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Litchfield, Connecticut Boat Rentals & Yacht Charters

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
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.

5.0
$85/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
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
Tubing and Water Fun on Candlewood Lake
Powerboats in New Fairfield · 8 guests

Tubing and Water Fun on Candlewood Lake

5.0
$195/hour
Slide Pontoon on Candlewood Lake
Powerboats in New Fairfield · 8 guests

Slide Pontoon on Candlewood Lake

5.0
$165+/hour
Rent a Celebrity Cruiser with Captain included in price
Water Sports in New Haven · 9 guests

Rent a Celebrity Cruiser with Captain included in price

New
$80+/hour
Luxury 10 Seater with Day Bed - 23ft Bennington Pontoon with Captain
Powerboats in Copake Lake · 10 guests

Luxury 10 Seater with Day Bed - 23ft Bennington Pontoon with Captain

New
$150/hour
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
40ft Private Yacht charter for all occasions in Branford and Thimble Islands.
Events in Branford · 10 guests

40ft Private Yacht charter for all occasions in Branford and Thimble Islands.

5.0
$199/hour
Get Ready To Have Fun Single Jet Ski Rental 2025 Yamaha Jetblaster Deluxe
Water Sports in Westfield · 3 guests

Get Ready To Have Fun Single Jet Ski Rental 2025 Yamaha Jetblaster Deluxe

New
$125+/hour
Get Ready To Have Fun Single Jet Ski Rental 2025 Yamaha Jetblaster Deluxe
Water Sports in Westfield · 2 guests

Get Ready To Have Fun Single Jet Ski Rental 2025 Yamaha Jetblaster Deluxe

New
$125+/hour
Bertram 46' Motor Yacht - Sunset Charters Or Swimming Off The Beach
Events in Bridgeport · 12 guests

Bertram 46' Motor Yacht - Sunset Charters Or Swimming Off The Beach

New
$650/hour
Sunset off Fairfield beach BEST RATES, BEST REVIEWS
Powerboats in Fairfield · 6 guests

Sunset off Fairfield beach BEST RATES, BEST REVIEWS

5.0
$235/hour
A boat charter to experience, BEST RATES, BEST REVIEWS
Powerboats in Westport · 6 guests

A boat charter to experience, BEST RATES, BEST REVIEWS

5.0
$235/hour
Sail the Hudson River in Kingston
Sailing in Kingston · 6 guests

Sail the Hudson River in Kingston

5.0
$125/hour
Great times around Norwalk,Westport,and Rowayton. BEST RATES,BEST REVIEWS
Events in Norwalk · 6 guests

Great times around Norwalk,Westport,and Rowayton. BEST RATES,BEST REVIEWS

4.8
$235/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
Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT
Sailing in Westport · 12 guests

Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT

4.7
Superowner
$200/hour
Welcome aboard on our 33ft charter have fun, relax & enjoy Sunset Cruises.
Events in Norwalk · 6 guests

Welcome aboard on our 33ft charter have fun, relax & enjoy Sunset Cruises.

New
$265+/hour
Formula 400SSC The Pinnacle of Luxury Boating - Rent this boat in Norwalk
Powerboats in Norwalk · 13 guests

Formula 400SSC The Pinnacle of Luxury Boating - Rent this boat in Norwalk

New
$700+/hour
Sunset, 3-6 Hour Cruises on Spacious Cruiser - Norwalk, Westport, Rowayton CT
Events in Norwalk · 6 guests

Sunset, 3-6 Hour Cruises on Spacious Cruiser - Norwalk, Westport, Rowayton CT

5.0
$375/hour
Luxe 68ft Fairline w/ A Paddleboard, Kayak & More in Northeast, USA
Events in Westbrook · 12 guests

Luxe 68ft Fairline w/ A Paddleboard, Kayak & More in Northeast, USA

New
$1,475+/hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/hour

Litchfield Reviews

  1. SK

    Sofiia

    40ft Private Yacht charter for all occasions in Branford and Thimble Islands.

    Yesterday we spent the day on this yacht, and we all had such an amazing experience! A huge thank you to our captain — he was incredibly attentive, professional, and made sure we were comfortable the entire time. He always asked if we wanted to stop somewhere, helped us find beautiful spots for photos, and even helped take pictures of us. 📸✨ I definitely recommend this experience! All of my friends said they would absolutely come back again — with family, for a birthday, a party, or even just a relaxing day on the water. Such a beautiful way to celebrate a special occasion or simply enjoy a perfect day with family and friends. 🛥️

  2. TR

    Timothy E

    40ft Private Yacht charter for all occasions in Branford and Thimble Islands.

    I was planning a surprise date at the last moment. In a matter of a few hourse I was able to customize our boat ride through Dana and the crew worked with us to make suggestions to ultimately provide the experience I was looking for. Our captain Joel was energetic and engaged thoughout. The boat was comfortable and spacious, and everything was very punctual. I would def recommend the experience to others.

  3. Gretchen

    Gretchen

    Sail the Hudson River in Kingston

    Cannot say enough about this experience. Loved the whole trip, great team at the helm, easy and accommodating and fun to spend the morning with. Highly recommend. Thank you so much!

  4. Irene

    Irene

    Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

    Nina is a fantastic person, fantastic captain and a fantastic company. 2 of us and a doggie went on a short adventure with her and it couldn’t have been a better experience. We had so much fun, laughter and comfort with her on her boat that i can barely put this in words. We will definitely do this over and over again. Highly recommend!

  5. 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.

  6. AB

    Alan

    Slide Pontoon on Candlewood Lake

    For those that don’t know Candlewood Lake. It is a great lake to boat in. We went to two different rope swings and a rock jump area. The boat we rented from Shannon was great. All ages of kids from high school and my seven-year-old all loved the slide which makes for extra fun when you’re just floating around. Shannon was easy to communicate with and we are a returning renter as we did the same last year