This is the Perfect Paddles SUP and Kayak Guide to Key West!
Are you interested in paddling the beautiful Florida Keys? Then check out exactly where to go by reading through our comprehensive guide below!
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Key West is an island that sits on the end of a series of islands off the coast of southern Florida collectively referred to as the Florida Keys. The islands are connected by a stretch of highway that sits above the beautiful turquoise waters. Each Key has its own personality and unique flare. Places to visit. Restaurants to eat in. And even their own small culture.
The largest island of the Keys is Key West. It is on this particular island you will find the majority of tourists visit each year. And with good reason. It’s the perfect place to enjoy the water, the views, and a unique bar scene.
It is also one of the places chosen by Ernest Hemingway to live and write. His house now stands on the island as a museum to his work and his life.
Among the many activities to enjoy while spending time on Key West is SUP. Here you will be able to explore the vast waterways, mangrove trails, and see manatees and other wildlife swimming through the water.
If you are a fan of SUP then Key West is a must-visit location for you. To plan the best vacation possible, use this Perfect Paddles guide full of inside information on what makes Key West an ideal spot to visit.
How This Guide Works
This guide is built with you in mind. Whether you are a seasoned paddler with years of experience, or a complete beginner who needs to rent a board for paddling, we have you covered.
For those with their own boards, think of the local paddle pros as resources for the best SUP info - where to paddle, what to look for, and when the best times to go. They know their area best and have launch location options, and “must-see/must-SUP” suggestions already planned for visitors. With that said, always reach out to the paddling pros listed in this guide to get started on your planning.
For short term visitors who need to rent a board while you’re in town, we’ll go over where you can pick up a board, what types of boards are available, and where you can launch your board on calmer waters.
Use this comprehensive guide as your key to the information you need to have the best possible time in Key West - both on and off the water.
Of course, if you have any questions about the area, you can always drop us a message and we’ll get back to you as soon as possible!
-Perfect Paddles Travel Brief-
Best Time of Year to Visit:
Key West is one of those few places that can be visited year-round. Whether you go in the heat of summer and enjoy the beautiful beaches, or during the winter for a fun time around the city in 70-75 degree weather, Key West can be enjoyed at any time.
However, if you want the best time to visit, it would have to be during the spring months - between March and May. During this time, the winter crowds leave, and the hotels are most affordable. Heads up, Key West does get a Spring Break crowd for the same reasons so plan accordingly
Wind and Weather and Where/When to Paddl
Due to Key West’s position in the ocean, it can get quite windy at times. To paddle during the calmest times it is recommended that you go early in the morning or late in the afternoon.
You can avoid most windy conditions by sticking to the protected mangrove areas. In these locations, you are often protected from the winds by the wildlife that grows there.
The weather in Key West is fairly consistent. In the morning, expect clear, blue skies. On occasion clouds can roll in during the early afternoons with an occasional rainstorm during the winter months.
Special Note: Hurricane season is official June 1st - November 30th Florida and the general region. Even though hurricanes may dissipate before they reach land they can still impact your paddling experience. Always refer to a wind and weather app before heading onto the water - or talk with a local paddling professional or outfitter to gain insider knowledge on the area.
Average Temperature/Seasons:
Much of the Keys have a hot and humid climate. During the summer months, the average daily high temperature hovers around 85-90°F with a low reaching around 65°F in the winter to 80°F during the summer months. Freezing temperatures never happen, even during the winter months.
SUP Environments to Paddle In
Atlantic Ocean
Intracoastal Waterways
SUP Activity Highlights:
SUP Yoga
Eco-Tours
Wildlife Tours
Potential Water Hazards
The waters that surround Key West are the open ocean. This can mean the direction and difficulty of the paddle can be greatly affected by the wind and tides.
It is always a great idea to consult a tide chart before you head onto the water. As well as a wind and weather app.
And before you decide to drop into the water, follow this simple checklist to make sure you and your paddling buddies are safe throughout your experience (source):
WEAR A PERSONAL FLOTATION DEVICE (PFD)!
Florida law requires a readily accessible Coast Guard approved PFD for each occupant. Children younger than six years-old are required to wear a PFD.
Know the waterway conditions and be aware of water levels and currents.
Tides and winds can significantly affect the difficulty of a trip. Under normal conditions, allow a minimum of two miles per hour paddling time.
FILE A FLOAT PLAN AND LEAVE IT WITH A RELIABLE PERSON.
