top Ratings in Key West
Top Things To Do In Key West For Columbus Day
Jet Ski Island Tour
Online Special From $139.95 $180
- Time: 9:30am, 11:30am, 1:30pm, 4:00pm
- Location: 2801 N. Roosevelt, Key West Florida
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1.5 Hour Tour, Brand New Jetskis, Rider On The Back Is FREE, FREE Shuttle Pick-up, 28 Mile Guided Tour, Over 4,000 5 Star Reviews For This Trip Alone!
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The best way to see Key West on your spring break. This action packed 1.5 hour guided tour around key west will take you to multiple historic stops and even to a secluded sandbar for a dip in the crystal clear waters. Voted Key West’s Best Jetski Tour.
Check In 45 Minutes Prior To Departure
Regulations: Riders under 18 must accompanied by a guardian. Must be 16 or older to drive a jetski.
Parasailing
Online Special From $55.95 $89.95
- Time: Daily 10am - 5pm
- Location: 201 Williams St, Key West Florida
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Highest & Longest Flights In Key West, Over 40 Years Of Key West Parasail Experience, Brand New Equipment, Most Fun You Can Have Parasailing Guaranteed, Lowest Prices In Key West.
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Key West’s most popular trip! We have been parasailing in Key West for over 40 years, longer than any other company. You won’t beat our parasailing trip or prices. We have multiple locations and 6 parasail boats. Come fly with Key West’s parasail experts.
Check In 45 Minutes Prior To Departure
Regulations: Riders under 18 must accompanied by a guardian.
Sunset Sail Booze Cruise w/Live Music, Appetizers & Open Well Bar
Online Special From $69.95 $89.95
- Time: 6pm
- Location: 201 Williams St, Key West Florida
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Appetizers, Live Music & Open Well Bar With Unlimited Draft Beer, Mixed Drinks, Margaritas, Rum Runners, Champagne, Wine & More. Key West’s Largest Sailing Catamaran Party!
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Key West’s Largest Sailing Spring Break Catamaran Party On The Sandie Cat. Includes great appetizers, live music and open well brand bar with draft beer, mixed well drinks, margaritas, rum runners, champagne, wine & more. You can’t beat this open well bar party on the water. The best booze cruise value in Key West.
Check In 45 Minutes Prior To Departure
Regulations: Riders under 18 must accompanied by a guardian. Must be 21 or older to consume alcohol.
COLUMBUS DAY WEEKEND
in KEY WEST 2026
The long weekend, October 9–12, is a great time for a Key West getaway. Restaurants, attractions, tours and watersports are open, with the Southernmost Half Marathon & 10K taking place Sunday, October 11. It’s also the weekend before Fantasy Fest begins, offering a chance to enjoy the island ahead of one of its busiest celebrations.
Get out on the water with Sunset Watersports for snorkeling, sandbar trips, parasailing, jet ski tours, dolphin watching and sunset cruises.
