Key West Weekend Guide: A 2-Day Itinerary

For the adventurous souls, explore the underwater world through snorkeling or diving expeditions, or set sail on a sunset cruise to witness the sky ablaze with color. And of course, no visit to Key West is complete without basking in the sun on its pristine beaches, where relaxation and rejuvenation are the order of the day.

Whether you’re seeking a romantic getaway, a family adventure or a solo escape, Key West has something extraordinary to offer to build an incredible two-day itinerary. Let this guide be your companion as you discover the hidden gems and iconic landmarks that make this island a true paradise.

Kick off your Key West getaway at Blue Heaven, a place that truly captures the island’s quirky charm. Nestled in the heart of the historic Bahama Village, Blue Heaven is famous not only for its inventive menu but also for its outdoor dining area, where chickens roam freely among the tables. The lobster Benedict here is a must-try, featuring freshly caught lobster and homemade hollandaise sauce atop a perfectly toasted English muffin. The atmosphere, with its eclectic decor and the shade of large almond trees, makes for a uniquely Key West breakfast experience.

For those on the move, Cuban Coffee Queen offers a quick yet memorable start to the day. Located conveniently at the Key West Historic Seaport, this bustling spot serves up robust Cuban coffee and a variety of delicious pastries, perfect for fueling your adventures around the island. The vibrant murals and the friendly banter of the staff add a splash of local color, making it more than just a coffee stop but a place to soak in the local culture and energy.

Hop on the Old Town Trolley Tours^® for a perfect introduction to Key West. These tours are fantastic for sightseeing on limited time. They feature live fully narrated excursions led by friendly and knowledgeable guides who delve into the island’s history and culture. Enjoy the flexibility of the hop-on, hop-off service as you visit iconic spots like the Ernest Hemingway Home & Museum, where you can explore the writer’s preserved study; Mallory Square, for its famous Sunset Celebrations and lively street performers; and the Southernmost Point, one of the most photographed locations in the U.S. This tour is an easy and enjoyable way to discover the best of a Key West getaway, ensuring you don’t miss out on any of the highlights.

Dive into the flavors of Cuba at El Meson de Pepe, conveniently located near Mallory Square. This restaurant is renowned for its authentic Cuban cuisine such as ropa vieja, a flavorful shredded beef dish, and sweet plantains that melt in your mouth. The ambiance here is filled with the rhythms of traditional Cuban music, enhancing the dining experience and embracing Key West’s Cuban connections.

For those seeking a quieter dining experience, Red Shoe Island Bistro offers a tranquil setting tucked away on a picturesque side street. Known for its refined menu, it features perfectly seared scallops served with a delicate lemon butter sauce and gourmet burgers crafted from locally sourced ingredients. The bistro’s calm, welcoming atmosphere makes it a perfect escape from the busier downtown buzz.

Lastly, Seaside Café at the Mansion boasts one of the best ocean views in Key West, located right on the water’s edge. Guests can enjoy fresh seafood dishes while overlooking the clear blue waters. Their lobster rolls are packed with fresh, succulent lobster meat, and their coconut shrimp comes with a homemade mango dipping sauce that adds a tropical twist to the meal. The cafe offers a relaxed and scenic dining experience, ideal for those who wish to dine amid the natural beauty of Key West.

Spend a peaceful afternoon at the Key West Butterfly & Nature Conservatory. Immerse yourself in a tranquil environment where hundreds of colorful butterflies flutter freely in a lush tropical setting. This conservatory is more than just a walk-through; it’s an interactive habitat where exotic birds also chirp melodiously from the foliage, adding to the serene atmosphere. The conservatory’s glass-enclosed environment is carefully controlled to mimic a natural rainforest, complete with waterfalls and rare tropical plants that provide a perfect backdrop for the butterflies and birds. This magical experience offers a unique opportunity to observe these beautiful creatures up close, making it a memorable part of any visit to Key West. The thoughtful layout and informative plaques throughout the conservatory educate visitors about the life cycle and conservation of butterflies, making it an enriching experience that connects you with nature’s delicate balance.

Savor a delightful dinner at Two Friends Patio Restaurant, where the setting buzzes with the sounds of local musicians playing classic and contemporary hits. This eatery is famous for its generous servings of classic American dishes like their signature Key West shrimp and grits. The casual, friendly environment makes it a great spot for enjoying a meal while soaking in the local culture.

Seafood lovers will relish the experience at A&B Lobster House, where gourmet dishes meet the backdrop of the ocean. Dine on exquisite seafood selections, such as fresh lobster tail and seared scallops, served alongside stunning views of the harbor. The restaurant’s elegant yet comfortable setting provides an ideal ambiance for a relaxing night out during a quick Key West getaway.

Cap your evening with a serene Fury Sunset Cruise. Glide across the waters as the sun dips below the horizon, casting a golden glow over the Gulf. This cruise not only offers breathtaking views but also a warm, welcoming atmosphere, allowing you to unwind fully as you take in the panoramic ocean vistas. It’s the perfect way to embody the relaxed essence of Key West, making for an unforgettable end to your day.

Start your day with something simple and quick to maximize your exploration time during your two days in Key West.

Start your day at Fort Zachary Taylor Beach, a serene retreat known for its clear waters and rich historical background. This beach is not just a place to relax; it’s part of a state park with a well-preserved fort that dates back to the Civil War. The beach offers exceptional snorkeling opportunities where you can explore vibrant marine life just offshore, or you can simply enjoy a peaceful morning sunbathing under the shade of Australian pines. What more could you ask for during a quick Key West getaway?

If you prefer a more dynamic setting, Smathers Beach is the place to be. It stretches along the southern shore of the island and is famous for its soft, sandy beachfront and gentle waves, making it perfect for volleyball, Jet Skiing or parasailing. Its wide expanse is dotted with coconut palms and provides ample space for sunbathers and picnickers. The atmosphere here is energetic, filled with the sounds of laughter and the gentle lapping of waves, offering a lively yet relaxing beach experience.

Spend your afternoon at the Key West Cooking School, where you can dive into the local cuisine with fun cooking classes led by expert chefs. These sessions are not just informative — they’re interactive and filled with fun, offering you a chance to learn about and enjoy making — and tasting — Key West’s signature dishes. You can walk away from your trip with skills to take home.

End your Key West weekend at Hot Tin Roof, where the menu’s fusion of tropical and Latin flavors is as enticing as the restaurant’s sophisticated ambiance. Located along the waterfront, diners can enjoy dishes like the zesty mango-glazed scallops or the savory churrasco steak, all while surrounded by elegant decor that features warm lighting and plush seating, creating a cozy yet refined dining atmosphere.

However, Latitudes on Sunset Key provides a uniquely intimate dining experience that’s just a short boat ride away. As you dine alfresco, you’ll be treated to stunning views of the Gulf of Mexico, making every meal feel like a private celebration. Latitudes is famous for its fresh seafood dishes, such as the pan-seared grouper on a bed of truffled risotto and its Key lime pie, acclaimed for its perfect balance of tart and sweet. The serene sound of the waves and the gentle ocean breeze add to the enchantment of dining at this secluded spot, making it an ideal choice for a romantic evening or a peaceful retreat from the bustle of Downtown Key West.