Our Favorite Islamorada Watersports & Aquatic Activities

Islamorada is surrounded by bright, warm, inviting waters, so it’s no surprise that any stay here revolves around the sea. Of course, we recommend that you try all the inviting aquatic activities and exciting watersports on offer. Read on to learn about the most popular ways to enjoy those beautiful Gulf waters.

Scuba Diving

The Florida Reef is one of the largest in the world, averaging four miles across and stretching over 150 miles from end to end. As the only living coral barrier reef in the US, it’s definitely worth exploring, and a scuba-diving session is the best way to do it. Get face to face with colorful marine life and explore enchanting shipwrecks up close.

Snorkeling

If you don’t want to bother with all the scuba gear, snorkeling is a great alternative. Keep things light, with just a mask and fins, and enjoy a glimpse into the vibrant underwater world. You’ll still be able to explore the reef and many of its most popular sites.

Hobie Cat Sailing

Hobie Cats are small sailboats that are easy to learn and operate. The design features two plastic hulls with a trampoline-style deck stretched between them, making the boat unsinkable. Unlike a traditional sailboat, there’s no boom, meaning Hobie Cats are also safer for beginners.

Parasailing

Parasailing is an exhilarating — yet perfectly safe — way to take in your scenic surroundings. Enjoy spectacular views from about 500 feet above the water as a boat tows you around the island. You might even catch a glimpse of dolphins playing in the surf!

Sunset Cruise

If that sounds like a bit too much adrenaline for you, opt for a soothing sunset cruise. Islamorada is known for its gorgeous sunsets, and trust us — they look even better from the deck of a sailboat. Enjoy being one with the water and not having to worry about a thing, and toast a glass of wine as the sun dips behind the waves.

Jet Skiing

If you prefer to be in the driving seat, then rent a jet ski and cruise the waves on your own or with a tour group. Feel the sea breeze and the wind in your hair as you race across the water, and get an up-close look at Florida’s wildlife in its natural habitat.

So which exciting water sport or soothing aquatic activity suits your style? If you’re planning a visit to Islamorada, book a stay at Cheeca Lodge, which offers all the above on property. Check out the resort’s activity page for pricing and availability.

Four Must-Try Summer Activities in Key West

Summertime in the Florida Keys is perfect for a relaxing getaway, with beaches to lounge on and marine life to discover. However, there’s a lot more to Key West than just scuba diving and suntanning. From the island’s fascinating history to its quirky culture, no trip would be complete without experiencing everything this picturesque destination has to offer. Read on to learn about four of our favorite activities in Key West.

Fort Zachary Taylor

Built in 1898, Fort Zachary Taylor is one of Key West’s most impressive historical sites. And thanks to its location, next to one of the island’s most beautiful beaches, you’ll probably find yourself in the area during your stay. Tour the fort to learn about its role in the US Civil War and to see the country’s largest collection of Civil War cannons.

Ernest Hemingway Home and Museum

One look at the tropical paradise of Key West, and it’s easy to see how Ernest Hemingway fell in love with the island. One of America’s most celebrated authors, Hemingway lived here with his wife for over ten years. Tour his exquisite colonial-style home, built in 1851, and admire the spectacular collection of furniture, art, and antiques, all carefully restored and preserved.

Duval Street and Mallory Square

When you’ve had enough history, it’s time to experience Key West’s vibrant contemporary culture. All the action is centered around Duval Street, where you’ll find lively bars, fun souvenir shops, and lovely restaurants. Enjoy an afternoon stroll along the thoroughfare, and time your walk to reach Mallory Square by sunset. Each night brings the Key West Sunset Celebration, with performers, artists, and food vendors creating a festive, party atmosphere.

Key West Butterfly and Nature Conservatory

For animal lovers, there’s more to see here than just the marine life. Key West Butterfly and Nature Conservatory is a glass-enclosed sanctuary that houses over 50 butterfly species and over 20 exotic bird species. Admire these colorful creatures and find out more about them in the learning center.

If the sun, sand, and sea weren’t enough to tempt you, these can’t-miss activities might just convince you to choose Key West for your summer getaway. If you do, a stay at Cheeca Lodge will put you in prime position to enjoy the best of the island. Browse our latest offers and discover Key West for yourself.

Blooming Islamorada Fruit Trees at Cheeca Lodge

Retreat to our seaside haven in the Florida Keys and enjoy all the benefits our lush tropical climate has to offer. If you walk along the grounds of Cheeca Lodge, you’ll notice a number of flowering trees in bloom, with an abundance of fresh fruit on their branches. Our fruit-bearing plants are scattered around the property and produce a variety of fruits at different times of the year. These fruits are highlighted in our restaurant menus and cocktails, and are there for our guests to enjoy.

Our Cheeca Lodge Staff encourages you to enjoy the fresh fruit and pick a few pieces to take with you to eat. We’re happy to answer any questions you may have about the various varieties of fruit.

Our lush, colorful property features the following fruit-bearing plants:

  • Four varieties of mango
  • Loquat
  • Jackfruit 
  • Lychee 
  • Carambola (star fruit) 
  • Guava
  • Six-plus varieties of banana
  • Barbados cherries 
  • Mulberry
  • Red papaya
  • Two varieties of fig
  • Pineapple

Enjoy a fruit-filled getaway to Islamorada when you reserve your stay at Cheeca Lodge today.


Three Reasons to Bring the Kids to Cheeca Lodge

Grab the kids and head to Florida! Cheeca Lodge is proud to be one of the top family friendly resorts in Islamorada. With an entire on-site camp for kids, our Florida Keys resort is full of fun activities for kids to enjoy

Camp Cheeca is Cheeca Lodge’s on-site kids’ camp, offering daily activities to educate children on the wildlife found in the Florida Keys. Leave the kids with us for a day of arts and crafts, exploration, outdoor activities, and more.

