Three nights, two people, and a little island time.
Key West is an easygoing getaway with colorful historic homes, waterfront restaurants, beautiful sunsets, and plenty to explore. Here’s a simple three-night itinerary for a long weekend.
Where to Stay
The Gardens Hotel — A quiet boutique hotel tucked into Old Town, surrounded by lush tropical gardens. A lovely choice for couples who prefer a more intimate stay.
Winslow’s Bungalows — A collection of charming island-style accommodations with three pools, tropical landscaping, and easy access to Duval Street. Great for couples who want a relaxed but social atmosphere.
Friday | Arrive & Settle In
- Afternoon: Check into your hotel and explore the colorful streets of Old Town.
- Evening: Head to Mallory Square for the famous sunset celebration and waterfront views.
- Dinner: El Mesón de Pepe for Cuban food and live music near Mallory Square.
Saturday | Explore Old Town
- Breakfast: Blue Heaven for an outdoor island-style breakfast.
- Morning: Visit the Ernest Hemingway Home & Museum, then browse the shops and galleries along Duval Street.
- Lunch: Moondog Café & Bakery for a casual meal or something sweet.
- Afternoon: Spend a few hours at Fort Zachary Taylor State Park. Swim, relax on the beach, or explore the historic fort.
- Dinner: Louie’s Backyard for an oceanfront dinner. Reservations recommended.
Sunday | A Little Adventure
- Morning: Grab Cuban coffee and breakfast at 5 Brothers Coffee.
- Late morning: Take a snorkeling excursion, dolphin-watching cruise, or guided kayak tour.
- Lunch: Enjoy fresh seafood near the Historic Seaport.
- Afternoon: Visit the Key West Garden Club at West Martello Tower, a beautiful hidden garden inside a historic fort.
- Evening: Book a sunset sail for a different view of the island.
- Dinner: El Siboney for a casual Cuban meal.
Monday | One Last Island Morning
- Breakfast: Coffee and pastries at a local café.
- Morning: Take a final walk through Old Town, pick up a souvenir, and enjoy one last slice of Key lime pie.
- Afternoon: Check out and head home.
A Few Things Worth Knowing
- Getting around: Old Town is easy to explore on foot or by bicycle. A rental car usually isn’t necessary.
- Best time to visit: November through April is a popular time for more comfortable temperatures.
- Book ahead: Reserve hotels, sunset cruises, and popular dinner spots early, especially for holiday weekends.
- Worth the detour: The Key West Garden Club is free to visit and a lovely alternative to the busier attractions.
Planning Your Own Key West Getaway?
This is just one way to spend a long weekend in Key West. Whether you’re looking for a romantic escape, a relaxing beach trip, or something a little more adventurous, your itinerary can be tailored to you.
