Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

Chesapeake Bay, US Boat Rentals & Yacht Charters

Page 3 of 9197 listings

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
Ride on our 49 Passenger Navigator Boat! Full bar options!
Events in Washington · 49 guests

Ride on our 49 Passenger Navigator Boat! Full bar options!

5.0
Superowner
$865+/hour
Let's Go Sail in Gloucester Point, Virginia
Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

5.0
Superowner
$117+/hour
26’ Pontoon Lounge on the Potomac
Powerboats in Washington · 6 guests

26’ Pontoon Lounge on the Potomac

5.0
Superowner
$200/hour
JetCar Bugatti in Washington DC for Luxury Experience!!
Powerboats in Washington · 5 guests

JetCar Bugatti in Washington DC for Luxury Experience!!

4.6
$300/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
8 People | Monterey 340 Sport Yacht
Events in Washington · 8 guests

8 People | Monterey 340 Sport Yacht

5.0
Superowner
$275/hour
Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia
Sailing in Kilmarnock · 4 guests

Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia

5.0
$15+/hour
2021 Sea Fox 226 dual console
Events in Deltaville · 8 guests

2021 Sea Fox 226 dual console

5.0
$76+/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
Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
Powerboats in Annapolis · 6 guests

Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

4.8
$95+/hour
Experience Colonial Beach in Style with SeaRay 220 Sundeck Bowrider Adventure!
Powerboats in Colonial Beach · 6 guests

Experience Colonial Beach in Style with SeaRay 220 Sundeck Bowrider Adventure!

5.0
$180/hour
$250 hr | 6 ppl | Grill and BBQ Family & Friends Boat
Powerboats in Washington · 8 guests

$250 hr | 6 ppl | Grill and BBQ Family & Friends Boat

5.0
Superowner
$250/hour
45' Sea Ray Luxury Yacht Stewardess, Crew and Captain Provided
Events in Washington · 10 guests

45' Sea Ray Luxury Yacht Stewardess, Crew and Captain Provided

5.0
Superowner
$600/hour
Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain
Powerboats in Annapolis · 6 guests

Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain

5.0
$115/hour
The Best Tiki/bar Cruise of the Summer in Dewey Beach
Powerboats in Dewey Beach · 18 guests

The Best Tiki/bar Cruise of the Summer in Dewey Beach

4.5
$450/hour
$350hr|11 people| Luxury Yacht
Events in Washington · 11 guests

$350hr|11 people| Luxury Yacht

5.0
Superowner
$350/hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$250+/hour
$275 HR | 8 people + Water Activities
Events in Washington · 9 guests

$275 HR | 8 people + Water Activities

5.0
Superowner
$275/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
$450/day
Wakeboarding & Tubing | $300hr | 8 PPL
Powerboats in Arlington · 8 guests

Wakeboarding & Tubing | $300hr | 8 PPL

5.0
Superowner
$300/hour
Brand New 25ft Crownline for Charter in Stone Harbor!
Powerboats in Stone Harbor · 6 guests

Brand New 25ft Crownline for Charter in Stone Harbor!

5.0
$200/hour
Enjoy the sights of Colonial Beach, VA ! Come boat with us!
Events in Colonial Beach · 6 guests

Enjoy the sights of Colonial Beach, VA ! Come boat with us!

5.0
$180/hour
$300 per hour | 8 PPl | Water Activity + Grill BBQ |
Events in Washington · 8 guests

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

5.0
Superowner
$300/hour

Chesapeake Bay Reviews

  1. AV

    Ali

    Ride on our 49 Passenger Navigator Boat! Full bar options!

    We scheduled a boat experience with Captain Q and her team. We had about 45+ guests and were celebrating our marriage. We brought our food and drinks, and their team helped make beautiful designs with the charcuterie board we brought. It was way better than whatever we originally had. They let us put on our music via Bluetooth, which was super easy. We also had some speeches, and they had a microphone that we could use, which made it easier than having to raise our voices. We scheduled a boat cruise originally, and though this wasn't able to happen due to a health issue, we still wanted to have this event on a boat, so we chose to stay dockside, which was still fun being in the marina and on a boat in the summertime. Their team is super professional and willing to work with you when possible, which I highly value.

  2. 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.

  3. 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.

  4. NM

    Nancy

    JetCar Bugatti in Washington DC for Luxury Experience!!

    JetcarDC went above and beyond to make our Jetcar experience memorable as well as enjoyable. I've never received such great customer service. What an experience!! Super fun jetcar ride, We loved it, I highly recommend it if your in the DC area, Thanks again Mr Pulpo!

  5. FC

    Francesco

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

    We simply loved our three days sailing excursion of the Chesapeake bay. The boat Icarus is very comfortable to maneuver and to live in for a family of four. The bay has numerous nice coves and spots were to stay for the night. Mr James help has been crucial for maximizing our time and energies on these limited days. Thank you Jiim!

  6. MI

    Maria

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

    One of the best sailing weekends we have ever experienced! The boat is manageable and in great shape! James is a great host, he explained everything when we got there, suggested an amazing route and was there when we got back to make sure everything went well. 100% recommended, we’ll definitely rent it again!