The Florida Keys are a tropical island chain stretching approximately 120 miles off the southern tip of Florida into the turquoise waters of the Atlantic Ocean and the Gulf of Mexico. This unique destination consists of over 1,700 islands connected by the iconic Overseas Highway, which offers one of the most scenic drives in the United States. From Key Largo in the north to Key West at the southernmost point of the continental United States, the Florida Keys provide visitors with crystal-clear waters, coral reefs, white sandy beaches, fresh seafood, and a laid-back island atmosphere unlike anywhere else in the country. Whether you’re interested in water sports, exploring national parks, discovering historical sites, or simply relaxing on pristine beaches surrounded by palm trees, the Florida Keys offer something for every type of traveler.
This comprehensive 5-day Florida Keys itinerary will guide you through the best things to do, the best places to eat, and the most beautiful places to stay throughout the Keys. From snorkeling tours above vibrant coral reefs to sunset sails in Key West, from visiting the Ernest Hemingway Home to exploring Bahia Honda State Park, this Florida Keys road trip covers all the highlights while leaving enough time to relax and soak in the tropical paradise. Whether you’re planning your first visit or returning to discover new spots, this guide provides everything you need for an unforgettable journey through one of Florida’s most beloved destinations.
5 Days in the Florida Keys
Getting to the Florida Keys
Most visitors begin their Florida Keys road trip by flying into Miami International Airport or Fort Lauderdale airport, both of which offer numerous flight options and competitive prices. From Miami Airport, it’s approximately a 3-hour drive to Key West, with Key Largo being just about an hour away. After landing, you’ll want to pick up a rental car to explore the different islands at your own pace. The drive from Miami to the Keys takes you along the Overseas Highway, a breathtaking route that connects the islands and provides stunning views of the Atlantic Ocean and the Gulf of Mexico throughout your journey.
Best Time to Visit the Florida Keys
The best time to visit the Florida Keys is typically between December and April when the weather is pleasant and you’ll avoid hurricane season, which runs from June through November. During the winter months, temperatures are comfortable, humidity is lower, and you’ll have the best chance for clear skies and calm waters, perfect for snorkeling tours, water sports, and exploring the coral reefs. However, this is also peak tourist season, so expect larger crowds at popular attractions like Mallory Square, Duval Street, and the southernmost point. For fewer crowds and lower prices, consider visiting during the shoulder seasons of late spring or early fall, though you should be prepared for warmer temperatures and the possibility of rain.
Day 1: Miami to Key Largo
Morning: Arrival and Drive to Key Largo
Begin your Florida Keys adventure with an early morning flight into Miami International Airport. After collecting your luggage and picking up your rental car, head south on the Overseas Highway toward Key Largo, the first stop on your Florida Keys road trip. The drive from Miami to Key Largo takes approximately one hour, making it an easy and convenient first destination.
Your first stop should be Key Largo Chocolates, a great place to sample the best key lime pie in the Florida Keys. This colorful shop with its lime green and pink exterior is not only a perfect spot for photos but also serves authentic key lime pie on a stick, a unique twist on the classic dessert. This is the perfect way to kick off your tropical island adventure and get your first taste of the local flavors that make the Florida Keys such a special culinary destination.
Afternoon: Check into Kona Kai Resort
Head to Kona Kai Resort in Key Largo, an intimate adults-only waterfront resort located on Florida Bay. This boutique property features only 13 guest rooms and suites, ensuring a quiet and serene atmosphere throughout your stay. The resort boasts a private white sand beach, waterfront pool and hot tub, hammocks scattered throughout the tropical botanic garden, and beach chairs positioned to take advantage of the stunning water views. The staff provides excellent service and helpful recommendations for exploring Key Largo and the surrounding areas of the upper Keys.
After checking in and changing into vacation attire, head to Marker 88 for a late lunch or early dinner. This waterfront restaurant is known for its creative cocktails, particularly their Bloody Marys, and offers beautiful views of Florida Bay. The fresh seafood menu showcases the best of what the Florida Keys have to offer, and dining here provides a relaxing introduction to the island lifestyle.
Evening: Florida Keys Brewing Company
Visit Florida Key Brewing Company for a brewery tour and tasting experience. This colorful brewery in the upper Keys offers a fantastic selection of craft beers, including the popular Smuggler’s Moon Oatmeal Stout and the unique Iguana Bait. The facility features an indoor bar area and an outdoor beer garden with live music, making it a great spot to spend an evening. The atmosphere is lively yet relaxed, and it’s a favorite spot among both locals and visitors looking for good drinks and entertainment.
