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Things to Do in Key West in October

jet ski in Key West

Key West is a unique place with a lively culture and vibe that marches to the beat of its own drum. This rings especially true during the fall. While visitors to other vacation destinations around the United States begin wearing scarves and drinking pumpkin spice lattes, visitors to Key West can enjoy watersports, outdoor festivals and other island pursuits that are typically associated with summer. Read our guide of things to do in Key West during October to experience this one-of-a-kind tropical paradise.

Wine and Dine Your Taste Buds

September 16 – October 16

Trade in your bathing suit and flip flops for a cocktail dress and heels during the annual WineDine KeyWest event. Enjoy the gourmet side of paradise without breaking the bank as you sample three-course prix-fixe menus at select fine dining restaurants. At $20 for lunch and $35 for dinner, the hardest part will be choosing which wine to pair with your appetizer.
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Double the Fun for the Price of One

Offer valid through October 15, 2016

Grab a sightseeing, history-loving partner for Historic Tours of America’s Key West BOGO offer. This special buy one, get one free vacation package includes a ride aboard the Conch Tour Train plus admission to Truman Little White House, Key West Aquarium and Key West Shipwreck Treasure Museum. Experience the best of Key West with The Nation’s Storyteller.
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Not Your Average Walk Along the Beach

October 6-9

Lace up your running shoes and grab an extra sweat towel, it’s time for the Southernmost Marathon & Half Marathon on October 8. And for those looking to put a little less mileage on their shoes, there’s also the Salute! 10K and 5K on October 9. Choose your distance, then hit the ground running on this fast and flat course. Don’t forget to wander around the expo during packet pickup on October 6 and 7.
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Get the Mustard Sauce Ready!

October 15

October marks a very special, and delicious, month in the Florida Keys. It’s the opening of stone crab season and all of the crustacean’s tasty goodness. The Florida Keys are a gold mine as about 40 percent of Florida’s stone crab harvest will come from these waters. Seafood lovers can enjoy the famed stone crab claws for the next seven months.

SUP, Competitor?

October 16

Whether you’re a paddling pro or you just enjoy a sunny day on the water, make your way to the Stand Up Paddle Invitational. The 2-mile paddle board and beach obstacle course is open for all skill levels and supports the Special Olympics Florida – Monroe County organization. Race entry includes a t-shirt plus it sponsors one Special Olympics Florida SUP athlete during race weekend. All events are located on Higgs Beach. Don’t have a paddle board but still want to participate? Lazy Dog will be renting boards at $10 each.
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Burn Calories for Halloween Candy

October 16

By this point in the month, Halloween candy is everywhere and your sweet tooth is aching. Burn off a few extra calories at the Halloween Half Marathon & 5K to make room for an extra chocolatey treat. All participants will receive a race medal and entry to the awards party at Schooner Wharf Bar. Costumes are welcome and a fun time is required!
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See Key West from Every Angle

Offer valid through January 31, 2017

It may be approaching the holiday season, but that doesn’t mean it’s time to pack away your beach gear. Join us for an epic adventure on the waters of Key West as we rev our engines for a Jet Ski Tour around the island. And for a limited time, purchase the Fury 360 package and experience Key West like never before. Included are a double rider Jet Ski Tour plus your choice of one or two additional trips for two people. Trip selections include Glass Bottom Boat or Glass Bottom Boat Sunset Combo, Parasail, Morning Snorkel, Double Dip Snorkel, Rum & Reggae snorkel and sunset combo and Reefs & Ritas afternoon snorkel. Pack the fun into one day or separate days to better fit your schedule. Either way, this is sure to be a check off the bucket list!
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Trick or Treat Key West Style

October 21-30

Who said you’re too old to dress up for Halloween? Certainly not a resident of Key West. The island’s premier, and perhaps most famous, annual event returns with even more festive flair. Get ready for 10 days of parades, adult beverages and shenanigans. Put on your best Halloween attire and leave the little ones at home for an adults’ night out (or week).
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Celebrate the Culture of Bahama Village

October 21-22

While the week-long party is for adults, Goombay Festival is for the families. Head over to Bahama Village for a street party celebrating island arts, crafts, music and food. Live entertainment will take place on stage at the corner of Petronia Street and Fort Street. Join either night for free.

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Dolphin Watch Eco Tour Eco Tour • Backcountry Snorkel
  • 9:00am, 12:00pm
  • 2.5 hrs
  • low
  • Beverages
Save 10% $67.46 Reg. $74.95
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Dolphin Watch Sunset Cruise Combo Eco Tour • Backcountry Snorkel • Sunset
  • 3:00pm
  • 3 hrs
  • low
  • Beverages
Save 10% $67.46 Reg. $74.95
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Double Dip Snorkel Sunset Combo Snorkel 2 Reef Locations
  • 3:45pm
  • 3 hrs
  • moderate
  • Beverages
Save 10% $44.95 Reg. $49.95
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Double Dip Snorkel Trip Snorkel 2 Reef Locations
  • 9:00am, 12:30pm
  • 3 hrs
  • moderate
  • Beverages
Starting at $36.85 Reg. $40.95
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Special Offer for Trips Taken Now Through Dec. 19, 2016*
Glass Bottom Boat & Sunset Cruise Special Offer
  • 4:00pm
  • 2 hrs
  • low
  • Snack Bar
Save 17% $40.95 Reg. $47.95
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Island Adventure & Sunset Cruise Combo Eco Tour • Snorkel • Kayak • Paddleboard
  • 2:00pm
  • 4.5 hrs
  • moderate
  • Food & Beverages
Save 10% $98.95 Reg. $109.95
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Island Adventure Eco Tour Eco Tour • Snorkel • Kayak • Paddleboard
  • 9:00am
  • 4.5 hrs
  • moderate
  • Food & Beverages
Save 10% $89.95 Reg. $99.95
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Key West Parasailing Fly Two or Three at a Time
  • 1 hr
  • low
Save 10% $49.45 Reg. $54.95
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Key West Snorkeling Morning Reef Snorkel
  • 9:30am
  • 3 hrs
  • moderate
  • Beverages
Save 10% $36.85 Reg. $40.95
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Key West Sunset Cruise Sunset Cruise • Champagne
  • 5:00pm
  • 2 hrs
  • low
  • Beverages
Save 10% $35.95 Reg. $39.95
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Save Up To $15
Land and Sail Package Trolley Tour • Sunset Sail
  • low
$64.95 Reg. $80.40
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Save Up To $11
Land and Sea Package Trolley Tour • Glass Bottom Boat
  • low
$64.95 Reg. $76.40
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Reef & Ritas Snorkeling Trip Afternoon Reef Snorkel
  • 1:00pm
  • 3 hrs
  • moderate
  • Beverages
Save 10% $43.15 Reg. $47.95
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Rum & Reggae Afternoon Reef Snorkel • Sunset Sail
  • 4:00pm
  • 3 hrs
  • moderate
  • Beverages
Save 10% $44.95 Reg. $49.95
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Ultimate Express Jet Ski • Parasail • Mini Water Park • Banana Boat
  • 12:45pm
  • 3.5 hrs
  • moderate
  • Food & Beverages
Save 10% $107.95 Reg. $119.95
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