This great Key West Day Trip includes a narrated tour of the scenic Overseas Highway and a thrilling parasailing flight above the blue waters of Key West.
Get free Pickup and Drop off at Downtown Miami & Miami Beach hotels
Ride down the incredible Overseas Highway
Enjoy a narrated tour of the Florida Keys
Cruise offshore for an exciting parasailing flight
Spend the afternoon enjoying tropical Key West
Go above and beyond the ordinary Miami to Key West Day Trip – add a Key West parasailing adventure to your visit to exciting Key West. This Key West tour combines sightseeing along the amazing Overseas Highway with a fun afternoon in tropical Key West, and the highlight of the day is a thrilling Key West parasailing flight 300 feet above the clear island waters.
Fast online booking with Cool Key West and convenient free pickup and drop-off service from most hotels in Sunny Isles Beach, Miami Beach, and Downtown Miami make this Key West day trip an easy 1-day escape from the city. It’s a different world down south in the Florida Keys, and you don’t want to miss the incredible views along the Overseas Highway or the Caribbean vibe of tropical Key West. Put some shopping, dining, and partying in the island city together with an adrenaline-pumping parasailing flight and you have an unforgettable adventure.
A complete tour of the Florida Keys is an essential part of any Miami vacation, and there is no better way to see the Keys than through the panoramic windows of a luxury touring coach piloted by a skilled professional. Riding in air-conditioned comfort without the stress of driving allows full appreciation of the scenic road trip down the Overseas Highway to Key West, renowned as one of America’s top sightseeing routes. A high-definition audio narration provides historical background and explains modern points of interest as the coach makes its way through one of the world’s foremost tropical marine wonderlands.
After crossing from the mainland to Key Largo, the U.S. Highway 1 becomes the famous Overseas Highway and passes over the entire string of narrow islands that make up the Florida Keys chain. The sightseeing is spectacular, with the roadway surrounded by emerald and turquoise waters. The coach crosses 31 Keys linked by over 40 bridges, including the spectacular Seven Mile Bridge. This engineering marvel jumps off from Knights Key at the western tip of Marathon Key and soars over 6.79 miles of open water. You will feel like the coach is flying over the water, and the views are so incredible that the Seven Mile Bridge is often used as a backdrop in action movies like True Lies and the Fast and Furious series.
Gliding off the Seven Mile Bridge onto Little Duck Key, the coach enters the Lower Keys. On this part of the journey, natural islands are set among broad bays and winding channels, lush foliage crowds the road, and small towns, marinas, and historic fishing camps recall times when life in the Keys was slower and simpler. Natural reserves that encompass land and water have preserved much of the original beauty of the Lower Florida Keys, and it is all on display during this epic tour.
Scheduled arrival in Key West is around 12:00 pm, and you have plenty of time to get down to the docks and check in for your parasailing flight. After a short run offshore in a specially-equipped 12-passenger parasailing boat, the excitement begins as intrepid fliers get harnessed in, step onto the launch platform, and soar gracefully into the air behind the boat without getting wet at all.
Rising up to nearly 300 feet, it impossible not to be inspired by amazing 360-degree panoramas of land and sea as the parasail glides through the sky with perfect safety and ease. The views of Key West are astounding and if your eyes are sharp, you may spot dolphins or other marine life below. It is awesome to feel the rush of ascending and descending under the canopy, and the landing back on the platform is gentle and dry. But if you would like to cool off in the water, just ask the captain for a toe dip!
When the parasailing session ends, the boat returns to shore and you have some time left over to enjoy Key West. Explore the streets of Old Town, check out the many excellent dining options, and step into one of the legendary Key West bars and lift a toast to high adventure. Enjoy a drink knowing that you can rest on the homeward journey while the coach returns you safely to Miami by about 10:00pm.
The Miami to Key West Day Trip with Parasailing delivers 3 great Florida attractions that should not be missed: an Overseas Highway tour, an afternoon in Key West, and a thrilling parasailing flight. Take advantage of our 100% secure online booking system to reserve your spot now!