A float plan contains information about your trip in the event that you do not return as scheduled. This includes a description of the vessel(s), names of all paddlers, planned course and stops, and an estimated time of return. Ask the person to notify the Coast Guard or local authorities if you do not return as scheduled. Don't forget to get in touch with your contact person and let them know when you return
Bring plenty of food and water.
Drinks should be in non-breakable containers . Food and gear should be stored in watertight containers. For day trips, 1/2 gallon of water per person in recommended. For overnight trips, one gallon of water per person each day is recommended.
Bring sunscreen and insect repellent.
Wear sunglasses, a hat, and long sleeves and pants even on cloudy days. Long sleeves and pants also helps prevent insect bites.
Watch for motorboats.
Stay on the right and turn into the boat's wake. Respect anglers by giving them plenty of room.
Bring a cell phone or VHF radio.
Cell phones are great for staying in communication, but coverage may be sporadic depending on your specific location.
Respect wildlife.
Do not approach or harass wildlife, as they can be dangerous. It is also illegal to feed them.
You may see: sea turtles, fish, eels, sharks, jellyfish, and tons of bottlenose dolphins. Also, a great area for sport fishing.
Something to be aware of when paddling in marshy areas and mangroves in the keys. There are four types of venomous snakes that may hang out: Cottonmouth, two types of rattlesnakes, and coral snakes
In addition, Key West can get American salt-water crocodiles in their waterways. To avoid any dangerous run-ins, it’s always best to stick to areas with higher boat traffic. Crocs (and other dangerous wildlife) are much more likely to be in areas where the water is calm and undisturbed.
Most crocodiles will stay away from anything that is bigger than them. If you are paddling a 10 '6' board’ up to a 14’ board you will likely scare off any smaller ones. If you happen to see a large croc in the area, calmly paddle away from it without making any loud noises or extra splashing motions.
Always be on the lookout when paddling in Florida!
Key West SUP Launch Locations
Key West is surrounded by beautiful turquoise waters, an abundance of wildlife, and pristine white sandy beaches just waiting to be explored.
From a paddler’s point of view, it can be easy to just drop your SUP in the water at any location. No matter where you go you will be surrounded by the beauty inherent to Key West. The Keys are part of the third largest barrier reef system in the world and there are few sandy beaches. Wear your water shoes and bring them with you on longer paddles so you can launch and, more importantly, get back on land if you end up returning to at a different location
However, to get the most out of your time there, we suggest making plans to visit at least a few of these choice launch locations. What follows are areas around Key West as well as locations within a day of driving to other Keys in the area where you will have the best views, the best beaches, and the best time on the water.
SUP Outfitters in the Area:
- Lazy Dog SUP
Location: 33040, Stock Island, Florida, United States
Best Offering: Key West paddle board Eco Tour - Paddle and explore the Key West backcountry at a relaxing pace. Keep an eye out for marine life like sea stars, tropical fish, and other creatures. - Paddle the Florida Keys
Location: 33070 Islamorada, Florida United States
Best Offering: Mangrove and Manatee Tours - see the real Florida Keys and interact with the manatees in the water! - Blue Balance Paddle Board
Location: Big Pine Key, Florida
Best Offering: SUP Yoga in Manatee Bay! Enjoy a revitalizing flow in a beautiful setting.
SUP Equipment Available to Rent
The available SUP shops in Key West rent your standard cruising boards perfect for beginners.
In Key West, Paddle the Florida Keys is your go-to spot for all types of trips and different renting options, especially if you want to rent for a few days in a row. Rentals come with life jackets and paddles and we never run out of gear. Book online or call us if you want to rent today! Free delivery from mm 100 to mm 80. Staying outside our delivery area, or want to explore on your own? They will strap your rentals to the top of your car or truck. They even lend you the straps and padding at no extra cost.
Fort Zachary Taylor
Fort Zachary Taylor is located on the southernmost tip of Key West. It’s surrounded by aquamarine water that makes for tremendous views from atop a SUP and even better views with snorkeling gear underneath your feet.
The entrance fee is very reasonable at just $4 per car. There are plenty of places to park. Unload your gear and go. Remember to bring your snorkeling gear to combine an afternoon of paddling in the ocean and diving underneath for a close encounter with the fish species swimming underneath. You’re likely to spot a dolphin or sea turtle!
The shoreline around the fort though is rocky and exposed to oceanic swells. And the channels can be full of boat traffic.
If you are still a beginner at SUP, you might want to look further down our list of launch locations where it will be easier. However, if you’re experienced, can handle changing conditions in currents and wind, and want to do some snorkeling while in Key West, this spot is our first choice.
