Key West

Florida | United States

Key West

The Conch Republic, in our opinion, is the very best Florida has to offer: spectacular beaches, rich history, excellent restaurants, and quaint architecture. Key West has homed some of the United States’ most famous writers and a US president. Get sun-drenched on the beach, explore the extensive rich history, snorkel in a National Park, have cocktails with your feet in the sand, enjoy one of the many fantastic restaurants, and explore a laid back music-focused nightlife.

Transportation: Bike and taxi/rideshare, possible rental car

Length: 4+ days

Guide Book: Fodor’s In Focus Florida Keys: with Key West, Moon Florida Keys, The Florida Keys Bucket List

Day 1

Day 2

Day 3

Day 4

Day 5

  • Pick up rental car and drive up the Keys
  • Big Pine Key
    • National Key Deer Refuge
    • Bahia Honda State Park
      • Sandspur Beach
      • Calusa Beach
      • Loggerhead Beach
      • Old Bahia Honda Bridge
  • Seven Mile Bridge
  • Marathon
    • Turtle Hospital
    • Dolphin Research Center
    • Curry Hammock State Park
  • Islamorada:
  • Key Largo
    • Keys Diver for John Pennekamp Coral State Park
    • The African Queen cruise
    • The Florida Keys Wild Bird Center
    • Caribbean Club’s claim to fame is that it was a filming site for the movie Key Largo (starring Humphrey Bogart) in 1947. It is the oldest bar in the Upper Keys.
    • Laura Quinn Wild Bird Sanctuary

In Depth Itinerary

Day 1

Welcome to Key West! The Conch Republic, as it’s fondly known, certainly knows a good time. But it’s also full of a rich history and beautiful beaches, marine life, and plenty of culture being closer to Cuba than Miami. The historic town, once the richest city per capita in the United States thanks to the salvage industry, is comprised of hundreds of candy-colored 19th century Victorian homes known as “conch houses” interspersed with tall banyan trees and bright tropical flowers. While in Key West you’ll only need your feet or a bike – it’s one of the best historic walking towns in the United States. Everything is close by, so a detour is barely a blip. If you don’t have time for something one day, visit it the next.

Take a rideshare (Uber/Lyft) or taxi from the airport to your lodging. We recommend picking up your bike first thing, or, depending where you’re staying, have the bike rental drop it off for you. There’s many bike rental companies in Key West, but We Cycle will deliver it to your rental.

If you need a pick-me-up you can stop for a cuban coffee at either Sandy’s Cafe or Cuban Coffee Queen before heading to the Ernest Hemingway House where the famous author lived and worked.

Have lunch after your museum visit. We recommend heading to Eaton Street Seafood Market for casual and excellent seafood. A closer option that’s also good is Moondog Cafe.

After lunch, take a guided tour the Truman Little White House where President Truman spent 175 days of his presidency. Once you get your fill of history continue to Duval Street, passing Mile Marker 0, to the Key West Butterfly and Nature Conservatory.

If you still have energy, pop into any of the many art galleries along Duval Street as you head towards the Southernmost Point. This is exactly what it sounds like, the southernmost point of the continental United States which is marked by a buoy. If you can elbow your way through the other tourists, snap a quick picture and make your way to the nearby Seaside Cafe at the Mansion for a sunset drink.

There are so many incredible places to eat in Key West. We can’t possibly have you eat at them all, so we’ll try and focus on our absolute favorites, but check out our Key West Restaurant Recommendations if you happen to be in town longer. Tonight we recommend either Blue Heaven or Salute.

Key West has one of the best night life of any city in the United States. While we’ll share our favorites, your best bet is wandering along Duval street and heading into any bar with music spilling out. It’s customary to tip the musicians who play, so try and have some small bills on hand. For tonight we recommend stopping by Green Parrot Bar, dating from 1890, and catching some live music.

Lodging in Key West can be expensive. We strongly recommend you stay in the old town to make it bikeable or walkable to everything. Pick a place with a pool. Don’t bother looking at AirBNBs – there’s a city-wide ordinance rentals can’t be shorter than 30 days. If you want to stay in the original hotel that started Key West’s elegance, stay at Casa Marina. Other good options include Scarlet Mango Inn, Traveler’s Palm Inn, Weatherstation Inn, The Saint Hotel Key West, Eden House, Marquesa Hotel, and the Southernmost House Hotel.

Day 2

For breakfast today you can try Key West’s iconic Cuban Coffee Queen Roasters or, if Cuban coffee is not your thing, Date and Thyme Organic Cafe which offers excellent matchas and smoothies.

After breakfast, consider the organized Lloyd’s bike tour which will take you to some of the most famous Key West sites or hop on the Conch Tour Train which similarly takes you around the old town. You can also opt to bike around the island yourself (or use a walking audio guide like this or this). Places to visit include: Garrison Bight, Key West Cemetery, Historic Seaport & Harbor Walk, Mallory Square, Southernmost Point, the St. Mary Star of the Sea, and the Key West Lighthouse, Higgs Beach, Smathers Beach, and East Martello Tower. The Key West Chamber of Commerce has plenty of maps for free for self guided bike tours.

