Standup Paddleboarding in Key West

Standup Paddleboarding, or SUP, is one of the fastest growing water sports worldwide, and Key West is an ideal place to get an introduction to this fun, safe, and easy pastime. Although standing upright on a large surfboard and paddling canoe-style undoubtedly dates back to the ancient Hawaiian roots of surfing, in its modern incarnation standup surfing was a pastime of the original Waikiki beachboys of the 1940’s and 50’s. In their work of introducing tourists to the sports of surfing and canoeing, the beachboys would stand on big, floaty longboards and move around with a canoe paddle, allowing for a good view of their charges and a more commanding platform from which to shout instructions. It was also a way to earn tips by paddling out with several tourist cameras hanging around the neck and snapping pictures of the happy visitors as they paddled canoes and surfboards around in classic Waikiki breaks like Old Man’s, Canoes, and Queen’s Surf.

About ten years ago, hardcore Hawaiian watermen like Robbie Naish, Brian and Rusty Keaulana, Dave Kalama, Laird Hamilton and several other leading lights of the Hawaiian islands big wave surfing and windsurfing scene began paddling around on flat water and into waves while standing up on big boards. The sport quickly went viral, and spread to both surf breaks and flat-water venues around the world within just a few years. Now, tourists in places like Key West can enjoy getting out on the water to feel the challenge and excitement of riding a maneuverable surfboard-like craft while reaping the health benefits of the solid core workout delivered by simultaneously maintaining balance and wielding a long-handled SUP paddle. As an added bonus, being positioned to look down into the water from above makes for good viewing of sea life when paddling in clear waters.

Standup paddleboarding has now become firmly established within the Key West watersports line up, and there are several competitions and special events held each year, including the Key West Paddle Board Classic, four days of events and races including a 12-mile race around the island. These events draw big crowds, and every year more people are introduced to SUP while visiting Key West. If you want to try it out for yourself, there are a few interesting options available on the island. Eco tours that feature paddles among the mangroves and along remote sandbars offer chances for exploration and wildlife viewing. Combination cruises give you a chance to try out multiple sports in one go as you paddleboard, kayak, and snorkel on the same trip offshore. Night paddling is a recent innovation that lets the paddler enjoy the unique experience of exploring moonlit waters on a lighted paddleboard that acts as a fish attractor to bring the creatures of the nighttime sea into good viewing range. And of course there are lessons available for those who would like a soft introduction to the sport, as well as the various races and competitions for visitors who are already at the expert end of the paddleboard spectrum.

The great thing about standup paddling is that it is a sport that you can take home to enjoy on your local lake or river. Then, as you gain skill, you can head out to the ocean and try it out in the waves if you want. Standup paddleboards work well in small waves, and offer an easy way to taste the thrill of wave riding without the long learning curve that traditional surfing requires. So, now that you know what’s SUP, take a chance to try out this great sport on your next visit to Key West.

Read More
Key West Sail, Snorkel, Kayak with Sunset Option
Likely to Sell Out
Top10Top 10 Tour Ranked using exclusive Attractions Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
Likely to Sell Out
4.5 or 6.5 hours (approx.) Free Cancellation Instant Confirmation
$99
$90

Key West Backcountry Safari
Likely to Sell Out
Top10Top 10 Tour Ranked using exclusive Attractions Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
Likely to Sell Out
4.5 or 6.5 hours (approx.) Free Cancellation Instant Confirmation
$120
$99

Key West 4-Seater Gas Powered Golf Cart Rental
Likely to Sell Out
Likely to Sell Out
3 hours and up Hotel pickup offered Free Cancellation Instant Confirmation
Best Rate
$90

Key West 8-Seater Gas Powered Golf Cart Rental
Likely to Sell Out
Likely to Sell Out
3 hours and up Hotel pickup offered Free Cancellation Instant Confirmation
Best Rate
$200

Key West 6 Seater Gas Powered Golf Cart Rental
3 hours and up Hotel pickup offered Free Cancellation Instant Confirmation
Best Rate
$170

Key West Split Fishing Charter
Likely to Sell Out
Top10Top 10 Tour Ranked using exclusive Attractions Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
Likely to Sell Out
4 or 6 hours (approx.) Free Cancellation
$350
$200

Key West Snuba® (No Dive Certification Required)
3 hours 30 minutes Instant Confirmation
from
$160

Key West Deep Sea Fishing Charter
Likely to Sell Out
Top10Top 10 Tour Ranked using exclusive Attractions Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
Likely to Sell Out
4, 6 or 8 hours (approx.) Free Cancellation
$1,000
$900

Key West Dolphin Watch & Snorkel
Top10Top 10 Tour Ranked using exclusive Attractions Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
3 hours 30 minutes (approx.) Hotel pickup offered Free Cancellation Instant Confirmation
Best Rate
$99

Miami to Key West Day Trip with Snorkeling
Likely to Sell Out
Top10Top 10 Tour Ranked using exclusive Attractions Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
Likely to Sell Out
6 hours in Key West (approx.) Hotel pickup offered Free Cancellation Instant Confirmation
$169
$119

Key West Party Boat Fishing Charter
6 hours (approx.) Free Cancellation Instant Confirmation
Best Rate
$69.69

Filter
Language
Currency

Site Settings

Activity name

Currency

Activity name

Sorting, ranking, and search results

Activity name

Attractions Key West wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Attractions Key West over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

Cool Rewards Terms & Conditions

Activity name

Cool Rewards

  • Cool Rewards is a loyalty program operated by Cool Destinations. Rewards may be earned by any eligible person holding a Cool Destinations account, subject to the Cool Destinations customer Terms of Use.

Earning rewards

  • Rewards can be earned by making bookings on the Cool Destinations website. You will be able to see the value of the rewards you can earn during the booking process.
  • Earned rewards will be issued in a pending state and will move to a confirmed state 24 hours after the start time of the experience.
  • Earned rewards will be available to redeem once they are no longer in a pending state.
  • For bookings that are moved to a different travel date, the rewards will be redeemable after the amended travel date.
  • If a booking where rewards were issued is canceled, the earned rewards will not be redeemable and will be moved to a canceled state.

Redeeming rewards

  • To redeem rewards, you must be logged into your Cool Destinations account.
  • Any available rewards will be automatically applied the next time you make a booking, and their value will be deducted from your order at checkout, unless you choose not to apply them, which requires you to indicate this via the toggle switch. Bookings made using rewards are subject to the standard Cool Destinations Customer Terms of Use.
  • You will not be able to redeem only a portion of your available rewards at checkout. It is only possible to redeem all or none of your available rewards.
  • There is no minimum order value required to redeem your rewards. This means that you can pay for 100% of your order with rewards.
  • Rewards are non-transferable and cannot be redeemed for cash.
  • If rewards are redeemed against a booking that is canceled or refunded, the rewards will be reissued to your account.

Miscellaneous

  • You can check your Cool Destinations account to see the rewards you have collected at any time. You are responsible for ensuring that your rewards balance is correct.
  • We reserve the right to modify these Cool Rewards Terms and Conditions at any time, with or without notice, including the rules for earning and redeeming rewards. Any changes will be reflected in the updated Terms and Conditions.
  • We reserve the right to terminate the Cool Rewards program and cease issuing any further rewards on future bookings. All pending and available rewards balances will be honored.
  • By earning and redeeming rewards, you agree to these Terms and Conditions, as well as any subsequent changes made to them.