Key West offers several wine-themed sunset cruises, combining local scenery with tastings.
These tours range from intimate champagne sails to larger catamaran trips with unlimited drinks. Some even include dolphin watching.
We love the small-group sailings for their personal touch and premium wine selections.
The classic schooner tours are also a favorite, offering a traditional sailing experience alongside wine tasting.
Check out our top picks for Key West wine tours below.
Good To Know
- Sunset cruises with unlimited wine, champagne, and gourmet offerings are highly rated by travelers, providing an intimate and scenic experience away from crowds.
- Small-group and private sunset sail options offer a more personalized wine-tasting experience with a variety of alcoholic and non-alcoholic beverages.
- Specialty cruises combine wine and champagne with additional activities like snorkeling, delivering a unique and adventurous wine tour in Key West.
- Sunset sail tours on classic schooners offer premium wine, craft beers, and gourmet hors-d’oeuvres, ranked among the top sunset sails in North America.
- Key West’s scenic views, including Mallory Square’s Sunset Celebration and Fort Zachary Taylor, enhance the wine tour experience with exceptional photo opportunities.
Adults Only Champagne Celebration Sunset Cruise From Key West
If you’re seeking a truly unforgettable sunset experience in Key West, the Adults Only Champagne Celebration Sunset Cruise is a must.
This 2-hour cruise is limited to just 14 passengers, providing a personalized and intimate setting. Aboard a 26-passenger catamaran, you’ll enjoy breathtaking views of Key West’s stunning sunsets away from the crowds at Mallory Square.
The cruise includes unlimited house champagne, premium wines, and a gourmet cheese buffet.
With its exceptional service, relaxing atmosphere, and quality of food and drinks, it’s no wonder the cruise is rated 4.9 out of 823 reviews, with a 98% traveler recommendation.
Read our full review: Adults Only Champagne Celebration Sunset Cruise From Key West Review
Book now: Check availability
Small-Group Key West Sunset Sail With Wine
One of the most popular sunset sailing experiences in Key West is the Small-Group Key West Sunset Sail with Wine.
You’ll cruise aboard a 65-foot schooner with a maximum of 26 travelers, ensuring a personalized experience. Sip up to eight wines and five beers as you take in the scenic sunset views.
Pair your drinks with a gourmet cheese buffet and appetizers. The experience includes unlimited beer, wine, and soft drinks, as well as gratuities.
Just be sure to arrive 30 minutes early for check-in, and keep in mind the minimum drinking age is 21.
With an impressive 98% traveler recommendation, this sunset sail is a must-do activity in Key West.
Read our full review: Small-Group Key West Sunset Sail With Wine Review
Book now: Check availability
Key West Sunset Champagne Catamaran Cruise
Experience the beauty of Key West’s stunning sunset aboard the 69-foot Sebago Key West Catamaran.
This 2-hour cruise is recommended by 92% of travelers, with 568 reviews and a Badge of Excellence. Enjoy the views of the island and marine life while sipping on a selection of drinks, including beer, wine, champagne, and sangria from the cash bar.
The cruise is priced at $59 and up, with all taxes and fees included. Boarding begins 30 minutes before departure, and the cruise accommodates a maximum of 86 travelers.
While most guests enjoyed the relaxing atmosphere and drink options, some had mixed feedback on communication and value for upgrades.
Read our full review: Key West Sunset Champagne Catamaran Cruise Review
Book now: Check availability
Key West Dolphin Watch Sunset Sail With Premium Wine, and Tapas Pairings
Looking to add more excitement to your Key West sunset adventure? Consider the Key West Dolphin Watch Sunset Sail With Premium Wine, and Tapas Pairings.
This 2.5-hour cruise offers an intimate experience for up to 50 travelers. Sail past Key West landmarks, watch for dolphins, and enjoy stunning sunset views from a luxury catamaran.
Sip premium wine, beer, and champagne, and indulge in a chef’s selection of tapas like shrimp cocktail.
With a 90% recommendation rate and 4.5-star average, this tour receives rave reviews for its friendly crew, beautiful scenery, and attentive service.
