Recent Searches
Clear

Top Key West Wine Tastings

Saved to wishlist!
Dates
Select Dates
Food Tours
Food Tours
Sailing
Sailing
Cruises & Sailing
Cruises & Sailing
On the Water
On the Water
Culinary & Gourmet Tour
Culinary & Gourmet Tour
Beer & Brewery Tours
Beer & Brewery Tours
Cultural Tours
Cultural Tours
Walking Tours
Walking Tours
Likely To Sell Out
Likely To Sell Out
Half-day Tours
Half-day Tours
Street Food Tours
Street Food Tours
Ghost & Vampire Tours
Ghost & Vampire Tours
Pub Tours
Pub Tours
When are you traveling?
Select Dates
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
Search tours and activities you can do from home.

You are viewing Virtual Experiences in Key West. See more Virtual Experiences around the globe. 🌎

Price
$0
$500+
Duration
Time of Day
RatingClear
Specials

13 results | All Key West Tours

Sort by: Featured

Key West Southernmost Food and Cultural Walking Tour

Key West Southernmost Food and Cultural Walking Tour

star-5
581
Eat your way around Key West on this food tour with a guide who introduces you to 'mom and pop' eateries in the Old Town historic district. Taste seafood, Cuban cuisine, and, of course, key lime pie. The walking tour route takes you off typical touristy streets so you can see Key West like a local, listening to insights about the city's food, architecture, and history along the way. Tastings are enough for a hearty lunch.
More
  • 3 hours
  • Free Cancellation
From
$88.68
From
$88.68

Key West Historic Seaport Food Tasting and Cultural Walking Tour
Likely to Sell OutLikely to Sell Out

Key West Historic Seaport Food Tasting and Cultural Walking Tour

star-5
277
Taste your way through Key West's Historic Seaport on a gourmet walking tour with a local guide. You'll stroll from the beach and docks into some of the most colorful neighborhoods in Key West, pausing to sample locally-caught fish tacos, Key West pink shrimp, spiny lobster, or other just-as-delicious non-seafood options, learning about Key West history along the way. Don't forget to save room for a refreshing glass of white wine and our famous key lime pie! Exploring Key West on foot is an ideal way to soak up the vibrant atmosphere, and group size is limited to 10 people to ensure personal service from your guide.
More
  • 3 hours
  • Free Cancellation
From
$88.68
From
$88.68

Key West Craft Cocktail Crawl

Key West Craft Cocktail Crawl

star-5
157
Explore Key West through the eyes of a local on a craft cocktail tour that stops at five off–the–beaten–path establishments, from a historic mansion to a boutique hotel that was once a hospital. In addition to navigating for you, your guide uses the city’s bar scene to give you an overview of its history and culture. The tour includes five craft cocktails and two gourmet food tastings.
More
  • 3 hours
  • Free Cancellation
From
$93.68
From
$93.68

Key West Pub Crawl

Key West Pub Crawl

star-4.5
175
Get ready to party in paradise on this guided, 2.5-hour Key West pub crawl. The beautiful island city of Key West is famous for its raucous bar scene. Visit some of its most popular and entertaining establishments, beginning downtown and then traveling to the historic seaport and back to busy Duval Street. Enjoy a domestic beer or mixed drink at each of the five locations and receive a free souvenir t-shirt to commemorate the event. Guests must be at least 21 years old to participate.
More
  • 2 hours 30 minutes
  • Free Cancellation
From
$37.57
From
$37.57

Key West Haunted Pub Crawl and Ghost Tour

Key West Haunted Pub Crawl and Ghost Tour

star-4
189
Experience Key West’s dark side on this fun yet frightening haunted bar crawl. Hear tales of known paranormal activity from your local guide and visit the most eerie bars in Old Town Key West – located in two haunted mansions and repurposed morgue. By the end of the 2‐hour tour, you’ll see ‘Bone Island’ in a different (and profoundly spookier) light.
More
  • 2 hours
  • Free Cancellation
From
$26.82
From
$26.82

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
Likely to Sell OutLikely to Sell Out

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

star-4.5
1187
Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.
More
  • 2 hours
  • Free Cancellation
From
$89.95
From
$89.95

Key West Ghost and Mysteries Guided Tour

Key West Ghost and Mysteries Guided Tour

star-4.5
824
Discover the spooky side to one of the country's most haunted cities on a 90-minute walking tour. Listen to hair-raising local legends as you follow your guide down the hidden alley's of Key West. See where Robert the Doll lived, learn about Count Von Cosel, and keep your eyes peeled for the ghost at La Concha. Learn how to attract spirit activity with dowsing rods and how to capture it with your camera.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$32.26
From
$32.26

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar
Likely to Sell OutLikely to Sell Out

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar

star-5
258
Enjoy the sunset from the water on this Key West cruise aboard a classic schooner. As you stand on the deck of the tall ship, pass by sights such as Mallory Square with its Sunset Celebration and the Navy Mole, where big ships dock. Hors d'oeuvres and unlimited drinks are included onboard. Take your pick of beer, wine, sparkling wine, cocktails, soda, and homemade tropical sangria.
More
  • 2 hours
  • Free Cancellation
From
$99.95
From
$99.95

