Key West Schooner: Day sail with drinks & local guide

Summary

Sail past Key West’s landmarks on a schooner with drinks included

You’ll board the famous Schooner America 2.0 for a day sail along Key West’s coast, with two included drinks and stories from your local guide as you pass Fort Zachary Taylor and Mallory Square. Expect salty air, laughter, and views you’ll remember long after the sails come down.

What’s the experience like?

First thing I noticed was the creak of the dock under my sandals — and then that schooner, America 2.0, just sitting there like it knew it was the best-looking boat in Key West. The crew greeted us with easy smiles (one guy, I think his name was Dave, had a sunburn that matched his shirt). We set off and right away you could smell salt and sunscreen mixing in the air. I picked a spot near the rail where you could see Fort Zachary Taylor in the distance — it looked smaller from the water than I expected, but somehow more mysterious too.

Our captain told stories about the original America schooner — apparently it won some big race back in 1851, which made me laugh because this replica still feels fast even when you’re just drifting along. The sails snapped overhead every time the wind shifted. There was this moment when we passed Mallory Square and people waved from shore; someone shouted something about happy hour and honestly, it felt like everyone in Key West was in on some inside joke except us. My drink (rum punch — strong) tasted better with all that breeze.

I tried to pronounce “Sand Key Light Tower” after our guide Li pointed it out — she laughed so hard I nearly spilled my second drink. Kids ran up and down the deck while their parents took photos of Sunset Pier glowing gold behind us. Soda and water were free but most folks stuck to their two included drinks (I saw one guy try for a third — no luck). The whole thing lasted about an hour and a half but time got weird out there; I kept thinking maybe we’d just keep sailing past sunset. Still think about that view sometimes, especially when I hear seagulls back home.

Step-by-step itinerary

Day 1 — Sail and Sightsee Key West Coast

• View Mallory Square from the schooner
• See Fort Zachary Taylor from the water
• Enjoy views of Sunset Pier and landmarks

Top questions

How long is the Key West day sail on Schooner America 2.0?

The sailing tour lasts approximately 1.5 hours along the Key West coast.

Are drinks included on the Schooner America 2.0 tour?

Yes, your ticket includes two alcoholic beverages for guests over 21 plus complimentary soda and water.

What landmarks will I see during this day sail?

You’ll see Fort Zachary Taylor, Mallory Square, Sunset Pier, and Sand Key Light Tower from the water.

Is there a local guide on board?

Yes, a local guide shares stories about Key West and points out landmarks during the sail.

Are children allowed on this sailing tour?

Yes, infants and small children can join; kids sail free on afternoon departures.

Where does the tour depart from?

The tour departs from a dock in Key West; check-in is required 15–30 minutes before departure at the ticket booth.

What’s included

Your day includes a 1.5-hour coastal sailing tour aboard Schooner America 2.0 with a local guide sharing stories along the way, two alcoholic drinks for adults plus unlimited soda and water for everyone before returning to shore together.