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    Sail Monterey

    Sail Monterey

    4.9 • 228 reviews
    Monterey, CA

    Sail Monterey invites you to experience the magic of Monterey Bay from the deck of a sleek catamaran or classic monohull. Family-run from Old Fisherman’s Wharf, this friendly crew blends decades of maritime expertise with a true l...

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    Book Sail Monterey

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    Coastal Navigation Course in Monterey

    Practice coastal navigation skills on the water in Monterey

    From$550person
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    ASA 103 Coastal Cruising Sailing Course in Monterey

    Learn coastal cruising skills in a 3-day ASA 103 course, capped at 4 students

    From$1,058person
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    Learn Keelboat Sailing in Monterey 3-4 Day Course

    Train to sail a 30-foot keelboat in a 3–4 day course (max 4 students)

    From$1,058person
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    2-Hour Sailing Lesson in Monterey

    Learn sailing basics in a 2-hour class from Old Fisherman’s Wharf

    From$168person
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    Sunset Catamaran Sailing Cruise in Monterey

    Sail Monterey Bay at sunset with a drink and snacks included

    $94.34person
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    Sail a Private Sunset Cruise in Monterey

    Private keelboat sailing for up to 6 from Old Fisherman’s Wharf

    $996.40
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    Sail Monterey Bay on a 30' Hunter Sailboat Rental

    Rent the 30' Hunter Willow and sail Monterey Bay your way

    $360.40boat
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    Sail a 24' Sloop Rental at Old Fisherman's Wharf

    Rent a classic 24-foot wooden sloop from Old Fisherman’s Wharf

    $312.70boat
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    Daytime Catamaran Sailing Cruise

    Relax on a 35-minute Monterey Bay sail with included drink and snacks

    From$62person

    Review summary

    4.9
    Excellent
    228 reviews

    LEI delivers consistently exceptional charter experiences, with reviewers praising everything from their well-maintained catamarans to their attentive crews. Nicole handles bookings with clear communication and helpful recommendations (including private chef referrals that guests rave about), while captains like Alex, Trevor, Guy, and Ross earn repeated mentions for being professional, personable, and great at making everyone feel comfortable. Multiple guests have returned for their third or fourth charters, which speaks volumes about the quality. The boats themselves impress, with several reviewers noting the Lagoon 42 and Bali 4.6 catamarans look even bigger and more beautiful in person. Crews provide snacks, drinks, and essentials while allowing you to bring your own food and wine for easy celebrations. There was one isolated timing hiccup where a dock mix-up delayed departure by 20 minutes without compensation, but this appears to be an outlier in an otherwise seamless operation. Perfect for bachelorette parties, birthdays, family gatherings, or just a luxurious day on the water with friends.