Simonton Street Beach
This may be the easiest launch location on our list. If you are a true beginner, start here.
Simonton Beach is located as far west as you can go on Key West. Which makes it pretty protected from the elements. But mostly, it’s the best place on the island to enjoy the sunset. The sand here is soft and so is the bottom in the ocean. Take your SUP and launch right from the beach, paddle in the water, and use your board as the best seat in the house to enjoy a magical sunset.
Smathers Beach
Smathers Beach is not your typical lazy day beach in Key West. Instead of the usual sunbathing crowd, you’re likely to find yourself amongst parasailing, wind sailing, kayaking, and other SUP fanatics.This is the place to go for a full day of fun with your family.
Smathers is the largest beach in Key West so be warned, if you’re looking for a private time, this is not the location for you. What you will find however, is plenty of action. The beaches here are white sand, and surrounded by turquoise waters. Paddle around the cove and you’ll find mangroves nearby for exploration.
If you’re a beginner, traveling with your family, or want a place with plenty of options for water sports outside of SUP, then head to Smathers Beach.
Higgs Beach
When you hear the name Higgs Beach we want you to think of one thing - the Caribbean. Higgs Beach is where you will have the views most similar to the Caribbean feel. We’re talking the whitest sand and the most turquoise clear water where you can see right to the bottom.
This is the beach you want to head to for the most stunning scenery. The water here is shallow so it is perfect for a beginner. You can launch right from the beach or take advantage of the wooden pier stretching into the ocean. Simply walk down, drop in, and paddle around.
Higgs Beach is our go-to spot to soak in the beauty that is Key West.
Stock Island
If you’re the adventurous type, Stock Island should be on your list to paddle. When we think of Florida, and especially southern Florida, the thought that always comes to mind is mangroves. The forests are teeming with wildlife and give the paddler a unique environment to explore on a SUP.
Stock Island has just that. There are mangrove highways you can paddle through. Plenty of wildlife to see and interact with, and an easy launch location right in the local marina full of boats.
If you’re looking for a different side of Key West, outside of the beaches, Stock Island should be your go-to.
Day Trips Near Key West
While Key West is a paddler’s dream - it is also a small island. And therefore, can be explored within a few days. If you are planning an extended stay on the island, we recommend you heading back east for a day trip or two. See more of the Keys and explore more on your SUP!
Sugarloaf Key
Sugarloaf Key is located about a 30 minute drive from the center of Key West and is an easy day trip to explore a different Key.
What makes Sugarloaf Key fun is the opposite of what makes our previous launch locations fun in Key West - it’s a more challenging paddle. Sugarloaf’s launch locations are tidal and can have a strong current in the water. Keep this in mind as you explore the shore. Because of this challenge, we only recommend it for experienced paddlers.
In addition, the paddling here is more remote. If you’re into solitude or need to escape the crowds in Key West, a trip out to Sugarloaf will provide the remedy.
One point of interest - look for the large bat tower in the middle of the mangrove ecosystem. This was put into place to help remedy the mosquito situation during the warm months. You’ll be able to see it right from the water!
The best launch location is the local marina. Keep in mind before you drop in to always check the tide and currents as well as the wind. Since this area is more remote, you’re not as likely to run into other paddlers on the water.
Seven Mile Bridge
Seven Mile Bridge is always part of a Key West bucket list for visitors. Why? Because the location has been featured in huge Hollywood blockbusters such as True Lies, License to Kill, Mission Impossible III, and 2 Fast 2 Furious.
You can experience it from the road and drive on the bridge to recall the most iconic scenes. Or you can take to the water and see it in a whole new way.
One word of warning - this is probably the most difficult paddling launch location on our list. The current here is strong and there is boat traffic. If you are not an experienced paddler then we recommend you choose a different location to enjoy the day on your SUP. But, if you’ve been around the block, why not see this famous location from the water? It’s worth the adventure.
Plus, next time you’re watching any of those movies with your friends, you can point out exactly where you paddled!
Dry Tortugas National Park
Dry Tortugas National Park is located 70 miles west of Key West. It consists of a 100-square mile park of open water with seven small islands. You can only access this National Park by boat or seaplane - but it’s worth the trip! Take a board with you on the boat (preferably an iSUP for ease of travel) and use it around the island!
