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Sailing

Set sail on the open water with sailing adventures! Whether you’re cruising along the coastline or heading out on a multi-day trip, sailing offers a unique way to explore the ocean at a relaxed pace. Perfect for adventure and leisure alike.

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5 trips for sailing

  • Sunset & Dinner Cruises

    Sunset Sip & Sail

    Sunset Watersports · Key West, Florida

    New on XBBook now: Sunset Sip & Sail
  • Explore Trips & Book Online

    Kids Sailing Camp

    Jamie O'Brien Surf Experience – NY · Montauk, New York

    Multi-dayEasy / familyLesson / course
    New on XBBook now: Kids Sailing Camp
  • Boat & Sailboat Rentals

    Hobie Cat Sailboat

    Navarre Beach Ski & Sail · Navarre, Florida

    Rental
    New on XBBook now: Hobie Cat Sailboat
  • Boat & Sailboat Rentals

    Hobie Cat Rental

    Key Sailing – Pensacola Beach · Gulf Breeze, Florida

    Rental
    New on XBBook now: Hobie Cat Rental
  • Explore Trips & Book Online

    Montauk Group Activity

    Jamie O'Brien Surf Experience – NY · Montauk, New York

    New on XBBook now: Montauk Group Activity

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