Key West, FL – Wind and Wine Sunset Sail

There is no doubt about it, Key West is an amazing vacation destination. The warm weather, blue ocean, laid back atmosphere all make it the perfect escape from the stress of real life. A few years ago, one of my favorite travel friends and I decided to create our own “fall break” and planned a trip down to Key West. Neither of us had been before so we had our wish list of things we wanted to experience. Starting with renting a car at Miami airport and driving across the keys. The 165-mile drive is an iconic American road trip and traversing the overwater highway makes the journey one of the most impressive parts of the trip.

We were traveling during late October, technically still hurricane season but late enough in the year that the risk of bad weather was fairly low. We rented a two-bedroom cottage just off Duval St. on the south side of the island. While we spent a fair amount of time simply lounging by our private pool, we ventured out plenty. We rode the Old Town Trolley, watched the sunset from Mallory Square, and sipped frozen drinks at Sloppy Joe’s. We drank every kind of rum cocktail imaginable, ate fresh seafood and key lime pie and spent a great afternoon on the “Reefs and Ritas” snorkeling tour. It was the perfect girl’s trip, late nights lots of laughs, unique adventures and plenty of time to relax in the sun.

While the entire week was wonderful, the most unforgettable part of the trip was an evening spent on a sailboat sipping wine as the sun set over the keys. There are dozens of sunset cruises that you can book in Key West, party boats, dinner cruises, tiki boat, glass bottom boat, truly an option for every taste. As I was browsing online looking for just the right sunset cruise I stumbled upon the Wind and Wine Sunset Sail. As wine lover, the whole idea of tasting wine while on a schooner at sunset was intriguing. As I booked the tickets I was immediately looking forward to what I expected to be a unique and memorable experience. It ended up exceeding all expectations.

Finding the departure location at the Danger Chandlery Store was easy. The ship left the dock right on time and the sails were up within minutes. Our group was small, less than 12 people.

It was mostly an older crowd made up primarily of couples though it didn’t feel at all awkward being one of only two singles on board. The staff was truly exceptional. More than just friendly and professional, they provided their guests with generous pours and a continual stream of appetizers. Delicious cheeses, summer sausages, different types of crackers and fruit. Passengers were given the option to taste eight different premium wines, both red and white or to simply pick a favorite. There were also numerous beer options available for the non-wine drinkers.

As we sailed through the waters off the island's west coast, the sun-set in spectacular fashion over the sea. The waters were calm, and the warm breeze was both comforting and soothing. While there was some discussion about the wine with our fellow passengers, it was not the pointed conversation one might have with a sommelier. No comments about the legs or tannins, hints of this or undertones of that. Rather, just simple, personal impressions. “I really like this one, nice and crisp” or “I’m not really a fan of red, I tend to stick to white”, or “I don’t really know much about wine, I only know what I like.” It was the type of laid-back chatter that you would expect in a place like Key West. Our fellow tourist were all friendly and fun to talk to. The entire experience felt sophisticated but not snobby, refined without being pretentious.

The time flew by faster than the wind in the sails and we were back on shore before any of us were quite ready to disembark. It was one of those remarkable evenings that can’t be captured in a Facebook Reel or Instagram photo. I remember snapping a few pictures during the cruise but feeling disappointed at how they turned out. It’s just one of those locations that a photograph can’t do justice.

I’m sure one day I will take another trip down to Key West and hope to explore some places that I didn’t get to visit the first time, the Hemmingway Home, the Dry Tortugas National Park and Butterfly and Nature Conservatory. I’m also sure that before I book tours or tickets for anything, the Wind and Wine Sunset Sail will be the first charge on my card.