The allures of Key West, located closer to Cuba than to Miami, are legendary. So it’s no surprise this slice of paradise at the southernmost part of Florida is the most popular, and arguably most famous, district in the Florida Keys archipelago. On this five-day itinerary, discover an eclectic mix of history, natural beauty, cultural diversity, and gorgeous architecture packed onto this seven-square-foot-mile island. It truly has something for everyone, from quiet sunsets to world-class restaurants and thrilling water sports.
Itinerary
PLAN YOUR TRIP
Day 1Arrival in Key West
After flying into Key West airport, take a taxi and check into Ocean Key Resort & Spa. The hotel’s perfect location is at the center of it all. Balconies have waterfront views or views over Duval Street, and nearly everything in Key West is accessible by foot, bike, or pedicab.
Outside the resort, get the lay of the land via the Conch Train Tour, which has been shuttling visitors around Key West since 1958. Stay on board for the entire 75-minute tour and listen to the knowledgeable guides deliver a fast-paced history of Key West as you ride by the island’s most famous sites. Or hop on and off at any stops that interest you, although you’ll have an opportunity to tour most of them during the next few days.
Before the sun starts to lower, head back to the resort for a dip in the pool and a seafood dinner with frozen drinks at the Sunset Pier. Watching the sunset here is a classic Key West experience. Hopefully, it will be just one of many on your trip.
Outside the resort, get the lay of the land via the Conch Train Tour, which has been shuttling visitors around Key West since 1958. Stay on board for the entire 75-minute tour and listen to the knowledgeable guides deliver a fast-paced history of Key West as you ride by the island’s most famous sites. Or hop on and off at any stops that interest you, although you’ll have an opportunity to tour most of them during the next few days.
Before the sun starts to lower, head back to the resort for a dip in the pool and a seafood dinner with frozen drinks at the Sunset Pier. Watching the sunset here is a classic Key West experience. Hopefully, it will be just one of many on your trip.
Day 2Hit the Town
Start your day with a delicious breakfast at the resort at Hot Tin Roof. Named after the famous play by Tennessee Williams, the menu pays homage to the writer from Mississippi. Dishes like the Rosemary & Brown Butter Biscuit and spicy sausage gravy blend Southern flavors with fresh touches.
Next is a visit to the Key West Aquarium to see alligators, jellyfish, sharks, and more. The touch tanks also contain conchs, sea stars, sea urchins, giant hermit crabs, and horseshoe crabs. Regular animal feedings are a particularly popular happening.
Then head south on Whitehead Street to visit the Audubon House & Tropical Gardens. Famous naturalist John James Audubon stayed here when he visited the Florida Keys during the 19th century and drew 25 new birds for his classic books. Lush gardens, orchids, and fruit trees surround the impeccably restored 19th-century Bahamian-Greek Revival home, which was owned by Captain John Huling Geiger.
The sun should be lower in the sky by now and that’s a sign to make your way to Mallory Square for the famous Sunset Celebration. People will gather about two hours before the big show to get a good viewing spot. Watch the street performers while you wait for the sun to drop beyond the horizon—there are musicians, of course, but you could also see a man swallowing swords or someone riding a unicycle.
After the show, make your way to the Flaming Buoy Fillet Co., a quintessential island restaurant with just a handful of orange and yellow wooden tables. Owners Fred Isch and Scot Forste turn out homestyle food sprinkled with tropical influences, like yellowtail snapper with grilled pineapple and banana salsa, and black grouper with lime butter sauce served with corn on the cob. The result: you feel like you’re at a friend’s house for a cozy dinner party.
Next is a visit to the Key West Aquarium to see alligators, jellyfish, sharks, and more. The touch tanks also contain conchs, sea stars, sea urchins, giant hermit crabs, and horseshoe crabs. Regular animal feedings are a particularly popular happening.
Then head south on Whitehead Street to visit the Audubon House & Tropical Gardens. Famous naturalist John James Audubon stayed here when he visited the Florida Keys during the 19th century and drew 25 new birds for his classic books. Lush gardens, orchids, and fruit trees surround the impeccably restored 19th-century Bahamian-Greek Revival home, which was owned by Captain John Huling Geiger.
The sun should be lower in the sky by now and that’s a sign to make your way to Mallory Square for the famous Sunset Celebration. People will gather about two hours before the big show to get a good viewing spot. Watch the street performers while you wait for the sun to drop beyond the horizon—there are musicians, of course, but you could also see a man swallowing swords or someone riding a unicycle.
