Key West: Schooner America 2.0 Sailing Tour & 2 Drinks

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Free cancellationExcellent quality

1/18

Duration1h 30m

GroupUp to 68

LanguagesEN

Mobile ticketAccepted

Sail the Schooner That Won the First America's Cup

You board the America 2.0 at the ticket booth after a 30-minute check-in, then spend 1.5 hours sailing past Fort Zachary Taylor, Sunset Pier, and Sand Key Light Tower with two included drinks in hand. The captain works the coast close enough to see the sights clearly but far enough out to feel like you're actually on the water. Kids sail free on afternoon departures, and the boat operates in all weather unless unsafe.

1h 30m

Step-by-step itinerary

Sail and view Key West landmarks

Board Schooner America 2.0
Sail along coast near Mallory Square
View Fort Zachary Taylor from water
See Sunset Pier and landmarks from boat
Enjoy two included drinks onboard

The Experience

The Schooner America 2.0 is a replica of the 1851 vessel that claimed the first America's Cup, and you're standing on her deck watching Fort Zachary Taylor slide past on the starboard side. The boat moves through clear Caribbean water with the kind of quiet efficiency that comes from 170 years of proven design — no engine noise, just the sound of canvas and the occasional call from the captain as he works the coast. The 1.5-hour sail takes you past Mallory Square, Sunset Pier, and Sand Key Light Tower, each one framed differently as the angle of the boat shifts and the light changes across the water.

Two alcoholic drinks come with your ticket (soda and water are free), and there's a rhythm to the afternoon that lets you actually taste them instead of just holding a cup. The captain hugs the shoreline deliberately, so you're close enough to see the architecture and the people on the docks, but far enough out that Key West looks like itself — not a postcard, but a working island with history stacked into every block. The boat handles all weather unless conditions turn genuinely unsafe, so you're sailing most days; just dress for wind and salt spray, which means layers and nothing you mind getting damp.

Arrive 30 to 45 minutes before departure to pick up your boarding pass at the ticket booth. Kids sail free on the afternoon departures, which changes the math if you're traveling with children — you only pay for the adults, and the boat doesn't feel crowded because of it. The sailing works for all fitness levels; there's no hiking or climbing involved, just boarding and finding a spot on deck or below if you want shade.

What’s included

Your day includes a 1.5-hour coastal sailing tour aboard the Schooner America 2.0, two alcoholic beverages (for those 21 and older), complimentary soda and water, and views of Fort Zachary Taylor, Mallory Square, Sunset Pier, and Sand Key Light Tower from the water. You'll need to arrive 30 to 45 minutes early for check-in at the ticket booth.

Good to know

Easy physical levelStroller friendlyPets welcomePublic transport nearby

Operated by Classic Harbor Line

Is this one for you?This works well if you want to see Key West's waterfront landmarks without arranging your own boat or timing a sunset perfectly — the fixed 1.5-hour route covers the main sights, and the two included drinks let you settle in instead of managing a tab.