Fishing

The kids will enjoy learning to fish off of Cheeca Lodge’s famous pier. Camp Cheeca provides bait, tackle, and fishing poles for a day of fun along the water.

Environmental Learning

Our knowledgeable counselors create interactive games to teach about the surrounding environment. We explore the beach looking for creatures and discover the importance of protecting our planet.

Sports

From coconut bowling and basketball to pickleball, tennis, and golf lessons, Camp Cheeca offers a bunch of ways for your kids to enjoy their day in Islamorada. If they love to ride bikes, our counselors are happy to go along for a guided ride with them.

Find the full list of Camp Cheeca activities and program details here.

The Best Father’s Day Activities in the Florida Keys

Since Father’s Day is right around the corner, celebrate dad with a relaxing trip to the Florida Keys. Treat him to the best activities the Florida Keys have to offer. Whether you prefer a fishing trip, a round of golf on the coast or a day of scuba diving, Cheeca Lodge offers outdoor activities that every dad is sure to enjoy.

Fishing Trips

Experience the excitement of the sportfishing capital of the world, right here in Islamorada. Fishing excursion options are endless at Cheeca Lodge. From backcountry fishing to open-reef or offshore excursions, each of our experiences makes for a perfect Father’s Day itinerary.

Golf

Perfect your golf game at our Florida Keys golf course. Our 9-hole, par-3 course is situated seaside and provides the ideal backdrop to a relaxing day with dad. Whether you’re a golf veteran or a relative newbie, the Cheeca Lodge golf facilities are enjoyable for golfers of any skill level. Stop by the course and set up your tee time today.

Water Activities

Spend your day with Dad on the water. Choose from a variety of water activities available from Cheeca Lodge’s inviting waterfront setting. Explore the clear waters of the Florida Keys with a snorkel trip, or book a scuba-diving session and discover the fascinating sea creatures below. Rather stay above water? Race jet skis with dad or test your skills at Hobie Cat sailing. Soar to new heights while parasailing behind a speedboat, or end the day with a picturesque sunset cruise and watch the sun disappear below the water.

Celebrate Father’s Week at Cheeca Lodge

We think Dad deserves more than just a day, so we’re dedicating an entire week to our favorite guy this summer. Book your stay with us week of June 10-16 and experience special Dad-approved features and amenities all week!

Featured

What to Pack For Your Trip to the Florida Keys

When packing for the Florida Keys, you want to make sure you have the absolute essentials. Flip Flops, a bathing suit, and sunscreen are all the basics required for a trip to paradise. But for the few items you may not remember to grab, we put together a list of what to pack for your trip to the Keys.

A Sense of Adventure

Pack your sense of adventure and take part in thrilling activities including jet skiing, parasailing, sport fishing, scuba diving, and more at Cheeca Lodge. Islamorada is full of action-packed activities to get you out of your comfort zone with new, exciting adventures.

The Urge to Learn

Islamorada has a rich history that goes way back to 1513 when the Spanish first discovered the Florida town. Satisfy your urge to learn about Florida history at numerous Islamorada museums during your visit to the Florida Keys. Stop by the Keys History and Discovery Center and the History of Diving Museum, both located near Cheeca Lodge in Islamorada.

An Empty Stomach

No matter what your taste buds crave, Islamorada offers flavorful dishes just waiting to be discovered. Bring your appetite and try authentic coastal cuisine at numerous restaurants across the Florida Keys. Our favorite restaurants in Islamorada include: Atlantic’s Edge, Mia Cucina, and Nikai Sushi Bar & Restaurant.

The Entire Family

Round up the entire family and travel to the Keys for your next vacation. With activities for both kids and adults alike, everyone is sure to enjoy their time in Florida. Drop the kids off at Camp Cheeca, where they’ll be entertained and educated, so you can enjoy some time to relax and unwind in Islamorada.

Leave Behind: Your Worries

Leave your worries behind when you travel to the Keys. Relax your mind, explore paradise, and enjoy yourself in Florida. Above all, Cheeca Lodge offers a tropical retreat for those looking to escape. Setting the standard for luxury amongst Islamorada hotels, we’re the ideal destination for a worry-free getaway.

Best Brunch Spots in Islamorada

A wise person once said, “Brunch without alcohol is just a sad breakfast”. We couldn’t agree more! Toast to the weekend at the best brunch spots in Islamorada. From your favorite breakfast items to refreshing mimosas and beautiful views, Islamorada is full of brunch spots that won’t soon be forgotten.

Marker 88

Offering beachside dining with fresh seafood, Marker 88 is an easy choice for brunch. Choose from classic selections with a coastal twist, like the lobster benedict, seafood omelette, and Hawaiian French toast. Pop some bubbly and enjoy endless mimosas, or try the Southern Bloody Mary for an extra kick!

Hungry Tarpon

Head down to the Hungry Tarpon for Caribbean cuisine in the Florida Keys. Here, brunch is offered every day of the week. Indulge in southern favorites, breakfast burritos, and champagne cocktails.

Chef Michael’s

Known for their dock-to-dish fish specialties, Chef Michael’s is a must-try Florida Keys experience. Conveniently located just around the corner from Cheeca Lodge, this spot’s  brunch offering includes Napoleon French toast, a lobster and asparagus omelet, and sauteed shrimp and grits. Be sure to try the hogfish, which is a local specialty. Pair any dish with a refreshing Island Sangria or a Good Morning Mary, made with TK.

Lorelei’s Restaurant

Have breakfast on the bay at Lorelei’s Restaurant. Their  Sunday School Specials include $3 bloody marys, screwdrivers, and mimosas. With traditional breakfast options and a laid-back local feel, Lorelei’s makes for the perfect way to start your day.