KEY WEST BOAT TOUR FIELD GUIDE
Schooner Sunset: A Stock Island Wind & Wine Sail Along Key West’s South Shore
A two-hour boutique sunset sail from Stock Island aboard a historic schooner that pairs a guided tasting of eight wines and premium beers with light hors d'oeuvres—this guide explains what to expect and how to prepare.
Schooner Sunset: A Stock Island Wind & Wine Sail Along Key West’s South Shore.
A small historic schooner slips away from Stock Island and eases along the south side of Key West as the light softens. Over two hours you’ll trade the raucous crowd scene of larger excursion boats for an intimate, calm tasting: a guided flight of eight wines complemented by craft and domestic beers and a spread of light hors d’oeuvres, all timed to a classic Key West sunset.
Highlights
Outing Highlights
A historic schooner and an uncrowded sail
This is a calm, uncrowded boutique sailing experience aboard a historic schooner—an intimate atmosphere that emphasizes relaxation over a party-boat vibe.
A guided tasting: eight wines, beers and small bites
The Wind & Wine sail includes a guided tasting of eight wines alongside craft and domestic beers, paired with light hors d'oeuvres such as crudités, meats, cheeses, crackers, fruit and chocolate.
Sunset and panoramic coastal views
With small group sizes and plenty of room to move, the sail offers panoramic views of Key West’s coastline and an unobstructed vantage for sunset photography.
What the day feels like
What the sail feels like
Boarding from Stock Island, the two-hour Wind & Wine Sunset Sail unfolds at an easy pace: cast off, settle into the schooner’s deck, and move between guided tasting stations and the rail as the crew navigates the south side of Key West. Conversation and photos are encouraged; the tasting and small bites are paced to coincide with the fading light.
THE BOAT
A historic schooner and an uncrowded sail
This is a calm, uncrowded boutique sailing experience aboard a historic schooner—an intimate atmosphere that emphasizes relaxation over a party-boat vibe.
THE TASTE
A guided tasting: eight wines, beers and small bites
The Wind & Wine sail includes a guided tasting of eight wines alongside craft and domestic beers, paired with light hors d'oeuvres such as crudités, meats, cheeses, crackers, fruit and chocolate.
THE VIEW
Sunset and panoramic coastal views
With small group sizes and plenty of room to move, the sail offers panoramic views of Key West’s coastline and an unobstructed vantage for sunset photography.
Suitability
Who it's for
Who this sail suits — and who should look elsewhere.
Practical planner
Details to review before reserving
The sail runs for approximately two hours.
The cruise embarks from Stock Island and sails the south side of Key West.
Bring sunglasses, a camera, photo ID, and a sweatshirt in the winter months.
The outing includes a guided tasting of eight wines, craft and domestic beers, and light hors d'oeuvres such as cheeses, meats, fruit and chocolate.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the Wind & Wine Sunset Sail?
The experience is a two-hour sail.
Where does the sail depart from?
The sail departs from Stock Island and follows the south side of Key West.
What food and drink are included?
Guests receive a guided tasting of eight wines, craft and domestic beers, and light hors d'oeuvres including crudités, meats, cheeses, crackers, fruit and chocolate.
Is this a party boat?
No—this is described as a calm, uncrowded, boutique sailing experience with an intimate, relaxed atmosphere rather than a party-boat environment.
Are there age restrictions?
Guests must be at least 13 years old to participate.
What should I bring aboard?
Bring sunglasses, a camera, photo ID, and a sweatshirt in the winter months.