Key West Sunset Sail: The Wind & Wine Schooner Cruise

Everybody in Key West watches the sunset. The question is from where. Mallory Square is the free show with the jugglers and the crowd. The Wind & Wine sail is the other way to do it: a wooden schooner, the engine off, a glass of something good in your hand, and the sun going down behind the backcountry islands with nobody between you and it.

This page covers what the sail is like, what it costs, who it is for, and the one rule that catches families out: it is 13 and up.

Why this made our list

There are a dozen sunset cruises in Key West, and most of them are catamarans with a bar. This one is different in three ways.

The boats. The company sails four wooden schooners, including a 48-foot Chesapeake skipjack replica and a 57-foot mini tall ship, and sails them by hand with the engine off whenever the breeze allows. The sound of a schooner heeling onto a reach as the sun drops is the thing people write about in the reviews.

The wine. Eight varieties a night, usually four reds, three whites and a sparkling, chosen from around the world and explained by the crew, alongside five premium beers and charcuterie boards that keep coming for two hours. It is one of the only sailing trips in the country that pours real wine rather than a punch.

The reputation. Coastal Living ranked the Wind & Wine one of the top two sunset sails in North America, the company has sailed nightly since 1993, and it holds a 4.9-star rating across 5,900 reviews, the highest of any sunset trip in Key West.

Why this operator

We compared the sunset options on boat, drinks, crowd and reviews. The Wind & Wine won on all four. The champagne sail on the big 105-foot schooner from the Seaport is the other great choice, a larger and more elegant yacht with champagne and hors d’oeuvres, and a fine pick if this one is sold out. The big catamaran sunset cruises with open bars and music are fun and cheaper, but they are parties, not sails.

What the Wind & Wine sunset sail is like

The sail runs two hours. Here is how it goes.

1. Check in at the shop. The schooner ticket shop is inside Opal Key Resort & Marina at 245 Front St, three minutes from Mallory Square. Check in 30 minutes early.
2. Board. The crew walks you down the dock to the schooner, hands you a glass and points you to a spot on deck. Cushioned seating runs along the rails; the bowsprit is the prize spot.
3. Motor out, sails up. The boat clears the harbor and the crew raises the sails. Guests who want to help haul a line are welcome. The engine goes off.
4. Sail west. The schooner reaches along the calm west side of the island toward the backcountry, with Sunset Key and Wisteria Island to one side and open horizon to the other. The crew pours the wines in order and talks about each.
5. Sunset. The captain positions the boat with the sun off the bow. Everyone goes quiet. Then the applause, the toast, and sometimes the green flash.
6. Sail home in the afterglow. The sky keeps changing for another 30 minutes. The boat ties up back at Opal Key at dark, two minutes from Duval.

Prices and what you get

The sail runs from about $109 per person plus tax and booking fees. That covers two hours on the water and everything served: eight wines, five beers, sodas, water, and the charcuterie boards with meats, cheeses, crackers, fruit, crudités and chocolate. Gratuity for the crew is extra and well earned.

Groups, proposals and weddings can charter an entire schooner for a private sunset sail with the same menu.

Who it’s for (and who should skip it)

Couples, friends, parents on a night off, wine people, and anyone who wants the sunset without the crowd. It is also the trip we recommend for a first night in Key West, because it orients you to the island from the water.

Skip it if you are traveling with children under 13; the age limit is firm. The afternoon sail, snorkel and kayak excursion from the same company welcomes all ages and ends at sunset. Skip it, too, if you want a loud party; the catamaran cruises from the Seaport are built for that.

The deck has steps and the gangway is short but can be steep at low tide. Guests with limited mobility should call the shop before booking.

Where to check in and how to get there

Opal Key Resort & Marina is at 245 Front St, on the waterfront between the cruise-ship pier and Mallory Square. From the north end of Duval it is a three-minute walk; from the Seaport, about 12 minutes along the Harbor Walk. Check in at the ticket shop 30 minutes before departure. The shop sells waterproof phone bags, sweatshirts and sunglasses if you forgot yours.

If you drive, the Mallory Square garage is across the street. Current sailing times, which shift with sunset, are on the booking page.

Best time to go

Time of year. November through April. The air is dry, the horizon is sharp, the trade winds are steady enough to actually sail, and the green flash is a real possibility. Summer sails are warmer and the skies are more dramatic with the afternoon storm clouds, but hazier at the horizon.

Time of trip. Book it for your first night so you can see the island, or your last night so you can say goodbye to it. Either way, book a week ahead in winter and over holidays; it sells out.

Local tips before you book

• Bring a layer. Even in March the breeze after sunset is cool on the water. The shop sells sweatshirts if you forget.
• Take the bowsprit. The net at the front of the boat is the best seat for the sunset and the most fun when the boat heels. Ask the crew.
• Pace the wines. Eight pours over two hours adds up. The crew brings water and the charcuterie keeps coming.
• Eat after, not before. The boards are generous. Plan a late dinner on Duval or at the Seaport.
• Check the departure time. It moves with the sun, from about 4:30 pm in December to 7 pm in June. Your confirmation has the exact time.
• Pair it with the sandbar day. The sandbar and dolphin trip gets back to the Seaport at 4, which leaves time to shower and walk to Opal Key. For a full week of ideas, see things to do in Key West.

The verdict

For a Key West sunset sail, this is the one we would book, and the one we do book when people visit. A wooden schooner sailed by hand, wine worth drinking, a quiet crowd and a 30-year crew who know exactly where to put the boat when the sun hits the water. Book the Wind & Wine a week ahead in winter, bring a sweatshirt, and take the bowsprit.