Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

All listings in Boston

Great sailboat rentals near Boston, Massachusetts.

Page 1 of 16 listings

Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$165/hour
Elegant 43ft Catamaran: Experience Boston Harbor in Style!
Sailing in Boston · 6 guests

Elegant 43ft Catamaran: Experience Boston Harbor in Style!

5.0
$313+/hour
Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!
Sailing in Gloucester · 6 guests

Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!

5.0
$250/hour
Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts
Sailing in Salem · 6 guests

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

5.0
$550/hour
Instant Book
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+/hour
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
$1,200+/hour

Sailing Reviews in Boston

  1. OO

    Olivia

    Elegant 43ft Catamaran: Experience Boston Harbor in Style!

    We had the best time on the boat with Alex, the boat was perfect, plenty of room to move around. The views were stunning, everything went so smooth from the pickup to departure. They accommodated us with everything we needed. Alex and his mate were super knowledgeable and friendly. We had the best time with them and can’t wait to book again’

  2. Brad

    Brad

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    We had a great day on the water with Captain Alan. Highly recommend this charter. Captain Alan is a knowledgeable and affable sailor. The trip consisted of myself and my wife, our twenty two year old daughter, and her two friends; the boat was easily accommodated all of us, Captain Alan and his first mate. Highly recommend Marblehead and the North Shore area for convenient and scenic sailing. We were even able to swim off the boat. Great day!

  3. WF

    William

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    Outstanding captain, flexible schedule, based on wind conditions. Knowledgeable captain, plan b to view the seals during calm wind conditions, that kept my grandsons (8,10) entertained. First mate Mable , very helpful, both with the boat and the boys.

  4. CO

    Christina

    Elegant 43ft Catamaran: Experience Boston Harbor in Style!

    We had a fantastic time cruising the harbor with Alex and Rich. They were so kind and welcoming as well as attentive to all of our needs. The absolute highlight of our trip to Boston my friends and I were so impressed to hear that Alex had refurbished the boat himself. She is a boat made beautiful from the care and attention of her crew and I highly recommend this catamaran for anyone interested.

  5. Joan

    Joan

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    Our party of 4 really enjoyed our sail. Captain Allen and first mate Mable were accommodating and nice. Captain Allen is an exceptional sailor and super chill. Highly recommend.

  6. CS

    Candace

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    Captain Allen and his crewmate Mable were great! They were very kind and accommodating And easy-going. Even in the pouring rain, they made our trip go well. I would highly recommend them.