Set sail on the Stock Island Wind & Wine Sunset Sail and enjoy eight exquisite wines, premium beers, and hors d'oeuvres as the sun dips below the horizon near Key West. Discover why this two-hour adventure is a favorite for relaxation and indulgence.
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Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for most fitness levels as it involves sitting or standing on the deck; minimal physical exertion required.
Wildlife
History
The schooner used for this sail reflects Key West's rich maritime heritage dating back to the 19th century.
Conservation
Danger Charters practices sustainable boating by minimizing waste and supporting local marine conservation efforts.
Danger Charters
Set sail on the Stock Island Wind & Wine Sunset Sail and enjoy eight exquisite wines, premium beers, and hors d'oeuvres as the sun dips below the horizon near Key West. Discover why this two-hour adventure is a favorite for relaxation and indulgence.
Danger Charters is a Key West, Florida-based charter company specializing in small-group sailing and private boat experiences aboard historic schooners and powerboats. The company operates a range of themed cruises and private charters, including a 4.5-hour Private Charter Sail, Snorkel & Kayak that pairs sailing with kayaking and snorkeling and includes complimentary drinks and snacks. The Key West Wind & Wine Sunset Sail features eight wines, craft beers, and hors d'oeuvres aboard a historic schooner for an intimate sunset experience.
For a shorter private option, the Private Powerboat Sunset Cruise offers a two-hour ride on a 24’ center console for up to six guests with space for personal music and beverages. Seasonal and holiday sails include a two-hour New Years Sunset Sail with fine wines and craft beers, a 1.5-hour St. Patrick’s Day Happy Hour Sail, a Cinco de Mayo celebratory 1.5-hour sail, and an Easter Weekend Hoppy Hour Sail with champagne and handcrafted cocktails. Special event options include morning Powerboat Races with mimosas, pastries, a catered lunch, unlimited drinks, and a guest limit of 24, plus Fourth of July combinations: a 3.5-hour Sunset Sail and Fireworks cruise and a 5-hour Snorkel and Fireworks trip. Every listing emphasizes small groups, curated food and beverage selections, and guided activities. Bookings accommodate a variety of occasions including holidays, celebrations, private gatherings, and sightseeing excursions around Key West harbor and nearby reefs for all experience levels.
Tours Offered
10
A variety of sails and charters
Guest Capacity
6–24 guests
Options from private to small groups
Vessel Types
Schooners & Powerboats
Historic schooners and center consoles
Included Extras
Drinks & Snacks
Wines, beers, hors d'oeuvres included
Book a private sail, snorkeling adventure, or holiday cruise in Key West — small-group availability and seasonal dates fill quickly.
Arrive Early to Settle In
Arriving 15 minutes before departure ensures a smooth boarding process and time to choose your favorite spot on the schooner.
Bring a Light Jacket
Evenings on the water can get cool, so a light jacket or wrap is recommended for comfort during the sail.
Limit Alcohol Intake
Enjoy the wine and beer selection responsibly to fully appreciate the experience and stay safe aboard.
Protect Against the Sun
Apply sunscreen before boarding, as the late afternoon sun can still be intense while sailing.
Light Jacket or Sweater
Keeps you warm during cooler evening breezes on the water.
fall
Sunscreen
Protects your skin from the strong afternoon sun before and during the sail.
summer
Sunglasses
Reduces glare off the water, making the views more comfortable to enjoy.
Non-slip Shoes
Provides stability and safety when moving around the boat’s deck.