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3 days in Key West

A day-by-day itinerary covering the must-sees of Key West plus one day trip — perfect for a long weekend or short vacation.

Key West, FL, USA· Airport: EYW
Key West — 3 days in | CheapoTrav travel guide

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Phone-only fares for Key West, 24/7.

Call (815) 991-4848

Key facts

  • Most attractions, restaurants, and bars are concentrated in Old Town, making it highly walkable.
  • Consider renting a scooter or bicycle for efficient travel beyond Duval Street's immediate vicinity.
  • The Harry S. Truman Little White House offers insight into presidential history and tropical retreats.
  • Catch a sunset celebration at Mallory Square, a daily tradition featuring street performers.
  • Explore the Ernest Hemingway Home and Museum, known for its resident six-toed cats.
  • Dry Tortugas National Park is a full-day commitment; book tickets well in advance if it's on your list.

Three days is a solid amount of time to get acquainted with Key West. It allows for exploration of the historic district, time on the water, and enough evenings to experience its unique atmosphere without feeling rushed. This itinerary focuses on making the most of your time, balancing iconic sights with opportunities to discover some of the island's quieter charm.

Key West is a walking town, particularly the Old Town area. You'll find many of its main attractions, restaurants, and bars within a compact footprint. Consider renting a bicycle or a golf cart for broader exploration, especially if your accommodation is a bit farther afield. Parking can be challenging and expensive, so planning your transportation is key.

The island's history is rich, from its maritime heritage to its role as a haven for artists and writers. Take time to step off the main thoroughfares; you'll uncover hidden gardens, quaint guesthouses, and independent shops. The pace here is generally relaxed, encouraging you to slow down and soak it all in.

Even with just a few days, you can experience a good cross-section of what Key West offers. From morning coffee to sunset celebrations, there's a rhythm to island life worth embracing. If you need help tailoring this to your specific interests, a travel agent can assist with personalized arrangements.

In this guide

  • Day 1: arrival and orientation
  • Day 2: top sights and food
  • Day 3: day trip or slow day
  • Where to stay
  • Cost breakdown

Frequently asked questions

What's the best way to get around Key West for three days?
For three days, the most efficient way to navigate Key West's Old Town is on foot. Most major attractions, dining, and nightlife are within a comfortable walking distance. For exploring areas slightly outside of Old Town, or if you prefer not to walk extensively, consider renting a bicycle, scooter, or golf cart. Public transportation via Duval Loop buses is also available and free, connecting many key points. Taxis and rideshares are present but can add up quickly.
Where should I stay in Key West for a 3-day trip?
Staying in Old Town Key West is generally recommended for a 3-day trip due to its central location and walkability to most attractions. Look for hotels or guesthouses near Duval Street, Mallory Square, or the Historic Seaport. This area puts you within easy reach of museums, restaurants, and nightlife. If you prefer a quieter experience, consider accommodations a few blocks away from the busiest sections of Duval Street, still within Old Town.
Call (815) 991-4848 for phone-only fares
Is Key West expensive for a short trip?
Key West can be an expensive destination, particularly for accommodation and dining, especially during peak season. However, a 3-day trip allows for careful budgeting. Many activities, such as watching the sunset at Mallory Square or exploring the architecture, are free. You can manage costs by choosing guesthouses over larger resorts, opting for casual eateries, and taking advantage of happy hour specials. Planning meals and activities in advance can help control spending.
What's a must-do activity in Key West if I only have three days?
If you only have three days in Key West, witnessing the sunset celebration at Mallory Square is a quintessential experience. It's a nightly tradition where locals and visitors gather to watch street performers, artisans, and the sun dip below the horizon. It's a vibrant, free event that captures the unique spirit of Key West and provides a memorable end to any day on the island. After, you're perfectly positioned for dinner in Old Town.
Call (815) 991-4848 for phone-only fares
Can I visit Dry Tortugas National Park in a 3-day Key West trip?
Yes, you can visit Dry Tortugas National Park, but it will consume one full day of your 3-day trip. The ferry departs early in the morning and returns in the late afternoon. Given the limited time, if Dry Tortugas is a priority, ensure you book your ferry or seaplane tickets well in advance, as they often sell out months ahead. It's a spectacular day trip but means less time for exploring Key West itself.
What are the best dining experiences to try in Key West for three days?
For three days in Key West, focus on fresh seafood and local Cuban-inspired flavors. Try conch fritters at a casual spot, savor fresh catch at a waterside restaurant in the Historic Seaport, and don't miss a slice of Key lime pie from a reputable bakery. Consider a brunch experience at a charming café in Old Town and explore some of the more established fine dining options for an evening meal if your budget allows. Reservations are advisable for popular spots.
Call (815) 991-4848 for phone-only fares

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