Departure date

Trip duration


Day trip
Multiple days
(Less than 1 week)
Weekly trip
Show boats that have weekly prices. Most weekly boats outside of the US are available only Saturday to Saturday.

Boat type

Boat length: 5ft -

Manufacturer

Boat model

Price

$
$

Captain

Boat build year: -

Amenities

Sort by:
Location
Reset
Dates
Filters
Reset

Departure date


Trip duration

Day trip
Multiple days
(Less than 1 week)
Weekly trip
Boat
Boat Details
Reset

Boat type

Boat length: 5ft -

Price: $ - $

Captain

Manufacturer

Boat model

Filters
Filters
Reset

Boat build year: -

Amenities

1 - 4 of 4 boats
  1. Home

Explore Chesapeake, VA with Sailo - an yachting playground waiting for you!

When visiting Chesapeake, one of the best things to do is enjoy some time on the water on a Sailo captained boat rental. From a sunset cruise, to a full day trip around the local waterways, rent a boat in Chesapeake to really make the most of your leisure time. A private yacht charter is a great way to spend time with your friends or family and enjoy an unforgettable experience in Chesapeake.

Our finest collection of Chesapeake, VA private yacht charters

Explore the beauty of Virginia state from Chesapeake with a yacht charter. You’ll find 4 boats to rent in Chesapeake with Sailo, for the best choice. Set sail on one of our several elegant sailboats. You can also choose from numerous catamarans, available to charter. What better way to discover the shores of Virginia than from the deck of a luxury motor yacht? Browse the multiple available on Sailo for your ideal boating trip. You’ll also find 4 larger party boats, perfect for groups of 13 or more available in Chesapeake, VA.

Learn how to find the right boat for great yachting experiences

Wondering how to find the best charter for a memorable experience on the water in Chesapeake, VA? We have created a set of advanced filters to help you navigate easily our database of Chesapeake boat rentals and yacht charters, and find the one for you. First pick a start date and then choose your trip duration. You can go for an extraordinary of 2, 4 hours or full day experience. Next, select the number of guests, the type of boat and the price range you are comfortable with. The crew filter helps you narrow down the results to the boats with the captain included in the price, or bareboats that you’ll captain yourself. Choose the boat you want in Virginia, to view more pics, read description and reviews. Message the owner if you have any questions or continue with your booking request.

How much does it cost to charter a yacht in Chesapeake, VA?

Chesapeake, VA yacht charters for daily trips are available at an average of $1100 per day. Cheaper boats (sometimes with no captain included) may be rented for $250. Our Chesapeake premium charters may have price tags up to $6500, with crew, fuel, docking fees and other extras added to your budget.

What is Sailo FREE 24 hours Reservation?

Not sure if the boat you like suits your vacation plans? You can place a free reservation for 24 hrs, no credit card required, for most of our weekly boat rentals, allowing you more time to discuss details with the boat owner, talk to your family or friends or customize your budget to suit your needs. Once you have placed the reservation, boat is blocked for 24 hours. During the 24 hours of your reservation, you can book the boat, cancel the reservation or ask for a one-time extension of 24 hours by contacting us at reserve@sailo.com. If you do nothing, your reservation will automatically expire and the boat will become available for other renters. Read more about free reservations.

Because we love the ocean

Sailing is a great way to experience nature. So we like to remind everyone that keeping nature as beautiful as possible involves a little effort from all of us. Some of our tips for responsible boating include:
  • Don’t litter or throw waste overboard - take rubbish home and dispose of it responsibly
  • Eco-friendly sunblock can help prevent damage to marine life
  • buy local and sustainable food products
However long you’re sailing for, a little goes a long way. Read more about responsible boating.