Easily accessible from the meeting point, this sail is stroller-friendly, though not wheelchair accessible.
Read our full review: Key West Dolphin Watch Sunset Sail With Premium Wine, and Tapas Pairings Review
Book now: Check availability
Private 2-Hour Wind and Wine Sunset Sail in Key West
The Private 2-Hour Wind and Wine Sunset Sail in Key West offers an intimate, private experience on a 65ft schooner.
Recommended by 98% of travelers with a 4.9 rating, this sail is ideal for groups and provides the perfect backdrop for memorable vacation photos.
You’ll savor a variety of hors d’oeuvres, including cheese skewers, accompanied by a selection of wines and beers from around the globe.
The sail departs from 255 Front St, Key West, FL, with a check-in 30 minutes prior.
While not wheelchair accessible, most travelers can participate in this private tour.
At $4,000 for up to 15 people, you can take advantage of the free cancellation policy up to 24 hours before the experience.
Read our full review: Private 2-Hour Wind and Wine Sunset Sail in Key West Review
Book now: Check availability
2-Hour Sunset Sailing With Wine In Stock Island
Set sail on a 2-hour sunset cruise in Stock Island, Key West, where you’ll savor a variety of wines as you take in breathtaking views.
This intimate experience accommodates up to 20 travelers, ensuring a peaceful atmosphere and personalized attention from the skilled schooner crew.
Indulge in a charcuterie board featuring meats, cheeses, crackers, and chocolate, along with eight wine varieties and five types of beer.
The tour’s 100% traveler recommendation and Danger Charters’ Badge of Excellence attest to its quality.
With free cancellation up to 24 hours in advance and a discounted price, this sunset sailing adventure is a must-try for oenophiles and sightseers alike.
Read our full review: 2-Hour Sunset Sailing With Wine In Stock Island Review
Book now: Check availability
Key West: Windjammer Champagne Sunset Sail
Set out on a captivating sunset sail aboard the majestic Appledore II, a 2-masted wooden schooner, and witness the iconic Key West skyline transform under the golden glow.
Depart from the southernmost point of the US for a 2-hour journey, where you’ll savor a variety of included beverages, from champagne and sangria to boutique wine and liquor.
Participate in raising the sails with the crew and enjoy scenic views of Key West’s historic landmarks, including the seaport, Mallory Square, and Fort Zachary Taylor.
With a perfect 5-star rating from 10 reviews, this sunset sail promises gorgeous views and an unforgettable experience.
Read our full review: Key West: Windjammer Champagne Sunset Sail Review
Book now: Check availability
Key West: Sunset Snorkel Cruise With Draft Beer & Wine
Enjoy a captivating sunset snorkel cruise in Key West, where you’ll explore the world’s third largest coral barrier reef.
The 3-hour cruise departs on a catamaran, offering a 1-hour snorkeling session followed by a leisurely sail back while enjoying unlimited cold draft beer and wine.
The cruise provides snorkeling gear, safety equipment, and transportation, with a panoramic view of the sunset over the Gulf of Mexico.
At $69.95 per person, this experience offers great value, with overwhelmingly positive reviews praising the friendly crew and stunning scenery.
Bring your passport, swimwear, towel, and sunscreen, and get ready for an unforgettable sunset adventure in Key West.
Read our full review: Key West: Sunset Snorkel Cruise With Draft Beer & Wine Review
Book now: Check availability
Key West Wind and Wine Sunset Sail Aboard Classic Schooner
For those seeking a more upscale and intimate sunset experience in Key West, the Key West Wind and Wine Sunset Sail aboard a classic schooner is a must-try.
This 2-hour sail departs from the Opal Key Resort & Marina, offering breathtaking coastal views and premium wine, beer, and gourmet hors-d’oeuvres. Priced from $128.89 per person, the experience is ranked among the top two sunset sails in North America by Coastal Living Magazine.
With free cancellation up to 24 hours in advance and a reserve now, pay later option, it’s an ideal choice for a relaxed and elevated evening on the water.
Don’t forget to bring a sweatshirt, sunglasses, and a camera to capture the stunning sunset.
