Best Sailboat Rentals Near Connecticut

Name: Sailing JOURNEY on the sound!
Rating: 5.0

Labor Day Weekend Boat Rentals

Our top sailboat rentals

$150+ /hour

Shelter Island Heights, NY

5.0 (23 bookings)

Sailing JOURNEY on the sound!

2 - 8 hours Captained

Up to 6 passengers

$331+ /hour

Greenport, NY

Sail on "Surprise", a beautiful and comfortable 50' wooden ketch

2 - 8 hours Captained

Up to 6 passengers

$184+ /hour

Stamford, CT

5.0 (10 bookings)

HUNTER LEGEND 35 SAILBOAT CRUISER MOTORSAILER

2 - 8 hours Captained

Up to 6 passengers

$359+ /hour

Sag Harbor, NY

Sailing Charter – Explore the Hamptons from Sag Harbor

4 - 8 hours Captained

Up to 6 passengers

$1,200+ /hour

Sag Harbor, NY

A Coast Guard Certified Classic Mahogany Trimaran

2 - 8 hours Captained

Up to 26 passengers

$725+ /hour

Greenport, NY

5.0 (2 bookings)

72-ft Traditional Schooner - Up to 20+ guests!

2 - 6 hours Captained

Up to 32 passengers

$1,063+ /hour

Sag Harbor, NY

5.0 (38 bookings)

62' sailing cat: bachelorette, sandbar, sunsets

3 - 8 hours Captained

Up to 12 passengers

$225+ /hour

Bridgeport, CT

5.0 (22 bookings)

2 - 4 hours Captained

Up to 6 passengers

$130+ /hour

Old Saybrook, CT

5.0 (5 bookings)

30' Nonsuch Classic for Sail in Old Saybrook, CT!

4 - 8 hours Captained

Up to 6 passengers

$312+ /hour

Sag Harbor, NY

5.0 (9 bookings)

Classic Beauty - 46 foot Bluewater Cruiser

2 - 8 hours Captained

Up to 6 passengers

$1,280+ /hour

Sag Harbor, NY

5.0 (5 bookings)

Luxurious Sailing Schooner for Events up to 41 guests.

2 - 8 hours Captained

Up to 41 passengers

Rent a Catalina sloop in Westbrook, CT near me

$300+ /hour

Westbrook, CT

5.0 (8 bookings)

A Long Island Sound Sailing Experience!

2 - 3 hours Captained

Up to 6 passengers

Top sailboat rentals reviews in Connecticut

303,393

Customers Reviews

4.95

Avg. Rating

5/5 stars

Sailing JOURNEY...

The boat is in great condition, in a great location and it sail very well. Highly recommended!

Andrea

Sep 2025
5/5 stars

Classic Beauty -...

Amazing day !
We booked a charter on Alan’s boat to celebrate my wife’s birthday. The experience was incredible ...

Colin

Aug 2025
5/5 stars

HUNTER LEGEND 35...

Boating is in excellent condition and is perfect for a day out. Being able to put the paddle board out for swimming...

Scott

Jul 2025
5/5 stars

Luxurious Sailing...

We had a great time! Captain Toby and his assistants were a delight. We will be making this a yearly tradition! My...

Karen

Jul 2025
5/5 stars

HUNTER LEGEND 35...

Marlene

Oct 2024
5/5 stars

HUNTER LEGEND 35...

Great boat with tons of space. Everything you need. It was just two of us on the boat along with Marco captaining. We...

Mike

Sep 2024
5/5 stars

HUNTER LEGEND 35...

Carlee

Sep 2024
5/5 stars

HUNTER LEGEND 35...

Had an amazing time! Marco was terrific! Made the evening absolutely amazing!! Great talk and accommodation!!

Maurice

Sep 2024
5/5 stars

Sailing JOURNEY...

We completed a summer bucket list item with Captain York aboard JOURNEY - sailing the Sound and finding the best...

Caroline

Sep 2024
5/5 stars

Classic Beauty -...

Perfect way to chill out and enjoy a relaxing time on the water instead of the beach. Boat comfortably accommodated 5...

carol

Aug 2024
5/5 stars

Tim and Sallie seriously made us all have one of our most favorite days ever! Started off with the most amazing boat...

Adelina

Aug 2024
5/5 stars

Sailing JOURNEY...

Clean and spacious

Joanna

Aug 2024

How to rent a sailboat in Connecticut?

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.