Reservations are REQUIRED for all bookings
Book Your Package On-Line and Receive Your Confirmation
Departure point: Detailed check-in instructions - including address, Google map, and parking information - will be included in your final confirmation email.
Duration: 6 Hours in Key West
Check-in time: Must be there by 7:15 am to check-in, boarding time will be at 7:40 am.
Round trip transportation from Miami
6 hours in Key West
A narrated tour of the Florida Keys
Awesome parasailing flight - see Key West safely from the air!
What To Bring
Confirmation Voucher (printed or mobile)
Any required or suggested items listed on your confirmation email.
Hotel pick-up is offered for this tour. Note: if you are booking within 24 hours of the tour/activity departure time, we cannot guarantee hotel pick-up. Once your purchase is complete, we will send you complete contact information (phone number, email address, etc.) for our local operator to organize pick-up arrangements.
Likely To Sell Out
Spaces are extremely limited this time of year so book early to ensure the date you want.
Voucher Confirmation Info
This tour accepts both printed and electronic vouchers (e-vouchers). You can either print the voucher and present a paper copy on the day of travel. Or, if you travel with a mobile device, simply show your Photo ID and present your voucher on your Smartphone or tablet on the day of travel.
Local Operator Information
Complete operator information, including local telephone number, will be included on your Confirmation Voucher.
You can cancel up to 24 hours in advance of the experience for a full refund.
For a full refund, you must cancel at least 24 hours before the experience’s start time.
If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
Any changes made less than 24 hours before the experience’s start time will not be accepted.
Cut-off times are based on the experience’s local time.
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Frequently Asked QuestionsFAQ
The answers provided below are based on answers previously given to customers' questions.
Will you take me back to my hotel after the tour?
Yes, after the tour, we will return you back to the hotel that we picked you up from. Cool Key West offers complimentary drop-off service to all hotels in Miami Beach and Downtown Miami.
Will you pick me up from my hotel?
Yes. Free pick-up is available from all hotels in South Beach, Miami Beach, and Downtown Miami.
Where is the meeting point for this activity?
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Miami to Key West Day Trip with Parasailing will be included in your confirmation email from Cool Key West. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Where can I park my car?
If required, parking instructions for the Miami to Key West Day Trip with Parasailing will be included in your confirmation email.
What is the weather cancellation policy?
If the Miami to Key West Day Trip with Parasailing must be canceled due to bad weather, and you cannot go on another day or time, you will be issued a refund by Cool Key West.
What is there to see in Key West?
You’ll have approximately 6 hours to explore Key West. Famous for its history, this tropical island is home to famous landmarks such as the Southernmost Point in the United States, Mel Fisher’s Treasure Hunting Museum, Ernest Hemingway’s House with the 6-toed cats, Fort Zachary Taylor, and a spooky above ground cemetery just to name a few. There’s also fun water activities, like snorkeling, a glass bottom boat ride, jet ski tours, and parasailing.
What happens if only my activity in Key West is cancelled?
On occasion, the activities in Key West will be canceled for bad weather. In those cases, you will be given a refund for the canceled part of your trip. Those refunds are as follows:
If Glass Bottom Boat Cruise is canceled due to weather you will be issued a $29 refund.
If Snorkeling Trip is canceled due to weather you will be issued a $29 refund.
If Parasailing is canceled due to weather you will be issued a $39 refund.
If Trolley is canceled due to weather you will be issued a $25 refund.
What are some good items to bring on the drive to Key West?
Here are some good things to bring to keep you comfortable on the trip: a smartphone, tablet computer, MP3 player, books, magazines, camera, snacks, sleeping shades, and a travel pillow.
Is there an age requirement for parasailing?
Yes, the minimum age to parasail is 6 years old. Participants under the age of 18 must have a parent or guardian sign their liability waiver prior to boarding the vessel. At Cool Key West safety is our number one priority. The minimum weight required for parasailing is roughly 90 pounds. If the flyer is less than 90 pounds, they will simply fly tandem with someone not to exceed roughly 450 pounds combined weight. Weight requirements may differ due to wind conditions.
How much free time do we have in Key West?
You’ll have approximately 6 hours to explore Key West at your leisure.
How long does it take to drive to Key West?
