Key West Schooner Open Bar: Drinks and Food on Each Sail

Every Key West schooner sunset sail but one includes drinks. America 2.0 pours beer, wine, champagne and soft drinks with a plate of hors d’oeuvres each; the Appledore adds a full cocktail bar and shrimp; Key West Schooners’ open-bar sail pours cocktails, beer, wine and champagne with no food listed; When and If pours select beer and wine, with a champagne toast at sunset included on the Viator booking; Danger Charters’ Wind and Wine sail is a guided wine tasting. The Jolly II Rover’s fare covers ice, cups, water and snacks, with no alcohol. You must be 21 to be served on all of them.

America 2.0’s sunset sail costs from $123 an adult on Viator (checked October 2026) and $123 on GetYourGuide (checked October 2026):

What each sail includes

Sail	Drinks	Food	From
America 2.0 at sunset	Beer, wine, champagne, soft drinks; cocktails to buy	A plate each: cheese and crackers, vegetables and dip, shrimp cocktail	$123
The Appledore at sunset	Premium beer, boutique wine, champagne, cocktails, soft drinks	The chef’s hors d’oeuvres and cocktail shrimp	$99
Schooner sunset sail, full open bar	A full open bar: cocktails, premium beer, wine, champagne	None listed	$109
When and If at sunset	Select beer and wine, soft drinks, a champagne toast at sunset (included on the Viator booking); bottle service extra	None listed	$117
Wind and Wine	A guided tasting of wines, beers, soft drinks	Meats, cheeses, crudites, fruit and chocolate	$135
Jolly II Rover at sunset	Ice, cups and bottled water; no alcohol in the fare	Snacks	$102
The Appledore by day	A full open bar	None listed	$54
America 2.0 by day	Two drinks, soda and water	None listed	$79

Prices per adult on Viator (checked October 2026); they change by date, and tips are not included. Inclusions from each listing and the operators’ own pages, read October 2026.

Check dates for America 2.0

The best value for drinkers

If the drinks matter most, Key West Schooners’ sails are built around them: the open-bar sunset sail pours a full bar of cocktails for two hours, and the afternoon sail does the same in daylight from $54 (checked October 2026). Their signature drinks are a Schooner Bloody Mary and a Dark and Stormy. America 2.0 pours beer, wine and champagne but sells its cocktails.

The best for food

America 2.0 and the Appledore sunset sail are the two that feed you: a plated selection on America 2.0, the chef’s hors d’oeuvres with cocktail shrimp on the Appledore. Danger Charters’ Wind and Wine pairs its wines with meats, cheeses and fruit, for ages 13 and up, from $135 (checked October 2026). None of the schooners serves a dinner; eat before or after on the harborwalk.

Illustration: guests seated on the varnished deck of a two-masted wooden schooner off Key West holding champagne flutes and wine glasses, a crew member passing a tray of hors d'oeuvres, the sun low over a flat sea horizon — Illustration. On America 2.0 and the Appledore the food comes round on deck.

Bringing your own

America 2.0: no. Bringing your own alcohol aboard is not allowed. On Viator, a bottle of champagne or white wine with souvenir glasses is a paid upgrade (two tickets minimum), and Thanksgiving, Christmas and New Year departures carry holiday rates (checked October 2026).
When and If: yes. Sunset Sail Key West welcomes guests to bring their own drinks and provides coolers of ice.
Jolly II Rover: her day sails are bring-your-own, with ice, chests, cups and bottle openers provided; the sunset sail’s fare covers ice, cups and water.

Where to check in

Map of where the Key West schooners check in around the Key West Bight: Schooner Wharf Bar at 202 William Street for America 2.0 and Key West Schooners, E dock by the Waterfront Brewery, the Jolly II Rover at Greene and Elizabeth streets, and Opal Key Resort on Front Street for Danger Charters' Wind and Wine sail — The bars of the schooners are a few minutes’ walk apart: most check in around Schooner Wharf Bar.

America 2.0 and the Appledores check in by Schooner Wharf Bar, the Jolly II Rover at Greene and Elizabeth streets and Danger Charters at Opal Key Resort on Front Street. The departure points guide has the walk and the parking.

The rules

Age: 21 to be served, with photo ID. Children sail on most schooners with an adult.
Tips: not included on any of them.
Weather: a captain’s weather cancellation gets you another date or your money back, and on Viator and GetYourGuide you can cancel up to 24 hours ahead for a full refund.

Key West Schooner with Open Bar: Drinks and Food Compared