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All listings in Middletown

Great sailboat rentals near Middletown, Rhode Island.

Page 1 of 15 listings

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
$260/hour
Newport RI: Sailing, Swimming and Sightseeing
Sailing in Newport · 6 guests

Newport RI: Sailing, Swimming and Sightseeing

5.0
$200/hour
Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$290/hour
Instant Book
63' Catamaran - Newport, RI - Luxury sailing for large groups!
Sailing in Newport · 40 guests

63' Catamaran - Newport, RI - Luxury sailing for large groups!

New
$833/hour
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
Snoozed - Active 02 Sep 2025

Sailing Reviews in Middletown

  1. ST

    Samantha

    Custom Sailing Charter - Newport/ Block Island

    We really enjoyed our sail with Candace, Stephanie and Matt - and we can't forget Eddie Spaghetti the daschaund! They told us a lot about the history of the area and made sure we were comfortable and well-taken care of on this sail. Many thanks to Stephanie too for the wonderful photos on the trip.

  2. Caroline

    Caroline

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

    David was amazing. He went above and beyond ensuring a smooth sail, pointing out key features and places, and getting us close to all of the action. Totally recommend

  3. JF

    Jamie

    Custom Sailing Charter - Newport/ Block Island

    Captain Don and Marsha were the best, we had a fantastic day out.

  4. MM

    Martez

    42ft J Boat Sailing Yacht in Newport, Rhode Island

    Captain Anthony created a wonderful experience for my family -- fun stories and sailing tutorials for the kids and knowledge information about sailing physics and "hands on" experience for the adults. A masterful conversationalist and a natural with people of all ages. Truly a gentleman and a terrific sailor. We highly recommend him to parties of all types, but especially families.

  5. MB

    Matt

    42ft J Boat Sailing Yacht in Newport, Rhode Island

    Couldn’t be happier with our experience with Tony and Parker. Easy communication, and Tony is a great host. We had so much fun, saw the beauty of Newport by boat, and even got some fun history lessons. Will definitely be booking with Tony again next time we’re in Newport!

  6. MS

    Mitchell

    42ft J Boat Sailing Yacht in Newport, Rhode Island

    Captain Tony and Parker were excellent! We had an incredible day out on the water, even with some rough wind. Not only did they provide an awesome experience and we’re incredibly accommodating to our itinerary requests, they even taught us a thing or two about sailing. I’d definitely recommend them and hope to charter them again in the future!