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Find Sailing Charters Near You

4.9
(4,908 Reviews)

Page 5 of 10240 listings

56' SeaRay Yacht in New York!
Events in Brooklyn · 12 guests

56' SeaRay Yacht in New York!

4.8
$475/hour
27  feet of fun in the summer sun, under sail!
Sailing in Brooklyn · 6 guests

27 feet of fun in the summer sun, under sail!

New
Snoozed - Active 02 Jun 2026
Sailing Charters in Wilmington NC
Sailing in Wilmington · 6 guests

Sailing Charters in Wilmington NC

5.0
$178/hour
Sailing Lesson in Little River, South Carolina
Tours in Little River · 1 guest

Sailing Lesson in Little River, South Carolina

New
$360/hour
Sunset Cruise in Myrtle Beach, South Carolina
Sailing in Little River · 6 guests

Sunset Cruise in Myrtle Beach, South Carolina

5.0
$450/hour
Ocean Inlet Captained Charter onboard Beneteau 39 Sailboat in Little River, South Carolina
Sailing in Little River · 6 guests

Ocean Inlet Captained Charter onboard Beneteau 39 Sailboat in Little River, South Carolina

5.0
$150/hour
Sailboat on the Hudson
Sailing in Ossining · 6 guests

Sailboat on the Hudson

New
$120+/hour
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
Limited Availability
30ft C&C 30 MK 1 Sailboat: Jersey City Harbor Sailing with Views of NYC Skyline
Sailing in Bronx · 6 guests

30ft C&C 30 MK 1 Sailboat: Jersey City Harbor Sailing with Views of NYC Skyline

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
Snoozed - Active 11 May 2026
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
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
$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
Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT
Sailing in Norwalk · 12 guests

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

4.7
Superowner
$200/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
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
Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin
Powerboats in Wisconsin · 8 guests

Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin

New
$449/day
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

5.0
$250/hour

Local Sailing Reviews

  1. DJ

    Duane

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

    We had a great time and even experienced sailing too. Went above and beyond and made sure we had a great time.

  2. HS

    Hillary

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

    Captain Jen was the most gracious host! The sailboat was immaculate and such a fun experience!

  3. David

    David

    56' SeaRay Yacht in New York!

    Had a really fantastic cruise with close friends -5 adults and 2 kids aged 9 and 11. Boat is fabulous, crew was great and Capt. Max was the best from start to finish. Listen to his recommendations - he knows what he’s doing. This was a special trip and one that my group will remember fondly for a long time.

  4. CQ

    Christopher

    56' SeaRay Yacht in New York!

    Captain Max and Ty were exceptional they went above and beyond for me and my group. They exceeded expectations and the vessel was just as beautiful as the pictures show definitely will be renting with you guys again. One of the best experiences of my lifetime

  5. MA

    Melinda

    56' SeaRay Yacht in New York!

    I highly recommend Captain Max and the Encore yacht. Follow the rules and you'll have an enjoyable time. Throughout the booking process, He is very responsive. It's a beautiful yacht! The main goal is to protect and maintain the yacht while delivering a fun day on the water. First Mate, MJ is amazing...skilled, helpful, and a great personality. You won't regret booking with Captain Max. This private charter saved my 40th birthday celebration since all other plans were cancelled due to covid.

  6. vito

    vito

    56' SeaRay Yacht in New York!

    We recommend this boat 100% took clients for 5 hours around the hudson and the vibe was perfect! Captain was very professional and the crew was super nice ! We had the crew always asking if we need it something! 5 stars for the boat and crew! We will def be back