Your ultimate five-day Florida Keys itinerary

The Florida Keys are a chain of tropical islands stretching off the southern tip of Florida, where turquoise water, laid-back towns, and ocean views define the experience.

While there are hundreds of islands, the most popular stops are Key Largo, Islamorada, and Key West, all sharing a relaxed lifestyle but each with its own highlights. Life moves at a slower pace here, as "island time" sets the day’s rhythm.

Linked by the Overseas Highway, the route spans more than 100 miles, crossing dozens of islands and over 40 bridges, with the Atlantic Ocean on one side and the Gulf of Mexico on the other.

This five-day Florida Keys itinerary follows that natural route from the Upper Keys to Key West, balancing time on the road with opportunities to explore coral reefs, enjoy world-class diving, and take in magnificent sunsets – along with plenty of key lime pie along the way.

Before you arrive, decide where you want to base yourself for the first part of the trip – either Key Largo or Islamorada, which are just a short drive apart and easy to explore without changing accommodation.

Key Largo is ideal for resort-style stays and romantic getaways, with properties like Bungalows Key Largo, an adults-only, all-inclusive retreat, alongside resorts such as Playa Largo and Baker’s Cay, known for their private beaches and ocean views.

Islamorada offers a slightly more laid-back feel, with a mix of boutique hotels and family-friendly resorts such as Chesapeake Beach Resort, La Siesta Resort, or Cheeca Lodge & Spa, known for its long fishing pier, oceanfront dining, and range of on-site activities. 

Morning

Most travelers arrive via Miami, so it’s best to keep your first day relaxed. After landing, pick up a rental car and head south along the Overseas Highway towards Key Largo, the gateway to the Florida Keys.

Within about an hour, the landscape begins to shift, with the mainland giving way to open water and a noticeably slower pace. Check in if your room is ready, or head straight out to explore.

Afternoon

Ease into the Keys with a low-key activity rather than a full excursion. A ride on the African Queen Steamboat—the historic vessel made famous by the 1951 movie—offers a relaxed way to get out on the water without committing to a long tour.

For lunch, both Key Largo and Islamorada offer excellent waterfront options. The Fish House is a long-standing favorite for fresh seafood, while Snappers Oceanfront Restaurant and Skipper’s Dockside offer a more casual setting with live music and ocean views.

From there, continue towards Islamorada and spend time around local docks, small beaches, and waterfront spots. A stop at Robbie’s Marina is a classic Keys experience, where you can feed tarpon, rent a jet ski, or watch the activity around the harbor.

Evening

Evenings are best spent by the water, whether that’s dinner at a marina-side restaurant or drinks on a laid-back floating tiki bar. A popular choice is Lorelei’s Restaurant & Cabana Bar, known for its sunset views, daily happy hour, and live music. The setting is casual, with tables right on the water, making it an easy and memorable first night.

Morning

The Florida Keys are home to the only living coral reef system in the continental United States, making it a standout experience. Aim for a morning arrival, as it's best enjoyed when conditions are typically calmer.

Start the day with one of the Florida Keys’ most defining experiences: time on the water. Head out early to John Pennekamp Coral Reef State Park, the first undersea park in the United States, where snorkeling and glass-bottom boat tours offer access to coral reefs and marine life just offshore.

If snorkeling isn’t your thing, consider a more social experience on the water. Hop on a boat tour to the Islamorada sandbar, a popular hot spot where locals and visitors gather to swim, float, and relax in shallow turquoise water.

Afternoon

After a morning on the water, stop for lunch at Islamorada Shrimp Shack, a local favorite known for its laid-back atmosphere and fresh seafood. 

Continue exploring Islamorada with a visit to Theater of the Sea, one of the Keys’ most well-known marine parks. Enjoy a mix of marine life encounters and live shows, with opportunities to see dolphins, sea lions, and tropical fish up close.

If you prefer something more relaxed, spend time exploring local stores or stop by Florida Keys Brewing Co. for a casual drink in its colorful outdoor setting.

Evening

For dinner, Islamorada offers some of the best waterfront dining in the Upper Keys. Square Grouper is a standout for its elevated seafood and marina views, while Islamorada Fish Company is a long-standing favorite known for its fresh local catch and relaxed atmosphere.

For something more casual, Papa Joe’s Waterfront pairs ocean views with a lively tiki bar setting, making it a great place to end the day.

Morning

Start the day with breakfast at Bob’s Bunz in Islamorada, a local favorite known for its casual atmosphere and hearty breakfasts.

From here, continue south along the Overseas Highway. This stretch of the drive is among the most scenic, with long stretches of road bordered by open water and small islands, creating the sense of driving across the ocean.

Afternoon

Cross the Seven Mile Bridge, one of the most sections of the drive and a highlight of any Florida Keys road trip. Stretching nearly seven miles, it connects the Middle and Lower Keys and offers uninterrupted views of the Atlantic Ocean and Gulf of Mexico on either side. 

Before continuing to Key West, stop at Bahia Honda State Park, known for its natural beaches, clear water, and panoramic views. It’s widely considered one of the best beach spots in the Keys, with opportunities to swim, snorkel, or walk along the shoreline. 

Evening

Arrive in Key West in the early evening and check into your accommodation. Drop your bags and head straight to Mallory Square for the nightly sunset celebration, where street performers, local vendors, and live music create a lively atmosphere as the sun dips below the horizon.

After sunset, continue into Old Town for dinner. Options nearby include Hot Tin Roof for a refined waterfront setting or El Mesón de Pepe, known for Cuban dishes and live music, both right on the square.

