What are the steps needed to rent a sailboat in Crisfield?

Best Sailboat Rentals Near Crisfield

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Our top sailboat rentals

$69+ /hour

Kilmarnock, VA

5.0 (14 bookings)

Skippered Chesapeake Bay sailing from Kilmarnock, Va

2 - 8 hours Captained

Up to 4 passengers

$144+ /hour

Deltaville, VA

Jeanneau SO 519 on Chesapeake Bay

8 hours Captained

Up to 6 passengers

$142+ /hour

Solomons, MD

"Hallelujah" Beneteau Oceanis 350 Sailboat

2 - 8 hours Captained

Up to 6 passengers

Top sailboat rentals reviews in Crisfield, MD

281,468

Customers Reviews

4.95

Avg. Rating

5/5 stars

Skippered...

We really enjoyed the sail, great weather and wind!

Ruth

Jun 2025
5/5 stars

Skippered...

Fun and informative!

Steve

Apr 2025
5/5 stars

Skippered...

We had a great day on the water with Capt. Russ! Great conversation and experience. Looking forward to another trip...

Marc

Aug 2024
5/5 stars

Skippered...

Had a great time sailing where I wanted to hone my skills.

Highly recommend

Scott

Jul 2024
5/5 stars

Skippered...

This was a perfect trip! Boat was nice and Captain Russell was very polite and accommodating and an excellent...

Jason

Aug 2023
5/5 stars

Skippered...

Our second trip with Capt. Russ. Had a fantastic time. Weather was great, winds were steady and great time was had by...

Jim

Jul 2023
5/5 stars

Skippered...

Russell was an excellent
captain. Very professional and safety oriented. He is knowledgeable about the area and...

Paul

Jul 2023
5/5 stars

Skippered...

We had a great time. Captain Russ was very knowledgable and we felt safe. The boat description is accurate...the...

Lisa

Jul 2022

How to rent a sailboat in Crisfield?

Find the perfect boat

Enter your desired location and date to explore our fleet of sailboats.

Select a captain

Choose to drive yourself or select a USCG licensed captain.

Book with ease

Connect with your boat owner and complete your booking online.

Set sail

Enjoy your day on the water with friends and family!

Why Boatsetter?

As the global leader in peer-to-peer boat rentals, Boatsetter offers an easy, safe and accessible way to experience on-the-water adventure. With boat rentals in 600+ locations, finding a boat is easy and with the option to tap into the largest network of USCG licensed captains, boating experience is not required.

Get out on the water worry-free, knowing our insurance covers every boating trip

Choosing the right boat rental platform is essential to your peace of mind while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

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Got questions?

Frequently asked questions

How much does it cost to rent a boat?

The cost to rent a boat depends on whether you are renting for a half-day or a full day, the boat features and the boat size can impact your boat rental price. Rental prices can range from $200 to $1,000 plus depending on the boat rental itself and the length of time of the rental.

How many people can fit on the boat rental?

The number of people who can fit on boat rental largely depends on the boat’s size and how many life jackets are on board. Currently the coast guard allows a maximum of 10-12 people on a Boatsetter boat rental.

How old do you have to be to rent a boat?

You must be 18 years old to rent a captained boat and 25 years old if you would like to rent a bareboat charter.

Do I need a boating license to rent a boat?

Boating license requirements vary from state to state. As a renter, you are responsible for understanding local state requirements.

How much does it cost to rent a boat for the day?

The cost of renting a boat for the day on average ranges from $200 to $1200. The cost to rent a boat varies depending on the size of the boat and the length of time that you will be using the boat.