Unwind, Explore and Play: The Perfect Family Getaway in Islamorada

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Advisor - Elissa Kole
Curated By

Elissa Kole

  • Florida

  • Family Travel

  • Beaches

  • Active Travel

  • Coastal

  • Local Culture

  • Local Food

A wooden pier with benches overlooks a calm sea under a clear blue sky.
Curator’s statement

Nestled in the heart of the Florida Keys, this resort provides an enchanting tropical escape with stunning ocean views and lush landscapes. At Cheeca Lodge, families can create unforgettable memories through a variety of activities. From kayaking and paddleboarding to snorkeling in vibrant coral reefs, there’s no shortage of outdoor fun. The resort’s spacious accommodations and family-friendly amenities ensure comfort and convenience, allowing everyone to unwind after a day of exploration. Additionally, the inviting atmosphere fosters togetherness, whether it’s enjoying meals at the beachfront restaurant, gathering around a fire pit at sunset or simply relaxing by the pool. Cheeca Lodge offers the opportunity for families to enjoy quality time together in a picturesque paradise.

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Where to stay in Islamorada

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Things to do in Islamorada

Kids are standing on a sandy pathway lined with lit torches and tropical vegetation at night.

Watersports at the resort: Cheeca Lodge boasts a full­-service watersports facility right on property for Islamorada snorkeling tours, fishing and more. Let the professional staff at Cheeca Watersports help you plan a perfect day on the water. Group tours, private excursions, fishing trips, equipment rentals and lessons are offered daily. You’ll find Cheeca Watersports conveniently located in the Tiki hut near the pier, right outside our luxurious family pool.

Swim, swim, swim: My kids favorite activity! Enjoy the resort pool year-round!

Snorkel beautiful coral reefs: Take a smooth ride out to one of the many coral reef patches that make this area so special. See an abundance of sea life and experience the only barrier reef system in North America!

Play golf at Cheeca Lodge: Cheeca’s golf course is first come, first served with no tee time required. Use of course, golf clubs, golf balls and tees are included in daily resort fee.

Play tennis or pickleball: Six lighted tennis courts give guests the opportunity to play tennis from sunrise to sunset — and beyond.

Kids can enjoy Camp Cheeca: A family-focused program designed to entertain your kids in the Florida Keys. Camp Cheeca offers daily activities that are enthralling and fun, with a unique combination of arts and crafts, exploration and outdoor activities led by knowledgeable counselors.

Theater of The Sea: Theater of the Sea lagoons and lush tropical gardens are home to dolphins, sea lions, sea turtles, fish, sharks, stingrays, alligators and birds, and the kids will love it!

Day trips:

Take a one hour 45-minute drive to Key West. Explore Duval Street, the lively main street filled with shops, restaurants, bars and entertainment. Visit Ernest Hemingway Home and Museum, the famous author's former residence, complete with beautiful gardens and six-toed cats. Stop by the Southernmost Point and snap a photo at this iconic landmark, marking the southernmost point in the continental United States. End your day in Mallory Square, home to the nightly sunset celebration, featuring street performers, local artisans and stunning views.

Places to eat & drink in Islamorada

A child fishing over the sea from a wooden pier.
  • Nikai Sushi Bar: This sushi restaurant is on property with rooftop seating, open for dinner.

  • Morada Bay: The resort offers a shuttle to this casual, outdoor eatery offering delicious food along with the ultimate Florida Keys vibes.

  • Pierres: Also accessible by the resort shuttle, this is an upscale French restaurant located next to Morada Bay Beach Cafe.

Advisor - Elissa Kole

Travel Advisor

Elissa Kole

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This guide is a part of our ongoing series on travel to Florida. For more travel tips, check out Fora Advisor Laura Rienas's guide, Adventurous Things to Do on a Vacation in Islamorada