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    Find Sailing Charters Near You

    4.8
    (5,135 Reviews)

    Page 5 of 10 • 240 listings

    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
    Sail the Hudson River in Kingston
    Sailing in Kingston · 6 guests

    Sail the Hudson River in Kingston

    5.0
    $125/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
    Limited Availability
    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
    Limited Availability
    Sail From Port Washington, NY with Hunter Passage 456 Sailing Yacht
    Sailing in Port Washington · 12 guests

    Sail From Port Washington, NY with Hunter Passage 456 Sailing Yacht

    4.8
    Superowner
    $219/hour
    Limited Availability
    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
    $225+/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
    $225+/hour
    Limited Availability
    Sail From Northport or Huntington, NY
    Sailing in Huntington · 12 guests

    Sail From Northport or Huntington, NY

    4.9
    Superowner
    $150/hour
    Limited Availability
    Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT
    Sailing in Westport · 12 guests

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

    4.7
    Superowner
    $200/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
    Snoozed - Active 17 Sep 2026
    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
    Snoozed - Active 17 Sep 2026
    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
    $240/hour
    Limited Availability
    Luxury BYOB Sailing in the Charleston Harbor
    Sailing in Charleston · 6 guests

    Luxury BYOB Sailing in the Charleston Harbor

    5.0
    Superowner
    $240/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
    Afternoon Sail | Private 50ft Jeanneau Sun Odyssey Sailing Yacht in Charleston
    Sailing in Mount Pleasant · 12 guests

    Afternoon Sail | Private 50ft Jeanneau Sun Odyssey Sailing Yacht in Charleston

    New
    $250/hour
    3-Hour Morning Sail | Private 50ft Luxury Sailing Yacht in Charleston
    Sailing in Mount Pleasant · 12 guests

    3-Hour Morning Sail | Private 50ft Luxury Sailing Yacht in Charleston

    New
    $250/hour
    High Demand
    Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston
    Sailing in Mount Pleasant · 12 guests

    Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston

    5.0
    $250/hour
    Limited Availability
    Luxury 42ft Catamaran Sailing Charter in Charleston Harbor
    Sailing in Mount Pleasant · 6 guests

    Luxury 42ft Catamaran Sailing Charter in Charleston Harbor

    5.0
    Superowner
    $235+/hour
    Limited Availability
    Shared Charleston Harbor Sunset Sail - 50ft Catamaran with Bar Onboard
    Sailing in Mount Pleasant · 100 guests

    Shared Charleston Harbor Sunset Sail - 50ft Catamaran with Bar Onboard

    New
    $375/hour
    Sunday Mimosa Brunch Sail: Shared Sail with Brunch Bites Included
    Sailing in Mount Pleasant · 100 guests

    Sunday Mimosa Brunch Sail: Shared Sail with Brunch Bites Included

    New
    $375/hour
    Limited Availability
    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
    $375/hour
    Private Charter Charleston Harbor Sail - 55ft Catamaran with Bar Onboard
    Sailing in Mount Pleasant · 100 guests

    Private Charter Charleston Harbor Sail - 55ft Catamaran with Bar Onboard

    New
    $1,625+/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
    $200/hour

    Top Destinations Nearby

    Local Sailing Reviews

    1. MC

      Mia

      Sail From Northport or Huntington, NY

      Captain Mark hosted us for my boyfriend’s surprise birthday party. Mark was extremely easy to plan with, accommodatingly sailed out of a more convenient port for us, and took us to two swim spots! The day was described as “the best outing ever” by many of our friends.

    2. AJ

      Aaron

      Sail From Northport or Huntington, NY

      Great captain, great experience. First time sailing for me and felt as comfortable as ever. Seamlessly kept me informed on the goings on with sailing so I felt at peace knowing what was happening. The boat was comfortable and safe. Captain mark was accommodating and friendly, good heart, good vibes! You'd be lucky to Have Captain Mark!

    3. LT

      Louis

      Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

      We had a great cruise on the sound. Marco was very personable and made sure everyone was comfortable and safe. I would highly recommend his boat. It is very well maintained and in excellent condition.

    4. CF

      Carlos

      Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

      Captain Marco was absolutely amazing! He was incredibly attentive to our entire group throughout our birthday party celebration and truly went above and beyond. His energy and hospitality made it such a special and memorable day for all of us. We would definitely recommend him to anyone looking for a perfect day on the water and we are already planning our future boat adventures with him!

    5. Mary Kate

      Mary Kate

      Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston

      Highly recommend this charter! Amazing charter for a girls day! Captain Jen and Janet are top notch!!

    6. Jon

      Jon

      Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

      Marco was a gracious host. The boat is beautiful, clean, and in great shape. We had a fantastic day on the water. I highly recommend!

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