Where Key West Sunset Sails Leave From
Where each Key West sunset sail checks in: Sebago, Fury, America 2.0, the Appledore and Sunset Watersports in the Historic Seaport, Danger Charters at Opal Key, the tiki boats at Garrison Bight, and parking.
Most Key West sunset sails leave from the Historic Seaport, the City of Key West’s marina at the Key West Bight, at 201 William Street. Its harborwalk runs along the water past the ends of Front, Greene, Elizabeth, William, Margaret and Grinnell streets, and the check-in booths sit along it a few minutes’ walk apart. Two exceptions: Danger Charters’ schooners leave from Opal Key Resort on Front Street, near Mallory Square, and the tiki boats from Garrison Bight on the other side of the island. Arrive 30 minutes before your sail; a few operators ask for 45 or 60.
Sebago’s sunset sail checks in on Lazy Way Lane, 205 Elizabeth Street. It is from $70 an adult on Viator (checked October 2026) and $70 on GetYourGuide (checked October 2026):
Check-in, sail by sail
| Sail | Where to check in | Arrive |
|---|---|---|
| Sebago (all its sunset sails) | Sebago’s office on Lazy Way Lane, 205 Elizabeth Street | 30 minutes before |
| Fury, Commotion on the Ocean | The booth at the corner of Greene and Elizabeth streets, next to Conch Republic Seafood Company | 45 minutes before |
| Sunset Watersports, Sip and Sail | Sunset Watersports’ booth, 201 William Street | 30 to 45 minutes before |
| Sunset Watersports, dinner cruise | Sunset Watersports’ booth, 201 William Street | 60 minutes before |
| Catamaran Echo | Dock D-30 by the Waterfront Brewery, 201 William Street; check in at the boat | 15 minutes before |
| America 2.0 | The ticket booth on the right of Schooner Wharf Bar (facing the water), 202 William Street | 30 to 45 minutes before |
| The Appledore (Key West Schooners) | The booth at the far end of William Street, right of the Western Union sign | 30 minutes before |
| Jolly II Rover | The ticket booth on the dock beside Conch Republic Seafood Company, Greene and Elizabeth streets | 15 minutes before |
| Floridays | The dock behind the Hyatt Centric, 601 Front Street, past the pool | 30 minutes before |
| Danger Charters | Danger’s chandlery at Opal Key Resort and Marina, 255 Front Street | 30 minutes before |
| Tiki bar sunset cruise | Garrison Bight Marina, Angelfish Pier, slip 8; entrance from Palm Avenue | 15 minutes before |
From the Viator listings and the operators’ own sites, read October 2026. Your booking confirmation has the final word on the place and time.
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.
Two that do not leave from the Seaport
Danger Charters sails its Wind and Wine schooners from Opal Key Resort and Marina on Front Street, a short walk from Mallory Square. The chandlery is at the top of the brick walkway between the resort and the Key West Museum of Art and History. Parking at the resort is usually full, and the street meters around it are pay-by-block, so walk if you can.
The tiki boats leave from Garrison Bight, on the north side of the island, with the entrance from Palm Avenue; parking there is free.
When and If, the 1939 schooner, sails from the Perry Marina on Stock Island on its own site, east of Key West, while its Viator listing gives a dock in the Key West Bight: go by your confirmation.
Parking near the Historic Seaport
- Old Town Parking Garage, 301 Grinnell Street at Caroline Street: 300 spaces, open 24 hours, $6 an hour or $48 a day plus tax (City of Key West, checked October 2026). The nearest garage to the Seaport.
- Key West Bight lot on Caroline Street: $6 an hour, $48 a day at most (City of Key West, checked October 2026).
- Conch Republic lot on Greene Street: $6 an hour, ten hours at most (City of Key West, checked October 2026).
Special-event rates can apply, so check the posted rate. The garage’s bus stop is across Caroline Street in front of West Marine.
Walking times
The Historic Seaport is at the north end of Old Town. From Mallory Square to the Seaport’s booths is less than ten minutes on foot along Front and Greene streets; from the middle of Duval Street, allow ten to fifteen. Give yourself the full check-in time on top: the boats leave at the listed time and do not wait.
Check In on Lazy Way Lane
Sebago's sunset sail checks in on the harborwalk in the Historic Seaport, 30 minutes before a two-hour sail with an open bar and live music.
Check dates