Best Sailboat Rentals Near Massachusetts

Name: Come Sailing on 'Our Passion'
Rating: 5.0

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Labor Day Weekend Boat Rentals

Our top sailboat rentals

Rent a Pearson Yachts classic in Tisbury, MA near me

$268+ /hour

Tisbury, MA

5.0 (1 booking)

Come Sailing on 'Our Passion'

3 - 8 hours Captained

Up to 6 passengers

$375+ /hour

Boston, MA

5.0 (30 bookings)

Private Luxury Catamaran Charter | 6 Guests | Boston Harbor

2 - 4 hours Captained

Up to 6 passengers

Rent a Other other in Gloucester, MA near me

$226+ /hour

Gloucester, MA

5.0 (18 bookings)

Day Sailing in New England is the best on our sailing yacht ARTEMIS

3 - 8 hours Captained

Up to 6 passengers

$188+ /hour

Hingham, MA

Islay

2 - 8 hours Captained

Up to 6 passengers

$182+ /hour

Newport, RI

5.0 (4 bookings)

Newport RI Sailing, sightseeing and swimming

2 - 4 hours Captained

Up to 6 passengers

$88+ /hour

East Providence, RI

1.0 (1 booking)

25' Catalina, Sail & Explore Narragansett Bay RI !

4 - 8 hours Captained

Up to 4 passengers

$200+ /hour

Newport, RI

5.0 (10 bookings)

Sail on Mariah- Catalina 320

2 - 8 hours Captained

Up to 6 passengers

$169+ /hour

Marblehead, MA

5.0 (110 bookings)

Sail from Marblehead Harbor

2 - 4 hours Captained

Up to 6 passengers

$825+ /hour

Nantucket, MA

65’ Classic Sailboat

3 - 6 hours Captained

Up to 6 passengers

$200+ /hour

Newport, RI

4.9 (34 bookings)

Sound Mariner Charters- Catalina 320 Mariah

2 - 8 hours Captained

Up to 6 passengers

$158+ /hour

New Bedford, MA

5.0 (18 bookings)

Spend the Day on Buzzards Bay / Pearson 35 Omoo

2 - 8 hours Captained

Up to 6 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 Massachusetts

302,354

Customers Reviews

4.95

Avg. Rating

5/5 stars

Sail from...

Erika

Sep 2025
5/5 stars

Private Luxury...

Perfect boat, outstanding crew!!! Everything went smooth!

Val

Aug 2025
5/5 stars

Spend the Day on...

Absolutely wonderful experience. Excellent communication, sailing and local knowledge, skillful sailing. Made it...

Heidi

Aug 2025
5/5 stars

Day Sailing in...

We had a fabulous time on our sail with Rick and Deb. Highly recommended. Our family of 6 enjoyed gliding across the...

David

Aug 2025
5/5 stars

Sail on Mariah-...

Thanks Perrin for taking us out for a sunset cruise! We really enjoyed it!

Isabelle

Aug 2025
5/5 stars

Private Luxury...

Incredible experience, highly recommend. Alex and Captain Rich were super responsive and helpful, made the experience...

Matthew

Aug 2025
5/5 stars

Sail on Mariah-...

Very nice time on the water and a perfect activity for 4 of us. Capt Kenny was great and we look forward to another...

Drew

Jul 2025
5/5 stars

Sail from...

Captain Allan made our day. We had a lovely sale, and he understood the assignment. He got us underway on sail, and...

Jeffrey

Jul 2025
5/5 stars

Come Sailing on...

Best boat trip ever and the captain and crew were the most delightful people we’ve met!

Matthew

Jul 2025
5/5 stars

Spend the Day on...

Thanks for a fun Father’s Day we learnt so
Much about sailing and our family
Is inspired to learn

sabrina

Jun 2025
5/5 stars

Spend the Day on...

We had an amazing trip with Captain Steve! He was fun, personable, and knowledgable. I would recommend BBYC to anyone.

Joe

Sep 2024
5/5 stars

Private Luxury...

Amelia

Sep 2024

How to rent a sailboat in Massachusetts?

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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.