Here at Islander Watersports we believe the best way to experience The Florida Keys is either on the water or in it….. our goal is to make it memorable!


water-sailEnjoy breathtaking sunsets aboard the “Horizon Cat” Islamorada’s only Sailing Catamaran.  No need to travel 2 more hours to Key West  to see our famous Sunsets here in the heart of the keys.  If you’re feeling adventurous you can help hoist the mainsail , trim the lines or the captain may even hand you the tiller.  In a relaxing mood? Just sit back and enjoy the wind in the sails, the tranquility of the seas and an unforgetable romantic view!  Our 40 foot 24 passenger Sailing Catamaran awaits your arrival.  Enjoy the beautiful warm evening weather and calm ride as the sun meets the sea.  Bring your camera and a loved one, you won’t want to miss this memorable trip!

2 Hour Sunset Cruise
Adults    $45
Children  (12 and under) $35  (0-3) free


water-breezeSome people only dream of getting close to the emerald waters of the caribbean.  Here at Islander Watersports we make dreams come true.  Join us aboard our 40 foot 24 passenger Sailing Catamaran and experience an underwater adventure like no other.

We have some of the most beautiful snorkeling sights in America including huge colorful coral heads, sea rays, fauna and a variety of tropical fish.  This “Horizon Cat” excursion includes a Sail and Snorkel to the nearby coral reefs such as “Cheeca Rocks” “Alligator Lighthouse” or “Hens and Chickens”. Swim, snorkel, or just relax in the sun and enjoy the tropical breeze.  Bring your underwater camera and capture the vast underwater sea life and spectacular views.

2 hour Snorkel Cruise
Adults $35
Children (12 and under) $25
(Gear additional)


water-boatHop aboard our comfortable 21ft Hurricane Deckboat and experience the Florida Keys wildlife within it’s natural habitat. We will take a tour through tropical foliage including rare and endangerd trees, flowers and mangroves.  You can expect to see species such as the great White Heron, Egrets, Ibis, and Roseate spoonbils in their nesting sites. We will also look for Manatees, Iquana, Bottle Nose Dolphin, Sea Turtles, White Pelicans, Cormorants, Osprey and even the American Bald Eagle.  Visit historical locations such as Indian Key or Lignumvitae Key and  explore some of Florida Keys natural paradise.  Each trip is an unforgettable and unique adventure you will want to share with family or friends so bring your camera.

2 Hour Tour
Adults   $40
Chidren (12 and under) $25
(4 person min)


water-baot-rental“Seas the Day” and Captain your own vessel! Check out the Florida Keys  the only way they were meant to be seen…..from the water!  Our 18ft unsinkable Boston Whalers will give you the perfect opportunity to safely navigate the pristine waters of the Atlantic Ocean.  For the novice or experienced boaters instruction is included.  We will get you started and suggest sights and activities so you can personalize your very own tropical paradise adventure. Take your friends or family to a restaurant on the water or visit the famous “Sandbar” . Go Snorkeling, fishing, and island exploring, The possiblities are endless and the day is yours to enjoy.
Fuel is included.

Half Day: $225  (up to 4hrs)
Full Day:$350  (up to 8hrs)
(Captain/guides for hire)


water-jetskiCheck out our all new Waverunner tours! Experience an adventure like no other in the “back country”. No roped off areas, no limit on destination. We’ll take you through mangrove tunnels, slalom courses, around islands, from the bayside over to the oceanside. Join us for a 2 hour tour and we’ll bring along snorkel gear and go snorkeling at one of our coral reefs, then visit the famous sandbar. We will make sure you see the Keys the way they were meant to be seen…on the water! Located at Islander Bayside, Mile Marker 81.4

Hourly: $99
Extra Rider: $10


water-hobieSailing is a great way to appreciate the tropical breezes that frequent Islamorada.  So, If you feel the wind is calling you then come sail with us!.  Your choice of Sailboats include a 12ft Hobie bravo, 14ft Hobie Waves, 17ft Hobie Getaway, and a Hunter 14 monohull.  These boats are great fun for the first time sailor (with just a one hour lesson) and for the experienced sailor that would like to raise a little HULL!

Hourly: $40
2 Hours: $60
4 Hours: $100


water-learn-sailA Sailing adventure awaits you. Whether you love the notion of sailing or have a passion for new and exciting experiences we can help. Sailing lessons are available for adults and children of all ages.  let our experienced instructors guide you through the basics of sailing and you’ll be tacting and jibing across the bright blue waters before you know it!

1 Hour Lesson: $50


water-kayakGet back to the peacefulness of nature while enjoying some fun in the sun.  Glide gracefully across the scenic waters of the Florida Keys in a kayak built for one or two. Whether paddling for adventure, sport or exercise our mainstream single and double kayaks are stable and comfortable. Cruise the shallow and safe waters near our extensive beach or venture out to the open sea and you can view some of the best wildlife encounters the Florida Keys have to offer.

Hourly: $20 single, $25 double
Half Day: $30 single, $40 double
Full Day: $40 single, $50 double


water-aquaPedaling one of our giant balloon tired Tri-cycles for two is a fun and easy way for two people to safely get out on the water. Kids and Adults love to ride our colorful Aqua Cycles enjoying the shallow and protected waters just off our beach. They are not only a great work- out but also an opportunity to view birds, rays and other marine life.

