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Old Lyme, Connecticut Boat Rentals

Page 1 of 124 listings

Overspray in Old Saybrook | 37ft Silverton Yacht
Powerboats in Old Saybrook · 6 guests

Overspray in Old Saybrook | 37ft Silverton Yacht

5.0
$300/hour
Instant Book
Luxury with No Limits - 43' Mystic Center Console
Powerboats in Old Saybrook · 13 guests

Luxury with No Limits - 43' Mystic Center Console

5.0
$800/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
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/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
Sail to Fishers Island on a fast and classy 35' Sailboat
Sailing in New London · 6 guests

Sail to Fishers Island on a fast and classy 35' Sailboat

5.0
Snoozed - Active 02 Jun 2026
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
31’ Bertram Classic with captain. Greenport NY
Events in Greenport · 6 guests

31’ Bertram Classic with captain. Greenport NY

New
$250/hour
Instant Book
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
💎 VIP experience - Vanquish VQ40 + SeaBob Rental in Greenport, New York
Events in Greenport · 12 guests

💎 VIP experience - Vanquish VQ40 + SeaBob Rental in Greenport, New York

New
$875+/hour
💎 VIP Experience: Sanlorenzo 88SX + SeaBob - NY
Events in Greenport · 12 guests

💎 VIP Experience: Sanlorenzo 88SX + SeaBob - NY

New
$2,063+/hour
Ride the Waves in Style with our 26ft Chaparral Surf Boat
Powerboats in Greenport West · 6 guests

Ride the Waves in Style with our 26ft Chaparral Surf Boat

New
$500+/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

New
$220+/hour
A large and luxurious French Sailing Yacht for up to 6
Sailing in Sag Harbor · 6 guests

A large and luxurious French Sailing Yacht for up to 6

New
$750+/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 2025
$1,500/hour
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
Sail on a classy and fast Sailing Yacht in the Hamptons, New York
Sailing in East Hampton · 6 guests

Sail on a classy and fast Sailing Yacht in the Hamptons, New York

5.0
Snoozed - Active 17 Jun 2026
42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

5.0
$312+/hour
62' Pershing + 2 Seabobs Yacht Charter in Sag Harbor, New York
Events in Sag Harbor · 12 guests

62' Pershing + 2 Seabobs Yacht Charter in Sag Harbor, New York

New
$2,384/hour
Sail the glamorous Hamptons in a 58ft Catana luxury catamaran
Sailing in Sag Harbor · 12 guests

Sail the glamorous Hamptons in a 58ft Catana luxury catamaran

New
$1,200/hour
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Sailing in Sag Harbor · 12 guests

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

5.0
$750+/hour
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
$310+/hour
Luxurious 80' San Lorenzo serving NY, Hamptons and New England
Events in Sag Harbor · 12 guests

Luxurious 80' San Lorenzo serving NY, Hamptons and New England

New
$2,750+/hour
Enjoy the Hamptons waters on wonderful and unique Classic Mahogany Trimaran
Sailing in Sag Harbor · 25 guests

Enjoy the Hamptons waters on wonderful and unique Classic Mahogany Trimaran

5.0
$750+/hour

Old Lyme Reviews

  1. LE

    Lara

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

    My girlfriends and I had the best time celebrating a bachelorette party with Captain Brian and his beautiful boat! From the very start Brian had quick communication and was helpful answering our questions. The actual boat was so nice, with a rustic charm. It comfortably fit all 10 girls. Brian made the day extra special - he’s so kind and fun. Would definitely recommend to this others and even hope to do another trip again!

  2. EC

    Emily

    42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

    Nate and Jaime were the absolute best from start to finish! Super great communication and excellent service - loved the swimming spot and how knowledgeable Nate was about the area and other boats. Exceeded our expectations, will definitely book with Nate again!

  3. KH

    Katy

    42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

    We are so happy we chose to book with Nate! The communication was clear and concise, we knew exactly where to go when our trip came! Nate and crew were beyond accommodating and the boat is so charming! This made our trip so special!

  4. 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!

  5. MM

    Molly

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

    Captain Alan and his boat are incredible!! We brought a group of girls for a bachelorette trip and spending the day out on the water was SO much fun. Captain Alan was so communicative and helpful throughout the process and leading up to the day of our charter. He had everything we could have needed on board and was so helpful the whole trip!! His deckie was also so incredibly helpful - we could not have asked for a better time!!! He even had floats and a paddleboard to use which was awesome. Highly recommend to anyone looking for a fun day on the water!! 10/10, no notes!!

  6. 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!