Once you reach, you can explore Fort Jefferson, Garden Key, or Loggerhead Key - all fantastic areas to drop a board into the water and paddle around. There are beautiful turquoise waters, coral reefs, plenty of marine life, and because it is so remote, it’s completely quiet on the island. A true digital detox.
Bonus - you can camp on site if you choose to stay the night. Just make sure to book your stay before you go. Wake up in the morning in complete silence, take in a beautiful sunrise, and go paddle. This location might be paradise on Earth.
Bahia Honda State Park
Bahia Honda State Park is about an hour drive east from Key West.
It boasts more pristine beaches, bright water, and plenty of space to explore on your own or find a private stretch of land on Sandspur Beach where you can relax underneath a palm tree and watch the sun set in the distance.
One tip - there are no places to rent a SUP for the day here. You will have to secure a board in Key West and bring it here if you want to paddle. But for the relaxing vibes and a chance to spend an afternoon on the beach by yourself, it’s worth the trouble!
Big Pine Key
Big Pine Key is located right before Bahia Honda State Park and is about a 45 minute drive from the center of Key West.
One interesting fact about Big Pine Key - it’s home to a deer refuge located at the inland parks. That’s right - deer at the beach!
Over the years this location has become one of the most popular for SUP. This is due to the mixture of perfect beaches and mangroves trails that have places where you can pull your board onto the sand to relax underneath some shade.
There are also SUP yoga classes offered by Blue Balance Paddle Board in Manatee Bay. If you want to go to one location outside of Key West for SUP, we recommend Big Pine Key.
John Pennekamp Coral Reef State Park - Key Largo
Our last location is also the farthest away from Key West. John Pennekamp Coral Reef State Park is located 2.5 hours east of Key West and is the first underwater park in the United States. That’s right - an underwater park. To us, that just means it’s perfect for SUP.
It consists of 50 miles of natural and preserved mangrove forests perfect for exploration. The wildlife here is diverse, the trails for paddling are endless, and it is worth a trip if you are looking for a new and completely unique place to paddle outside of Key West.
Bonus: There are rentals available inside the park so there is no need to travel with all your equipment!
Additional Activities When You Are Not on the Water
Notable Restaurants in Key West:
Latitudes
This beautiful restaurant is located in the Sunset Key Guest Cottages overlooking the Gulf of Mexico. It is an outdoor seating area with a casual yet elegant atmosphere. Latitudes Beach Cafe offers aromatic flavors of the island in the form of fresh local seafood and seasonal fruit salsas. If you are a guest at the Westin resort, you enjoy a complimentary breakfast as well.
Red Shoe Island Bistro
This restaurant specializes in fresh Key West fish and shrimp delivered daily from the fishery here, and never uses frozen products. In addition to the local seafood, this restaurant bakes its own Key Lime Pie the old-fashioned way.
Origami
Operating here for more than a dozen years, Origami is run by Kiyoto and Kuma. They have worked hard and their small sushi restaurant has been named "Best Sushi Bar" in a local poll. You can relish the choice selections either in air-conditioned comfort or outside in a pleasant garden patio. On the menu are tempura and teriyaki selections, as well as children's choices for sophisticated kiddies.
Little Pearl
Neighborhood restaurant & wine bar focusing on local seafood.Nestled in the heart of Old Town and away from the bustling downtown streets of Key West, Florida, sits an excellent spot for fresh local catch and innovative cuisine with a tropical twist. Make a reservation today, book us for your next event, or simply just drop in!
Additional Attractions if the Wind and Weather Don’t Cooperate (Click on the links for additional information on each location):
Night Time Kayaking in Key West
If you'd rather sit down instead of stand while paddling, there are options for great nighttime kayak tours. Paddle around the waterways that surround Key West with a great group of friends. To know everything you need to know before you head out, read this excellent piece by our friends at The Roam Wild HERE.
Fort Zachary Taylor Historic State Park
The Fort Zachary Taylor Historic State Park, better known simply as Fort Taylor, is a Florida State Park and National Historic Landmark centered on a Civil War-era fort located near the southern tip of Key West, Florida.
Butterfly and Nature Conservatory
If you're a fan of the delicate winged creatures, then this is definitely the place for you. The Butterfly and Nature Conservatory, which treats visitors to amazing sights and smells of mother earth, has a climate controlled enclosure for about 60 species of butterflies. The colors, size, shape, history and lifespan can be studied at the Learning Center - a great experience for children and adults alike. The gallery and gift shop have lots more in store.
