2 Days to See Key West

Whether you're a first-time visitor or returning to this enchanting island, Key West offers a wealth of experiences packed into a small area. This vibrant 2-by-4-mile island is rich in history, from its time as Florida's largest city to its tales of treasure and piracy, U.S. military exploits, Cuban connections, and famous authors like Ernest Hemingway. It is also a paradise for artists, featuring unique architecture and diverse fishing opportunities.

Explore Old Town and New Town

Begin your adventure in "Old Town," the historic heart of Key West. This area stretches from the elegant Casa Marina Resort to the historic Fort Zachary Taylor, and along the western channel to the northern harbors. Once home to naval bases, the harbor now hosts fishing charters and yachts. "New Town," on the island's east side, offers a glimpse into mid-century Key West with its concrete homes, shopping centers, and local life.

Discover Fort Zachary Taylor

For a tranquil beach experience, head to Fort Zachary Taylor State Park. Known for its natural beauty and seclusion, this beach offers a perfect spot to watch sailboats and sunsets. Bring your snorkel gear and a picnic to make the most of this natural haven. If you're feeling adventurous, you can even grill your own Mahi sandwiches with just a few ingredients. The park is a pack-in, pack-out area, so be prepared to take everything you need with you.

Historical Tours

To get acquainted with Key West, start with a 90-minute historical tour. The Conch Tour Train offers an open-air ride through the island's rich past, while the Old Town Trolley provides a hop-on, hop-off option with stops at 13 different attractions. These tours give you a great overview and help you decide which sights to explore further.

Breakfast Spots

Begin your day with breakfast at one of Key West's beloved eateries:

• Pepe’s Cafe & Steakhouse: Established in 1909, Pepe's is the oldest eatery in the Keys, offering a charming rustic atmosphere. Located at 806 Caroline Street, it serves cafe-style breakfasts from 7:30 am to noon and lunch until 5 pm.

• Moondog Cafe & Bakery: Located at 823 Whitehead Street, Moondog offers a vibrant breakfast menu with options like avocado toast, Benedicts, and fresh pastries. The relaxed setting and friendly staff make it a great spot to start your day.

• Banana Cafe & Creperie: Situated at 1215 Duval Street, Banana Cafe serves delicious breakfast options, including crepes, omelets, and seafood specialties. This spot also offers salads, sandwiches, wines, and beer, making it a local favorite.

• Sandy’s Cafe: For a quick grab-and-go option, stop by Sandy's Cafe on White Street for Cuban coffee and sandwiches. It's perfect for a busy day ahead.

Adventure on the Water

Make the most of Key West's stunning waters with a morning snorkeling trip. Visibility is best between 10 am and 3 pm, so head out early to explore the reefs or a shipwreck site. Fury and Sebago catamarans offer excellent snorkeling tours, ensuring you experience the tranquility and excitement of marine life.

If the weather turns rainy, consider a half-day fishing trip instead. Fish are active even in the rain, so seize the opportunity to enjoy the beautiful waters.

Experience Key West Sunsets

Don’t miss Key West's famous sunsets. Plan to catch at least two: one from the lively Mallory Square and another from a serene sunset sail. Fury and Sebago offer sunset cruises, as do several schooners and smaller charters for a personalized experience.

Dining and Nightlife

After a day of adventure, unwind with Key West's vibrant nightlife. Here are some dining and entertainment recommendations:

• The Boat House Bar & Grill: Located at the Key West Bight Marina, The Boat House offers a casual dining experience with a focus on fresh seafood and grilled meats. Enjoy their famous "Boat House Bucket," filled with a variety of seafood, or try their delicious steaks and burgers. The waterfront views and laid-back atmosphere make it a perfect spot for a relaxing dinner.

• Alonzo’s Oyster Bar: Situated at the Key West Historic Seaport, Alonzo's Oyster Bar is renowned for its wide selection of fresh seafood, especially oysters. Their happy hour from 4 pm to 6:30 pm features fantastic deals on drinks and appetizers. Enjoy the lively seaport ambiance while savoring dishes like crab cakes, lobster, and fish tacos.

• Hot Tin Roof: Located in the Ocean Key Resort & Spa, Hot Tin Roof offers an upscale dining experience with stunning views of the Gulf of Mexico. The menu blends Caribbean and Latin flavors, featuring dishes such as yellowtail snapper, filet mignon, and paella. The romantic setting is perfect for a special evening out, and their extensive wine list complements the exquisite cuisine.

As the night unfolds, head to Duval and Green Streets, the epicenter of Key West's nightlife. Visit the world-famous Sloppy Joe’s Bar for a taste of history, or explore Rick’s Bar & Complex across the street. Let the music guide you through Duval Street's lively atmosphere, and embrace the spontaneity of the night.

Stay Safe and Enjoy

Key West offers late-night food spots for a quick recharge, ensuring you can safely enjoy the island's vibrant scene. Plan to meet up with friends and ensure everyone gets home safely after a night of fun.

Enjoy your two days in Key West, making the most of its unique blend of history, culture, and natural beauty. Whether you're exploring its waters or savoring its cuisine, Key West promises an unforgettable experience.