
$4000 | 49 Guests | 2hrs | Annapolis
Sailing in Annapolis · 49 guests

$4000 | 49 Guests | 2hrs | Annapolis

5.0
Superowner
$2,200/hour
$750hr | 14 Guests | 4hr Min
Events in Washington · 14 guests

$750hr | 14 Guests | 4hr Min

New
Superowner
$750/hour
2023 Yamaha AR190 - Perfect Day on the Water!
Powerboats in Virginia Beach · 7 guests

2023 Yamaha AR190 - Perfect Day on the Water!

5.0
$200/hour

Chesapeake Bay Reviews

  1. CJ

    Clarissa

    $350hr|11 Guests | Water Toys

    A fun and relaxing way to spend the day on the water. The boat was beautiful, the views were great, and the captain made the experience easy and enjoyable. Would definitely do it again!

  2. angel

    angel

    Sanpan 2500 RE Pontoon in Washington, Living room comfort on the water!

    MIKE was AMAZINGGG!! Worth every penny! Extremely patience, generous, and helpful!! I would book again! He made my experience so much easier and enjoyable!!

  3. Hawa

    Hawa

    $300 per hour | 8 Guests | Water Activity + Grill BBQ |

    Such a good experience! I literally booked the boat about 3 hours before and they were super responsive and made everything really easy from the start. Once we got there, they were so welcoming and sweet. The whole vibe was comfortable and relaxed, and they really made us feel taken care of. I honestly appreciated how smooth everything was, especially with me booking so last minute. We had such a good time and I would definitely book with them again. If you’re thinking about it, do it!

  4. JP

    John

    Let's Go Sail in Gloucester Point, Virginia

    Captain Bill was a fantastic host for our inaugural sailing adventure in the York River out of Gloucester Point, VA. We booked him for a Saturday afternoon in June for a 2:30 to 5:30 cruise and it was everything we could have asked for and more. He explained the region's waters and relation to the Chesapeake Bay as well as the naval and nautical history of the area in addition to teaching us about his boat and how to sail it properly. We wanted to be immersed in the experience and he let us be very hands on, giving direction for assisting with deploying the sails, commanding the helm, reading the wind and performing the tacking maneuvers while being at the helm. We also had a chance to relax on the forward section of the deck as Bill took over, he passed our libations to us and helped us enjoy the experience of sailing while soft music played that even invited an interaction with one of the regions local dolphin who accompanied and entertained us for well over a half an hour on our return up the river. What an awesome way to spend an afternoon.

  5. DH

    Dan

    Let's Go Sail in Gloucester Point, Virginia

    Bill was awesome. Very communicative leading up to the sail with weather, directions, and other logistical specifics. The trip left and returned on time, Bill was very knowledgeable about the boat and the area, let my wife and I take the helm several times and the boat was in great condition. Would totally sail with Cpt Bill again.

  6. RD

    Ryan

    Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine

    Mike and Norma were absolutely phenomenal! I booked a boat with them for my proposal, and they went above and beyond to make the entire experience unforgettable. From the planning process to the day itself, they were professional, accommodating, and genuinely invested in making everything perfect. Their attention to detail and hospitality helped create a memory that my fiancée and I will cherish forever. I highly recommend booking with them if you're looking for a special and stress-free experience on the water.