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All listings near me

Find Sailing Charters Near You

4.9
(5,010 Reviews)

Page 7 of 10240 listings

SAIL Historic Southern Lake Champlain on 30ft Catalina Sailboat
Sailing in New York · 6 guests

SAIL Historic Southern Lake Champlain on 30ft Catalina Sailboat

New
$150/hour
Large and Luxuriously Appointed Schooner for Private Daysails, Swims and Sunsets
Sailing in Sag Harbor · 41 guests

Large and Luxuriously Appointed Schooner for Private Daysails, Swims and Sunsets

5.0
$1,100+/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
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
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
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
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
Private Sailing Charter – Explore the Hamptons from Sag Harbor Aboard a Beneteau
Sailing in Sag Harbor · 6 guests

Private Sailing Charter – Explore the Hamptons from Sag Harbor Aboard a Beneteau

New
$230+/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
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
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
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
Sailing and Kitesurf Onboard Hunter 260 Sailboat
Sailing in Brossard · 6 guests

Sailing and Kitesurf Onboard Hunter 260 Sailboat

New
$145/hour
Luxury 62' Lagoon Catamaran
Sailing in Warwick · 12 guests

Luxury 62' Lagoon Catamaran

5.0
$1,325/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
$350/hour
Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
Sailing in Newport · 6 guests

Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

5.0
Best of 2025
$180/hour
63' Catamaran - Newport, RI - Luxury sailing for large groups!
Sailing in Newport · 40 guests

63' Catamaran - Newport, RI - Luxury sailing for large groups!

New
$833/hour
42ft J Boat Sailing Yacht in Newport, Rhode Island
Sailing in Newport · 4 guests

42ft J Boat Sailing Yacht in Newport, Rhode Island

5.0
$260/hour
Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$290/hour
Instant Book
Newport RI: Sailing, Swimming and Sightseeing
Sailing in Newport · 6 guests

Newport RI: Sailing, Swimming and Sightseeing

5.0
$200/hour
43' Sailboat, Bristol RI & Beyond
Sailing in Bristol · 6 guests

43' Sailboat, Bristol RI & Beyond

5.0
$199/hour
Padanaram / Dartmouth Harbor Sailboat Cruise 42ft "Our Passion"
Sailing in Dartmouth · 6 guests

Padanaram / Dartmouth Harbor Sailboat Cruise 42ft "Our Passion"

5.0
Superowner
$250/hour
Spend the Day on Buzzards Bay - Sail on "Omoo" a Pearson 35 Cruising Yacht
Sailing in New Bedford · 6 guests

Spend the Day on Buzzards Bay - Sail on "Omoo" a Pearson 35 Cruising Yacht

5.0
$180/hour

Local Sailing Reviews

  1. cC

    chris

    43' Sailboat, Bristol RI & Beyond

    This was an incredible sail. We had to cancel our initial trip due to very bad storms with 65 knot winds and flooding rains early in the season. We rebooked and had a fabulous, relaxing time. The Capt' is both entertaining and a wealth of information and just makes the entire experience what you would want.....sublime.

  2. BA

    Bridget

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    Our sail with Captain Perrin was an absolute dream. We were lucky enough to have gorgeous weather for our sunset sail and Perrin could not have been more accommodating. Our bachelorette party of five loved his historic tidbits and great vibes. Would definitely book again when back in the area!

  3. AH

    Anne

    43' Sailboat, Bristol RI & Beyond

    Four of us had a great sail with Captain Francis. He struck the right balance between chatting with us and letting us talk amongst ourselves. We wanted to sail by a specific area and he graciously complied. I thought the value for the sailing experience was great. Highly recommend.

  4. MH

    Melissa

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    We had a great trip with Kenny - highly recommend. Very prompt, communicative, and clear in departure directions. We had a great sail with beautiful conditions and Kenny is personable and knowledgeable. Highly recommend for a great time on the water, we’ll definitely go sailing with him again next time!

  5. SC

    Steven

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    This wasn’t just a sail—it was an adventure filled with stories, laughter, and the kind of peaceful moments you only find out on the water. I can’t recommend Kenneth highly enough if you’re looking for a memorable and truly enjoyable sailing experience. Highly recommend! 🚤⛵️

  6. VS

    Vicky

    42ft J Boat Sailing Yacht in Newport, Rhode Island

    We had a great day out exploring the bay with Captain Tony. It was a wonderful sailboat experience, that included a swim in a quiet cove and tour of notable homes on the coast. The ride come with a free lesson on the History of Newport, if you would like one. We look forward to seeing the Captain again soon!