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  1. The Ultimate List: 15 Best Things to Do in San Diego (Updated 2026)
  2. Wake2Wake

    Wake2Wake

    5.0 • 333 reviews
    St. Augustine, FL

    Wake2Wake FL offers a fun, laid-back way to experience St. Augustine from the water. Led by Captain Grant, a lifelong boater with a genuine love for local adventure, each private trip is designed to feel personal, easy, and memora...

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    Book Wake2Wake

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    St. Augustine Sunset Cruise

    Private twilight cruising with historic waterfront views and chances to spot marine life

    $336
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    Wakeboarding & Wakesurfing Lessons in St. Augustine

    Build confidence on the water with private coaching from experienced rider Grant G’Sell

    From$84person
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    Sandbar Boat Charter in St. Augustine

    Make your private St. Augustine boat day your own with a local captain

    From$224boat
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    Nights of Lights Private Cruise in St. Augustine

    See St. Augustine's holiday lights from a private boat with warm drinks and a licensed captain

    $336
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    Private Dolphin & History Cruise in St. Augustine

    Private 90-minute boat tour for dolphins and St. Augustine history

    $308

    Review summary

    5.0
    Excellent
    333 reviews•Google Maps
    250
    0
    0
    0
    2

    Captain Grant is the kind of guide who makes a place feel like it belongs to you. Knowledgeable about St. Augustine's history, ecology, and hidden spots, he weaves local storytelling into every outing while keeping things relaxed and fun. Repeat visitors are common, with several reviewers booking again on the same trip or returning for milestone occasions like bachelorette parties and family reunions. The boats are consistently described as clean, comfortable, and well-equipped, and Grant's communication before and during trips earns special praise. He monitors weather closely, checks in with guests about what they want from the day, and adjusts accordingly. Dogs are welcome, and the crew has a knack for handling groups of all sizes and energy levels. Hidden sandbars, dolphin sightings, Driftwood Beach, and sunset bar hops are among the highlights guests mention most. Josh also gets a nod as a great co-captain on select trips. If you're looking for a water experience in St. Augustine that feels personal rather than generic, this crew delivers consistently.

    What people are saying

    Review 1 of 5
    5/5

    We did a sunset cruise the Captain was very informative and showed us some neat spots. Saw lots of dolphins as well, we will be back!

    Photo of Rylee Kraichely

    Rylee Kraichely

    October 15, 2026

    Review 1 of 1
    5/5

    We did a sunset cruise the Captain was very informative and showed us some neat spots. Saw lots of dolphins as well, we will be back!

    Photo of Rylee Kraichely

    Rylee Kraichely

    October 15, 2026