Half Hour: $15
Hourly: $25


water-bikeCome out to the Islander Watersports beach hut and check out our beach cruisers. Take advantage of the natural beauty in our nearby surroundings.  Bicycling is a great way to visit our local shopping and restaurant district or just to get a little sunshine and exercise.  We have light weight aluminum bicycles for men, women, and children.  Baby seats are also available on request.  Helmets are available for adults and required for children 14 and under.

Hourly: $5
Half Day: $15
Full Day: $20


water-fishingTest your skills right from our fishing pier with a full day fishing rod rental!  You can also rent a mask & snorkel for the day and Investigate the nearby shallow water flats, sea grass beds, and the ocean bottom within the swimming area.  You have a choice and a chance to see a variety of fish including, mangrove snapper, grouper, box fish, grunts, needle nose, or even a spiny Florida lobster!

Fishing Rod Full Day: $10
Snorkel Set ( Mask & Snorkel): $5


water-sunHad enough of the sun?  You can still have the view and the relaxation.  We will set up a beach umbrella or a canopy at the pool or your favorite spot on the beach. Whether all day sun protection is what your looking for or just a temporary break from the Florida Sunshine,  our 8ft umbrellas and 10×10 canopies are a great way to extend your time outdoors by providing enough shade for everyone to enjoy.

Beach Umbrella
Half Day $10
Full Day $15

10 x 10 Canopy
Half Day $15
Full Day $20


water-privateNeed something more personal?  Whether your planning your vacation, family gathering, romantic getaway, or corporate event, we want to make your experience special.  From private charters to creative itineraries we can offer a variety of options to help customize any venture. Just e-mail us your information along with any ideas you may have to sales@guyharveyoutpostislamorada.com.  We look forward to getting you on the water!


Islander Water Sports - Bicycles, Sailing, Kayaks, Water Trykes, Rafts, Snorkel Gear, Sun Covers… Everything you need for a great day on the beach.


Scuba AdventuresScuba Adventures

Located in the middle of some of the best diving the Florida Keys have to offer, you will have the pleasure of diving or snokeling many popular reefs and wrecks from Islamorada to Key Largo! The list is long, but here are a few of our favorites Davis Reef, Pleasure Reef, Crocker Wall, Snapper Ledge


glassbottomThe Keys ONLY Glass Bottom / Snorkel boat!

Enjoy a glass bottom boat tour over a beautiful shallow reef. See the beautiful tropical fish, coral and plethora of marine life – all without ever having to get in the water! After the main tour we anchor the boat. Snorkelers will then have up to 45 minutes to snorkel while passengers continue viewing the reef through the glass bottom while anchored.

This is something the ENTIRE family, from children to grandparents, can enjoy together. You don’t have to get wet, if you don’t want to, to enjoy the beauty of the colorful reefs of the Florida Keys!


Yankee Freedom
Dry Tortugas and Fort Jefferson Ferry Service
Almost 70 miles, 112.9 km, west of Key West, Florida lies a cluster of seven islands called the Dry Tortugas. These islands, along with surrounding coral reefs and waters, make up the Dry Tortugas National Park. Snorkeling, kayaking, camping, legends of pirates and sunken gold have drawn visitors to this national park from all over the world.

Easy Adventures

(305) 852-4553 or 305-451-8393
Located at World Wide Sportsman in Islamorada
Mile Marker 81.5 Bayside
Easy Adventures offers fun fishing, snorkeling and eco-tours. We specialize in teaching kids and beginners how to fish or snorkel. Lessons are taught patiently without pressure at your own pace.

islamorada-boat-tourIslamorada Boat Tours
Mile Marker 83.4 Oceanside


Offering snorkeling, eco-historical, and sunset cruises on a brand new 45′ Catamaran – Docked at Whale Harbor Marina.

hangglideParadise Hang Gliding, Inc.
Mile Marker 83.4

Tandem Hang Gliding above the Florida Keys with a Certified Instructor is a truly world-class experience for all ages. No experience is necessary, and each flight is a lesson as well as a spectacular & thrilling aerial eco-tour. Soar above the sparkling waters of Islamorada in a state-of-the-art, HGMA Certified tandem hang glider. Your instructor will allow you to fly the glider and teach you the basics of speed control, level flight, and turns, all while enjoying breathtaking views and spotting abundant marine life. Landing is similar to a seaplane on their large pontoons, and the tow boat simply lifts glider & passengers back onto the deck, ready for another flight. Reservations required, please call or see website for more details.

kiteboardINGSeven Sports / 7 Kite Boarding
Mile Marker 84.7 at Whale Harbor

(305) 664-2463


Florida Keys Kiteboarding Adventures with Seven Sports is the ultimate way to experience kiteboarding in the Keys. Seven’s team has the resources and experience to accommodate you and your group. We are experts in Ocean and Bay excursions from Key Largo to Key West.  Weather you seek a simple short morning or afternoon session or multi-day adventure we make it happen.

othersideOtherside Boardsports

305-853-9728 · Fax: 305-853-9689
Email: shana@othersideboardsports.com
83292 Oversea Hwy. (Mile Marker 83.2 Bayside) · Islamorada, Florida 33036

The best in Kite boarding, wakeboarding, paddle-boarding and Skateboarding equipment sales and lessons. Excellent service, expert teachers !

Very Friendly !


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