Parasail from Smathers Beach with a 10–12 minute flight and up to 1 hour on the boat
Up to 1 hour
Up to 12 people
Safety equipment, 10–12 min flight
Parasail from Smathers Beach and take off and land right from the boat for sweeping views over Key West. Spend up to 1 hour on the water with an industry-leading 10–12 minute flight time.
Solo or tandem flights are determined on site based on weight distribution for safety.
Full refund with 24-hour notice of cancellation. Full refund if the operator cancels due to weather or other unforeseen circumstances. No-shows will be charged the full price.
Product ID: K38EHC
Solo, tandem, and triple flights are available, with final groupings decided on site based on weight distribution.
The parasail boats can take up to 12 passengers.
All takeoffs and landings are done directly from the boat.
1901 S. Roosevelt, Key West FL 33040
Smathers Beach stretches along the southern shore of Key West as the island's longest natural beach, a half-mile ribbon of imported sand fringed by swaying palms and the impossibly clear, shallow waters of the Atlantic. It is the launching point for one of the most exhilarating ways to experience the Florida Keys: soaring high above the turquoise shallows on a parasail. From the moment you step onto the soft sand at Smathers Beach, the horizon opens up in every direction, with calm blue water in front and the easy rhythm of Key West life behind. The protected, gently sloping waters off Smathers Beach make conditions ideal for parasailing, which is why this stretch of coast has become the go-to spot for visitors who want a thrill without the chop of open ocean.
The adventure begins with a short, scenic boat ride out from Smathers Beach, where the captain and crew guide you through the safety briefing and harness you in. As the line releases, you lift gently into the sky, climbing higher and higher until the entire shoreline of Smathers Beach unfurls below you like a postcard. From up there, the water glows in shifting shades of jade, aquamarine, and deep sapphire, and you can often spot sea turtles, rays, and schools of fish gliding through the shallows. The flight is surprisingly peaceful, just the whisper of the wind and a panoramic view of the Keys spreading out toward the reef.
This experience is perfect for couples chasing a romantic bucket-list moment, families with older kids ready for their first taste of flight, and travelers who want the iconic Key West memory without needing prior experience. Solo adventurers and friend groups love it too, since tandem and triple flights make it easy to share the rush. If you are looking for the signature view of Smathers Beach and the surrounding turquoise water, lifting off from the sand here turns an ordinary beach day into the highlight of your Key West trip.
Sunset Watersports offers a solid range of activities from parasailing and jet skiing to snorkeling trips and dinner cruises, with most visitors leaving genuinely impressed. The parasailing consistently gets rave reviews, with guests like Wyatt and various captains earning specific shoutouts for making the experience memorable and capturing great photos. The dinner cruises seem to be another winner, with Captain Kristen, Captain Logan, and others praised for their knowledge and service. People love the combination of sunset views, live music, cocktails, and the overall atmosphere. The snorkeling excursions also get strong marks, particularly when captains like Kristen find calm spots on the reef and crews like Kevin, Maggie, Helen, and McKenzie take time to explain everything thoroughly. That said, there are some hiccups worth noting. One detailed review painted a concerning picture of the water adventure park experience, citing inattentive staff more focused on their phones than guest safety, mediocre food (boiled hot dogs and chicken nuggets), and a snorkeling setup that felt underwhelming. Another guest had a truly disappointing sunset sail where the crew couldn't even get the sail up, leading to an hour spent circling near the dock with static-filled music and subpar food and drinks. While these negative experiences seem to be outliers given the overwhelmingly positive feedback, they suggest consistency can vary depending on which activity you book and which crew you get. The jet skiing and parasailing appear to be the safest bets if you're trying to decide what to book.
Hubby and I experienced Key West like never before aboard The Sandie Cat for a luxury catamaran sunset sail. The beautiful sunset and tropical views were only part of the experience. The cruise included great appetizers and an unlimited open bar offering rum runners, margaritas, mixed drinks, draft beer, wine, champagne and soft drinks. The staff was extremely accommodating, and the DJ was excellent—keeping the music going and encouraging guests to dance throughout the catamaran. I did so much dancing that I probably should have brought a tip box! 🤣💃🏾 Captain Ana was equally impressive. We stayed to watch her dock the catamaran and were amazed by her precision and skill. My husband has been an aanother platform and boater throughout his life, so he understands the expertise required to safely maneuver a vessel of that size. He made a point of personally commending Captain Ana on a job exceptionally well done. From the attentive staff and energetic DJ to the appetizers, unlimited cocktails and excellent captain, the entire experience was enjoyable and well executed. We captured wonderful photos, made great memories and would absolutely recommend The Sunset Motorsports Key West Sandie Cat sunset sail to anyone looking for a memorable way to experience Key West from the water.
Arleen Davis-Slagle
September 1, 2026
Hubby and I experienced Key West like never before aboard The Sandie Cat for a luxury catamaran sunset sail. The beautiful sunset and tropical views were only part of the experience. The cruise included great appetizers and an unlimited open bar offering rum runners, margaritas, mixed drinks, draft beer, wine, champagne and soft drinks. The staff was extremely accommodating, and the DJ was excellent—keeping the music going and encouraging guests to dance throughout the catamaran. I did so much dancing that I probably should have brought a tip box! 🤣💃🏾 Captain Ana was equally impressive. We stayed to watch her dock the catamaran and were amazed by her precision and skill. My husband has been an aanother platform and boater throughout his life, so he understands the expertise required to safely maneuver a vessel of that size. He made a point of personally commending Captain Ana on a job exceptionally well done. From the attentive staff and energetic DJ to the appetizers, unlimited cocktails and excellent captain, the entire experience was enjoyable and well executed. We captured wonderful photos, made great memories and would absolutely recommend The Sunset Motorsports Key West Sandie Cat sunset sail to anyone looking for a memorable way to experience Key West from the water.
Arleen Davis-Slagle
September 1, 2026
Ride a jet ski around Key West with 5–6 scenic stops and a free shuttle
Enjoy a high-flying 10–12 minute parasail ride with sweeping views of Key West
Snorkel Key West’s vibrant reef aboard a fast catamaran with breakfast and post-trip drinks.
Captain a two-person boat to secluded sandbars and mangrove islands.
Swim at a secluded sandbar and watch playful wild dolphins up close, with lunch and unlimited beer and wine included.
Paddle mangrove tunnels then relax on a secluded sandbar with lunch and unlimited drinks