Where the Key West Schooners Leave From
Where each Key West schooner checks in: Schooner Wharf Bar for America 2.0, the Western Union sign for the Appledore, Greene and Elizabeth, Opal Key, parking.
Three of the four Key West schooners check in within a minute’s walk of each other at the Key West Bight, the old harbour the City calls the Key West Historic Seaport: America 2.0 at Classic Harbor Line’s booth beside Schooner Wharf Bar, 202 William Street; the Appledores at Key West Schooners’ booth at the very end of William Street; and the Jolly II Rover at Greene and Elizabeth streets. Danger Charters’ schooners leave from Opal Key Resort on Front Street, by Mallory Square, and When and If from the Perry Marina on Stock Island, 6 km east.
America 2.0’s sunset sail costs from $123 an adult on Viator (checked October 2026) and $123 on GetYourGuide (checked October 2026):
The check-in points
| Schooner | Check in | Arrive |
|---|---|---|
| America 2.0 | Classic Harbor Line’s booth on the right side of Schooner Wharf Bar, 202 William Street, as you face the water | 30 to 45 minutes before |
| The Appledores | Key West Schooners’ booth at the very end of William Street, right of the Western Union sign | Boarding starts 30 minutes before |
| Jolly II Rover | The ticket booth on the dock beside Conch Republic Seafood Company, Greene and Elizabeth streets | 15 minutes before |
| Danger Charters | Danger’s chandlery at the base of Opal Key Resort, 255 Front Street: up the ramp between the resort and the art museum, second shop on the left | 30 minutes before |
| When and If | The dock on your confirmation: E dock in front of the Waterfront Brewery on the listing, the Perry Marina on Stock Island on her own site | 15 to 30 minutes before |
From the Viator listings and the operators’ own pages, read October 2026.
Schooner Wharf Bar and the end of William Street
Schooner Wharf Bar is the open-air bar on the water at the foot of William Street, and two schooner companies have their booths beside it. From Elizabeth Street, keep the water on your left and follow Lazy Way Lane past the shops, with the Marker Resort on your right and Schooner Wharf Bar on your left: Key West Schooners’ booth is just past the bar. Classic Harbor Line’s booth is on the right side of the bar as you face the water, and America 2.0 docks behind it. There are no restrooms at Key West Schooners’ booth; each of its ships has one.
Greene and Elizabeth streets
The Jolly II Rover’s ticket booth stands on the dock beside Conch Republic Seafood Company, at the corner of Greene and Elizabeth streets, a two-minute walk west of Schooner Wharf Bar along the harborwalk.
Opal Key Resort
Danger Charters’ schooners leave from the Danger chandlery at Opal Key Resort and Marina on Front Street, a short walk from Mallory Square and about ten minutes on foot from the Bight. The resort’s address is 245 Front Street; the chandlery uses 255. Its own lot is often full, so walk or use the meters nearby. A second Wind and Wine departure leaves from the Perry Marina on Stock Island.
The Perry Marina, Stock Island
When and If’s own site sails her from the Perry Marina, 7001 Shrimp Road on Stock Island, about 6 km east of the Bight beyond the bridge from Key West: a marina of 288 slips with a hotel, bars and restaurants. You need a car or a taxi to get there. Her Viator listing meets at E dock in the Bight instead, so go by your confirmation.
Parking and the bus
| Where | Rate |
|---|---|
| Key West Bight lot, Caroline Street at William Street | $6 an hour, $48 a day |
| Old Town Garage, 301 Grinnell Street at Caroline Street | $6 an hour, $48 a day, plus tax; 300 spaces |
City of Key West rates, read October 2026; special-event rates may apply.
The free Duval Loop bus stops at Caroline and William streets, a block from Schooner Wharf Bar.
Which schooner from which dock
Key West Sunset Sail on the Schooner America 2.0
America 2.0 from the booth beside Schooner Wharf Bar: two hours at sunset, drinks and a plate each.
Check dates →Key West Sunset Sail on the Schooner Appledore
The Appledore from the booth by the Western Union sign: help raise the sails, cocktails and shrimp.
See the Appledore →Key West Sunset Sail on the Jolly II Rover
The Jolly II Rover from the booth by Conch Republic Seafood Company: red sails and cannons.
See the Rover →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.
Other Key West Sails with Open Dates
More Key West Boat Trips with Open Dates
Sunset sails, schooners and snorkel trips, with live availability. Times and cancellation terms are on each listing.
Sail from Schooner Wharf
America 2.0 checks in at the booth beside Schooner Wharf Bar: two hours at sunset with beer, wine, champagne and a plate of hors d'oeuvres each.
Check dates