We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

All listings in Connecticut

Incredible sailboat rentals in Connecticut, United States.

5.0(Average of 113 reviews in this area)
22 listings
Charter Sailboat Cruiser in Stamford, Connecticut
Sailing in Stamford · 6 guests

Charter Sailboat Cruiser in Stamford, Connecticut

5.0
Superowner
$170-195hour
A wonderful USCG Inspected Trimaran For up to 18 Guests
Events in Sag Harbor · 18 guests

A wonderful USCG Inspected Trimaran For up to 18 Guests

5.0
$1,100hour
Sail from Norwalk, CT - $220/Hour - $37/Person
Sailing in Norwalk · 10 guests

Sail from Norwalk, CT - $220/Hour - $37/Person

4.6
Superowner
Best of 2022
$36person
42' Catalina Sailing Yacht in the Hamptons - 4 Hours
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - 4 Hours

5.0
$325hour
Classic Beauty: Nautor Swan 46 Bluewater Cruiser, Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Classic Beauty: Nautor Swan 46 Bluewater Cruiser, Sag Harbor, New York

5.0
$300hour
Casa Sul Mare - Home on the sea
Events in Sag Harbor · 12 guests

Casa Sul Mare - Home on the sea

5.0
$1,250hour
Sail the Thimble Islands on the classy 35' Dufour 4800 Sailboat
Sailing in Branford · 6 guests

Sail the Thimble Islands on the classy 35' Dufour 4800 Sailboat

5.0
$200hour
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
42' Catalina Sailing Yacht in the Hamptons - 3 Hours
Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - 3 Hours

New
$350hour
A Large, Comfortable and Spacious Luxury Sailing Yacht in Sag Harbor
Sailing in Sag Harbor · 12 guests

A Large, Comfortable and Spacious Luxury Sailing Yacht in Sag Harbor

5.0
$800hour
Wonderful Luxury Schooner Perfect for Private Sails and Events for 12-41
Sailing in Sag Harbor · 41 guests

Wonderful Luxury Schooner Perfect for Private Sails and Events for 12-41

5.0
$1,150hour
Charter on 50ft Beneteau Sailing Yacht in Greenport, New York
Sailing in Greenport · 6 guests

Charter on 50ft Beneteau Sailing Yacht in Greenport, New York

5.0
$213-275hour
Sailing JOURNEY on the Sound
Sailing in Stamford · 6 guests

Sailing JOURNEY on the Sound

New
$262hour
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
35ft Dufour 4800 Sloop Boat Charter in Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

35ft Dufour 4800 Sloop Boat Charter in Sag Harbor, New York

New
$300hour
Hunter 170 Sailboat with Honda motor in Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Hunter 170 Sailboat with Honda motor in Sag Harbor, New York

New
$129hour
22ft Catalina Daysailer Boat Rental in Montauk, New York
Sailing in Montauk · 5 guests

22ft Catalina Daysailer Boat Rental in Montauk, New York

New
$125-145hour
Hobie One 12 ft Sailboat for rent in Sag Harbor
Sailing in Sag Harbor · 3 guests

Hobie One 12 ft Sailboat for rent in Sag Harbor

New
$99hour
40' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Sailing in Sag Harbor · 6 guests

40' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

New
$600hour
40' Sailing Catamaran for charter in Montauk
Sailing in Montauk · 8 guests

40' Sailing Catamaran for charter in Montauk

New
$300hour
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

Top Destinations Nearby

Sailing Reviews in Connecticut

  1. Maria
    Maria
    Classic Beauty: Nautor Swan 46 Bluewater Cruiser, Sag Harbor, New York

    Everything was top notch, Alan was very considerable and did everything to make this trip as pleasant for us as possible. The vessel is amazing and the experience was outstanding. I traveled with my two children (3&5) and it worked out really well. Highly recommend!

  2. Paul
    Paul
    Charter 36ft Sloop In Westbrook, Connecticut

    Captain Joy is an outstanding captain and we really enjoyed sailing with her on her beautiful sailboat on the Long Island Sound! We would definitely hang with Captain Joy again!!

  3. MD
    Miranda
    Classic Beauty: Nautor Swan 46 Bluewater Cruiser, Sag Harbor, New York

    Had a great time with Captain Alan! Very comfortable ride, and great communication prior to departure. An excellent choice if you are looking for a sailing trip around Sag Harbor!

  4. DD
    Daniel
    Sail from Norwalk, CT - $220/Hour - $37/Person

    Booked Mark’s boat for a maternity photo shoot. Everything was perfect! He was very communicative and made the whole process very easy. He even came to pick us up from the beach. The boat is gorgeous and we had an amazing time. Would definitely recommend. Thanks Mark!

  5. JL
    Jon
    Sail from Norwalk, CT - $220/Hour - $37/Person

    Our family of 5 all enjoyed a beautiful sail with Mark. Lovely boat with comfortable seating for all. Mark was very flexible with booking a time that worked for us and a very pleasant and knowledgeable captain. Recommend!

  6. TO
    Theresa
    Charter Sailboat Cruiser in Stamford, Connecticut

    We highly recommend Marco!! His boat is beautiful and he is a true professional!!! We had an amazing day on the water!!!