Key West: Schooner Sunset Sail Tour with Food & Drinks

There are plenty of ways to watch the sunset in Key West, but few feel as timeless as doing it from the deck of a tall-masted schooner. This is a sailing experience first: no booming speakers or crowded dance floor, just the creak of rigging, the snap of canvas and a slow glide toward the horizon.

The schooner is a 105-foot replica of a celebrated 1851 racing yacht, the kind of vessel that once outran an entire fleet of British challengers. She's built with teak decks and mahogany trim, and she carries roughly 3,600 square feet of sail. Once the crew hoists the canvas and shuts off the engine, you'll feel the boat lean gently into the wind. That quiet, steady motion is something a motorized cruise can't match. Seating is on comfortable benches along the deck, and the crew serves drinks to you rather than sending you to a bar.

After leaving the harbor, the schooner follows Key West's western waterfront. You'll pass Mallory Square, where the nightly sunset celebration draws street performers and crowds, and the old brick walls of Fort Zachary Taylor, built in the mid-1800s to guard the harbor. Farther out, look south toward the Sand Key lighthouse, an iron tower that marks one of the area's best-known reefs. Dolphins, sea turtles and seabirds often appear along the way. This isn't a dedicated dolphin-watching trip, so any sighting is a bonus.

As the sun sinks, the sky and water glow orange and rose, and the crew sets a course for the clearest view. On a clear evening with a flat horizon, watch the very last sliver of the sun closely. For a split second, it can turn bright green. This "green flash" happens when the atmosphere bends sunlight like a prism, and Key West's open western horizon is one of the best places in the U.S. to see it. After sunset, stay on deck as the first stars come out on the sail back.

Each guest gets an individually plated selection of hors d'oeuvres, served by the crew. Complimentary beer, wine, champagne and soft drinks flow throughout the sail, so you can sit back and enjoy the evening.

• The closest public parking is the city lot on Caroline Street, a short walk from the dock. It fills up before sunset, so arrive early.
• Bring a passport or driver's license. You'll need it to be served alcohol, and the drinking age is 21.
• Seating may be assigned. Arriving early for check-in gives you the best chance of sitting with your group.
• This is a sunset sail, not a dolphin tour. Wildlife sightings happen often, but they aren't guaranteed.
• Tips for spotting the green flash. It needs a clear, cloud-free horizon. Avoid staring at the sun as it sets, and look only at the final moment as the last edge disappears. Sunglasses help.
• Dress for cooler air. It's usually cooler on the water than in town, especially after dark and in winter, so bring a light jacket.
• Wear flat, rubber-soled shoes. Teak decks can be slippery, and the boat heels slightly under sail.
• Departure times follow the sunset. Key West sunset ranges from roughly 5:45 p.m. in late fall to about 8:20 p.m. in early summer, so confirm the time on your ticket.
• Holiday dates sell out fast. Book well ahead for the Christmas and New Year's sailings.