After the show, make your way to the Flaming Buoy Fillet Co., a quintessential island restaurant with just a handful of orange and yellow wooden tables. Owners Fred Isch and Scot Forste turn out homestyle food sprinkled with tropical influences, like yellowtail snapper with grilled pineapple and banana salsa, and black grouper with lime butter sauce served with corn on the cob. The result: you feel like you’re at a friend’s house for a cozy dinner party.
Day 3Discover History and Paradise
After rising early for breakfast at the hotel, pack a small bag with drinking water, sunscreen, a bathing suit, a towel, snorkel gear, and whatever else you’d need for a day at the beach. Then, it’s time to make your way to Dry Tortugas National Park.
Located 70 miles west of Key West across open water, it claims the title of the country’s most remote national park. There’s no road here—you need to take a 2.5-hour ferry or 45-minute seaplane ride to reach it.
First, tour the massive 19th-century fort crowned with a lighthouse and encircled by a moat. After that, spend the rest of the day at the beach. However, birders might want to search for endangered sooty terns because Dry Tortugas is the only place in the continental U.S. where they nest.
It will be dinnertime upon returning to Key West in the evening. Head to Seven Fish, popular with visitors and locals alike. After 20 years in a smaller setting, the restaurant has expanded into a breezy space on Truman Avenue. But the menu still lists tried-and-true favorites like seafood dishes and grilled banana chicken with caramelized walnuts.
By now, you understand why the Keys are known for beautiful beaches and breathtaking sunsets. Tonight you’ll learn why it’s also famous for nightlife as you bar hop along Duval Street. Whether you want live music, cabaret events, or dancing, it’s all here.
Located 70 miles west of Key West across open water, it claims the title of the country’s most remote national park. There’s no road here—you need to take a 2.5-hour ferry or 45-minute seaplane ride to reach it.
First, tour the massive 19th-century fort crowned with a lighthouse and encircled by a moat. After that, spend the rest of the day at the beach. However, birders might want to search for endangered sooty terns because Dry Tortugas is the only place in the continental U.S. where they nest.
It will be dinnertime upon returning to Key West in the evening. Head to Seven Fish, popular with visitors and locals alike. After 20 years in a smaller setting, the restaurant has expanded into a breezy space on Truman Avenue. But the menu still lists tried-and-true favorites like seafood dishes and grilled banana chicken with caramelized walnuts.
By now, you understand why the Keys are known for beautiful beaches and breathtaking sunsets. Tonight you’ll learn why it’s also famous for nightlife as you bar hop along Duval Street. Whether you want live music, cabaret events, or dancing, it’s all here.
Day 4Rest and Relaxation
After a late night out, why not indulge in room service and a leisurely breakfast in bed this morning? Take your time getting ready before departing for the Key West Butterfly & Nature Conservatory. It will be a nice reprieve from the crowds from the night before. Find more than 50 fluttering butterfly species, as well as a vast variety of plants and upwards of 20 species of exotic birds, soaring inside the glass aviary.
Now would also be an excellent time to tour the Little White House, where President Harry Truman spent 175 days of his presidency. Afterward, return to the resort for some rest and relaxation. A visit to Spaterre, where body scrubs, facials, and other treatments mix Balinese influences with local flair, is in order.
For dinner tonight, you’ll make your way to Louie’s Backyard for Caribbean-American food, served alfresco or inside a converted Victorian home. There’s Bahamian Conch Chowder with Bird Pepper Hot Sauce and Crumb Crusted King Salmon with Chayote Relish & Cajun Tartar Sauce since 1971. Then, if you’re feeling up for it, hit Duval Street one last time.
Now would also be an excellent time to tour the Little White House, where President Harry Truman spent 175 days of his presidency. Afterward, return to the resort for some rest and relaxation. A visit to Spaterre, where body scrubs, facials, and other treatments mix Balinese influences with local flair, is in order.
For dinner tonight, you’ll make your way to Louie’s Backyard for Caribbean-American food, served alfresco or inside a converted Victorian home. There’s Bahamian Conch Chowder with Bird Pepper Hot Sauce and Crumb Crusted King Salmon with Chayote Relish & Cajun Tartar Sauce since 1971. Then, if you’re feeling up for it, hit Duval Street one last time.