Key West Sunset Cruise with Live Island Music

Key West Sunset Cruise with Live Island Music

star-4.5
536
Jam to island beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Unlimited drinks and appetizers included; multiple departure times available to suit your schedule.
More
  • 2 hours
  • Free Cancellation
From
$85.07
From
$85.07

Key West Sunset Champagne Catamaran Cruise
Likely to Sell OutLikely to Sell Out

Key West Sunset Champagne Catamaran Cruise

star-4.5
342
Experience a sunset you’ll never forget on this 2-hour catamaran cruise in Key West. Sip on your choice of wine, champagne, beer or sangria as you watch the sun go down over the water. As you sail you’ll catch glimpses of the island and marvel at the views from the turquoise water. Cocktails are also available at a cash bar on board.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$51.95
From
$51.95

Key West Florida Reef Half-Day Snorkeling Excursion

Key West Florida Reef Half-Day Snorkeling Excursion

star-4.5
724
Enjoy an afternoon of swimming and snorkeling on this cruise off the coast of Key West. Spend a relaxing afternoon on a 69-foot catamaran headed to North America's only living coral barrier reef for the adventure of a lifetime. Pass some of Key West’s top attractions on the way, then dive right in to see more than 600 species of colorful fish, coral, and other sea life. This cruise includes professional snorkeling gear and instruction plus beer, wine, and soft drinks.
More
  • 3 hours
  • Free Cancellation
From
$45.95
From
$45.95

Key West Historic Homes and Island History - Small Group Walking Tour
Likely to Sell OutLikely to Sell Out

Key West Historic Homes and Island History - Small Group Walking Tour

star-5
98
Key West is home to many unique architectural landmarks and historic homes. Rather than wandering around alone, you can learn the fascinating stories of each by taking a guided tour. This small-group walking tour provides in-depth insights into the people and places of historic Key West.
More
  • 2 hours
  • Free Cancellation
From
$45.00
From
$45.00

Private 2-Hour Wind and Wine Sunset Sail in Key West

Private 2-Hour Wind and Wine Sunset Sail in Key West

star-5
23
This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There will be hors d'oeuvres passed around throughout the trip. A great way to have a private sail with your friends, family, or co-workers.
More
  • 2 hours
From
$2,299.00
per group
From
$2,299.00
per group

Filters

What people are saying about Wine Tastings in Key West

star-5
Key West Southernmost Food and Cultural Walking Tour
"Great tour! Meredith was very knowledgeable and interesting! We saw some interesting places and tried some yummy foods."..."
star-5
Key West Historic Seaport Food Tasting and Cultural Walking Tour
"The background on the area was very interesting. Meredith was incredible in her knowledge and caring. The food was great!"..."
star-5
Key West Craft Cocktail Crawl
"So much fun! This tour gives you the opportunity to get off of Duval street and get a great drink! Max was an awesome tour, 100% would recommend this!"..."
star-5
Key West Pub Crawl
"Our tour guide Mike did a great job sharing some of the interesting stories about locations and history. Great Job!!"..."
star-5
Key West Haunted Pub Crawl and Ghost Tour
"JD was an excellent tour guide, funny, animated and an excellent story teller. My family loved the haunted pub crawl!"..."
star-5
Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
"Being able to enjoy the adventure with my loved one. Good Food, Drink and entertainment. Would recommend this trip to anyone."..."
star-5
Key West Ghost and Mysteries Guided Tour
"My husband and I had a great time! Our tour guide was an excellent storyteller, and we were completely engaged. I liked the focus on history! I would highly recommend this to anyone interested in ghosts."..."
star-5
Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar
"Service was excellent, Sunset was wonderful, and Sail boat very clean and comfortable We will come back!! loved it !!"..."
star-5
Key West Sunset Cruise with Live Island Music
"What an amazing night. Loved the staff, the unlimited drinks, the food and the band. We lucked out and had an beautiful sunset. We had so much fun and cannot wait to return. Highly recommend ❀"..."
star-5
Key West Sunset Champagne Catamaran Cruise
"We sailed into the evening with a beautiful sunset. The crew was very attentive. Plenty of space on the sailboat."..."
star-5
Key West Florida Reef Half-Day Snorkeling Excursion
"Well organized crew Excellent but unobtrusive service (loved getting beers brought to us on the deck) The snorkeling was good but not great but only 50 yards or so from anchorage"..."
star-5
Key West Historic Homes and Island History - Small Group Walking Tour
"Loved learning more about KW architecture and hearing stories about the history of the homes and their historic inhabitants. Our guide, Richard, an old conch, was very interesting."..."

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Wine Tastings in Key West?
Q:
What Wine Tastings in Key West are taking additional safety precautions?
Q:
What Wine Tastings in Key West are good for avoiding crowds?