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    5. /Private Waterfront Bar Hop Boat Cruise Near Key West
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    Private Waterfront Bar Hop Boat Cruise Near Key West

    Pair Stock Island’s waterfront scenery with marina bars, seafood, and tacos

    5.0 stars• 49 reviews

    Duration

    4 hrs

    Ideal For

    Up to 6 people

    Includes

    Water, cooler with ice, speaker

    Highlights

    Explore Stock Island by water on a private cruise aboard a 20 ft Pioneer Islander. Glide past working docks and colorful marinas, with island music setting a relaxed pace between waterfront food and drink stops.

    • Unwind at Hurricane Hole, a laid-back marina bar with harbor views
    • Discover Hogfish Bar & Grill, known for fresh seafood, funky charm, and its hogfish sandwich
    • Sample tacos and creative bites by the water at Bad Boy Taqueria

    Itinerary

    Trip starts at 2:00pm. Arrive at the first bar at 2:15pm depart at 3:15pm Arrive at the second bar at 3:30PM depart at 4:30pm Arrive at the third bar at 4:45pm Depart at 5:45pm Stop to watch the sunset on the water Arrive back to the departure location at 6:00pm

    What's Included

    • Bottled water
    • Cooler with ice
    • Bluetooth speaker system

    Important details

    • Requires navigating a 2-foot step between the dock and boat
    • Not wheelchair accessible
    • Life jackets are required for children under 6
    • The trip is weather dependent
    Split the cost with your group

    This booking is for the whole experience, which fits up to 6 guests.

    From$120per person
    Split with

    Cancellation Policy

    Cancel at least 24 hours in advance for a full refund or credit. If the operator cancels due to weather or other unforeseen circumstances, you'll receive a full refund or credit. No-shows are charged the full price.

    Product ID: 8QXUEM

    FAQs

    No. Food and alcoholic beverages are not included in the listed price. Bring your own food and drinks, plus cash or a card for purchases at the waterfront restaurants and bars.

    Wear clothing suitable for boating and casual restaurants, and bring sunscreen.

    Meeting details

    Seawall south of the gas dock, Oceans Edge Marina, 5950 Peninsular Ave, Key West, FL 33040

    Experience provided by Stock Island Charters

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Private sunset cruise

    $721.50

    Fits up to 6 guests · 4 hrs

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    49 reviews•Google Maps
    47
    0
    0
    0
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    Captain Donnie has built a loyal following in Key West, and it's easy to see why. Reviewers consistently praise his deep knowledge of the local waterways, his easygoing personality, and his ability to take guests to spots that feel genuinely off the beaten path. The boat is a 23-foot center console, perfect for small groups who want a more personal experience than the big crowded charters offer. Sandbars and sunset cruises are the most popular trips, and both get glowing feedback. Donnie is flexible with scheduling, proactive about weather concerns, and communicates well before the trip so guests know exactly what to expect. One reviewer even mentioned he reached out days in advance to reschedule around bad weather, which says a lot about how he runs things. The boat is also dog-friendly, which is a nice bonus for travelers bringing pets along. With a perfect rating across dozens of reviews, there are no real concerns to flag here. This looks like a genuinely reliable option for anyone wanting to get out on the water in Key West.

    What people are saying

    Review 1 of 5
    5/5

    We did a sunset cruise and had such a great time! Don was amazing and especially great with our kids (who were full of questions!). He even went back to fetch my daughter’s hat when she accidentally dropped it in the water. We enjoyed learning about the islands and then getting to enjoy the sunset. It was just fantastic. We will definitely use Stock Island Charters again next time we visit!

    Photo of Jenny Molton

    Jenny Molton

    July 1, 2026

    Review 1 of 1
    5/5

    We did a sunset cruise and had such a great time! Don was amazing and especially great with our kids (who were full of questions!). He even went back to fetch my daughter’s hat when she accidentally dropped it in the water. We enjoyed learning about the islands and then getting to enjoy the sunset. It was just fantastic. We will definitely use Stock Island Charters again next time we visit!

    Photo of Jenny Molton

    Jenny Molton

    July 1, 2026

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