Watersports Adventures in Islamorada

Explore the best of Islamorada with the Ultimate Thrill Ride! Maximum of 2 adults per jet ski. Three passengers are only allowed if 2 adults have one small child or one adult and two kids. Hop on our incredible island jet ski tour as it takes you through over 26 miles of the most beautiful waters and scenery the Florida Keys has to offer. This tour is perfect for thrill-seekers and nature lovers alike, providing an unforgettable experience on the water. With top-of-the-line jet skis and expert guides, you'll navigate through lush paths and open waters, making stops at iconic locations like the sandbar and coral reefs.

Discover the beauty of Islamorada with our newest adventure, the Catboat Tour! A maximum of 2 people per boat. Perfect for all ages, this tour offers a unique experience on the water with our state-of-the-art catboats. Enjoy a leisurely ride through the stunning waters of the Florida Keys, taking in the breathtaking scenery and wildlife. Our experienced guides will ensure a safe and enjoyable journey, providing insights into the local environment and history. Book now to experience the ultimate relaxation and exploration on the water!

Two of the Florida Keys’ most iconic experiences — reef snorkeling and the famous Islamorada sandbar — combined into one unforgettable trip aboard the brand-new 55-foot Isle Legacy.

This adventure begins with a scenic cruise through the beautiful waters surrounding Islamorada as your captain heads toward one of the area’s coral reef or patch reef snorkel sites. Slip into the clear, tropical water and explore a vibrant underwater world filled with colorful fish, coral formations, and other marine life that make the Florida Keys reef system so special.

After snorkeling, the experience continues with a visit to the world-famous Islamorada sandbar, where shallow, crystal-clear water creates the perfect place to swim, float, and relax. Stretch out on premium SunChill floating loungers, wade in calm waist-deep water, or unwind aboard the spacious catamaran while soaking in the island scenery.

With a comfortable ride, professional crew, and two unforgettable destinations in one trip, this experience is perfect for families, couples, and groups looking to make the most of their time on the water in Islamorada.

Enjoy the Florida Keys’ most famous sandbar aboard the brand-new 55-foot Isle Legacy. Departing from Three Waters Resort & Marina, the closest marina to the Islamorada sandbar, Isle Legacy offers a brief scenic ride before anchoring in clear, shallow turquoise waters. The short transit maximizes your sandbar experience so you can swim, float, relax, and socialize longer.

Stretch out on premium SunChill floating loungers, wade in calm waist-deep water, or unwind aboard a spacious, stable catamaran featuring both shaded seating and an open sun deck. With an onboard restroom and generous room to move about, Isle Legacy offers a comfortable and easygoing sandbar trip ideal for families, couples, friend groups, celebrations, and visitors enjoying the Keys.

Explore the colorful underwater world of the Florida Keys on this dedicated reef snorkeling adventure aboard the brand-new 55-foot Isle Legacy.

Departing from the marina at Three Waters Resort & Marina, this trip offers quick access to nearby coral reef and patch reef snorkeling sites so you can spend more time in the water and less time traveling.

Once anchored, you’ll have the opportunity to snorkel in clear tropical water filled with vibrant reef fish, coral formations, and other marine life that make the Florida Keys reef system one of the most unique ecosystems in North America.

When conditions allow, trips may visit well-known snorkel areas such as Hens and Chickens Reef or Cheeca Rocks, both known for shallow coral formations and abundant marine life. On calm days with favorable conditions, offshore locations near Alligator Reef Light may also be explored.

Whether it’s your first time snorkeling or you’re an experienced ocean explorer, this trip offers a relaxed and memorable way to experience the natural beauty of Islamorada’s reef environment.

End your day on the water with a relaxed Islamorada sunset cruise aboard the brand-new 55-foot Isle Legacy. Departing from a convenient Islamorada marina, you’ll glide through calm Florida Bay and Atlantic waters as the sky transforms into brilliant shades of gold, orange, and pink. Tropical music and laid-back island vibes create the perfect atmosphere while you relax and enjoy the scenery.

Designed for guests seeking a peaceful and scenic experience on the water, this cruise is perfect for couples, families, celebrations, and visitors looking to unwind in comfort. The wide, stable catamaran offers generous space to move about, relax with friends, and take in panoramic views as the sun dips below the horizon.

As the evening colors peak, guests 21+ are invited to enjoy a complimentary champagne sunset toast, adding a celebratory touch to an already unforgettable setting. Whether you're marking a special occasion or simply unwinding after a day in the sun, this is an easygoing and memorable way to experience Islamorada.

Set sail on our custom Tiki Cruise Boat for an unforgettable adventure in the beautiful waters of Islamorada. Perfect for groups of up to 18, this private charter offers a unique way to celebrate special occasions or simply enjoy a day on the water with friends and family.

Private Tiki Bar Boat Charters and Tours in Islamorada!

Have more than 6 people in your group? U.S. Coast Guard requirements limit most Florida Keys commercial vessels to only 6 passengers, but not us! With our USCG Certified vessel rating of 18, there’s no need to split up your group on multiple boats!

About the Tiki Boat:
Our brand new tiki bar boat, “Tropic Like It’s Hot”, was custom built to be the best sandbar party and sunset cruise boat in the Florida Keys. Designed for up to 18 passengers (though we think groups of 8 – 14 will be the most comfortable), Tropic Like It’s Hot offers everything you need for the perfect day on the water in Islamorada. Perfect for large family or friend groups, wedding parties, bachelorette / bachelor parties, and corporate outings.

Experience the thrill of riding a high-performance jet ski in the beautiful waters of Islamorada. Each jet ski accommodates a maximum of 2 adults. Three passengers are allowed only if they consist of 2 adults with one small child or 1 adult with two kids. Our top-of-the-line jet skis provide a safe and exciting ride, perfect for both beginners and experienced riders..