Stock Island Wind & Wine Sunset Sail Aboard Classic Schooner

Set sail on a captivating journey with the Stock Island Wind & Wine Sunset Sail Aboard a Classic Schooner. This enchanting 2-hour cruise immerses guests in the picturesque waters of Key West, where they’ll savor premium wines, gourmet hors-d’oeuvres, and captivating commentary from a live guide. Rated among North America’s top sunset excursions, this intimate experience blends relaxation and scenic beauty, making it an ideal choice for romantic evenings or gatherings with friends. Discover why this sunset sail has captured the hearts of visitors, and uncover the hidden gems that await you on the open waters.

This experience made our list of the 25 Best Cruises And Boat Tours In Key West.

Key Points

• Classic schooner cruise around the scenic Key West waters, lasting approximately 2 hours and departing from the Perry Hotel & Marina.
• Gourmet hors-d’oeuvres, including a selection of 8 wines and 5 premium beers, complementing the scenic sunset experience.
• Recognized as one of the top sunset excursions in North America, offering an upscale, relaxed, and intimate atmosphere.
• Accessible amenities, including bathrooms and complimentary soda and bottled water, allowing guests to focus on the enjoyment of the experience.
• Flexible booking system with free cancellation up to 24 hours in advance, ensuring a stress-free planning experience for travelers.

You can check if your dates are available here:

Experience Overview

The Stock Island Wind & Wine Sunset Sail offers guests a unique opportunity to experience a classic schooner cruise around the scenic waters of Key West.

The 2-hour activity departs from the Perry Hotel & Marina, with guests meeting the captain 30 minutes prior at the nearby Bad Boy Taqueria & Tequila. A live tour guide accompanies the group, providing commentary in English throughout the journey.

Aboard the classic schooner, guests can enjoy an array of red, white, and sparkling wines, as well as premium beers, paired with gourmet hors-d’oeuvres.

The sail is rated as one of the top sunset excursions in North America, offering an upscale and intimate atmosphere to mingle with friends or enjoy a romantic evening.

Pricing and Booking

Pricing for the Stock Island Wind & Wine Sunset Sail starts from €115.48 per person.

Customers can reserve their spot without any upfront payment, paying later instead. Cancelations are also hassle-free, as the company offers free cancelation up to 24 hours in advance for a full refund.

This flexible booking system makes it easy for travelers to plan their sunset sail experience. Whether you’re looking for a romantic evening or a fun outing with friends, the Stock Island Wind & Wine Sunset Sail offers an excellent value proposition, allowing you to secure your spot without any financial commitment upfront.

Culinary Offerings

An impressive selection of 8 varieties of wine (4 red, 3 white, 1 Champagne) and 5 premium beers (both imported and domestic) are offered aboard the Stock Island Wind & Wine Sunset Sail. Guests can enjoy a gourmet selection of hors-d’oeuvres, including charcuterie boards with meats, cheeses, crackers, fruit, crudités, and chocolate. The culinary offerings provide a perfect accompaniment to the scenic sunset sail.

Wine Varieties	Beer Selections
4 Red Wines	3 Domestic Beers
3 White Wines	2 Imported Beers
1 Champagne

Highlights and Unique Features

One of the highlights of the Stock Island Wind & Wine Sunset Sail is its recognition as one of the top two Sunset Sails in North America by Coastal Living Magazine.

This unique experience offers an upscale, relaxed, and intimate atmosphere that sets it apart. Plus, it’s the only sailing excursion in the U.S. that serves "real" wine, allowing guests to enjoy a wide variety of red, white, and champagne options.

The opportunity to mingle with friends or enjoy a romantic evening under the setting sun further enhances the appeal of this sought-after activity.

• Rated as a top Sunset Sail in North America
• Serves "real" wine, a rarity for sailing excursions
• Offers an upscale, relaxed, and intimate atmosphere

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What to Bring and Amenities

Guests should plan to bring a sweatshirt, especially during the winter months, as well as sunglasses and a camera to capture the stunning sunset views.

Photo ID is also required for boarding. The schooners offer bathrooms for use before and during the excursion, providing a convenient amenity.

Plus, complimentary soda and bottled water are provided to ensure guests stay hydrated throughout the sail.

The excursion’s accessible and well-equipped nature allows visitors to focus on enjoying the scenic views, live music, and exceptional wine and hors-d’oeuvres offerings without having to worry about the logistical details.

Departure Point and Meeting Location

The departure point for the Stock Island Wind & Wine Sunset Sail is the Perry Hotel & Marina, located at 7011 Shrimp Road on Stock Island, Florida.

Passengers are asked to meet the captain at the Bad Boy Taqueria & Tequila, a nearby restaurant, 30 minutes prior to the sail’s scheduled departure. This allows ample time for check-in and boarding the classic schooner.

The meeting location offers several convenient features:

1. Centrally located adjacent to the departure point
2. Provides a comfortable space to gather before the voyage
3. Allows the captain to greet and assist passengers prior to setting sail

Duration and Language

For the Stock Island Wind & Wine Sunset Sail, the experience lasts approximately 2 hours.

During this time, guests will enjoy a leisurely sail aboard a classic schooner. The tour is conducted entirely in English, with a knowledgeable live guide providing commentary and insights throughout the journey.

This allows visitors to fully enjoy the experience and learn about the local history, wildlife, and landmarks as they sip premium wines and savor gourmet hors-d’oeuvres.

With its convenient departure from the Perry Hotel & Marina on Stock Island, the sunset sail offers a unique and unforgettable way to experience the Florida Keys.

Cancellation Policy

Free cancellation up to 24 hours in advance allows guests to plan their visit with flexibility. This policy offers several benefits:

1. Peace of mind – Travelers can book their sail without the worry of losing their money if plans change.

2. Stress-free rescheduling – Should the need arise, guests can easily move their sail to another date.

3. Full refund – In the event of a cancellation, customers receive a 100% refund, enabling them to explore alternative options.

This generous cancellation policy underscores the company’s commitment to providing an exceptional customer experience, ensuring guests can fully enjoy the Stock Island Wind & Wine Sunset Sail aboard the classic schooner.

Frequently Asked Questions

Can I Bring My Own Alcoholic Beverages on the Sail?

No, passengers cannot bring their own alcoholic beverages on the sail. The experience includes a selection of wine and beer provided by the tour operator, so outside drinks are not permitted.

Is There a Dress Code for the Sunset Sail?

There isn’t a strict dress code for the sunset sail, but passengers are encouraged to dress comfortably and in casual attire suitable for an evening on the water, such as lightweight clothing and closed-toe shoes.

Are Children Allowed on the Sailing Tour?

Children are welcome on the sailing tour. There’s no age limit, but the tour operator recommends it’s suitable for kids aged 6 and up who can safely enjoy the 2-hour experience.

Can I Bring My Pet on the Sailing Excursion?

Pets are not permitted on the sailing excursion. The tour operator’s policies prohibit bringing animals aboard for safety and liability reasons. Only service animals required for a disability are allowed on the sailing tour.

Is Gratuity Included in the Tour Price?

Gratuity is not included in the tour price. Guests are expected to tip the crew at their discretion, typically between 15-20% of the total cost of the experience.

Recap

The Stock Island Wind & Wine Sunset Sail aboard a Classic Schooner offers an unforgettable experience, blending relaxation, stunning scenery, and delectable culinary offerings. Whether seeking a romantic evening or a gathering with friends, this top-rated sunset excursion provides the perfect opportunity to take in the picturesque Key West waters and enjoy the captivating commentary from a live guide.

You can check if your dates are available here: