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The experience we enjoyed for this review of the Danger Charters Wind & Wine Sunset Cruise was complimentary. As always, the opinions expressed are our own.

Our review of Danger Charters’ Wind & Wine Sunset Sail

As the sun slipped below the horizon in the fiery orange sky, a cheer went up from those on deck of the sailboat. Glasses were raised, toasts made, and everyone on board realized they’d just shared a magical moment, made possible by Danger Charters in Key West, Fla.

Ann and I have been visiting Key West for years, but had never taken a sunset cruise. So, when the opportunity arose for us to experience a sunset sail, we jumped at it. Our sunset sail was hosted by Danger Charters and The Florida Keys & Key West.

Booking is easy

To book your sunset sail, just go onto the Danger Charters website and select the tour you’d like. They offer a variety of tours both during the day and evening. We took the Key West Wind & Wine Sunset Sail. Choose your date, fill out the forms and you’ll be all set. If you do have a question, just give them a call and an actual human will usually answer the phone. I know, that rarely happens any more.

Steve and Ann Teget of postcard jar on danger charter cruise

As of May 2023, the Key West Wind & Wine Sunset Sail we took was $109 for adults ages 13+. However, watch the Danger Charters website for specials and discount codes.

Review of Danger Charter cruise: What to bring

You won’t need much for your Danger Charter cruise. We suggest bringing a tightly fitting hat, sunglasses, a smart phone or camera, and cash for tipping. That’s it. Since the boat does rock a bit, if you’re shooting video you might want to bring a hand held stabilizing device such as a gimbal. If you arrive early, you may also want to bring a bottle of water to drink while you wait. Water is provided on the cruise.

shooting video on a sunset cruise

What not wear on a Danger Charter sunset cruise

While dressing up in a long flowy maxi dress with high heels might seem like the perfect attire for a romantic sunset sail, we don’t recommend it. You will need to navigate a few steps (perhaps in the wind) to get on and off of the boat. Also, to use the bathroom, you’ll need to climb down and up a narrow staircase where others might be below. A hat helps block the early sun and keep your hair from flying around. Just be sure to bring one that stays securely on your head or has a strap, in case it’s windy.


an honest review of danger charters wind and wine sunset sail by postcard jar

Honest review of Danger Charters: Check-in is a snap

The check-in process for the cruise is simple and well-organized. Just step into the Danger Chandlery Store at 255 Front Street in Key West. Give the host your name, and they’ll mark you present. Then, they will give you a laminated, colored boarding pass and ask you to wait outside in the plaza area for your boat’s captain. There is limited seating outside, so be prepared to stand for a bit.

outside danger charters cruise in key west

As the time for your cruise draws near, the boat captains will approach the group, and each will call folks based on the color of their boarding passes. From the shop, you’ll stroll with your captain a block or two along the marina to the sailboats. You’ll want to wear sensible shoes that are good for both walking and standing on a boat deck.

PRO-TIP: Late in the day while you wait for your cruise, there isn’t a ton of shade and Key West’s sun can be warm and bright. As such, you should bring a hat, sunglasses, and maybe a bottle of water. 

Boarding the sail boat

When you step onboard, you’ll meet the rest of the crew who will show you where to sit and give a concise safety briefing. Seating is on the deck facing out, and every seat on board is a good one.

danger charter review of sunset wine cruise

No review of Danger Charters would be complete without telling you the boat is exceptionally clean and well-maintained. Even better, the friendly crew work hard to quickly put everyone at ease in a relaxed atmosphere. Very Key West of them.

What to expect during the cruise

The cruise is on a sailboat large enough to comfortably accommodate 25-30 people, but it isn’t a huge boat. On our craft, there were no seat backs. There is a bathroom on board, accessed by climbing down a short ladder into the main cabin.

The boat departs the harbor and heads out onto the waters west of Key West. Once you’re clear of the marina, there’s a flurry of activity as the crew raises the sails. Before you know it, you’re gliding through the water powered only by the wind. With no motor constantly making noise, it’s a different, more relaxing experience than other powered boat trips you may have taken.

explaining wines

Crew turn on some upbeat tropical music (think Jimmy Buffet) that is not so loud that you can’t visit. Then, they give an overview of the wines you’re going to taste. Folks start sipping wine and chatting with those around them. We loved meeting new people like Biscuit (pictured below). He told us he enjoyed the sunset cruise so much that he’s taken it dozens of times.

biscuit on a danger charter

Acquaintances are made, and bursts of laughter break out here and there. A tropical breeze blows across your face as everyone watches the sun sink lower and lower in the sky.

A word about motion sickness on the boat

Before setting sail, Ann was a little worried about the movement of the boat and whether she’d feel motion sickness.The boat stayed in the lee of the island so the seas weren’t too big. Plus, being on deck watching the sun set puts your focus on the horizon while providing plenty of fresh air. As a result, motion sickness wasn’t a problem for Ann or any of the 25 passengers onboard despite it being a breezy day.

Ann Teget snacking on Danger Charter sunset cruise

Review of Danger Charters wine and food

The food and drinks on Danger Charters were a definite step above most excursion cruises we’ve taken. Instead of watered down drinks and cheap wines, we enjoyed tastings from seven quality bottles of wine. We started with refreshing whites and progressed through hearty reds.

wines on danger charter sunset cruise

Each pour was just a few of sips, but if you wanted more of anything, they were happy to serve it. Every person tasted at her/his own pace, and the crew, somehow, kept track of where everyone was in the progression. The quality of this wine tasting is a definite plus in our review of Danger Charters.

serving caprese skewers on danger charter cruise

Along with each wine, another crew member served small bites like caprese skewers, meats, cheeses, crackers, and fruit. There were also a variety of quality beers available as well as bottled water. Note the snacks are appetizer portions. You’ll still want to go somewhere for dinner either before or after your cruise especially since you’ll be tasting a number of wines.

PRO-TIP: If you drove, be sure to designate a driver before you start your tour. 

Don’t forget to tip the crew

As we wrote this review of our experience on Danger Charters, we were reminded of the awesome crew. They were personable, knowledgeable, and well-experienced. They worked hard throughout our cruise to make sure every guest had a relaxing and memorable experience.

The crew kept our glasses full and made sure we had whatever we needed for our two-hour voyage through the waters near Key West. They were happy to answer questions, keep us informed, and share additional information about The Florida Keys.

PRO-TIP: Crew members work for tips, so if you have a good experience, please remember them with an appropriate gratuity as you step off the boat. A 15-20% tip for the $109 cruise is $16.35 to $21.80 per person. Of course, you can always tip more. 

The sunset is the highlight of the trip

Sunsets in Key West are famous, and with good reason. They’re simply magnificent. And when you’re out on the water, your view is second-to-none. Check out this video to see what we mean.

About accessibility

Sadly, The Key West Wind & Wine Sunset Sail is not wheelchair accessible. However, a staff member told us that they have had guests who used a wheelchair to get to the pier and down the ramp before stepping onto the boat. For more detailed information about accessibility, call Danger Charters at 1 (305) 304-7999.

Have you taken a sunset cruise in Key West? What did you think? Let us know in the comments below.

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