Why Book Through Us?
No paid listings. No fluff. Just the best of Key West.
We live here. We’ve done it all. These are the tours we trust and book for our own friends.
Key West Florida Fishing
Blind Squirrel Private Fishing Charter (Up to 41!)
Experience the only Coast Guard-certified private fishing charter in Key West for large groups. Spacious, air-conditioned, and led by renowned Captain Mike Weinhofer.
Compass Rose (Up to 6)
Light tackle fishing with Captain Mike Weinhofer. Ideal for all skill levels seeking a personalized and memorable fishing adventure.
Key West’s Premier Private Fishing Adventure for 6 – Windy Day
Key West’s Premier Private Fishing Adventure for 6 – Windy Day
Join Captain Steve on a 40’ SeaHunter for a smooth, spacious, and expertly guided fishing trip tailored to your group’s preferences.
Sandbar Charters
Salty Bottom Boats
Barefoot Billy’s Private Charter
Barefoot Billy’s Private Charter
Private sandbar charters perfect for groups seeking a fun and relaxing day on the water. Enjoy floating docks, music, and unforgettable memories.
Barefoot Billy’s Private Charter
Barefoot Billy’s Private Charter
Barefoot Billy’s Private Charter
Set sail in comfort with Key West’s most trusted family-owned watersports company. This private charter offers a smooth ride, personalized service, and endless options—from sandbars to snorkeling. Relax or explore—it’s your day, your way. Special requests? Call us!
Fishing & Sandbar Combo Charter
Barefoot Billy’s Private Charter
Fishing & Sandbar Combo Charter
Start the day reeling in dinner, then unwind at a stunning Key West sandbar. This combo charter blends action and relaxation with expert captains, top-tier gear, and plenty of time to float, sip, and soak it all in.
Key West's best Sunset Sail & Cruise
Sunset on Schooner America 2.0
Sunset on Schooner America 2.0
Sunset on Schooner America 2.0
RETURNS IN NOVEMBER
Sushi & Sunset Cruise
Sunset on Schooner America 2.0
Sunset on Schooner America 2.0
Glide past Key West’s landmarks on a 45’ power catamaran while enjoying fresh sushi, local drinks, and unbeatable views. This laid-back cruise is anything but average—and Billy’s signature hospitality seals the deal.
Key West Sailing
Sail into Elegance: Sunset on Schooner America 2.0
Set Sail for Adventure: Join the Iconic Wreckers Race Aboard Schooner America 2.0
Set Sail for Adventure on the Iconic Schooner America 2.0!
Discover the romance of Key West aboard the iconic Schooner America 2.0. This 2-hour champagne sunset sail offers plush seating, stunning ocean views, and the chance to see dolphins, sea turtles, and the legendary “Green Flash.” With hors d’oeuvres and refreshments served by a friendly crew, this is more than a sunset—it's your story of Key West elegance.
Set Sail for Adventure on the Iconic Schooner America 2.0!
Set Sail for Adventure: Join the Iconic Wreckers Race Aboard Schooner America 2.0
Set Sail for Adventure on the Iconic Schooner America 2.0!
Experience the thrill of Key West’s turquoise waters aboard Schooner America 2.0, the stunning 105-foot replica of the first America's Cup champion. Glide effortlessly under 3,600 square feet of sail while enjoying expert narration, complimentary refreshments, and breathtaking views of iconic landmarks. Whether spotting dolphins or feeling the warm breeze, this 1.5-hour day sail is your ticket to a classic Key West adventure. Book your journey now and make memories to last a lifetime!
Set Sail for Adventure: Join the Iconic Wreckers Race Aboard Schooner America 2.0
Set Sail for Adventure: Join the Iconic Wreckers Race Aboard Schooner America 2.0
Set Sail for Adventure: Join the Iconic Wreckers Race Aboard Schooner America 2.0
Set sail on the legendary Schooner America 2.0 for Key West’s thrilling Wreckers Race! Feel the excitement as schooners race to Sand Key Lighthouse, enjoy a delicious lunch from Old Town Bakery, and toast the adventure with beer, wine, or champagne. History, adventure, and ocean views await—book your spot now!
Sail Under the Stars: Astronomer-Guided Stargazing Cruise
Sail by Moonlight: Full Moon Cruise Aboard Schooner America 2.0
Set Sail for Adventure: Join the Iconic Wreckers Race Aboard Schooner America 2.0
Embark on a 1.75-hour starlit sailing adventure aboard the breathtaking Schooner America 2.0. Guided by a NASA Solar System Ambassador, you’ll explore the night sky like never before. Relax, sip your favorite drink, and marvel at the cosmos as you sail the tranquil Key West waters. A truly magical evening awaits!
Sail by Moonlight: Full Moon Cruise Aboard Schooner America 2.0
Sail by Moonlight: Full Moon Cruise Aboard Schooner America 2.0
Sail by Moonlight: Full Moon Cruise Aboard Schooner America 2.0
Experience the magic of a 1.5-hour moonlit sail aboard the stunning Schooner America 2.0. Glide silently across Key West’s waters under the glow of the full moon, with twinkling stars above and golden reflections dancing on the waves. Perfect for date nights, quiet reflection, or unforgettable evenings with friends.
Snorkeling & Dolphin Watching
Private Dolphin Watch & Snorkel
Private Dolphin Watch & Snorkel
Private Dolphin Watch & Snorkel
Cruise like a local on Barefoot Billy’s custom 26’ tritoon. Snorkel reefs, spot dolphins, chill at the sandbar—your pace, your playlist. Up to 6 guests. From $750.
Dolphin Watch and Snorkel Tour
Private Dolphin Watch & Snorkel
Private Dolphin Watch & Snorkel
Board the Seabreeze for a relaxed, small-group eco tour. Watch wild dolphins play, then snorkel coral reefs teeming with tropical fish. Always local-led. Always unforgettable.
Key West's Original Island Jet Ski Tour
The Original Key West Jet Ski Tour
Ride all 27 miles around the island on this fast, fun, and locally led tour. From sandbars to secret spots, this is the jet ski adventure everyone talks about—for good reason.
Kayaking in Key West
Kayak the Mangroves with the Locals
Glide through mangroves, spot wildlife (yes, sometimes manatees), and paddle peaceful waters with the most trusted guides in town. Easy, scenic, and pure Key West.