For lunch we recommend grabbing Cuban Sandwiches at Sandy’s Cafe before heading to the beach. While Key West isn’t exactly known for sandy beaches, there are definite exceptions. If you prefer to snorkel and visit a Civil War Fort, bike to Fort Zachary Taylor State Park, a state park with plenty of shade and good snorkeling, and enough of a sandy beach to lie out. That being said, this beach is generally rocky, and while pretty, most of the shade is set up and off of the sand. If you prefer calm water and pristine sand Smather’s Beach may be your best option. It’s a pristine and beautiful beach, but a poor place to snorkel. If you don’t like beaches, enjoy the afternoon at your hotel’s pool, or select an activity off of Day 4.

For pre-dinner drinks keep your feet in the sand at Louie’s/the Afterdeck Bar or for excellent craft cocktails and live music try Key West’s rum distillery Papa Pilar’s Rum Distillery.

For dinner tonight, head to our personal favorite, Little Pearl for their casual tasting menu or select from Key West Restaurant Recommendations.

Finish your evening at the Little Room Jazz Club, enjoying both the music and ambience.

Day 3

Have breakfast early, grabbing one of the phenomenal donuts at Glazed Donuts before catching the ferry to Dry Tortugas National Park. Yes, it’s one of the most difficult national parks to get to, but it’s well-worth it for spectacular snorkeling (gear provided on your trip). This is an all-day adventure but you’ll get to explore one of the prettiest coral reefs in the world. While you can also get there quicker by helicopter tour, we recommend the ferry.

Once you return home, take a quick shower and head to Sunset Pier for sunset drinks before having dinner at Thirsty Mermaid or Nine One Five. If it’s Monday, have one (or more) martinis at Virgilio’s or if it’s another day, stop by Hog’s Breath Saloon for great live music.

Day 4

If this is your last day in Key West, decide if you want to stay on the island or rent a car and head up the keys. If you choose the latter, check out our itinerary recommendation for Day 5.

If you choose the former, grab breakfast at the Keys Coffee Company.

For the day you get to make some choices. You could take a dolphin tour with Honest Eco, a kayak or paddle board trip with Lazy Dog Adventures, or scuba with Captain’s Corner Dive Center: Vandenberg Wreck Dive. There are many museums you can visit including the Audubon Museum, a historic house featuring Audubon’s paintings, the Mel Fisher Maritime Museum, the Key West Museum of Art and History, or the Oldest House and Gardens. You can also visit the Key West Lighthouse, take a Literary Walking Tour, or a sunset sail.

At some point today we recommend you get lunch at the Half Shell Raw Bar, have key lime pie at Old Town Bakery and enjoy a drink at Sloppy Joe’s.

Day 5

Pick up your rental car and drive up the Keys. The hundreds that make up the “keys” or Florida’s archipelago are joined by a series of overwater bridges, the longest being the Seven Mile Bridge. The Florida Keys Overseas Highway offers one of the prettiest road trips in the US. In 100 miles you can jump from key to key enjoying the pristine turquoise water and stopping along the way to snorkel, eat, and shop.

While you can drive the length of the Keys and back in a day (about 4 hours total driving), it may be more pleasant to plan and stay over in Key Largo or end and fly home out of Miami. The best sites are on Pine Key and Key Largo, so decide if you feel like stopping in between. You won’t have time to stop and do everything, but these are some of the most interesting and worthwhile things to do.

First you will come to Big Pine and the most nature-forward of the Keys. This is most popular for two things: the National Key Deer Refuge and Bahia Honda State Park. The Refuge was founded to protect the tiny Key deer and here is your opportunity to see them along with alligators and great white herons. The state park offers snorkeling along Looe Key Reef and lots of hiking trails. Some of the best beaches here include Sandspur Beach, Calusa Beach, and Loggerhead Beach. Or go diving near at the wreck dive, Adolphus Busch Sr.

Next you’ll drive across the famous Seven Mile Bridge, which is the longest bridge in the Keys. You’ll literally be driving over the vivid water. From here you will see the old railway bridge, the original way tourists made it down to Key West, destroyed by a hurricane in 1935.

The next place you’ll reach is Marathon which has two interesting stops: the Dolphin Research Center and Turtle Hospital, both which are conservation and rehabilitation sites for the species. If you’re not planning to go further, you can finish with the beach at Curry Hammock State Park.

Islamorada makes a great stop for lunch on the water at Morada Bay Beach Café or to quench your thirst at Florida Keys Brewing Company and see some art at the Morada Way Art Walk.

Key Largo is one of the most northernmost Keys closest to Miami and known as The Dive Capital of the World. It’s worth spending most of the day or even an overnight here if you plan on diving. John Pennekamp Coral Reef State Park lets you explore shipwrecks and a live coral barrier reef by scuba. If you’re not a diver or snorkler there’s still plenty to do. Take a glass-bottom boat to see the Florida Keys National Marine Sanctuary, take a cruise on Humphrey Bogart’s The African Queen, or check out the Florida Keys Wild Bird Center. Have a drink at the Caribbean Club, a filming site for Humphrey Bogart’s movie Key Largo and the oldest bar in the Upper Keys. Consider dinner here if you’re heading back to Key West this night at the Key Largo Conch House or The Fish House.

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