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    Find Sailing Charters Near You

    4.9
    (4,327 Reviews)

    Page 5 of 10 • 240 listings

    Sailing Charters in Wilmington NC
    Sailing in Wilmington · 6 guests

    Sailing Charters in Wilmington NC

    5.0
    $89person
    Sailing Lesson in Little River, South Carolina
    Tours in Little River · 1 guest

    Sailing Lesson in Little River, South Carolina

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

    Sunset Cruise in Myrtle Beach, South Carolina

    5.0
    $450hour
    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
    $150hour
    Private Schooner in NY
    Sailing in Queens · 6 guests

    Private Schooner in NY

    New
    $1,500day
    Cruising Monohull Rental in Kingston
    Sailing in Kingston · 6 guests

    Cruising Monohull Rental in Kingston

    5.0
    $125hour
    Sunset cruise outside of NYC: the beauty of Long Island
    Sailing · 6 guests

    Sunset cruise outside of NYC: the beauty of Long Island

    New
    $95person
    ASA practice sailing exercizes
    Tours in Bronx · 6 guests

    ASA practice sailing exercizes

    New
    $95person
    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
    $95person
    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
    $350hour
    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
    $100person
    Sailing Long Island Sound with Captain Steve
    Sailing in Port Washington · 6 guests

    Sailing Long Island Sound with Captain Steve

    5.0
    $199hour
    Sail From Port Washington, NY - $219/Hour - $37/Person
    Sailing in Port Washington · 6 guests

    Sail From Port Washington, NY - $219/Hour - $37/Person

    4.7
    Superowner
    Best of 2023
    $37person
    25' Bayliner for rent in East Rockaway
    Powerboats in Freeport · 7 guests

    25' Bayliner for rent in East Rockaway

    New
    $113-$150hour
    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!

    New
    $175-$275hour
    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
    Sailing in Stamford · 6 guests

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    5.0
    Superowner
    $37person
    Sailing JOURNEY on the Sound
    Sailing in Stamford · 6 guests

    Sailing JOURNEY on the Sound

    New
    $262hour
    Sail From Northport or Huntington, NY - $215/Hour - $36 Per Person
    Sailing in Huntington · 6 guests

    Sail From Northport or Huntington, NY - $215/Hour - $36 Per Person

    5.0
    Superowner
    Best of 2023
    $50person
    Sail from Norwalk, CT - $220/Hour - $37/Person
    Sailing in Norwalk · 10 guests

    Sail from Norwalk, CT - $220/Hour - $37/Person

    4.6
    Superowner
    Best of 2023
    $36person
    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
    $160hour
    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
    $85hour
    Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin
    Powerboats in Wisconsin · 8 guests

    Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin

    New
    $500day
    Private Luxury BYOB Sailing in the Charleston Harbor
    Sailing in Charleston · 6 guests

    Private Luxury BYOB Sailing in the Charleston Harbor

    5.0
    Superowner
    Best of 2023
    $200hour
    Luxury BYOB Sailing in the Charleston Harbor
    Sailing in Charleston · 6 guests

    Luxury BYOB Sailing in the Charleston Harbor

    5.0
    Superowner
    Best of 2023
    $220hour

    Local Sailing Reviews

    1. CV

      Carlee

      Luxury BYOB Sailing in the Charleston Harbor

      We had a blast sailing! Our captain was very friendly and made sure to answer all of our questions about the area. There was plenty of room to spread out on the boat and they made sure to make us feel welcome and serve us our refreshments we brought on board :) Would book again!

    2. CG

      Carlos

      Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

      Captain Nina is amazing! I planned a surprise for my then gf now fiancée and Captain Nina made the experience special!

    3. AG

      Amberlyn

      Luxury BYOB Sailing in the Charleston Harbor

      One of the best adventures I’ve been on with my girlies! Would rate him 100 stars if I could! Thank you so much for making us feel comfortable and so accommodating

    4. KM

      Krista

      Sailing Charters in Wilmington NC

      Oliver is a very experienced sailor and Captain and super nice too!

    5. BS

      Brooke

      Sailing Charters in Wilmington NC

      Oliver is an amazing captain! My husband and I celebrated our anniversary aboard Oliver’s sailboat and it was an amazing experience. He’s extremely personable, knowledgeable, and safe! We loved having the opportunity to help steer, put sails up, and dock the boat. We also loved the relaxing moments where we could soak up the sun and the view! We will definitely be booking other Oliver again and highly suggest him for anyone looking to do a boat ride in Wilmington. This is a must do!!

    6. JK

      Jorn

      Sailing Charters in Wilmington NC

      I would recommend this to anyone that would like the experience and feeling of being on a sailboat in a safe and peaceful manner. Captain Oliver was knowledgeable and a very pleasant person. More wind would have been appreciated but who’s in control of that.

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