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All listings near me

Find Sailing Charters Near You

4.9
(4,553 Reviews)

Page 5 of 10240 listings

Sailboat on the Hudson
Sailing in Ossining · 6 guests

Sailboat on the Hudson

New
$120+/hour
Sail NYC in Style: Luxury Private Charter Aboard the Sleek NEEL 47 Trimaran
Sailing in Bronx · 12 guests

Sail NYC in Style: Luxury Private Charter Aboard the Sleek NEEL 47 Trimaran

New
$813+/hour
Instant Book
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/hour
2 Hour Sunset Sail in Wrightsville Beach
Sailing in Wrightsville Beach · 6 guests

2 Hour Sunset Sail in Wrightsville Beach

New
$175/hour
Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!
Sailing in Bronx · 6 guests

Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!

New
$150/hour
ASA practice sailing exercizes
Tours in Bronx · 6 guests

ASA practice sailing exercizes

New
$150/hour
Fun in the Sun with Manhattan skyline in the background
Sailing in Bronx · 6 guests

Fun in the Sun with Manhattan skyline in the background

New
$150/hour
Shamrock-Classic 42 foot Allied XL Yawl Wilmington, NC
Sailing in Wilmington · 6 guests

Shamrock-Classic 42 foot Allied XL Yawl Wilmington, NC

5.0
$350/hour
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Sailing in Mamaroneck · 10 guests

Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

5.0
$50/hour
Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis
Sailing in Port Washington · 6 guests

Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

5.0
$169+/hour
Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
Sailing in Oyster Bay · 6 guests

Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

5.0
$190+/hour
Instant Book
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
Best of 2025
$225+/hour
Sailing JOURNEY on the Sound
Sailing in Stamford · 6 guests

Sailing JOURNEY on the Sound

New
$262/hour
Sail From Northport or Huntington, NY
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY

4.8
Superowner
$150/hour
Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin
Powerboats in Wisconsin · 8 guests

Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin

New
$449/day
Private Luxury Sailing in the Charleston Harbor — Captain Included, BYOB
Sailing in Charleston · 6 guests

Private Luxury Sailing in the Charleston Harbor — Captain Included, BYOB

5.0
Superowner
$220/hour
Luxury BYOB Sailing in the Charleston Harbor
Sailing in Charleston · 6 guests

Luxury BYOB Sailing in the Charleston Harbor

5.0
Superowner
$220/hour
Instant Book
Charleston's Largest Private Luxury Sailing Yacht 50ft Windchaser Custom Cruises
Sailing in Mount Pleasant · 12 guests

Charleston's Largest Private Luxury Sailing Yacht 50ft Windchaser Custom Cruises

New
$250/hour
Charleston Luxury Shared Sunset Sail - 50ft Catamaran Enjoy the Bar
Sailing in Mount Pleasant · 100 guests

Charleston Luxury Shared Sunset Sail - 50ft Catamaran Enjoy the Bar

New
$225/hour
Sunday Funday Mimosa Bar Shared Sail– Ultimate Brunch on the Water! Catamaran
Sailing in Mount Pleasant · 100 guests

Sunday Funday Mimosa Bar Shared Sail– Ultimate Brunch on the Water! Catamaran

New
$135/hour
Shared Party Boat Sail w/Bar: Charleston Harbor - Perfect for Bach or Birthday
Sailing in Mount Pleasant · 100 guests

Shared Party Boat Sail w/Bar: Charleston Harbor - Perfect for Bach or Birthday

5.0
$370/hour
Private Events Charleston's Luxury 50ft Catamaran w/Bar Party Sail
Sailing in Mount Pleasant · 100 guests

Private Events Charleston's Luxury 50ft Catamaran w/Bar Party Sail

New
$1,625+/hour
 CATAMARAN/DOLPHIN SAIL  FOLLY BEACH SC
Sailing in Folly Beach · 6 guests

CATAMARAN/DOLPHIN SAIL FOLLY BEACH SC

5.0
Best of 2025
$190/hour
FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr
Sailing in Folly Beach · 6 guests

FOLLY BEACH CATAMARAN SUNSET SAIL, departing Folly River boat landing 190/hr

5.0
Best of 2025
$200/hour

Local Sailing Reviews

  1. NT

    Nick

    Sail From Northport or Huntington, NY

    Mark is a wonderful captain and person all around. He is very communicative and informative both before and while we were on his sailboat. We had the best time sailing from Huntington to Northport. He sang a Happy Birthday to our Mom and brought out his guitar! Thanks so much, Captain Mark!

  2. Tarik

    Tarik

    Cruising Monohull Rental in Kingston

    Great sail. Our captain Rob was very knowledgeable and easy to talk to. He let us help with some of the sailing and then we sat at the front of the boat and enjoy the view. It was a perfect day weather wise. Had a great time overall.

  3. MR

    Madeleine

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Such a fun evening on the water with Marco. A very comfortable boat, easy to access and a beautiful cruise! Highly recommend and we look forward to going out again.

  4. DL

    Dana

    Cruising Monohull Rental in Kingston

    Excellent trip, exactly as described if not better! Karin convinced us to sail at sunset and it was absolutely beautiful. Do not hesitate to book!

  5. LF

    Liza

    Cruising Monohull Rental in Kingston

    This was the perfect choice for my birthday boating goal. Captains were incredible, fun and knowledgeable and even the day showed up as perfect. I can’t wait to do this again VERY soon.

  6. Tal

    Tal

    Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

    From the moment we stepped aboard, it was clear this yacht was something special. Impeccably maintained with every detail thoughtfully cared for, the vessel was not only stunning but also incredibly comfortable and inviting. What truly set this experience apart was our captain. An absolute gem- professional, patient, and genuinely kind. John’s calm demeanor and warm personality created an atmosphere of ease and enjoyment throughout the entire time. Whether it was navigating the waters flawlessly or ensuring everyone felt safe and cared for, this captain went above and beyond. This was more than just a ride—it was a luxury experience wrapped in beauty, serenity, and top-tier hospitality. Highly recommend for anyone looking to create lasting memories on the water. We will definitely be back❤️