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    Find Sailing Charters Near You

    4.9
    (4,915 Reviews)

    Page 5 of 10 • 240 listings

    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
    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
    $350/hour
    Limited Availability
    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
    $208+/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
    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
    Limited Availability
    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
    Limited Availability
    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
    $240/hour
    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
    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
    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
    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
    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
    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
    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
    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

    Top Destinations Nearby

    Local Sailing Reviews

    1. PC

      Peter

      Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

      Had a GREAT day on the sound with Captain Rick. His boat is in excellent condition clean comfortable and so well maintained. Rick is a very experienced sailor with whom we always felt safe. He showed us all over Long Island Sound, which he knows so well. I highly recommend Rick for a great day on the water!!

    2. Laura

      Laura

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

      I would highly recommend sailing with Captain Steve! He is extremely knowledgeable and an excellent sailor. We loved our sail with him!

    3. MW

      Megan

      Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston

      Jennifer was an amazing captain. We had an amazing time on the wind chaser. She had everything we needed & gave us a wonderful & smooth ride! We couldn't recommend this excursion more!

    4. jj

      joy

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

      stellar experience overall, great memories with my family and learned a little history about oyster Bay.

    5. CM

      Cara

      Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston

      Jen and Janet were great! They made us feel so warm, welcome, and a lot of fun! They were amazing and I would highly recommend.

    6. Sarah

      Sarah

      Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston

      We had a great time with Jen and Janet. They were passionate sailors that put the needs and safety of the passengers first.

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