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Boston, Massachusetts Boat Rentals & Yacht Charters

Page 3 of 3 • 53 listings

Beautiful  Like New Rinker Fiesta Vee 31' Cruiser
Powerboats in Gloucester · 6 guests

Beautiful Like New Rinker Fiesta Vee 31' Cruiser

New
$175+/hour
Fast and Fun Fishing or Cruising Boat | 27' Mako Center Console
Fishing in Winthrop · 6 guests

Fast and Fun Fishing or Cruising Boat | 27' Mako Center Console

New
$200/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
Limited Availability
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
Snoozed - Active 05 Oct 2026
Boston Harbor Cruise & Fishing Trip on 29ft Rejoyce
Fishing in Boston · 8 guests

Boston Harbor Cruise & Fishing Trip on 29ft Rejoyce

New
Snoozed - Active 04 Oct 2026

Boston Reviews

  1. Jen

    Jen

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    My sister and I had a wonderful time with Captain Allan and we had perfect weather all day. He was very knowledgable about the local area and a very skilled captain, making us feel comfortable throughout the whole experience. We played music and had such a great time talking with him. Would absolutely recommend and definitely use Captain Allan 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. 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. SA

    Sarah

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    The experience was incredible and so fun! Captain Allan was so great to sail with and taught us so much and made us feel so comfortable and we can’t wait to get back out on the water with him in the future!

  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.