Key West Watersports Adventures – Lowest Prices!

Top Trips & Tours

Featuring The “Do It All”  Watersports Adventure

Guaranteed To Wear You Out!

12 Activities, 6 Hrs of Fun, 1 Low Price

Including jetskis, parasailing, snorkeling, banana boat rides & more. Includes grilled lunch and draft beer on the ride back. Book online & Save or give us a call today 855-378-6386. 

Sunset Watersports – Key West Watersports Tours and Activities

Popular Trips & Tours

Do It All Adventure with Parasailing

$149 $139 

  • 6 Hour Trip
  • 13 Activities
  • Grilled Lunch & Drinks


Dinner Cruise

$69 $59 

  • 2 Hr Trip
  • Live Music
  • Open Bar
  • Tropical Buffet


Jetski Tour

$140 $130 

  • 1.5/2 Hr Tour
  • Free 2nd Rider
  • Free Shuttle
  • 28 Mile Tour


Jetski Tour Special

$140 $119 

  • 9:30am & 5:30pm Only
  • 1.5/2 Hr Tour
  • Free Second Rider
  • Free Shuttle
  • 28 Mile Tour


Do It All Adventure

$139 $129 

  • 6 Hour Trip
  • 12 Activities
  • Grilled Lunch & Drinks



from $50 

  • Multiple Locations
  • Longest Flight Time
  • Amazing Beach Views
  • All New Equipment


Parasail 9am Special

from $45 

  • Longest Flight Time
  • Great Historic Views
  • All New Equipment

Sunset Sail Cruise

$59 $49 

  • 2 Hr Trip
  • Open Bar
  • Live Music
  • Great Appetizers


Rise & Reef  – Morning Snorkel Special

$45 $40 

  • 3 Hour Trip
  • Includes Breakfast
  • Brand New Snorkel Boat


Dip & Sip – Afternoon Snorkel

$49 $45 

  • 3 Hr Trip
  • Includes Open Bar
  • Brand New Snorkel Boat
  • Best Reef Snorkel


Dolphin Watch & Snorkel Combo

$74 $64 

  • 3 Hr Tour
  • Dolphin Watch
  • Reef Snorkel
  • Draft Beer


Sunset Cruise, Dolphin Watch & Reef Snorkel Triple Combo

$74 $64 

  • 3 Hr Tour
  • Dolphin Watch
  • Reef Snorkeling
  • Sunset Cruise with Beer


Safari Eco Excursion with Snorkel

$178 $168 

  • 2.5 Hour Trip
  • Captain Your Own Boat
  • Explore The Back-country
  • Go Where Locals Go


Boat Rentals

from $225 

  • Full & Half Day Rentals
  • Largest Selection 
  • Lowest Prices
  • Fishing, Pontoon Boats


Beach Pass with Parasailing

$89 $79 

  • All Day Rentals
  • Kayaks, Paddleboards
  • Parasail Ride
  • 28 Mile Tour


Golf Cart Rentals

from $90

  • FREE Shuttle Pick Up
  • 4 & 6 Passenger Carts
  • 3, 8 & 24 Hour Rentals
  • Brand New Golf Carts


About Us In

Key West, Florida – Sunset Watersports Trips, Rentals & Key West Water Adventures

Sunset Watersports is Key West’s origianl watersports company, establish in early 1984. Sunset Watersports has been family owned and operated since inception. Starting out on Smathers Beach as the first parasailing operation, not only in Key West but the United States. Since our origination in 1984, Sunset Watersports has consistently grown to continue to offer new and original watersports to our Key West locals and visitors alike.

Sunset Watersports is also the home of the World’s 1st ALL DAY WATERSPORTS ADVENTURE the “DO IT ALL.” Offering 13 different watersports activities for one low price.  Activites include waverunners, parasail, snorkeling, banana boat rides, paddle boards, windsurfing, hydro bikes, watersking, ice berg, giant inflatable slides, knee boards, kayaking and water trampoline.   This Key West adventure is GUARANTEED TO WEAR YOU OUT!

Our mission is to provide first class watersports activities at a reasonable price with first class service and equipment. Additionaly we strive to provide an atmosphere where our employees can advance and be part of the Key West community, raise families and give to those less fortunate. We believe that providing a fun filled, drug free atmosphere is essential to achieving the goal of good family values. Sunset Watersports Key West offers more watersports activities, trips and tours than any other Key West watersports Company and is the oldest existing Parasail company in the USA

A message from the Owner

We believe in respecting all races, genders and religions so that we may advance as one human family.  Welcome to Sunset Watersports Key West.
– Richard C. Welter President

KEY WEST SAFARI SPEED BOAT SNORKEL TOURS-be your own captain and drive a mini speed boat deep into the Florida Keys National Marine Sanctuary, walk along deserted beaches and snorkel in pristine waters off Key West. Our KEY WEST BOAT RENTALS are the Lowest Priced Boat Rentals in Key West and the largest selection of Key West Boat Rentals.

