Catamaran or Schooner for a Key West Sunset Sail
Catamaran or schooner for a Key West sunset sail: the big open-bar catamarans, Fury against Sunset Watersports, the schooners America 2.0, Appledore and Danger's, and the tiki boats.
A catamaran is the easy sunset sail: a wide, steady boat with two hulls, shade, restrooms, an open bar and, on several, live music, for between 14 and 149 guests depending on the boat. A schooner is a traditional two-masted sailing ship: fewer guests, more canvas, a quieter deck, and on most of them you can help raise the sails or take the wheel. Pick the catamaran for a lively evening and the drinks; pick a schooner for the sailing and the calm.
For a first sunset sail, Sebago’s catamaran is the safe pick: two hours with an open bar, hors d’oeuvres and local musicians, from $70 an adult on Viator (checked October 2026) and $70 on GetYourGuide (checked October 2026):
In Key West “sunset sail” and “sunset cruise” are used for the same evening. The difference that matters is whether the sails go up: Sebago, Fury and Sunset Watersports’ Sandie Cat are sailing catamarans, the schooners sail by definition, while the dinner catamaran and the tiki boats are sold as cruises rather than sails.
The catamarans
| Boat | Operator | Size | Drinks | Music | From |
|---|---|---|---|---|---|
| Sunset sail | Sebago | Sailing catamaran | Open bar: cocktails, champagne, sangria, wine, beer | Live local musicians | $70 |
| Commotion on the Ocean | Fury | 65-foot catamaran | Margaritas, champagne, beer, wine | A full live band | $73 |
| Sandie Cat, Sunset Sip and Sail | Sunset Watersports | 65-foot sailing catamaran, up to 149 guests | Open well bar: mixed drinks, rum runners, margaritas, beer, wine, champagne | Live music | $77 |
| Party Cat, sunset dinner cruise | Sunset Watersports | 65-foot catamaran with an air-conditioned dining room | Open well bar | Live music | $93 |
| Sunset and Moet | Catamaran Echo | 28-person sailing catamaran, at most 14 guests | Chandon Brut, eight wines, beer | None listed | $109 |
| Champagne sunset sail | Sebago | 60-foot sailing catamaran | Wine, sparkling wine, beer, sangria | None listed | $43 |
Prices per adult on Viator (checked October 2026); they change by date. Boat sizes from the operators’ own pages, read October 2026.
Fury or Sunset Watersports? Both run 65-foot catamarans for two hours from the Historic Seaport with live music. Fury’s Commotion on the Ocean has a full band and pours margaritas, champagne, beer and wine; Sunset Watersports’ Sandie Cat pours an open well bar with mixed drinks and rum runners, and carries up to 149 people on three decks. If you want spirits in the glass, Sunset Watersports or Sebago; if you want a band to dance to, Fury.
The schooners
| Schooner | Operator | What it is | Drinks and food | From |
|---|---|---|---|---|
| America 2.0 | Classic Harbor Line | 105-foot schooner built in 2011, a revival of an 1851 design; Key West from November to May | Beer, wine, champagne, soda; a plate of hors d’oeuvres each | $123 |
| Appledore | Key West Schooners | Two-masted wooden schooner; help raise the sails | Wine, beer, cocktails, soft drinks | $99 |
| Wind and Wine | Danger Charters | Schooners of 48 to 57 feet, up to 26 guests; ages 13 and up | A guided wine tasting, beers, hors d’oeuvres | $135 |
| Jolly II Rover | Schooner Jolly II Rover | 80-foot square-rigged topsail schooner with red sails and cannons | Ice, water and snacks; no band | $102 |
| When and If | Sunset Sail Key West | Wooden schooner built in 1939 for General George Patton | A champagne toast, drinks on board | $117 |
Prices per adult on Viator (checked October 2026); they change by date. Boat details from the operators’ own pages, read October 2026.
America 2.0 is the most polished of them, with plated food; the Appledore lets you work the sails; Danger Charters’ sail is the one built around wine and a small group. When and If’s own site puts its departures at the Perry Marina on Stock Island, east of Key West’s Old Town, while the Viator listing gives a dock in the Key West Bight, so read your confirmation before you set off.
Who each one suits
Book whichever fits your evening:
Key West Sunset Sail with Open Bar, Live Music and Hors d'Oeuvres
A big, steady catamaran with the bar open from the start, hors d'oeuvres and live music. Easy with friends or older children.
Check dates →Key West Wind and Wine Sunset Sail on a Schooner
A schooner, a small group and a guided tasting of wines, no band. For a date or a birthday. Ages 13 and up.
See the wine sail →Key West Sunset Sail on the Schooner America 2.0
105 feet of schooner and 3,600 square feet of canvas, with drinks and plated hors d'oeuvres. November to May only.
See America 2.0 →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 they leave from
Both kinds leave from the same few blocks. The catamarans of Sebago, Fury and Sunset Watersports check in along the harborwalk between Greene and William streets; America 2.0 and the Appledore by Schooner Wharf Bar at the end of William Street; Danger Charters’ schooners at Opal Key Resort on Front Street, near Mallory Square. The tiki boats are the exception: the tiki-bar sunset cruise, six guests at most and bring your own drinks, leaves from Garrison Bight on the other side of the island. The departure points guide has the details.
What to know before you choose
- Seasickness: a catamaran’s two hulls keep it level; a schooner heels a little under sail. If you are prone to seasickness, the catamaran is the gentler ride.
- Children: the catamarans and most schooners take all ages; Danger Charters’ sail is 13 and up, and Catamaran Echo’s 21 and up.
- Size: the big catamarans carry a crowd; the schooners and Catamaran Echo keep it small. If a quiet deck matters, ask the operator how many are booked on your date.
Other Key West Trips with Open Dates
More Key West Boat Trips with Open Dates
Sunset sails, snorkelling, dolphins and the sandbar, with live availability. Times and cancellation terms are on each listing.
Start with the Catamaran
Sebago's sailing catamaran from Lazy Way Lane: two hours, an open bar, hors d'oeuvres and live music, with room to move about.
Check dates