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Florida Keys Paddleboarding

The storied Florida Keys set the stage for some of the best paddling in the world. Tranquil blue & green seas stretch as far as the eye can see into both the Florida Bay and the Atlantic Ocean. Clear, calm, shallow waters host an incredibly rich eco system above and below the surface and we can't wait to share your paddleboarding or Kayaking adventure with you! Let us guide you to the very best secret spots, or choose to rent our top notch equipment and explore on your own.

Find us on the water at Lorelei Restaurant 96 Madeira Rd, Islamorada, FL 33036. Call us at 305-853-9728

Let's get your paddle on!






Follow the beach and you will find our paddle shack nestled among the mangroves our guides on hand with their toes in the sand!

Open at breakfast, lunch & dinner, reservations can be made for private or group tours at anytime by calling 305.853.9728; our rentals are available by the hour between 10 & 6 daily, weather permitting.

The Lorelei, a bayside property is notorious for the spectacular sunset views; but for oTHErside paddlers, it provides much, much more. Situated at the tip of Little Basin the Lorelei is the perfect launch for adventure. Rich with our wild residents the basin stretches across a 1/2 mile of shallow waters & is surrounded by a ring of mangrove islands. These islands not only provide the humans with a wind shield but also a home and breeding ground for wadding birds and fish. Adolescent sharks, starfish, rays, lobsters, manatee and many others call this home and make up the incredibly rich ecosystem.

Cross the famous florida flatts & visit our favorite places along the way including a downed ship, and for the dedicated, the southern portion of the basin is lined with mangrove tunnels, great to explore and is certainly worth going the distance. On a given day, paddlers can expect to spot a variety of critters in, on, under and soaring above the water.        

This location offers both paddleboard and kayak rentals and serves as our trail head for tours.

Especially for beginner paddleboarders, May we recommend our guided eco tour.

Not only do you get to go through the best routes, but you get some paddling advice and instruction along the way.

No experience is necessary! Minimum of two people to book a tour and reservations are recommended.

oTHErside also offers advanced excursions for experienced paddlers that include two of our offshore state parks (Indian Key State Historic Site, Lignumvitae Key Botanical State Park) as well as paddle/snorkel trips to Alligator Reef Lighthouse, Cheeca Rocks or Caloosa Gardens. 

Paddleboard yoga classes are available upon request with our certified yoga instructors. Call 305-853-9728

New! GoPro Photo Package.  Your guide will capture you looking like a pro along with all the beauty of the Florida Keys above and below the water.  You'll leave your experience with hundreds of photos and videos just like may of the ones you see on this page.


#2. oTHErside Boardsports Headquarters, retail hub & extended rental pick up MM 83 


Enter the oTHErside- the heart of operations, open 364 days a year from 10- 6!

The shop is home to our extended rental fleet- 24 hrs & weekly rates- paddle chat included & free delivery available; call 305-853-9728!

All extended rentals include the soft rack system compatible with any 4 door vehicle.

Don't stress, its super simple and it gives you the freedom to move your rentals from location to location, the house,  your resort, that super secret spot the gal at the inn told you about- you know, wherever your heart desires throughout the keys :)

Pop on in for Paddle-board sales & service, lifestyle apparel & accessories for the board-sport enthusiast- island vibes are always in stock, alongside boardshorts, bikinis, rash guards and all your watersports needs.  


#3. oTHErside Adventure Park MM59 (Lake Paddling and long-term rentals)


Our Eco Park is known for its main attraction, Keys Cable Wakeboard Park, but it offers much more. We can teach anyone to learn to wakeboard on our 7 acre salt-water lake, but we also take advantage of beginner paddleboarding here in a controlled, contained environment. Long term and off-site rentals are also available, with the same soft rack system used at MM83 location. Also ask about our weekly Paddleboard Yoga classes! We're also happy to deliver to the Duck Key and Marathon area with proper notice. Call 305-414-8245