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    Find Sailing Charters Near You

    4.9
    (4,334 Reviews)

    Page 8 of 10 • 240 listings

    Sailing Adventure Aboard 44' Hunter Sailboat
    Sailing in New Castle · 6 guests

    Sailing Adventure Aboard 44' Hunter Sailboat

    New
    $175-$220hour
    Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin
    Sailing in Shalimar · 6 guests

    Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin

    5.0
    $150hour
    2019 HOBIE MIRAGE ADVENTURE ISLAND SAILBOAT IN JACKSONVILLE
    Sailing in Jacksonville · 2 guests

    2019 HOBIE MIRAGE ADVENTURE ISLAND SAILBOAT IN JACKSONVILLE

    New
    $40hour
    Private Sunset Cruise (2-Hours) in Destin, Florida
    Powerboats in Destin · 6 guests

    Private Sunset Cruise (2-Hours) in Destin, Florida

    5.0
    $175hour
    3-Hour Daytime Cruise in Destin, Florida
    Sailing in Destin · 6 guests

    3-Hour Daytime Cruise in Destin, Florida

    5.0
    $150hour
    4-Hour Private Charter in Destin, Florida! Crab Island, Snorkeling, Dolphins & More!
    Sailing in Destin · 6 guests

    4-Hour Private Charter in Destin, Florida! Crab Island, Snorkeling, Dolphins & More!

    5.0
    $150hour
    The "Original Redneck Pontoon" Crab Island / Dolphin / Snorkeling Adventures
    Powerboats in Destin · 6 guests

    The "Original Redneck Pontoon" Crab Island / Dolphin / Snorkeling Adventures

    New
    $110hour
    Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins
    Sailing in Fort Walton Beach · 6 guests

    Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

    5.0
    $149hour
    64' Roberts Sailing Ketch for Charter in Jacksonville Area
    Sailing in Green Cove Springs · 6 guests

    64' Roberts Sailing Ketch for Charter in Jacksonville Area

    5.0
    $138-$217hour
    Full or Half Day Private Charter Aboard 50' Ohana in Panama City, Florida
    Sailing in Panama City · 12 guests

    Full or Half Day Private Charter Aboard 50' Ohana in Panama City, Florida

    5.0
    $299-$320hour
    Morgan 382 Sailboat for charter in Pensacola, Florida
    Sailing in Pensacola · 6 guests

    Morgan 382 Sailboat for charter in Pensacola, Florida

    5.0
    $75hour
    50 foot sailing yacht offering day and term charters out of Portland, Maine
    Sailing in Portland · 6 guests

    50 foot sailing yacht offering day and term charters out of Portland, Maine

    New
    $850day
    Lake boat day! Enjoy beautiful Maine at the Lake!
    Powerboats in Nobleboro · 8 guests

    Lake boat day! Enjoy beautiful Maine at the Lake!

    New
    $245-$350day
    32ft Classic Swedish Sloop Sailing Charter
    Sailing in Rockland · 6 guests

    32ft Classic Swedish Sloop Sailing Charter

    5.0
    $150hour
    ★ 28' Classic Schooner in Rockland, Maine ★
    Sailing in Rockland · 6 guests

    ★ 28' Classic Schooner in Rockland, Maine ★

    5.0
    $175hour
    ★Midcoast Maine aboard the Schooner Yacht Meteor ★
    Sailing in Rockland · 4 guests

    ★Midcoast Maine aboard the Schooner Yacht Meteor ★

    5.0
    $175hour
    Experience Maine on 65ft Classic Schooner Yacht
    Sailing in Rockport · 30 guests

    Experience Maine on 65ft Classic Schooner Yacht

    5.0
    $65person
    Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!
    Sailing in New Orleans · 6 guests

    Sailing on Lake Pontchartrain with 52ft Shannon Sailing Yacht!

    5.0
    $110hour
    Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana
    Sailing in New Orleans · 6 guests

    Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana

    5.0
    $110hour
    52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana
    Sailing in New Orleans · 6 guests

    52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana

    5.0
    $110hour
    Tampa Bay - Clearwater Area with a perfect & elegant Carver Mariner 38 x 190$/h
    Powerboats in Tampa · 12 guests

    Tampa Bay - Clearwater Area with a perfect & elegant Carver Mariner 38 x 190$/h

    New
    $250hour
    ''Razor's Edge'' Yacht Rental in Cape Canaveral, Fl
    Events in Cape Canaveral · 11 guests

    ''Razor's Edge'' Yacht Rental in Cape Canaveral, Fl

    5.0
    $382hour
    Silverwave 22' Pontoon Rental from Downtown Tampa Area /Sunset & Evening Cruises
    Powerboats in Tampa · 12 guests

    Silverwave 22' Pontoon Rental from Downtown Tampa Area /Sunset & Evening Cruises

    4.8
    $90hour
    55ft "Poseidon SR" Sea Ray Flybridge Power MegaYacht Charter in Tampa, Florida
    Events in Tampa · 13 guests

    55ft "Poseidon SR" Sea Ray Flybridge Power MegaYacht Charter in Tampa, Florida

    New
    $801hour

    Local Sailing Reviews

    1. Lauren

      Lauren

      Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin

      Wonderful time out on the water with Captain Bill! Very accommodating, kind and knowledgeable. Weather wasn’t cooperative but he was able to be flexible and come up with an alternative itinerary. Definitely recommend!

    2. DJ

      Darren

      52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana

      The working of the sails to listening to the captain about how the sailboat works was very interesting , enjoyed the whole experience on such a beautiful sail boat

    3. BH

      Bradlee

      52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana

      Jim was an amazing captain! He helped us create some amazing engagement photos!

    4. TW

      Thomas

      Shannon Cruising 52' Sailboat on Lake Pontchartrain, Louisiana

      This is a very nice large boat which is very comfortable on the water. Look forward to sailing again with Captain Jim in a few weeks.

    5. AB

      Allison

      Morgan 382 Sailboat for charter in Pensacola, Florida

      The sailboat is beautiful & Robert and his wife were very friendly and hospitable. We had a wonderful time and the sunset views were beautiful!

    6. JF

      Joey

      Private Sunset Cruise (2-Hours) in Destin, Florida

      Ladd was our captain for this trip. We couldn’t ask for a better crew than him and Sebastian. We had to delay our trip a day because of a storm but they more than made up for it. They also documented our trip with photos that they emailed to us. It was very relaxing and informative. We also got to see some dolphins. Very nice people. Overall, a 10 star outing!

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