Chasin Surf is a travel blog that consists of a compilation of posts to inspire people to keep traveling and feed their souls with new key west family trip itinerary cultures, food and beautiful sights that will leave a mark on their life. In addition to travel, we write about the gear we use, lifestyle we live and people we meet along the way.
Ultimate Key West Family Trip Itinerary: Sun, Fun, and Unforgettable Moments
Planning a family vacation to Key West? Whether you’re looking for sun, history, nature, or just a relaxing getaway, this island paradise offers the perfect mix of activities for all ages. Here’s a fun, stress-free itinerary to make the most of your family trip to Key West.
Day 1: Arrival and Island Passion
Morning:
Fly to Key West or take a scenic drive along the exotic highway.
Check into a family-friendly hotel or resort like Parrot Key Hotel & Villas or Hyatt Centric Key West.
Afternoon:
Have lunch at Conch Republic Seafood Company — kid-friendly and right on the water.
Head to Mallory Square for your first taste of local life.
Evening:
Enjoy the sunset celebration at Mallory Square with live music, street performers, and breathtaking views.
Dine on Cuban cuisine and a lively family atmosphere at El Maison de Pepe.
Day 2: Sea Adventures and Island Exploration
Morning:
Start your day with a family snorkeling tour at Fort Zachary Taylor State Park or book a half-day excursion with Furious Water Adventures.
For younger kids, the Key West Aquarium offers a more relaxed marine experience.
Afternoon:
Refuel with fish tacos at B.O.'s Fish Wagon or a smoothie from The Smoothie Shuttle.
Visit the Key West Butterfly and Nature Conservatory—a magical hit for both kids and their parents.
Evening:
Salute! Enjoy dinner on the beach, then take a nighttime glass-bottom boat tour for a unique view of the underwater past.
Day 3: History meets nature
Morning:
Visit the Ernest Hemingway Home and Museum - older kids will love the stories (and the famous six-toed cat).
Walk to the southernmost point for an iconic family photo.
Afternoon:
Take a conch train to see the island's attractions while resting tired feet.
Have a late lunch at Blue Haven, known for its fun atmosphere and outdoor seating under the trees.
Evening:
Relax by the hotel pool or take an evening stroll down Duval Street (a quiet, family-friendly street closest to the south).
Day 4: Dolphin Watching and Farewell
Morning:
Take a dolphin-watching tour - many tours guarantee sightings and offer snorkeling stops in calm, clear waters.
Or rent a bike and explore the island together.
Afternoon:
Have a last-minute lunch at Hogfish Bar & Grill on Stock Island — it’s a hidden gem just a short drive away.
Shop for souvenirs at a local boutique or art gallery before heading home.
Bonus Tips for a Smooth Trip
Pack sunscreen, a hat, and refillable water bottles — the Key West sun is intense!
Book your favorite tours in advance, especially during peak season.
Use downtime to lounge by the pool or beach so everyone can relax and unwind.
Summary: A family trip to Key West is key west family trip itinerary the perfect mix of adventure and fun. From coral reefs and dolphins to quirky museums and colorful sunsets, every day brings something new and exciting. With this itinerary, you’re sure to create unforgettable memories that your family will talk about for years to come.