The road trip takes about 4 hours. Driving the Overseas Highway is a one-of-a-kind experience. You will see some of the most spectacular scenery in the State. You will literally be driving right over the ocean and across a thin chain of islands and bridges, including the famous 7-Mile Bridge. These bridges connect 34 islands that make up the Florida Keys.
How do people dress in Key West?
Key West is super casual. A sundress for ladies and khaki shorts for the gets is as dressed up as anyone usually gets.
Do you have to know how to swim in order to parasail?
Although it is best for you to be comfortable in the water, you do not have to know how to swim. Each guest is provided with a buoyancy compensator (BC) that will assist with flotation.
Do we stop on the way to Key West?
It depends. If passengers wish to take a break, we will stop at the McDonalds in Tavernier at approximately 9:00 AM. There is also a convince store and a grocery store in the same vicinity.
Can I bring luggage on the bus?
Yes, you may bring one piece of luggage and one carry on bag, per person.
Are there beaches in Key West?
There are several beaches in Key West, with the most popular being located at Fort Zachary Taylor State Park. Key West is a great watersports destination, so bring a bathing suit and sunscreen, if you plan to get wet.
Are there any weight restrictions for parasailing?
Minimum weight to fly alone is 90 lbs; not exceeding 450 lbs in tandem or triple (the captain may change these safety restrictions due to weather conditions).
Average 4.71 out of 5 stars based on 1642 verified reviews from Cool Key West and TripAdvisor
Petribe_R, May 2023 Verified
This was our first time going to Key West & it was a great time. We choose the package with snorkeling activity. The reef was very pretty and the amount of time out in the reef was great to explore the reef, get a tan and spend quality time with the girls. The margaritas that was provided on the boat were so good and they staff there made sure that no one had their cups empty the entire time. Very pleased with the entire trip. Would definitely recommend. It was a holiday weekend and there was a game playing that night so time management was at the forefront of everything.
Xiuwen_L, May 2023 Verified
It was our first time parasailing, great experience. I had Scotty and Maddie. Wonderful people! Would definitely go back
Ross_C, May 2023 Verified
It’s a long day but couldn’t recommend it highly enough - Tour guide was excellent and very informative, stopped for breakfast on the way and then got 6 hours in Key West before journey home. Great city!
Isela M, May 2023 Verified
Tour guides were very nice and informative I was picked up on time. Loved it. Definitely recommend for solo trip or family
yangxihua, May 2023 Verified
Totally enjoyed this tour. Lewis is a very good guide, every thing was well organised and very clear.
A550BUconnors, May 2023 Verified
Pick up was prompt, within ten minutes of the allocated time and right outside our hotel. The guide was very informative, telling us about the history of the Keys. The bus was comfy and had power outlets too, and there’s a stop for breakfast along the way in case you wish to buy some. We just had transport to Key West and had six whole hours to spend on arrival, which was more than enough time. Very central drop off location in Key West and easy to find to come back. We were dropped off at our South Beach hotel between 9-10 pm so it really is a full day out.
Rongen_Z, May 2023 Verified
Good communication. The guide David thoughtfully put us on another bus coming back since the lower level was too hot. Would recommend to others
Angela_F, May 2023 Verified
My most memorable was the trolley ride through the city and stop in to see all the different stores, ice cream parlor. Nice restaurants in the city and all the history behind Key West and some of it was tied in with my hometown Macon, Georgia.
Marina_T, May 2023 Verified
We loved our guide very informative and made sure everyone got to where they needed to be , the snorkelling was beautiful ! And Key West has such a vibe !!
priship2023, May 2023 Verified
The entire day trip to Key West was filled with amazing people and staff. Everything was on time and the staff on the bus (Lili) was incredibly sweet and helpful. Her instructions were super clear plus the staff on the boat when we went snorkeling was just super helpful and professional beyond my expectations. I personally panicked when I went inside the water and the life guard (not sure about the name) saw me struggle and he promptly reached towards me and offered to help. Even though I was very nervous, he went out of his way to calm me down and offered to help. Highly recommend booking this trip because for the price it is so much worth it. Hope this helps.
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