KEY WEST PARASAILING from 2 locations:
Parasail over beautiful Key West Smathers Beach located at 1901 South Roosevelt Blvd. and enjoy this spectacular view of our wonderful island.  Choose to parasail at the Key West Seaport located at 201 William St and you will get a first hand view of the Key West Harbor any location you choose to parasail in Key West will leave you a memorable experience of Key West ‘s best view.  

KEY WEST SUNSET CRUISE from the upper deck of the Party Cat is the best Sunset Cruise in Key West at the LOWEST PRICE KEY WEST DINNER CRUISE is the only Key West Dinner Cruise with an air conditioned main cabin offering a Key West Tropical food buffet, FREE Margaritas, Rum runners, Mixed drinks, beer, wine and champagne. This is the best valued Sunset Cruise in Key West.

KEY WEST WAVERUNNER/JETSKI TOURS AND RENTALS. Brand new waverunners at the lowest price in Key West. This Key West waverunner tour is 1 ½ hours long, be prepared for a thrilling fast paced tour as you go completely around Key West. Visit the Southernmost point, Sub Marine pits and stop at the Boca Chica sand bar for some free style riding. Follow your local guide around Key West on this 28 mile tour. The waverunner tours depart from 2801 North Roosevelt Blvd. (US 1) at the Parrot Key Resort. We do have hourly rentals as well.

Sunset Watersports has 2 locations on KEY WEST BEACHES.  One location Key West Beach Location is in front of the Sheraton Resort at 2001 South Roosevelt Blvd (A1A) on Smathers Beach Key West. Key West Beach Rentals are Hobie Cat Sailboats, Paddle boards, Kayaks, Windsurfing and chair and umbrellas rentals. Our 2nd Key West Smathers Beach is on the corner of South Roosevelt Blvd and Bertha St. the address is 1901 South Roosevelt Blvd on Smathers Beach Key West  This Smathers Beach location is the original Sunset Watersports location started back in 1984. This Key West Smathers Beach Location offers parasail rides, Hobie Cat Sailboats, Windsurfing, Paddle boards, Kayak rentals and chair and umbrella rentals.

The KEY WEST BEACH  PASS is the best way to spend the day on a Key West beach for one price. You get 1 parasail ride and unlimited Hobie Cat sailing, Windsurfing, Stand up Paddle Boards, Kayaks and Volleyball. There are 2 Key West Beaches to choose from, both Key West beach locations are on Smathers Beach located at 1901 South Roosevelt Blvd and in front of the Sheraton Resort at 2001 South Roosevelt Blvd (A1A) on Smathers Beach Key West.

Sunset Watersports KEY WEST SNORKEL Reef trip RISE AND REEF offers a lite breakfast as you Snorkel the only living coral reef in the US. This is a Key West Snorkel trip you should not miss. You will be whisked out to the Key West coral reef on a new state of the art Sailing catamaran boat. The friendly crew will instruct you to use the snorkel equipment and we have a safety line floating behind the boat for those that are less experienced. There are Snorkel vests and swim noodles to make you feel comfortable while you snorkel this magnificent coral reef. We also offers the afternoon SIP AND SAIL where you will snorkel the coral reef and enjoy a cold beer and soda on the way in.

KEY WEST DOLPHIN WATCH by Sunset Watersports is a magical Key West adventure for the whole family. Venture out on a 40 foot dolphin watch boat that takes you for a brief Key West snorkel adventure and then to the dolphin playground to see dolphins in their natural habitat. Watch the dolphins as they interact with each other and, at times, perform stunning acrobatics. Don’t forget your camera because on the way back to Key West you will enjoy the famous Key West sunset. We provide all snorkel safety gear and equipment. Enjoy a cool complimentary refreshment of soft drinks, beer and water.

for all different occasions: Weddings on the beach, Boat Weddings on our fleet of 65′ luxury Catamarans as well as fully catered wedding receptions, rehearsal dinners and more. If you need a private charter for 2 to 149 people Sunset Watersports offers boats from 17 feet to 65 feet for all your charter needs. For more info on our wedding offerings please visit our wedding page by clicking here. Or visit ur wedding site for Weddings On The Water Key West   

Sunset Watersports proudly presents its newest addition Hammer Head Surf Shop located at 201 William St on the Key West Seaport board walk. 

Sunset Watersports

Looking for discounts, deals & updates?

Join our mailing list to receive the latest from our Key West team.

You have Successfully Subscribed!