Best Spots For Paddleboarding and Kayaking in Key West

May 24, 2022

If you haven’t had the opportunity to go kayaking or standup paddleboarding (SUP)… You have to carve out some time to do it on your next vacation. There is no better way to explore nature and see the beautiful sites of Key West, Florida than floating through the water on a board. Below you will find our list of the best spots for kayaking and standup paddleboarding in Key West!

Here is some research I did before my excursion. I hope this helps you in your adventures! If you are going on a guided tour or renting gear the average price for any of these varies on the options so make sure to book ahead! Generally, you will be starting at around $50 per person in most cases but there are some packages that get as high as $500 with many really cool perks included! If you own your own gear I am also including some “must see” locations so you have an idea of what you are getting into.

Paddleboarding spots in Key West

SUP Key West

The owners of SUP Key West have extensive experience in marine biology and ecology. They offer a “personable experience” in the mangrove forest and they pride themselves on keeping the tours small to achieve this. One of the owners holds a PhD in Marine Ecology so they can pass their knowledge of nature and its surroundings down to the tourists that come through.

They offer a variety of lessons, “We offer morning and afternoon lessons and tours. Customized lessons where you pick the structure and the times can be arranged as well. Private lessons or charters can be arranged for groups of 6 and less.” (Source) Because Key West is home to two national wildlife refuges there are many different kinds of birds including seven different species of hero and also, “cormorants, egrets, pelicans and more!! In the water … fish, rays, small sharks and perhaps a manatee or a dolphin. We have also seen many turtles!” (Source)

The office is easy to find on 5001 5th Ave. You can call for more information by dialing 305.240.1426. And be sure to visit the website too by clicking here.Paddle boarding in the Keys


Key West Paddle

Another good place to check out is Key West Paddle located at 3841 North Roosevelt Boulevard. Imagine kayaking at night with a glass bottom kayak that lights up! “We had an idea to put lights on the glass bottom kayak and go out on the water at night. We wanted to do this to provide Key West visitors with a unique way to experience the beauty and wildlife that exists here.” They are the first company in Florida to do the glass bottom and one of the first in the world.

This family owned company has been at it since 2012 and they offer “a magical experience with well-prepared equipment and highly trained guides. Our local guides know this area well, and they will take you on a night kayak tour of those out of the way, hidden spots to experience the nocturnal marine life of the Keys.” (Source)

They offer two tours on their website but be sure to book ahead as they book up fast! The Night Kayak Tour “Get a single or double glass-bottom kayak illuminated with lights and follow our tour guide on this one of a kind, unforgettable and simply magical adventure.” (Source) Is $60 per person to book. The Key West Sandbar Trip is a group trip (up to six people) “Key West sandbars are our local well kept secret. This is where we take our families to hang out and relax on our days off. This is the perk of our island lifestyle. Now we want to share this experience with you.” (Source)

Best kayak spots in Key West

Lazy Dog

Another good option for everything paddleboarding and kayaking is Lazy Dog located at 5114 Overseas HIghway. A high level executive left the corporate world in 1997 to “live the life I wanted: to live on an island, open my own business and have a dog.” (Source) In 1998 the kayaking and t-shirt company was officially opened. In 2007 they purchased some paddleboards “for fun” and they decided to rent those out as well. By 2009 they had the largest paddleboarding fleet in Key West. “We began traveling the country, racing paddle boards, taking classes, clinics and getting certified to bring back paddleboarding to Key West the right way. All the while bringing our brand with us and setting up booths at events.” Aside from the rentals they also offer tours and lessons. Be sure to check out all the offerings by going here.

Best kayaking spots in Key West

Sunset Watersports

This rental company offers tours on the largest beach in Key West at Smathers Beach. “Jump on a paddle board, kayak or hobie cat and explore the Key West Atlantic coast. Sail through the crystal clear waters as you explore the largest beach in Key West. This pass includes your choice of a parasailing ride or chair & umbrella.” (Source) Rentals and tours are available from 9:00 a.m. to 5:00 p.m. You get an all day pass that gives you a great experience in a safe environment with trained professionals. They offer a lot more than paddleboarding tours so be sure to check out their website here for all the info on Dolphin adventures and more!

Where Are The Best Spots?

Now that you have some good rental options. If you just rent and don’t do a tour – you need to have some scenic places to check out! Stock Island is a favorite in Key West. “Stock Island offers incredible wildlife through mangrove highways, clear waters to the bottom in the bays, and perfectly chilled out vibes. If you are after a casual SUP session then this is the place for you!” (Source)

Another hidden gem is Sugarloaf Key because it is a “superb spot for paddling through wildlife and escaping the crowds of the southern parts of Key West. This is a good place for beginners to start challenging themselves and explore further afield with tidal currents to consider.”

Simonton Street Beach is a small beach off of Key West Harbor. It has concession stands with chairs and tables or you can bring a towel to mark your spot. This quite and often clear water spot is a perfect low-key location to paddle board and take in the sunset. Parking is very limited so either walk in or grab a bike to make it easier to get in and out. The cost is free so this is a good place to have in your back pocket when you don’t want to spend much.

Next up on the list is Clarence S. Higgs Memorial Beach Park… a 16.5 acres ocean vista that offers a lot of family fun on the water and the sand. This includes a Civil War era fort, a “caribbean-influenced take on Italian classics” (Source), “swimming, snorkeling, sunbathing, beach volleyball, tennis, pickleball, and a beachside Children’s Playground” (Source). You can rent the following: rent including beach chairs, umbrellas, kayaks, and paddleboards. “For animal lovers, the Park hosts a large and actively utilized dog park with separate runs for small and large dogs.” (Source)

Smathers Beach is another great spot for beginner paddleboarders. “Parasailing, SUPs, kayaks, wind sailing, and more. Smathers Beach is fully loaded to have an ultimate day of fun with the family. This is the largest beach in the Florida Keys offering rentals, pristine waters, perfectly white sand, and nearby mangroves to explore.” (Source) If you are interested in seeing Mile Marker 0 then this is the place to go! It starts there and it is located on the south side of the island on the Atlantic Ocean and State Road. It is rumored that the white sand was imported from the Bahamas but that’s a lot of sand to cover 2 miles! There are food trucks, public restrooms and showers also available. This is a free beach so you won’t have to worry about any extra fees to access the beach. This is also home to Sunset Watersports which I mentioned earlier in the post.

Ready to Race?

For most of us, standup paddleboarding is a relaxing hobby where we experience beautiful adventures on the water. For others, paddleboarding is used for intense exercise and competition. If you are ready for the challenge there is a yearly race in Key West called the Key West Paddle Classic. This race includes a route around the whole island with individuals and teams battling it out. This October 1st will actually be the 25th anniversary of the event! You can learn more about it here: Key West Paddle Classic 2022

Share Your Key West Paddleboarding Adventures

We hope this post helps you find your next adventure on the water! Be sure to share your Key West Traveler adventures with us on Facebook or Instagram (#keywesttravelers). Until next time… safe travels!


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