Top Florida Custom Private Tours

We loved our sunset sail with Key West Wind and Wine By Cool Destinations. Everything was very organized. Captain Tony and his delightful crew were wonderful,friendly and very attentive. The choice of wines were great and varied . The passed nibbles were nicely curated. Highly recommend this as a perfect way to end the day in Key West. Nicely appointed and ideal for a relaxing evening. No loud music 👍👍and Not Crowded ❤️

As a solo traveler, I was hesitant to book this tour. But I’m so glad I did! It was the highlight of my Key West trip. The crew members were friendly, the wine and snacks were tasty, and the sailing and views were spectacular. Great way to experience the sunset. Highly recommend.

We had our family vacation in the Florida Keys in July. There were nine of us total with my wife, our four boys (ages 17-25) and their significant others. We planned a fishing trip in advance. My one goal was for everyone to catch fish. This fishing trip delivered on that request! We caught over 100 fish. Everyone each caught at least 10. Our Captain Tash was incredible along with her First Mate Chris. Tash was very knowledgeable about every aspect of fishing and boating. We also learned a lot about the area from Tash and even saw some dolphin pods. My son’s girlfriend got motion sickness on the boat and Tash took great care of her and got us into calmer waters to fish. We ordered lunch in advance and they had it waiting for us on the boat. This was nice so we didn’t need to bring anything with us. After fishing, Tash filleted our fish for us and put it into multiple bags for meals to accommodate all 9 of us. We took some to a local restaurant and they made us some delicious tacos. The remainder we brought to our VRBO and we were able to cook fish for a couple of meals. I would highly recommend this company for any fishing excursion in the Keys. Their attention to detail and making sure everyone was happy and catching fish was great!

Tosh and Gil got us on the fish right away and Tosh was great with my 3 & 6 year old boys. Everyone on the boat caught fish including grandma! Lots of space on the boat and nice calm water made for a great morning.

Was really such an enjoyable experience on a wonderful weather evening and captured a great sunset. The crew was fun and made it very enjoyable. Highlight of our long weekend in KW

Of all the things we did on our Key West vacation, this was our very favorite excursion. Capt Mike and his crew, Allie and Rocky were on top of everything and so pleasant to boot. And the wine and snacks were great. If you’re torn on which sunset cruise to pick, you won’t go wrong with this one!

Captain Tosh was great! Kids had a blast and caught lots of fish!

Would definitely book through this captain again!!

Wonderful evening on the Sarah sailing ship and great way to end a fun Key West day. Respect Capt'n Brad's decision to end the sail a little early due to changing weather conditions. Crew was attentive and apps and beverages suited everyone's tastes. Well done and great job.

We enjoyed the cruise, it would have been nice to sail a bit more and not just sit, but perhaps we misunderstood what it was. Cruising allows for a breeze and it's just nice to be moving on the water. Great wine and staff.

All went well. Staff was awesome.

We loved the sunset sail. The crew was friendly and very accommodating. The wine was top notch.

We had so much fun on the wind/wine evening sailboat ride. The crew were awesome, funny and friendly. The captain piloted the perfect route to give us a great view of Key West. The crew service was fantastic as they made their way around the boat. Stories and fun was the nights pleasure to have. Me and my group would highly recommend this adventure and we will do it again!!

The crew was amazing, and the sail was smooth even with a stiff breeze. Katie and Dani provided plenty of information along with the different wines and snacks.

Awsaome ride and great crew from Tennessee. Captain noticed my friend had some sea sickness and tacked the boatto stay behind the island. The whole crew took care of us. Cheerful fun Crew.

My husband and I enjoyed the sunset sail. It was our favorite thing we did on our trip to Key West. The captain and other staff were great and the sunset was beautiful.