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All listings in Boston

Great sailboat rentals near Boston, Massachusetts.

Page 1 of 16 listings

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

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$165/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. CL

    Cong

    Elegant 43ft Catamaran: Experience Boston Harbor in Style!

    I had a fantastic evening on this beautiful catamaran with a successful proposal to my now fiancee with sunset. Alex was so professional and accommodating, which led to the success. He was fast to respond, accommodating my date change request due to the weather forecast change even though it was within five days. Alex also coordinated well with my photographer, allowing him to board early before picking us up, which kept the proposal a surprise.

  2. Mike

    Mike

    Elegant 43ft Catamaran: Experience Boston Harbor in Style!

    Perfect way to spend a day in Boston Harbor. The crew was so incredible and took amazing care of us. They had everything we would need, including snacks and towels (we usually bring our own, but totally didn't need to!). Would 100% recommend for a relaxing time on the water!

  3. 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’

  4. 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!

  5. GP

    George

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    Had a great time with Captain Allan, truly a fun time and he was very concerned about us enjoying the experience. We highly recommend him and his service. You won’t be disappointed!

  6. 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.