End your first day with dinner at Tides Beachside Bar & Grill at the Islander Resort. The resort’s grounds are beautiful, and the restaurant offers a casual atmosphere perfect for your first night in the Keys. Order the Blackened Fish Sandwich, a local favorite that showcases the fresh seafood available throughout the islands, and don’t skip dessert – try another version of key lime pie to compare with your earlier tasting.
Day 2: Exploring Key Largo and Islamorada
Morning: Relaxation at Kona Kai
Start your day with the complimentary light breakfast served at Kona Kai Resort, which includes bagels, pastries, fresh fruit, and coffee. Take the morning to relax and explore the resort property. Lounge in a hammock, take a dip in the pool, or simply enjoy the peaceful atmosphere of this beautiful place before heading out for the day’s adventures.
Lunch: Key Largo Conch House
For lunch, visit Key Largo Conch House, a highly-recommended restaurant that delivers on both atmosphere and flavor. The menu features excellent seafood options, with the Grilled Mahi Tacos being a standout dish. The casual setting and good food make this a perfect spot to fuel up before an afternoon of water activities.
Afternoon: John Pennekamp Coral Reef State Park
John Pennekamp Coral Reef State Park is a must-visit destination for anyone interested in exploring the coral reefs and marine life of the Florida Keys. As the first undersea park in the United States, this protected area offers some of the best snorkeling and diving opportunities in the Keys. Join a snorkeling tour to explore the shallow water coral reefs, where you’ll encounter colorful tropical fish, sea turtles, and vibrant coral formations. Depending on weather conditions, your snorkeling tour may include a visit to the famous Christ of the Deep statue, an underwater sculpture that has become an iconic landmark.
The park also offers glass-bottom boat tours for those who prefer to stay dry while viewing the underwater world, as well as kayaking opportunities through the mangrove forests. The visitor center provides educational information about the delicate ecosystem and the importance of coral reef conservation. This is truly one of the best things to do in Key Largo and provides an unforgettable introduction to the natural beauty of the Florida Keys.
Evening: Robbie’s Marina in Islamorada
Drive south to Islamorada, located in the middle Keys, to visit Robbie’s Marina, a Florida Keys institution that has been entertaining visitors for decades. If you arrive during daylight hours, participate in the famous tarpon feeding experience where you can hand-feed these massive fish from the dock. The marina also features a gift shop and several food vendors offering different ways to enjoy fresh seafood.
Dine at Hungry Tarpon, the on-site restaurant at Robbie’s Marina. Ask your server for recommendations, as the menu changes based on the fresh catch of the day. Excellent options include a Blueberry Mojito, Chef’s Peel & Eat Shrimp, Thai Fish Fingers, and Ahi Tuna Tacos. The casual waterfront atmosphere and delicious meal make this a great spot to experience authentic Keys dining. The combination of good food, live music, and waterfront views creates a memorable evening in the middle Keys.
Day 3: Key Largo to Key West
Morning: Checkout and Journey South
After enjoying breakfast at Kona Kai Resort, check out and begin your drive south along the Overseas Highway toward Key West. This scenic route takes you through the middle Keys and offers numerous opportunities for photo stops and quick explorations. Consider stopping at Drop Anchor Resort to capture photos of its colorful, Instagram-worthy exterior, a perfect representation of the vibrant Keys aesthetic.
Another recommended quick stop is Isla Bella Beach Resort, a stunning property that showcases the luxury waterfront resorts available throughout the Florida Keys. Even if you’re not staying here, the beautiful place is worth a visit to admire the architecture and grounds.
Afternoon: Lunch at Mangrove Mama’s
Stop for lunch at Mangrove Mama’s on Sugarloaf Key, a great place to break up the drive to Key West. This casual restaurant is a local favorite known for its fresh seafood and island atmosphere. The Blackened Mahi Tacos here feature mahi, bacon, and slaw, creating a delicious combination that may be the best version you’ll try during your entire Florida Keys road trip. The quirky decor and laid-back vibe make this a quintessential Keys dining experience.
Late Afternoon: The Perry Hotel on Stock Island
Check into The Perry Hotel on Stock Island, located just before Key West proper. While not technically in Old Town Key West, this waterfront property offers excellent amenities including a waterfront pool, marina views, scooter rentals for exploring the area, and a dog-friendly policy. The hotel provides a more tranquil base while still being close enough to easily access all the attractions, restaurants, and nightlife of Key West. Upon arrival, you’ll be greeted with champagne and stunning views of the harbor.