Read our full review: Key West Wind and Wine Sunset Sail Aboard Classic Schooner Review
Book now: Check availability
Stock Island Wind & Wine Sunset Sail Aboard Classic Schooner
A classic Key West schooner awaits you for an unforgettable 2-hour sunset sail along the picturesque Stock Island coastline.
Rated one of the top two sunset sails in North America, this nightly experience offers premium wine, craft beers, and gourmet hors-d’oeuvres.
Depart from the Perry Hotel & Marina, where you’ll be escorted to the boat in slip J5 after checking in at the nearby Bad Boy Taqueria & Tequila.
Relax and soak up the stunning views as the sun dips below the horizon.
With free cancellation up to 24 hours prior, you can reserve your spot now and pay later for this unbeatable Key West wine tour.
Read our full review: Stock Island Wind & Wine Sunset Sail Aboard Classic Schooner Review
Book now: Check availability
Key Wests Schooner Appledore Star Champagne Sunset Sail
As the sun begins to dip below the horizon, step aboard the majestic 2-masted schooner Appledore Star for an unforgettable champagne sunset sail in Key West.
Priced from $2,571 per person, this 2-hour English-language tour includes a live guide and free cancellation up to 24 hours in advance.
Enjoy spacious decks, participate in sailing, and savor a chef’s selection of gourmet hors d’oeuvres and unlimited champagne, wine, beer, and soft drinks.
You’ll take in iconic views of Mallory Square’s Sunset Celebration, Navy Mole, and Fort Zachary Taylor as the experienced captain positions the schooner for the best sunset views.
Don’t forget to bring a valid ID for alcohol consumption.
Read our full review: Key Wests Schooner Appledore Star Champagne Sunset Sail Review
Book now: Check availability
Key West: Catamaran Champagne Sunset Sail
Set out on a captivating 1.5-hour champagne sunset sail aboard a spacious 60-foot catamaran departing from the Key West Historic Seaport.
Arrive 30 minutes early to the local partner’s office on Lazy Way Lane.
Enjoy breathtaking views of iconic landmarks like Mallory Square and Fort Zachary Taylor as you toast with unlimited beverages, including wines, beer, champagne, sangria, water, and soft drinks.
The experienced captain positions the boat for optimal sunset viewing, and two marine heads are available onboard.
With an overall rating of 4.7/5 from previous travelers, this activity offers a comfortable setting for gathering with friends and family while experiencing Key West’s stunning sunset.
Read our full review: Key West: Catamaran Champagne Sunset Sail Review
Book now: Check availability
Frequently Asked Questions
Can I Bring My Own Wine or Alcohol on the Tour?
No, you can’t bring your own wine or alcohol on the tour. Most wine tour companies have strict policies prohibiting outside beverages to ensure the safety and enjoyment of all participants. Check with the specific tour provider for their exact rules.
Do the Tours Provide Transportation to and From the Departure Location?
Most wine tours provide transportation to and from the departure location. They’ll typically pick you up from your hotel or a central meeting point, so you don’t have to worry about driving. This makes the experience more convenient and enjoyable.
Are There Discounts Available for Locals or Military Members?
Many wine tour operators offer discounts for locals and military members. Check with the specific company to see if they have any special offers or reduced rates available. These discounts can help make the tour more affordable.
Can I Request a Specific Seating or Viewing Location on the Boat?
Yes, you can request a specific seating or viewing location on the boat. Many wine tour operators offer this option, allowing you to choose the best spot to enjoy the scenic sights during your excursion.
Do the Tours Accommodate Dietary Restrictions or Food Allergies?
Yes, the tours typically accommodate dietary restrictions or food allergies. You’ll want to let the tour operator know about any special needs when you book your trip so they can make the necessary arrangements.
The Sum Up
You’ve got plenty of options for wine-fueled sunset sails in Key West. Whether you prefer a small-group cruise, a private sail, or a champagne-filled celebration, you can find the perfect wine tour to suit your taste. Just choose the one that fits your budget and vibe, and get ready to soak up the stunning Florida sunset with a glass of your favorite vintage in hand.