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All listings in Massachusetts

Incredible sailboat rentals in Massachusetts, United States.

Page 1 of 124 listings

Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
Sailing in Newport · 6 guests

Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

5.0
$200hour
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$150hour
42ft J Boat Sailing Yacht in Newport, Rhode Island
Sailing in Newport · 4 guests

42ft J Boat Sailing Yacht in Newport, Rhode Island

5.0
$260hour
4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!
Sailing in North Kingstown · 6 guests

4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!

5.0
$150hour
Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht
Sailing in Newport · 6 guests

Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht

5.0
$200hour
Sail with us aboard ARTEMIS in Gloucester MA and New England
Sailing in Gloucester · 6 guests

Sail with us aboard ARTEMIS in Gloucester MA and New England

5.0
$250hour
60' Cruising Monohull Ketch in Vineyard Haven, MA
Sailing in Tisbury · 12 guests

60' Cruising Monohull Ketch in Vineyard Haven, MA

5.0
$200-$275hour
Sail to Fishers Island on a fast and classy 35' Sailboat
Sailing in New London · 6 guests

Sail to Fishers Island on a fast and classy 35' Sailboat

5.0
$150person
Captained Sailboat Charter in Salisbury 2 hr sails 4 persons
Sailing in Salisbury · 4 guests

Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

5.0
$160hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$145person
41' Catana Cruising Catamaran for Charter in Newport, RI
Sailing in Newport · 6 guests

41' Catana Cruising Catamaran for Charter in Newport, RI

5.0
$290hour
Private Charters on Classic 80' Schooner yacht in Salem, Massachusetts
Sailing in Salem · 6 guests

Private Charters on Classic 80' Schooner yacht in Salem, Massachusetts

5.0
$498-$550hour
Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$290hour
Spend the Day on Buzzards Bay - Sail on a J/105 or Cruise on a Dyer 29 Powerboat
Sailing in Mattapoisett · 6 guests

Spend the Day on Buzzards Bay - Sail on a J/105 or Cruise on a Dyer 29 Powerboat

New
$70person
Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.
Sailing in Salisbury · 2 guests

Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

New
$85hour
Sunset Sail Buzzards Bay in a Classic Sloop!
Sailing in Fairhaven · 4 guests

Sunset Sail Buzzards Bay in a Classic Sloop!

New
$150hour
Private Sailing Charter Newport, Bristol RI | Captain and Crew
Sailing in Newport · 6 guests

Private Sailing Charter Newport, Bristol RI | Captain and Crew

New
$120-$175hour
Instant Book
Sail World-Famous Newport & Narragansett Bay Aboard Tartan 34 Classic
Sailing in East Providence · 6 guests

Sail World-Famous Newport & Narragansett Bay Aboard Tartan 34 Classic

4.0
$200hour
Private Sailing Charter Bristol/ Newport RI | Captain and Crew
Sailing in Bristol · 6 guests

Private Sailing Charter Bristol/ Newport RI | Captain and Crew

New
$120-$175hour
Instant Book
Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston
Sailing in Boston · 6 guests

Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston

New
$500hour
Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!
Sailing in Gloucester · 6 guests

Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!

New
$175-$225hour
Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!
Sailing in Gloucester · 60 guests

Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!

New
$1,150-$1,300hour
43' Sailboat, Bristol RI & Beyond
Sailing in Bristol · 6 guests

43' Sailboat, Bristol RI & Beyond

New
$199hour
Able Custom 42' Chartered Sailing Experience in Stonington, CT
Sailing in Stonington · 3 guests

Able Custom 42' Chartered Sailing Experience in Stonington, CT

New
$200-$215hour

Sailing Reviews in Massachusetts

  1. Paula

    Paula

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    I loved my experience going on a boat trip with Kenneth! He’s very professional but also easy going and fun to be around! He was very accommodating with my requests (I’m a photographer and rented the boat for a couple session). I’d 100% recommend his service and I’m already looking forward for a next trip!

  2. Seth

    Seth

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    Kenny and Perrin were fantastic with communication throughout the process of booking and getting us out for a sunset cruise! Our family had a great time with Perrin and he is very knowledgeable about the area and has tons of experience. We felt right at home on Mariah! We will definitely be back. Great boat, great captain, and a great experience all around. Highly recommend. Seth

  3. CM

    Cindy

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    Perrin was amazing! The whole process was such a breeze and we had a great couple of hours out on the water. Really knowledgeable (and we tested him haha) and had great insight about the area and the other boats around us. Would definitely recommend!

  4. KB

    Kerry

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    My sisters and I had a wonderful experience with Captain Allan Waldman. We rented the Emma Rose to take our mother’s ashes and scatter them in the ocean out of Marblehead Harbor, where the boat is conveniently located. We were transported to and from the boat by independent launch from Commercial Street Wharf. The weather was luckily beautiful and the trip was made quite memorable by Captain Allan’s sensitivity to our needs. He is comfortable with people and gave us the time to absorb the experience we had and also enjoy the beauty of the afternoon.

  5. DB

    Dylan

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    I booked this trip to propose to my girlfriend and Allen made this very memorable. The harbor and surrounding area in Marblehead was beautiful, and seeing all the other sails in the horizon is a scene that makes this experience worth every penny. Allen was friendly and very knowledgeable. I had never been on a sailboat before but the classic look and close quarters seating area of this vessel made for a romantic setting. Absolutely recommend for a date, special occasion, or just a casual sail around the Gold Coast.

  6. BG

    Briana

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    Awesome experience & an amazing captain. The trip was relaxing and fun. Allan is super experienced, kind, and knowledgeable. He managed to smoothly sail through a sailboat race, without interfering with the race and showed us cute seals and beautiful mansions !!