Open Bar, Champagne, Wine or Dinner on a Key West Sunset Sail

Nearly every Key West sunset sail includes the drinks. What differs is the bar. Sebago and Sunset Watersports pour an open bar with mixed drinks; Fury pours margaritas, champagne, beer and wine; Catamaran Echo is bottomless champagne for adults only; Danger Charters runs a wine tasting on a schooner; Sunset Watersports’ dinner cruise adds a buffet; and on the tiki boats you bring your own. Everywhere, you must be 21 to drink and should carry photo ID.

For cocktails, the open bar to pick is Sebago’s: two hours on a sailing catamaran with cocktails, champagne, sangria, boutique wine and premium beer, the chef’s hors d’oeuvres and live music. It is from $70 an adult on Viator (checked October 2026) and $70 on GetYourGuide (checked October 2026); a premium-liquor upgrade costs extra on Sebago’s own site:

What each sail pours and serves

From the Viator listings and the operators’ own pages, read October 2026.

Open bar: what “well” means

An open well bar pours mixed drinks made with the house liquors, plus margaritas and rum runners. For top-shelf brands, Sunset Watersports and Sebago both sell a premium-liquor upgrade at extra cost. Fury’s live-band sail pours margaritas, champagne, beer and wine rather than a full bar.

Champagne

Two sails are built around it. Catamaran Echo’s adults-only Sunset and Moet pours bottomless Chandon Brut with eight wines, beer and White Claw and a cheese buffet, for at most 14 adults on a catamaran that seats 28; Moet champagnes can be bought on board. It is from $109 (checked October 2026), and on Viator all sales are final, so book it only for a date you are sure of. Sebago’s 90-minute champagne sunset sail is the low-cost option, from $43 (checked October 2026), with no food listed.

Wine

Danger Charters’ Wind and Wine sail is a guided tasting on a schooner: eight wines (four red, three white and a sparkling), five premium beers and charcuterie boards, for ages 13 and up, from $135 on Viator (checked October 2026). It is the quietest of the drinks-led sails: no band, a small group, and a crew that talks you through the glasses.

Dinner

Sunset Watersports’ sunset dinner cruise is the one with a meal: a Caribbean buffet in an air-conditioned dining room (blackened mahi, mojo pulled pork, jerk chicken, black beans and yellow rice, plantains, salads and churros on the Viator menu), then an open well bar and live music on the upper deck as the sun goes down. It is from $93 (checked October 2026); check in an hour before. On every other sail the food is hors d’oeuvres, so plan dinner in Old Town after you land.

Bring your own

Sunset Watersports, Sebago and Classic Harbor Line include the drinks, and bringing your own alcohol onto America 2.0 is not allowed. The bring-your-own option is the tiki-bar sunset cruise from Garrison Bight: a thatched-roof boat for up to six, booked by the seat, with ice, cups and water provided, leaving about 75 minutes before sunset, from $81 (checked October 2026).

Pick by the glass

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.

For tips: gratuities are not in the ticket price on Sebago’s, Fury’s or Classic Harbor Line’s listings, and Fury adds an automatic 10% gratuity for groups of eight or more on its snorkel trip.