Sunset sail and wine tasting… it doesn’t get much better
(Or… the Adventures of Tide Stick Man and the Bluefin Tuna)


As Terry, Ellen, Richard and I began making plans for a recent trip to Florida, one of the most important things for all of us was a return to Key West. We had never been there together as a group of four, but all of us had traveled to the Keys… and all of us love the area. We wanted to spend at least one night in Key West… perhaps two. But amazingly, since we had all seen the Hemingway House and other landmarks, we couldn’t quickly identify a specific thing to do that we hadn’t already done in some way.

Enter Danger Charters.

Key West is legendary for sunset. Whether enjoyed on the water or experienced at Mallory Square, a sunset viewed while in Key West is one of those things you should just put on your I’d-love-to-do list right now. Because it’s not just an amazing and wonderful thing… which a beautiful sunset is when viewed from so many fantastic locations. A sunset in Key West is a celebration.

By some miracle of search engine good fortune, Ellen and I eventually both stumbled across a combination of words when looking for things to do. We didn’t enter them in as the actual search, but we spotted them in one of the results…

Key West…



Wine tasting…

Hold on… a sailboat out of Key West that offers a wine tasting at sunset? We reacted about as enthusiastically as Peter does on Family Guy when he comes across the red feety-pajamas.

Although we weren’t familiar with the name, we quickly decided to take a chance and book our evening with Danger Charters. And on May 5, 2009, we hopped on board and left the dock for one of the most fun, laughter filled, life-long memories experiences we have ever had.

~ ~ ~ ~ ~

On a Tuesday evening, we arrive in Key West. A trip to the hotel… bags left behind… and a cab called. We’re heading across the island of Key West, to a boat belonging to Danger Charters.

We arrived a little more than an hour before we were scheduled to board, and this presented a slightly unexpected problem… what to do. See… it was warm and muggy for an early May evening. And you don’t exactly head to Key West hoping to enjoy the air conditioning. So there we were… dressed for the casual formalities of a wine tasting cruise, to be followed by an evening on the town… looking for something to do that didn’t involve a ton of physical activity that would leave us hot and drenched before we even got on the boat.

Funny thing… if it weren’t so warm that evening, the area around the marina would have been perfect for wasting that hour. A few shops, a couple of food options, and even a restroom were all within short distance of the dock. We stopped for some ice cream… which was ok, but amazingly overpriced… wandered through a couple of stores, and then eventually settled near the hut we checked in at for the final fifteen or so minutes until the crew came to pick up our full group and walk us to the boat. And from that point on… it was a great evening…

What had been hot, muggy and downright uncomfortable was… no surprise here for those that sail often… absolutely beautiful and perfect once we were moving on the water. Our three-person crew for the evening consisted of Haig (the captain), Don (first mate) and Sarah.

The cruise featured an assortment of wine and promised a variety of appetizers. Actually, let me quote the web site on this one: “In addition, an array of quality beer, and hors d’oeuvres are also served…” You’ll notice the word “quality” doesn’t appear next to the food. There’s a reason for that… the food was average. (Ok… look… it wasn’t bad. Veggies and dip… cheese and crackers… more cheese… more veggies. But heck… let’s face it… if you’re out on the water for a Key West sunset, the quality of the veggies shouldn’t be determining whether or not you had a good time.)

The wine was outstanding. Haig and Don both credited Sarah for making the selections. And, unless they were pulling our legs about it (highly possible), she did a fabulous job. We started the evening with a Grandial sparkling wine that everyone agreed was pretty good and had a nice taste. We progressed through a Lurton Pinot Gris that was very good into a Yangarra Chardonnay that we all felt was ok. After that… a rose and on to some red wines… and the boat was on open water, the sun was going down, and my notes don’t cover everything else that was poured for us. I was distracted by, well, everything. (I do recall later being served a Fresca, which was a completely unexpected treat and kicked off a string of Caddyshack sailing with Judge Smails jokes. “How about a Fresca?”… “Spalding, get your foot off the boat.”… “You’ll get nothing, and like it!”)

So, the wine was outstanding and… most importantly… plentiful. The crew was wonderful, including lots of jokes and stories playing out over the night. One of them started when Haig and I had a discussion, which I made up and blamed Don for, about an encounter with a legendary Bluefin Tuna. That one kind of died quickly, but the conversation kept moving when someone spilled wine on Haig’s shirt. Ellen pulled out a Tide stick, Terry took care of the stains, and the next thing you now… the legend of Tide Stick Man took over the night.

And the other reason for the cruise? The sunset. And… well… words fail.

As I mentioned, Key West is one of those places where a sunset isn’t simply a part of every day. I wouldn’t be surprised to learn that “Key West Sunset” is actually a religion. And quite worthy of such a possibility, the sunset we viewed on the boat certainly could be credited as evidence of a higher power.

At the end of our sail, we stepped off the boat and it was still early. A fantastic evening would have been had by all if the night simply ended there. But we had more to do… and Duval Street was just a few steps away.

~ ~ ~ ~ ~

If you go…

Danger Charters runs sail excursions out of Key West. The marina they operate out of is at the corner of Whitehead and Greene streets. Whitehead is notorious for… along with several other things… Mile Marker 0 of Route 1 and the Southernmost Point Buoy. You’ll be very close to the mile marker while at the marina… not so much the buoy. In addition to the sunset sail, they also offer trips for snorkeling and other possibilities.

Now, let’s get the serious stuff out of the way… there is alcohol involved. My guess is you have a hotel room booked, possibly on Key West, so call for a cab and get a ride down to the marina. It’s pretty reasonable cost-wise to get a ride across the entire island of Key West, and Duval Street really is within incredibly easy walking distance of the dock. You know you’re going to drink… I know you’re going to drink… so don’t fight it. Kick back, relax, and leave the driving to someone else. You’ll be very happy that this has been taken care of, and that you’re free to enjoy anything and everything.

Camera. Don’t forget a camera. Sunglasses… yes. Suntan lotion… sure. Tide stick… now I’m just trying your patience to make a funny connection to our story. But your cell phone is not going to capture the true beauty and fantastic colors. Bring a camera.

Food. I hate to say this… but the food on the boat was fine and that’s it. We’re talking veggies and dip… cheese and crackers. Not chicken skewers… not unlimited shrimp or steak… they will not be airing any footage of your journey on Top Chef or the Food Network. In fact, to use a thought from the classic world of South Park, the food on this boat is what you eat to make you hungry. So plan on having a late lunch or early dinner before you head out to the boat. And if you are debating it at all… see the note above about Duval Street. You’re probably planning on the Crawl and not fine dining options for after the boat ride. (Maybe you are. Whatever. Just do not expect an endless and diverse assortment of overflowing trays to parade past you for two or three hours. Ain’t happening.)

And... to wrap it up... if Haig, Don or Sarah are introduced as part of your crew, say hello for us. Then relax... because you’re in great hands and you’ll have a fabulous time.

If you have any comments or questions, please e-mail me at