Evening: Sunset Sail with Fury
Head into Old Town Key West for a sunset sail with Fury Water Adventures. The Commotion on the Ocean Sunset Cruise is a perfect way to experience the famous Key West sunset from the water. This 2-hour cruise includes live music, unlimited drinks including margaritas, champagne, beer, and wine, plus appetizers. Sailing on the turquoise water as the sun sets over the Gulf of Mexico creates an unforgettable experience and is one of the best things to do in Key West. The relaxed atmosphere and beautiful views make this an ideal activity whether it’s your first visit or your tenth trip to the southernmost point of the United States.
After your sunset sail, enjoy dinner at Azur, a Mediterranean-inspired restaurant in Old Town Key West. The menu features excellent small plates perfect for sharing. Recommended dishes include the Steamed Mussels, Pulpo (grilled octopus), Steamed Clams & Chorizo, and Goat Cheese Salad. The intimate atmosphere and creative menu make this a nice place for dinner after a day of travel.
Day 4: Full Day in Key West
Morning: Parasailing with Fury
Start your day with an exhilarating parasailing adventure with Fury Water Adventures. Even first-time parasailers will find the experience thrilling yet manageable. The boats depart regularly throughout the day, but booking in advance ensures you get your preferred time slot. Groups of two ascend together for approximately 12 minutes of flying above the crystal-clear waters, providing breathtaking views of Key West and the surrounding islands. The perspective from above gives you a unique appreciation for the tropical island chain and the beautiful turquoise water that defines the Florida Keys.
Late Morning: Conch Train Tour
After returning to land, grab coffee and join the Conch Train Tour, one of the best ways to get oriented in Old Town Key West. This narrated tour takes you through the historic streets while providing interesting facts about the area’s history, architecture, and famous residents. You’ll learn about Key West’s role in various historical events and get a sense of where different places are located, making it easier to navigate on your own later. These self-guided tour options are a perfect way to cover a lot of ground quickly while learning about this unique destination.
Afternoon: Old Town Trolley and Lunch in Bahama Village
Hop on the Old Town Trolley to reach the Bahama Village area of Key West, a neighborhood known for its Caribbean influence and vibrant culture. While Blue Heaven is a popular choice for meals, if it’s closed, Rams Head Southernmost is an excellent alternative. This colorful restaurant features a great atmosphere, creative cocktails like the Rum Runner, and delicious food options. Try the Peel & Eat Gulf Shrimp and the refreshing Tomato & Watermelon Salad, perfect for a hot day. Rams Head is particularly famous for its Build Your Own Bloody Mary Bar, a great spot for brunch if you visit earlier in the day.
Mid-Afternoon: Ernest Hemingway Home and Museum
No trip to Key West is complete without visiting the Ernest Hemingway Home and Museum. This beautiful property was the residence of the famous author during the 1930s and has been preserved to reflect that era. The home features the first swimming pool built in Key West and was one of the first houses on the island fitted with indoor plumbing. The property is also home to descendants of Hemingway’s six and seven-toed cats, which roam the grounds freely. The self-guided tour allows you to explore at your own pace while learning about Hemingway’s life and work during his years in the Florida Keys.
Late Afternoon: Pool Time at The Perry Hotel
Return to The Perry Hotel to enjoy some downtime at the waterfront pool. After a busy day of activities in the heat, relaxing by the pool provides a perfect break before dinner. The peaceful atmosphere and marina views offer a nice contrast to the busier streets of Key West.
Evening: Dinner at Matt’s Stock Island Kitchen
Dine at Matt’s Stock Island Kitchen, the on-site restaurant at The Perry Hotel. Request a table overlooking the marina for the best views, especially at sunset. The menu features creative dishes using fresh, local ingredients. Start with a Pineapple Jalapeno Mojito and order the Commodore Tower appetizer to share. For the main course, the Black Grouper is exceptional and showcases the fresh seafood that makes Florida Keys cuisine so special. This is truly one of the best restaurants in the Key West area and provides a delicious meal in a more relaxed setting than the busy restaurants of Duval Street.
Night: Ghosts and Gravestones Tour
End your evening with the Ghosts and Gravestones Tour, a fun way to learn about Key West’s spooky history and haunted locations. The tour takes you to various historical sites while sharing tales of ghosts, mysteries, and the island’s colorful past. The entertaining guides bring the stories to life, making this much fun for both believers and skeptics. These evening tours provide a different perspective on Key West’s history and are a great spot to spend your final night in town.
Day 5: Final Morning in Key West and Return to Miami
Morning: Breakfast at Fisherman’s Cafe
Check out of The Perry Hotel and head to Fisherman’s Cafe in Old Town Key West for a memorable final meal. This unassuming restaurant serves exceptional Cuban-inspired breakfast dishes that will leave you thinking about the food long after you leave. Order the “El Cubano” Breakfast Sandwich, Yuca Fries, and Plantains for an authentic taste of the Caribbean influence that permeates Key West culture. The generous portions and bold flavors make this a favorite spot among locals and visitors alike.
