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All listings near me

Find Sailing Charters Near You

4.9
(4,576 Reviews)

Page 6 of 10240 listings

Sailing The Edge of America - Folly Beach
Sailing in Folly Beach · 6 guests

Sailing The Edge of America - Folly Beach

5.0
$200/hour
Well Appointed Beneteau 32, Folly Beach, SC
Sailing in Folly Beach · 6 guests

Well Appointed Beneteau 32, Folly Beach, SC

5.0
Best of 2025
$190/hour
🎉🐬⛵️HUGE Sailing Catamaran Yacht in Charleston on Folly Beach, South Carolina
Sailing in Folly Beach · 6 guests

🎉🐬⛵️HUGE Sailing Catamaran Yacht in Charleston on Folly Beach, South Carolina

5.0
Superowner
$300/hour
Sail the Adirondack Mountain Lakes
Sailing in New York · 4 guests

Sail the Adirondack Mountain Lakes

New
$160/hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/hour
26ft Beach Cat Private Charter in Savannah GA *COI Vessel
Powerboats in Savannah · 17 guests

26ft Beach Cat Private Charter in Savannah GA *COI Vessel

5.0
$450/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
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
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
$143/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
Limited Availability
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
Limited Availability
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

Local Sailing Reviews

  1. JG

    Jen

    Well Appointed Beneteau 32, Folly Beach, SC

    Loved our sunset cruise with Greg for my friends birthday. Beautiful boat, scenery, and weather! It was so relaxing to sail, watch the dolphins and catch a gorgeous sunset on the water. Greg was super nice, took pics of our group, and made the trip more enjoyable with his easygoing personality. We would sail again with Greg anytime!

  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. 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!

  4. 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! 🚤⛵️

  5. 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!

  6. Joe

    Joe

    26ft Beach Cat Private Charter in Savannah GA *COI Vessel

    Great day out on the water with the family. Couldn’t ask for a better crew! Capt Tim and Missy were awesome. Pickup and drop off was very smooth, the boat was clean and it was a perfect day!