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Stonington, Connecticut Boat Rentals & Yacht Charters

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+/hour
36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island
Sailing in Stonington · 6 guests

36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island

5.0
$220+/hour
97ft Guy Couach Mega Yacht Charter in Montauk Harbor, New York
Events in Montauk · 12 guests

97ft Guy Couach Mega Yacht Charter in Montauk Harbor, New York

New
Superowner
Best of 2026
$1,875/hour
Instant Book
80' Roscioli Luxury Offshore Fishing & Yacht Charters in Montauk & The Hamptons
Fishing in Montauk · 12 guests

80' Roscioli Luxury Offshore Fishing & Yacht Charters in Montauk & The Hamptons

New
$1,725/hour
36' 2021 Aquila Catamaran + Seabob Boat Rental in Montauk, New York
Powerboats in Montauk · 12 guests

36' 2021 Aquila Catamaran + Seabob Boat Rental in Montauk, New York

New
$1,247/hour
Beautiful 88' Ferretti serving NY, Hamptons and New England
Events in Montauk · 12 guests

Beautiful 88' Ferretti serving NY, Hamptons and New England

New
$3,125+/hour
Gorgeous Italian Yacht: Ferrari of the Sea
Events in Montauk · 6 guests

Gorgeous Italian Yacht: Ferrari of the Sea

New
$599/hour
Your Own Boat to Sail on Block Island! Low cost - sailing should be for all!
Sailing in New Shoreham · 2 guests

Your Own Boat to Sail on Block Island! Low cost - sailing should be for all!

New
$50/hour
Enjoy Fishing in Narragansett, Rhode Island with Captain Scott
Fishing in Narragansett · 6 guests

Enjoy Fishing in Narragansett, Rhode Island with Captain Scott

5.0
$119+/hour
36ft Sportfisherman Boat Charter in Point Judith, Rhode Island
Powerboats in Narragansett · 6 guests

36ft Sportfisherman Boat Charter in Point Judith, Rhode Island

New
$960/day
80ft Pershing Yacht Charter in Montauk for Day Trips and Celebrations
Events in Montauk · 13 guests

80ft Pershing Yacht Charter in Montauk for Day Trips and Celebrations

New
Superowner
Best of 2026
$3,000/hour
Instant Book
Overspray in Old Saybrook | 37ft Silverton Yacht
Powerboats in Old Saybrook · 6 guests

Overspray in Old Saybrook | 37ft Silverton Yacht

5.0
$400/hour
85 Pacific Mariner-Serving Luxury to Connecticut and Eastern Long Island
Events in Old Saybrook · 12 guests

85 Pacific Mariner-Serving Luxury to Connecticut and Eastern Long Island

New
$2,250+/hour
57’ 2023 Okean + 2 Seabobs in East Hampton, New York
Events in East Hampton · 12 guests

57’ 2023 Okean + 2 Seabobs in East Hampton, New York

New
$1,750/hour
51' 2022 Azimut Atlantis + 2 Seabobs Yacht Charter in East Hampton, New York
Events in East Hampton · 12 guests

51' 2022 Azimut Atlantis + 2 Seabobs Yacht Charter in East Hampton, New York

New
$1,632+/hour
36' 2023 Aquila Catamaran + Seabob Yacht Rental in East Hampton, New York
Powerboats in East Hampton · 12 guests

36' 2023 Aquila Catamaran + Seabob Yacht Rental in East Hampton, New York

New
$1,247/hour
50' 2023 Jubilance (2-49 Guests) +2 Seabobs Boat Rental in East Hampton
Powerboats in East Hampton · 12 guests

50' 2023 Jubilance (2-49 Guests) +2 Seabobs Boat Rental in East Hampton

New
$1,650/hour
20' Palm boat for the perfect day on the water - Fishing, watersports, swimming
Powerboats in East Hampton · 6 guests

20' Palm boat for the perfect day on the water - Fishing, watersports, swimming

New
$250+/hour
Charter a 30' Classic Wooden Motor Boat in East Hampton, NY
Events in East Hampton · 6 guests

Charter a 30' Classic Wooden Motor Boat in East Hampton, NY

5.0
$388+/hour
Captained sail on a beautiful and comfortable 50' wooden ketch
Sailing in Greenport · 6 guests

Captained sail on a beautiful and comfortable 50' wooden ketch

New
$475/hour
40 Foot Tiara Motor Yacht Rental in Greenport, New York
Powerboats in Greenport · 6 guests

40 Foot Tiara Motor Yacht Rental in Greenport, New York

New
$600/hour
31’ Bertram Classic with captain. Greenport NY
Events in Greenport · 6 guests

31’ Bertram Classic with captain. Greenport NY

5.0
$250/hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$275/hour
Come Sail Newport, Narragansett Bay & Beyond with 50ft Jeanneau Sun Odyssey
Sailing in Jamestown · 6 guests

Come Sail Newport, Narragansett Bay & Beyond with 50ft Jeanneau Sun Odyssey

New
Snoozed - Active 26 Jun 2026

Stonington Reviews

  1. DK

    Dmitri

    Charter 36ft Sloop In Westbrook, Connecticut

    We had a fantastic 2-hour sail out of Westbrook! The boat was in great shape, and Captain Joy was a Joy to sail with: she was professional, friendly, and very experienced. She made us feel safe and relaxed the entire time, and even shared some interesting local facts and recommendations along the way. The views were beautiful and the whole trip was smooth and enjoyable. Highly recommend booking with this captain – we’ll definitely be back!

  2. KF

    Karly

    36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island

    We booked a 2 hour boat trip to celebrate my parents retirement and Francisco was amazing! The boat was beautiful, clean and exactly as listed. He was an incredibly gracious host and took us on a lovely sail! Will definitely be back!

  3. JL

    Jaclyn

    Overspray in Old Saybrook | 37ft Silverton Yacht

    We had a beautiful day out on the CT river for my sister’s birthday! Pick up/drop off was incredibly easy, boat was in great condition, and the crew was very accommodating - would definitely recommend!

  4. HE

    Holly

    Charter 36ft Sloop In Westbrook, Connecticut

    Our first sailing experience was memorable and joyful thanks to Captain Joy! We enjoyed learning about the skills needed to interpret wind and water conditions and seeing the nesting snowy egrets:)

  5. 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!!

  6. BH

    Bailey

    Charter a 30' Classic Wooden Motor Boat in East Hampton, NY

    This is an incredible boat and Scott is a perfect captain. We had an amazing trip including a gorgeous sunset. We will definitely be back!