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Connecticut, US Boat Rentals & Yacht Charters

Page 2 of 597 listings

Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$275/hour
80ft Chris-Craft Yacht Charter in New York for 40 Guests
Events in Sag Harbor · 40 guests

80ft Chris-Craft Yacht Charter in New York for 40 Guests

New
Superowner
Best of 2026
$1,375+/hour
Instant Book
SeaRay Sundancer 41' Power Sport Yacht Crusie in Sag Harbor
Events in Sag Harbor · 6 guests

SeaRay Sundancer 41' Power Sport Yacht Crusie in Sag Harbor

5.0
$700/hour
Sea Ray 39ft Yacht Charter in Deep River.  A great day on the water !
Events in Clinton · 6 guests

Sea Ray 39ft Yacht Charter in Deep River. A great day on the water !

5.0
$175+/hour
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
$160/hour
Captained Modern Luxurious 58' Princess Motor Yacht in the Hamptons
Events in Sag Harbor · 12 guests

Captained Modern Luxurious 58' Princess Motor Yacht in the Hamptons

5.0
$1,000+/hour
Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience
Sailing in Sag Harbor · 41 guests

Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience

5.0
$1,100+/hour
61ft Sirena Flybridge Yacht For 12 In Sag Harbour/Montauk!!!
Events in Sag Harbor · 12 guests

61ft Sirena Flybridge Yacht For 12 In Sag Harbour/Montauk!!!

New
Superowner
Best of 2026
$1,469+/hour
Instant Book
July Special 4 Hours $3200   53 ft. Luxury Yacht    Sag Harbor  East Hampton
Powerboats in Sag Harbor · 10 guests

July Special 4 Hours $3200 53 ft. Luxury Yacht Sag Harbor East Hampton

5.0
$800/hour
20ft Nautique Ski Boat: Ski Instruction, Tubing, Fishing and Fun on Lake Zoar
Powerboats in Connecticut · 7 guests

20ft Nautique Ski Boat: Ski Instruction, Tubing, Fishing and Fun on Lake Zoar

5.0
$140/hour
Luxe 68' Galeon: 3 Staterooms, Bar and Water Toys serving South, FL
Powerboats in Sag Harbor · 12 guests

Luxe 68' Galeon: 3 Staterooms, Bar and Water Toys serving South, FL

5.0
$1,300+/hour
110ft Horizon FD110 Luxury Yacht Charter Sag Harbor & Montauk, NY
Events in Sag Harbor · 12 guests

110ft Horizon FD110 Luxury Yacht Charter Sag Harbor & Montauk, NY

New
Superowner
Best of 2026
$3,125/hour
18' 2025 Small "Ken" Fun Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 12 guests

18' 2025 Small "Ken" Fun Boat Rental in Sag Harbor, New York

New
$545/hour
22' 2025 Bayliner Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 8 guests

22' 2025 Bayliner Boat Rental in Sag Harbor, New York

New
$514/hour
Robalo 207 Center Console for Rent in Norwalk
Powerboats in Norwalk · 6 guests

Robalo 207 Center Console for Rent in Norwalk

5.0
$200/hour
Experience New York Like Never Before — Aboard Our Stunning 76ft Riva Yacht
Events in Sag Harbor · 12 guests

Experience New York Like Never Before — Aboard Our Stunning 76ft Riva Yacht

New
Superowner
Best of 2026
$1,500/hour
Instant Book
Enjoy Fishing or Cruising on a Downeast-Style Boat
Fishing in Branford · 6 guests

Enjoy Fishing or Cruising on a Downeast-Style Boat

5.0
$190/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
52' Santasevera The Ultimate 2026 Day Boat in Sag Harbor, New York
Events in Sag Harbor · 12 guests

52' Santasevera The Ultimate 2026 Day Boat in Sag Harbor, New York

New
$3,080/hour
Learn To Sail 23' Pearson With Instructor In Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Learn To Sail 23' Pearson With Instructor In Sag Harbor, New York

New
$249/hour
Experience the Nautique G23 Paragon Surf, Wakeboard, or Just Hang Out
Powerboats in New Milford · 8 guests

Experience the Nautique G23 Paragon Surf, Wakeboard, or Just Hang Out

5.0
$275+/hour
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
22' 2023 Bayliner Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 8 guests

22' 2023 Bayliner Boat Rental in Sag Harbor, New York

New
$514/hour

Connecticut 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. CV

    Cheryl

    Sea Ray 39ft Yacht Charter in Deep River. A great day on the water !

    Rob and mellie were amazing, they made our boat excursion for a 40th bday extra special, with so many great touches. Mellie was so great helping with our theme and putting together food and drinks for us. She went above and beyond. Rob was great at communicating with me during the whole planning process and answered all my questions . We never felt rushed and they made sure we had good time , we will be booking again next summer , can't wait !!!!

  3. WB

    Wayne

    Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

    I really appreciate how Captain Nina accommodated me last minute after I had a lesson scheduled at a sailing school. Saved my plans for the weekend. She did a great job adjusting the experience to my level, and keeping the whole time chill and conversational.

  4. Mayuri

    Mayuri

    Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience

    If you are looking for an amazing time, do not hesitate booking the Luna! Toby and his staff take care of you every step of the way. The boat is well equipped with servingware, water, and ice for your event. Fun bean bags are plenty aboard. Our guests enjoyed the awning and swim spot on a hot day, as well. Just a fabulous experience from start to finish!

  5. GR

    Gillean

    Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

    Nina was great, and the sail was so relaxing and peaceful. Not too many powerboats out like you see on so many other lakes, so it was smooth sailing all the way. I’d highly recommend a sail with Captain Nina on this lovely lake.

  6. ML

    Margaux

    Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience

    We had such a fabulous time on this beautiful boat. Our captain, JM, and the crew Liz and Andrew were so friendly and attentive and amazing with all the kids we had. It was a wonderful afternoon and we can’t wait to do it again!