Key West Sunset Sail

Key West is the last island on the Overseas Highway, and its Old Town looks west across open water, so the sun goes down over the sea in every month of the year. A sunset sail is the way to watch it from the water: two hours on a sailing catamaran or a schooner from the Historic Seaport, the old harbor the locals call the Key West Bight, out past Mallory Square and Sunset Key while the sky changes colour. Sunset in Key West falls between 5:38 pm in early December and 8:20 pm in late June and early July, by the U.S. Naval Observatory’s figures, and the boats move their departures with it.

The short answer

For one evening, take Sebago’s sunset sail: two hours on a sailing catamaran with an open bar (cocktails, champagne, sangria, wine and beer), the chef’s hors d’oeuvres and live music from local musicians. It costs from $70 an adult on Viator, rated 4.7 from 3,884 reviews on Viator and Tripadvisor (checked October 2026), and the same sail is on GetYourGuide from $70 (checked October 2026). The price moves with the date on both. Check in at Sebago’s office on Lazy Way Lane in the Historic Seaport 30 minutes before; all ages can sail, and you must be 21 to drink.

Check dates for the sunset sail

If you want something quieter, a schooner or a small group with wine suits you better; if you want dinner, one catamaran serves a buffet.

Pick the sail

Prices, ratings and review counts from the Viator listings (checked October 2026). Operators price by date and season, so treat the figures as the shape of the market, not a quote.

Where the boats leave from

Most sunset sails check in a few minutes’ walk apart in the Historic Seaport, the City of Key West’s marina at 201 William Street, and along the harborwalk around it; Danger Charters is on Front Street, by Mallory Square:

The departure points guide has a close-up map, the parking garages and their rates.

When the boats leave

The sails leave earlier in winter and later in summer, always so that the sun goes down while you are out. Sebago’s Viator schedule for its sunset sail starts at 4:30 pm in November and December, 5:00 pm from January to early March, 6:00 pm in mid-March, 6:30 pm from April to August, 6:00 pm in September and 5:30 pm in October (read October 2026). That puts the departure between about 50 minutes and just under two hours before sunset, and the sunset inside the two hours on every date. Clocks go back on 1 November 2026 and forward on 14 March 2027, which moves both the sunset and the departures by an hour overnight. The sunset times guide has every month.

Catamaran or schooner

A sailing catamaran is wide and stable, with room to walk about, shade and restrooms; it is where the open bars and the bands are. A schooner is a traditional two-masted sailing ship: smaller groups, more sail, quieter decks, and on several of them you can help raise the sails or take the wheel. The catamaran or schooner guide compares them, boat by boat.

What is included

Almost every Key West sunset sail includes drinks. The difference is what kind: an open bar with cocktails (Sebago, Sunset Watersports), beer, wine, champagne and margaritas (Fury), a wine tasting (Danger Charters), champagne by the bottle as an upgrade (America 2.0), or bring your own on a tiki boat. Food runs from hors d’oeuvres to a full buffet dinner. The open bar, champagne or dinner guide sorts them, and the prices guide lines up what each costs.

Who should pick something else

• Only want to see the sunset: the Sunset Celebration on Mallory Square is free every night, with street performers from about two hours before sunset. The Mallory Square guide compares it with a sail.
• A quiet evening for two: a schooner or Catamaran Echo’s adults-only champagne sail, at most 14 guests, rather than a big catamaran with a band.
• Dinner as well: the sunset dinner cruise serves a buffet; on the other sails the food is hors d’oeuvres.
• Snorkelling first: Fury’s Rum and Reggae trip snorkels the reef in the afternoon and sails back at sunset.