Pair Stock Island’s waterfront scenery with marina bars, seafood, and tacos
4 hrs
Up to 6 people
Water, cooler with ice, speaker
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.
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
This booking is for the whole experience, which fits up to 6 guests.
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
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.
Seawall south of the gas dock, Oceans Edge Marina, 5950 Peninsular Ave, Key West, FL 33040
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.
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!
Jenny Molton
July 1, 2026
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!
Jenny Molton
July 1, 2026
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