After dinner, walk towards Duval Street, where bars and nightlife line the island’s most famous strip, including the historic Sloppy Joe’s Bar, once a favorite of Ernest Hemingway.

Whether you choose a relaxed evening or something more lively, this is your first introduction to Key West’s energy.

Morning

Begin the day in Old Town, where colorful conch-style houses, leafy streets, and historic landmarks define the island’s character.

Start at Moondog Café & Bakery for coffee, pastries, or a relaxed breakfast. After breakfast, consider a hop-on hop-off trolley tour, an easy way to get an overview of Key West’s historic landmarks before continuing on foot.

Visit the Ernest Hemingway Home and Museum and see where the author once lived when writing, which is now home to dozens of descendants of his original six-toed cat. Across the street, climb the Key West Lighthouse for panoramic views over the island and surrounding turquoise waters.

If you’re planning a longer stay or want a full-day alternative, consider a trip to Dry Tortugas National Park, located about 70 miles west of Key West and accessible by ferry or seaplane. The journey takes most of the day, but you’ll return in the late afternoon just in time to enjoy Key West’s sunset celebrations.

Afternoon

Stop by the Southernmost Point buoy for a photo, marking the southernmost point of the continental United States and just 90 miles from Cuba. The original buoy is currently undergoing repairs, but a temporary replica has been placed nearby along Duval Street so visitors can still capture the photo.

From there, head to Duval Street, the lively heart of Key West. Lined with cafés, stores, and galleries, it’s easy to spend a few hours browsing and exploring at your own pace.

Make your way to the Key West Butterfly and Nature Conservatory, where tropical butterflies and birds fill a glass-enclosed habitat, offering a calm break from the busier streets. 

On your way, stop at Kermit’s Key Lime Pie Shop for one of the island’s most famous desserts.

If you’d rather spend the afternoon by the water, head to Smathers Beach or Fort Zachary Taylor State Park, both offering opportunities to swim, snorkel, or just relax by the shoreline.

Evening

For something more unique, consider a night kayaking tour, where glowing LED-lit or glass-bottom kayaks take you through mangrove tunnels to spot nocturnal marine life. There are also plenty of sunset cruises and schooner sails if you prefer to sit back and relax.

Alternatively, enjoy Key West’s live music scene at spots like Green Parrot Bar or Hog’s Breath Saloon, both known for their lively, laid-back atmosphere.

For a more historic setting, stop by Captain Tony’s Saloon, one of the island’s oldest bars, or keep things relaxed at Margaritaville, inspired by Jimmy Buffett’s connection to the Keys.

Morning

Start your final day with breakfast at Banana Café & Creperie, known for its banana foster waffles, savory crepes, and French-inspired menu.

Take a short walk through Old Town afterwards or revisit a favorite spot before leaving Key West behind.

Afternoon

Spend the afternoon in Marathon, the heart of the Florida Keys, located about one hour north along the Overseas Highway. Relax at Sombrero Beach for a final swim in calm, turquoise water, or explore the area’s marine life experiences. For something more educational, the Turtle Hospital offers guided tours focused on sea turtle rescue and rehabilitation.

Evening

Marathon is an ideal place to slow down before the final leg of your trip. Stay overnight at a waterfront resort to break up the journey and enjoy one last evening in the Keys.

For dinner, local favorites like Hideaway Café or Burdine’s Waterfront serve fresh seafood in a casual, dockside setting.

Depending on your travel plans, you can easily drive back to Miami in the evening, but staying overnight allows for a more relaxed departure the next day.

To help you plan a smooth trip, here are a few essential tips and practical things to know before visiting the Florida Keys.

• Plan your driving time carefully: Distances may look short, but the Overseas Highway is a single main road with limited passing, so allow extra time between stops, especially on holiday weekends.
• Book key experiences in advance: Snorkeling, diving, and boat tours are popular and can fill up quickly, especially during peak season.
• Use reef-safe sunscreen: Reef-safe sunscreen helps protect the Keys’ delicate coral reef ecosystem while you swim or snorkel.
• Consider the time of year: Winter, spring, and peak summer holiday weekends are the busiest periods, so expect higher prices.
• Getting around: A car is essential for exploring the Keys, but in Key West, consider renting a bicycle to navigate Old Town’s narrow streets.

If you’re working with fewer days, focus on experiences that capture the Florida Keys lifestyle. Whether it’s a weekend getaway or a quick excursion from Miami, these highlights can be easily mixed and matched.

• Explore Key Largo and Islamorada before crossing the Seven Mile Bridge on your way to Key West.
• Snorkel the coral reefs at John Pennekamp Coral Reef State Park.
• Spend an evening in Key West, including sunset at Mallory Square and a walk along Duval Street.
• Relax at Bahia Honda State Park or another Keys beach for clear water and scenic views.
• Visit Robbie’s Marina to feed the tarpon and experience one of the Keys’ most stops.

The Florida Keys offer a unique travel experience, where the journey between destinations is just as memorable as the stops themselves. Over five days, you’ll enjoy scenic drives, time on the water, and moments to slow down, creating a trip that feels both relaxed and immersive. 

Whether followed in full or adapted for a shorter stay, it provides a flexible way to explore one of Florida’s most distinctive destinations. By the end of your trip, you’ll be accustomed to island time, where days unfold slowly and it always feels like it’s five o’clock somewhere.

Disclaimer: The views and opinions expressed are those of the author and don't necessarily reflect the official policy or position of our company.