KEY WEST TRAVEL GUIDE

Author: Nathan Knight

Sunset Watersports or Barefoot Billy’s? A Guide to Key West’s Top Rated Activities

You are researching the best “things to do in Key West.” Here is why these two local names keep popping up.

As the undisputed leaders in island watersports, these two companies appear everywhere because they have survived the test of time. But for the traveler trying to finalize an itinerary, the choice can be difficult. The good news? When you are deciding between these two local legends, there is no wrong answer—only the best fit for your specific needs. This guide breaks down exactly how they compare and why these two brands remain the gold standard for activities in Key West.

Here is a breakdown of why these two companies are the “Gold Standard” for Key West activities.

The “Locally Owned & Operated” Difference

In an era of big corporate buyouts, knowing who you are booking with matters. Both Sunset Watersports and Barefoot Billy’s are locally owned and operated since their beginning.

• Sunset Watersports is the original watersports company, established in 1984. Sunset Watersports is known for their incredible sunset cruises, sandbar charters and their all inclusive watersports adventure. Additionally, Sunset Watersports is the 1st parasailing company in the state of Florida.

• Barefoot Billy’s has been a local Key West staple since 1992. Barefoot Billy’s is the home of Key West’s original jetski tour, golf cart rentals, snorkeling tours,  kayak rentals and much more.

Between them, that is over 60 years of combined experience navigating our local reefs, sandbars, weather and currents. When you book any activity with them, you are supporting local families, captains and crew who know this island better than anyone. From the owners to the maintenance team, they are 100% Florida Keys locals.

Convenience Near Me Locations (Duval St, Southernmost Point & Downtown)

The biggest difference for most travelers is simply where you are staying.

• Staying near the Historic Seaport or Downtown? Sunset Watersports has a major hub right on the harbor walk. It’s perfect if you want to finish your activity and walk straight to dinner.

• Cruise Ship Visitors? Both companies offer shuttle pick ups for select tours and Sunset Watersports is a quick 5 minute walk from your port.
• Staying on the south side of Key West? Barefoot Billy’s is conveniently located a 5 minute walk from the Southernmost Point

• Staying at a Resort? Barefoot Billy’s operates out of several premier properties, including The Reach and Casa Marina, offering an exclusive “resort-style” convenience. While Sunset Watersports has a location at Parrot Key Resort and Villas.

Safety & Satisfaction: The 5-Star Standard

For many travelers, especially those organizing trips for children or grandchildren, safety is the number one priority. This is where “big” is better.

• Verified Excellence: Both companies boast over 10,000 5-star reviews. This volume of positive feedback is your safety net. It means thousands of travelers before you have tested the experience and loved it.

• New Equipment: Nothing ruins a vacation faster than a broken-down rental. Both companies operate the newest fleets of boats, golf carts and jet skis on the island.

• The Guarantee: Both operators back their activities with a 100% satisfaction guarantee. They have been in business for three decades because they treat people right.

Most Flexible Cancellation Policy (Risk-Free Booking)

When you are planning your vacation, the last thing you want is to feel trapped by a reservation. Weather changes, travel plans shift, and life happens. Unfortunately, many third-party booking sites and corporate travel agencies force you to lock into committed bookings months in advance with zero wiggle room.

This is where the “locally owned” difference truly shines.

Both Sunset Watersports and Barefoot Billy’s believe that treating guests fairly is just the right thing to do. That is why both companies offer the island’s most flexible cancellation policy.

• The 24-Hour Freedom Window: Unlike strict competitors, both Sunset and Billy’s offer free cancellations up to 24 hours before your trip.

• No Questions Asked: If anything comes up outside of that 24-hour window, you aren’t stuck. You can choose a full refund or simply reschedule your activity for a better time.

• Book Direct for Peace of Mind: When you book with big online travel agencies, you are often battling a call center halfway across the world to get your money back. When you book with these local teams, you are dealing with real people in Key West who understand that flexibility matters.

Next Key West Tip: Top 5 Key West Trips & Tours