Day 5The Grand Finale
On your final full day in Key West, you’ll see some of the island’s most iconic sites. But first, for breakfast, pop into Cuban Coffee Queen, located in front of the harbor, for some cafe con leche or a fresh smoothie and Cuban breakfast sandwiches.
Then make your way to the Hemingway House, the island’s most famous site. Ernest Hemingway bought this gorgeous Spanish colonial home, where he finished A Farewell to Arms and started For Whom the Bell Tolls, in 1931. The lush gardens surrounding the home and pool are stunning. The interior contains Hemingway’s furnishings, personal photographs, and lots of stuffed fish. Also find the ancestors of Hemingway’s cat, Snowball, who famously had six toes. Now more than 50 of her six-toed descendants roam the property.
After the tour, the Key West Lighthouse and Bahama Village are located nearby. The structure was built in 1825 to guide ships navigating the reefs while trying to make it to port. If you want to get your heart thumping, climb to the top for breathtaking views of Key West and the ocean. Also, find the Keeper’s Quarters for displays of antique furniture, nautical artifacts, and vintage maps.
The adjacent Bahama Village neighborhood covers a 16-block area bordered by Fort, Louisa, Southard, and Whitehead streets. A decorative arch welcomes you to explore this area, a remnant of Key West’s Caribbean heritage, where the first black Bahamian settlers arrived in the 19th century. Don’t be surprised if you hear reggae or calypso tunes pouring out from the buildings as you wander the narrow streets. The outdoor market will surely cover your souvenir needs with its huge selection of seashells, straw hats, and t-shirts galore.
Many credit neighborhood restaurant Blue Heaven with the revival of the area, so make a point to have lunch or dinner here if you can snag a table. It would make a fitting send-off for your final full day in Key West. A typical meal there usually includes dining in the backyard while live music plays and chickens and cats circle your feet. But the unique atmosphere isn’t a gimmick—the food is the stuff of legends, blending Caribbean and Keys ingredients and influences. Think Jamaican jerk chicken and Caribbean “BBQ” Shrimp Pan-blackened Key West shrimp deglazed with Red Stripe beer.
In just five days, you’ve experienced the best of what Key West has to offer. You might consider the highlight to be the local cuisine, the historical attractions, or the idyllic beaches. But one thing’s for sure–no matter how many sunsets you’ve watched on the island, you’ll always leave wanting more.
Then make your way to the Hemingway House, the island’s most famous site. Ernest Hemingway bought this gorgeous Spanish colonial home, where he finished A Farewell to Arms and started For Whom the Bell Tolls, in 1931. The lush gardens surrounding the home and pool are stunning. The interior contains Hemingway’s furnishings, personal photographs, and lots of stuffed fish. Also find the ancestors of Hemingway’s cat, Snowball, who famously had six toes. Now more than 50 of her six-toed descendants roam the property.
After the tour, the Key West Lighthouse and Bahama Village are located nearby. The structure was built in 1825 to guide ships navigating the reefs while trying to make it to port. If you want to get your heart thumping, climb to the top for breathtaking views of Key West and the ocean. Also, find the Keeper’s Quarters for displays of antique furniture, nautical artifacts, and vintage maps.
The adjacent Bahama Village neighborhood covers a 16-block area bordered by Fort, Louisa, Southard, and Whitehead streets. A decorative arch welcomes you to explore this area, a remnant of Key West’s Caribbean heritage, where the first black Bahamian settlers arrived in the 19th century. Don’t be surprised if you hear reggae or calypso tunes pouring out from the buildings as you wander the narrow streets. The outdoor market will surely cover your souvenir needs with its huge selection of seashells, straw hats, and t-shirts galore.
Many credit neighborhood restaurant Blue Heaven with the revival of the area, so make a point to have lunch or dinner here if you can snag a table. It would make a fitting send-off for your final full day in Key West. A typical meal there usually includes dining in the backyard while live music plays and chickens and cats circle your feet. But the unique atmosphere isn’t a gimmick—the food is the stuff of legends, blending Caribbean and Keys ingredients and influences. Think Jamaican jerk chicken and Caribbean “BBQ” Shrimp Pan-blackened Key West shrimp deglazed with Red Stripe beer.
In just five days, you’ve experienced the best of what Key West has to offer. You might consider the highlight to be the local cuisine, the historical attractions, or the idyllic beaches. But one thing’s for sure–no matter how many sunsets you’ve watched on the island, you’ll always leave wanting more.