Mallory Square
Located by the historic Key West waterfront, this open-air marketplace and entertainment complex is a great place to start or end your visit to Key West. Known for its magnificent sunsets, the area is also home to many shops, including Shell Warehouse, Key West Sponge Market and Caribbean Cargo. The Square also features daily entertainment, which includes guitar music, juggling, and animal performances. Local sightseeing tours also depart from the Square.
Harry S. Truman Little White House
Nestled in the recesses of the historic Old Town, the Little White House is a startling canopy of pristine white, which lends deep insights into the Truman Presidency. Formerly a naval base which served as the White House of America for the winter session until 1952 , this site is more like a breathing museum entrenched in a long-standing military history. To this day, functions, meetings and private events are held here, whereas elaborate tours unfold layers of the house's presidential and political history. Part of the U.S. National Register of Historic Places, this white-washed house yet retains some of its ancient features like well-furnished spaces including bedrooms and dining halls, treasured documents and opulent furniture. Harry S. Truman Little White House is an integral edifice etched on the pages of America's political history.
Ernest Hemingway House and Museum
The Ernest Hemingway House was the residence of American writer Ernest Hemingway in the 1930s. The house is situated on the island of Key West in Florida. It is at 907 Whitehead Street, across from the Key West Lighthouse, close to the southern coast of the island. Due to its association with Hemingway, the property is the most popular tourist attraction in Key West.
Audubon House and Tropical Gardens
The Audubon House & Tropical Gardens is located at 205 Whitehead Street, Key West, Florida. Brick-pathed gardens offer a lush 1-acre view of orchids, bromeliads, and other tropical foliage, an herb garden and 1840-style nursery.
Key West Lighthouse and Keeper’s Quarters Museum
Long ago, hazardous reefs off Key West wrecked many ships. To keep ships off the reefs, a lighthouse was built in 1825. Although it was destroyed in 1846, it was later rebuilt inland on Whitehead Street and was manned for more than 120 years. It's now open for those who can climb the 88 steps to the top of the tower, and tour the grounds. A small museum of nautical artifacts and vintage photos has been set up in the Keeper's Quarters.
Fun Key West Area Info (source):
- There are 42 bridges that connect Key West to the mainland of Florida.
- The third-largest coral reef in the world is off the coast of Key West.
- All of the sand on the beaches of Key West were shipped in from the Caribbean.
- Because it can be accessed by land Key West is known as the Southernmost city in the country. It is closer to Cuba than it is to Miami.
- Facts About Key West - bridges of the florida keys
- People born in Key West are called Conchs.
- There are three Civil War forts located on Key West.
- Key West has the highest average temperature in the United States. It is the only city in the country that never gets frost.
- Key West was home to the writer Ernest Hemingway, treasure hunter Mel Fisher, baseball player Boog Powell, and many other well-known figures.
- Hemingway House was the first home in Key West to boast such luxuries as running water and a swimming pool.
- Hemingway house is home to more than 60 six-toed cats that are direct descendants of a six-toed cat given to Hemingway by a friend.
- The Naval Air Station in Key West takes up most of the island. It was selected because flight conditions are better in the Florida Keys than anywhere else in the US.
- The original name for Key West was Cayo Hueso meaning: Island of Bones.
- Duval Street in Key West is known as the longest street in the world because it runs from coast to coast.
- In Pre-Columbian times Key West was inhabited by the Calusa people.
Hotels/Price Ranges
There are numerous places to stay in Key West. We always recommend doing your own research before booking. However, to give you an idea on the prices you should expect we’ve listed a few options below.
The Marker Key West Harbor Resort $755/night
Margaritaville Beach House Key West $795/night
Eden House $565/night
Ambrosia Key West Tropical Lodging $449/night
The Cabana Inn $459/night
Camping Locations
Lazy Lakes RV Resort, Sugarloaf Key
Bluewater Key, Key West
Big Pine Key Fishing Lodge, Big Pine Key
Breezy Pines RV Park, Big Pine Key
The Florida Fun Continues…
We hope you enjoyed our Perfect Paddles Guide to Key West. These small chains of islands lying south of Florida have plenty to offer the paddling enthusiast - and then some!
Here you can paddle the back bays, the beautiful canals, mangrove forests or take to the turquoise ocean for unbelievable views while the sun sets. With so many locations to drop in and paddle around, you must put Key West and the areas around it on your paddling list.
Looking for a location outside of Key West? Then check out the rest of our Florida resources by clicking on our SUP Search section on Perfect Paddles! The fun in Florida never ends and we hope to help guide you in creating the perfect trip down south!
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