Helicopter Rides, Parasailing and Skydiving in the Florida Keys

As relaxing as the Florida Keys and Key West are, there is also an extreme side to island life, from floating hundreds of feet in the air for remarkable aerial views to plunging 90 feet below the sea for a look at depths unknown. Experience phenomenal helicopter tours, parasailing and skydiving in the Florida Keys with our quick guide to extreme adventures.

For Extreme Adventures, please select an island location:

Key Largo

Key West

Key Largo
Caribbean Parasailing

There is nothing quite as exciting as the chance to fly. When you go on a parasailing adventure, you have the chance to fly with the birds and see the Florida Keys from their vantage point.

Location: Hilton of Key Largo
Cost: Single – $70
Times Offered: Departs hourly from 10:30 – 4:00
Duration: 15 minutes
Activity Level: High


Marathon offers the ultimate Extreme Adventures with a real Jet Fighter Ride over the Middle Keys or Jump out of an airplane during the “Keys Boogie” skydiving in Florida event. Cruise low and slow over the clear shallow waters along the Marine Sanctuary Coral Reef and see sharks and a multitude of sea life activity. Add Extreme to your list of FUN!
Helicopter Tours of the Florida Keys
Welcome! Soar through the clouds and above the technicolor tides for a true bird’s-eye view of the Florida Keys. A variety of Florida helicopter rides to some of the most scenic locations in the archipelago are available.

Location: Marathon Airport MM 52
6 – 60 -minute tours packages available
Photo flights
Charters available
Times Offered: Daily tours by reservation or Walk Ins Welcome
Activity Level: Medium

Request Reservation or more information

Keys Boogie Skydiving Fest – Nov. 9-12
With water stretching as far as the eye can see, skydiving in the Florida Keys is a unique adventure offering a perfect birds-eye view of the island chain. And during the ninth annual Keys Boogie Skydiving Fest, the experience becomes even more exceptional with a Super Otter, Twin Otter, Pac 750 and helicopter set to carry jumpers aloft. The helicopter jump is truly unique because it gives skydivers the true sensation of falling straight down, rather than “flying” from a moving airplane. Tandem and single jumps are available with landings scheduled for Sombrero Beach in Marathon.

Location: Marathon
Cost: Until Oct. 15 (prices to rise after Oct. 15)
$45 registration fee per person
$65 registration fee plus event T-shirt, per person
Jump tickets available separately
Times Offered: Nov. 9-12
Activity Level: High
Requirements: A C license and flotation device are required of all skydivers.

Request Reservation or more information

Tropical Fighters
Boasting a colorful military history, the Florida Keys offers visitors a chance to bring history to life – flying high above the islands in a fighter jet. Whether an experienced pilot or a first-timer, thrills are guaranteed as FAA-certified flight instructors demonstrate aerobatics, combat maneuvers and customized instruction in modern air-conditioned, pressurized Fighter Jets.

Location: Marathon Airport
Cost: Starting at $950.00
Times offered: Tuesday – Saturday, 8AM – 5PM. Reservations required.
Activity Level: High

Request Reservation or more information

Conch Air
You will enjoy the open air exhilaration in a luxurious classic Waco Bi-plane. This 1935 designed and FAA certified plane has recently re-entered production with many modern improvements for safety, comfort and ease of communication. Her beautiful lines and great flying qualities, with the capability to carry a pilot and two passengers in a leather wrapped open cockpit, allow you and a friend to enjoy flying in a way that lured thousands to become pilots.

Location: Marathon Airport, MM 52 bayside
Cost: Scenic Flights begin at $74 per person, based on 2 passengers
Activity Level: High

Request Reservation or more information

Key West

Experience flying like a bird while Parasailing above the crystal clear water surrounding Key West. Taking a sightseeing ride on a Float Plane to the Dry Tortugas is an excellent Adventure for the day.

Dry Tortugas Sea Plan Trip – Sea Planes of Key West
A unique seaplane adventure featuring low altitude sightseeing, marine life, snorkeling, history, bird spotting, white beaches and more. Morning, Afternoon and full day tours.

Location: Key West International Airport
Cost: Adults – $199 per person; 12 & under – $149 per person; 6 & under – $119 per person
Times Offered: 8AM, 10AM, 12PM, 2PM
Duration: 4 hours
Activity Level: Easy

Request Reservation or more information

Parasail Ride – Key West Water Tours
Experience a view of Key West that can only be seen from the air by parasail. You may also see a wide array of marine life such as dolphins, manta rays and living coral patch reefs.

Location: Hurricane Hole Marina (Stock Island)
Cost: Single – $65; Double – $85
Times Offered: Daylight Hours (beginning at 9AM)
Duration: 15-30 minutes
Activity Level: High

Request Reservation or more information

Contact Us

"Stay" Safe with KeysCaribbean - Information about what we are doing to Help Slow the Spread of COVID-19

We’re preparing for a safe re-opening soon (June 1st is our goal date) with additional measures to keep you, your family, our employees, and contractors as safe as possible during your return to our Florida Keys paradise.

1. As recommended by the CDC’s social distancing guidelines, guests shall be advised to practice physical distancing by standing at least six feet away from other groups of people not traveling with them, including any area where guests or employees queue.

2. During all times in which the usage of masks/face coverings is recommended by the CDC and/or other local health authorities guests and employees or contractor will be required to wear a mask/face covering if unable to maintain 6 ft distance or inside of any building other than the guests rented space.

3. Contactless Check-In. Pre-arrival instructions including a digital door lock code will be emailed to each guest prior to arrival. No need to meet anyone face-to-face before entering the rental space.

4. If not wearing protective gloves, all employees shall follow CDC guidance regarding hand-washing. Employees shall wash their hands for at least 20 seconds, or use sanitizer when a sink is not available, after any of the following activities: using the restroom, sneezing, touching the face, cleaning, smoking, eating, drinking, accepting items from a guest, taking a break, and before a shift and as needed throughout the shift. When possible, employees shall wear gloves for added protection
and sanitation efforts. Proper hand hygiene, in accordance with CDC guidelines, should be followed prior to and after removing the gloves.

5. Cleaning products and protocols shall include EPA-approved disinfectants that meet CDC requirements for use and effectiveness against viruses, bacteria and other airborne and bloodborne pathogens.

6. ULV Fogging between guest stays with EPA-approved, non-toxic disinfectants that meet CDC requirements for use and effectiveness against viruses, bacteria and other airborne and bloodborne pathogens. ULV fogging will also be concentrated on non-removable bedding in each rental space.

7. In anticipation of individual concerns of guests, housekeeping shall not enter a guest room during a stay unless specifically requested, or approved, by the guest, or to comply with established safety protocols. Housekeeping shall maintain the practice of cleaning rooms thoroughly following check-out.

8. Professionally laundered linens and towels with the warmest allowable temperature so as not to degrade the quality of the product.

9. Non-emergency maintenance issues will be scheduled after guest departure to reduce contact risks for both our guests and our contractors. If assistance is needed during your stay we will ask for permission to enter the rental space to conduct necessary repairs as timely as we possibly can, however, please keep in mind delays could occur as our contractors do provide services to others outside of KeysCaribbean.