The Perfect 5-Day Key West Itinerary

No Key West itinerary would be complete without biking! Key West is a small 2-mile wide by 4-mile long island. You’ll easily miss so much driving a rental car and searching for parking. Biking allows you to slow down and appreciate pastel Conch houses, bright bougainvillea hedges, banyan trees and the local chickens. I always love biking around Old Town. I recommend scheduling cruiser bike rentals before you arrive from We Cycle. They deliver and pick up your bikes, so you’re ready to go.

My favorite spot to bike is through the Key West Cemetery. Pick up a self-guided map of historical gravestones and enjoy a peaceful ride down lanes dotted with unique burial sites, sunbathing iguanas, and beautiful red Royal Poinciana trees. Key West Historic Seaport and Mallory Square are must-sees for other attractions to cruise around.

When you’re ready to lock up your bikes, spend the afternoon strolling down Duval Street. There are many galleries, shops, restaurants and bars. I recommend stopping at The Green Pineapple, La Grignote, Grand Vin Wine Bar and Key West Pottery.

Try The Flaming Buoy, a funky yet intimate spot serving comfort fare and catch-of-the-day fish for dinner.

You’ll be down the street from Sloppy Joe’s, a popular bar once frequented by Ernest Hemingway. The Bull & Whistle Bar is down the block, where I’ve enjoyed a cocktail or two on the second-floor balcony. While it’s not fancy, it offers a great view of Duval’s rowdy nightlife. You can also try Sunset Pier or Sunset Tiki Bar for an ocean view.

After a hotel breakfast, start the day kayaking or paddle boarding through the mangroves. It’s ideal to go in the morning before the temps increase with the day. I recommend booking a private sunrise tour with Paddlin’ Madeleine. She’s a local guide who knows the winding mangrove tunnels like the back of her hand. Her excursions are low-key and peaceful. Or you can get picked up right from your hotel by Key West Eco Tours and follow their nature guides through Key West’s National Wildlife Refuge.

Grab lunch off-the-beaten-path at Hogfish Grill on Stock Island, a dockside restaurant with open-air dining. Their grilled hogfish sandwich on Cuban bread hits the spot after an active morning on the water.

After lunch, head back to Old Town to peek at the buoy marking the Southernmost Point of the Continental U.S.A. Around the corner is The Key West Butterfly & Nature Conservatory, where you can meet two striking flamingos who live amongst hundreds of butterflies and other exotic birds. From there, you’ll be across the street from Southernmost Beach Cafe. Take the rest of the afternoon to lounge on the beach with a frozen daiquiri.

Have an elegant and relaxing dinner at Louie’s Backyard. This fine dining restaurant is known for its small plates, outstanding entrees, panoramic ocean views, extensive wine list and professional service.

Stop at Keys Coffee Co., a quaint coffee shop off Southard St, before heading to the beach. The hot or iced coconut breve, made with fresh coconut milk, is delicious, as are their sandwiches. Order some for a picnic on the beach.

Fort Zachary Taylor Historic State Park is a well-maintained 54-acre park steeped in wartime history. You can easily spend a whole day here on the natural coral beach or roaming the nature trails and historic fort. Join the daily guided tour of Fort Zach to learn its story within the Civil and Spanish-American Wars. A cafe, lounge chairs, umbrellas, snorkel gear rentals, picnic tables and plenty of trees to sit in the shade are on the beach.

Garbo’s Grill, an Airstream food truck tucked behind Hank’s Hair of the Dog Saloon, is a seven-minute bike ride from Fort Zach. I highly recommend trying the cayo fish tacos or the Korean BBQ burrito. They’re open from 11 AM to midnight, perfect for lunch, happy hour or a late-night bite.

For more historical sightseeing in the afternoon, Hemingway Home & Museum and the Key West Lighthouse are kitty-corner from each other on Whitehead Street. The Hemingway house is a must-see of Key West. Each tour guide is funny, charming and eager to share stories of Hemingway and the six-toed cats that now call the estate their home. Cross the street and climb up the tower of the Key West Lighthouse for a panoramic view of Old Town.

For happy hour or dinner, Thirsty Mermaid offers excellent and beautifully presented fresh seafood from rotating oysters, local catch and a full raw bar.

One of the best local dive bars in Key West is the Green Parrot Bar. This saloon is an icon of the island and a favorite of locals. Its interior is relaxed, funky and caked with history, with an open-air design allowing anyone nearby to hear the night’s live music.

The turquoise waters of Key West are a luxury, so it’s only suitable to spend a whole day on the ocean. Bottoms Up Key West offers all-inclusive, private excursions to dive shipwrecks or reefs, lounge around on sandbars, snorkel or learn how to swim like a mermaid.

When you return to land, I recommend dinner at Tavern N Town, Nine One Five or Antonia’s.

On the last day of this 5-day Key West itinerary, bike over to Pepe’s Cafe & Steakhouse for a hearty breakfast and fresh squeezed mimosas. Pepe’s is the oldest eatery in Key West, serving the island for over 100 years.

Afterward, make your way to the other side of the island to the West Martello Tower and Key West Garden Club. The former Civil War fort turned botanical garden is a peaceful oasis beside the ocean. Wander through corridors and courtyards filled with lush tropical flora, or sit under a gazebo to enjoy the beautiful ocean view.

On either side of the garden are Higgs Beach and White Street Pier. Umbrellas and chairs are available to rent, so you can spend the whole day between sunbathing, wading in the clear water and napping in the shade.

Keep your feet in the sand and enjoy a relaxing lunch at Salute! On The Beach. This casual beachfront restaurant is located right on Higgs, with light Italian dishes and fresh seafood.

In the late afternoon, grab a seat at the Conch Republic Seafood Company bar or patio. Conch Farm is a casual, open-air restaurant that looks out over the marina with a 2-for-1 drink special during happy hour. Take advantage of their secret menu item, peel-n-eat Royal Red Shrimp.

To end your island getaway, climb aboard a schooner for a romantic, upscale sunset sail with Danger Charters. They provide craft and domestic beers, various wines and hors d’oeuvres to enjoy while sailing into the sunset.