Customize your Key West day on a private boat with snorkeling gear and sandbar stops included
4 hrs
Up to 6 people
Captain, snorkel gear, drinks
Embark on a private captain-guided cruise through Key West’s clear waters to secluded sandbars and reefs. Decide your itinerary on arrival and enjoy snorkeling, dolphin watching and sun-soaked relaxation.
Trip accommodates up to six guests. Dolphin sightings are possible but not guaranteed. Please list your preferred departure marina in the booking notes. Options are:
This booking is for the whole experience, which fits up to 6 guests.
Free cancellation up to 72 hours before start; within 72 hours reservations are non-refundable. One rebooking may be requested within 72 hours for a fee, subject to availability. If a deposit was used, the remaining balance is charged 72 hours before departure. Operator is not liable for arrival issues.
Product ID: AW39UD
Yes. Masks, fins, snorkels, safety gear, and winter wetsuits are included.
Yes. You choose your itinerary the day of your trip, including sandbars, snorkeling, or dolphin cruising.
Bottled water, soda, and light snacks are included. You may bring any additional food or alcoholic beverages.
Opal Key Resort & Marina 255 Front St Key West, FL 33040
Key West sailing doesn't get much better than this, according to travelers who consistently rave about their time on the water here. Whether you're booking the adventure combo with snorkeling and kayaking through the mangroves or opting for the more leisurely sunset wine cruise, you're apparently in for something special. The crew members get called out by name again and again, with captains like Mary, Janet, Anthony, and Micah earning particular praise for being knowledgeable, professional, and genuinely fun to be around. People love that these aren't massive cattle-call operations. Groups tend to max out around 16 passengers, which creates an intimate vibe where the crew can actually give you personal attention and fellow travelers become part of the experience rather than just anonymous faces. The full-day excursions seem to be the showstoppers. You're looking at snorkeling (though not on a reef, so temper expectations accordingly), kayaking around mangrove islands with solid ecology commentary, plus snacks and unlimited drinks throughout. One couple said it was the best day of a rough year, which speaks volumes. The sunset sails hit differently too, with proper wine flights paired with cheese and appetizers, all enjoyed under actual sail power. A few practical notes: the snacks are described as good but light, so consider bringing extra food if you're prone to getting hungry. Weather can look sketchy before departure but often clears up, and you might even spot manatees at the dock. Multiple repeat customers say this is their go-to charter year after year, which tells you everything about consistency.
We recently were on Vacation in Key West where we scheduled the Key West Wind and Wine sailing. The crew was amazing, the wine was amazing as were the Hors d'oeuvres. Do not worry if you do not like wine there are other options like soft drinks or beer. One thing I really loved about this sailboat with Danger - it was far more intimate than the larger options with MANY people. We went at the end of August and it was hot and the breeze lower than normal and we still had an amazing time. One of my favorite nights out that week and you can’t beat the views on the water! And that day we actually saw a few water spouts!
Tricia Craft
August 31, 2026
We recently were on Vacation in Key West where we scheduled the Key West Wind and Wine sailing. The crew was amazing, the wine was amazing as were the Hors d'oeuvres. Do not worry if you do not like wine there are other options like soft drinks or beer. One thing I really loved about this sailboat with Danger - it was far more intimate than the larger options with MANY people. We went at the end of August and it was hot and the breeze lower than normal and we still had an amazing time. One of my favorite nights out that week and you can’t beat the views on the water! And that day we actually saw a few water spouts!
Tricia Craft
August 31, 2026
Sail Key West's clear waters, kayak mangrove islands, snorkel vibrant reefs, and refuel with a buffet lunch—all in one day.
Private Key West schooner charter with snorkeling, kayaking, drinks, and snacks
Sail a historic schooner at sunset with wine, beer, and small bites
Sail, snorkel, and kayak on a historic schooner with drinks and snacks included
Charter a private historic schooner sail with drinks and snacks included
Sail a historic schooner, snorkel and kayak, then cruise into the Key West sunset