Late Morning: Final Exploration of Key West
Spend your remaining time exploring the streets of Old Town Key West. Walk down Duval Street, the main thoroughfare known for its lively bars, restaurants, and shops. Stop for a photo at the Mile 0 sign marking the beginning of US Route 1, and visit the iconic Southernmost Point buoy, one of the most photographed spots in the Florida Keys. If time permits, tour Truman’s Little White House, the former vacation home of President Harry S. Truman that now serves as a museum showcasing presidential history.
Take time to simply wander through the charming streets, admiring the unique architecture, colorful buildings, and tropical vegetation that make Key West such a beautiful place. Browse local shops, watch street performers, and soak in the laid-back atmosphere one last time before beginning your journey back to Miami.
Afternoon: Return Drive to Miami International Airport
Begin the 3-hour drive back to Miami International Airport for your departure flight. While it may seem like a long journey, the Overseas Highway provides one of the most scenic drives in the United States, with stunning views of the Atlantic Ocean and the Gulf of Mexico throughout the route. The drive takes you across the famous Seven Mile Bridge and past numerous small islands, each with its own character and charm. Plan for enough time to account for potential traffic, especially if you’re traveling on a weekend or during peak season. Most visitors should allow at least four hours between leaving Key West and their flight departure time to ensure a stress-free journey.
Additional Florida Keys Attractions and Activities
While this 5-day itinerary covers many highlights, the Florida Keys offer numerous other attractions worth considering if you have more time or are planning a return visit. Here are some of the best places and best things to do that didn’t fit into this particular itinerary:
Bahia Honda State Park
Located in the lower Keys, Bahia Honda State Park features some of the best white sandy beaches in the entire island chain. The park offers swimming, snorkeling, kayaking, and nature trails through the tropical landscape. The old Bahia Honda Rail Bridge provides a unique photo opportunity and a glimpse into the area’s history. This is an ideal place for couples or families looking to spend a day enjoying natural beauty away from the more developed areas.
Dry Tortugas National Park
For adventurous travelers with an extra day, Dry Tortugas National Park is accessible by ferry or seaplane from Key West. This remote national park features Fort Jefferson, crystal-clear waters, excellent snorkeling opportunities, and abundant marine life including sea turtles. The park’s isolation makes it one of the best places to experience pristine coral reefs and enjoy the natural environment with fewer crowds than other popular snorkeling spots.
National Key Deer Refuge on Big Pine Key
The National Key Deer Refuge on Big Pine Key protects the endangered Key deer, a small subspecies found only in the Florida Keys. Visitors can spot these diminutive deer along the trails and roads throughout the refuge. The area also offers hiking opportunities and access to beautiful natural areas away from the more touristed spots.
Dolphin Research Center
Animal lovers should visit the Dolphin Research Center in the middle Keys, where you can learn about dolphin behavior, conservation efforts, and even participate in structured encounters with these intelligent marine mammals. The center focuses on education and research while providing opportunities for visitors to observe and interact with dolphins in a responsible environment.
Turtle Hospital
The Turtle Hospital in Marathon provides care for injured sea turtles and educates visitors about sea turtle conservation. The facility offers tours where you can learn about different sea turtle species, the threats they face, and the rehabilitation process. This is a great place for families and anyone interested in marine conservation.
Everglades National Park and Biscayne National Park
Though not technically part of the Florida Keys, both Everglades National Park and Biscayne National Park are located nearby and can be incorporated into an extended trip. These national parks offer unique ecosystems, wildlife viewing, and outdoor activities that complement a Florida Keys road trip. Biscayne National Park, in particular, features excellent snorkeling and diving opportunities among coral reefs similar to those found in the Keys.
Best Restaurants and Bars to Add to Your List
The Florida Keys are home to countless excellent restaurants and bars, many specializing in fresh seafood and Caribbean-inspired cuisine. Here are some of the best restaurants and favorite spots that come highly recommended but weren’t included in the main itinerary:
Blue Heaven (Key West)
This legendary Key West restaurant features a garden setting complete with roaming chickens, live music, and a menu showcasing local favorites. While it can have long waits, especially for breakfast, many consider it worth the time. The restaurant occupies a historic property and offers a quintessential Key West dining experience.
Santiago’s Bodega (Key West)
Santiago’s Bodega offers creative tapas and Spanish-inspired dishes in a cozy, intimate setting. The menu changes seasonally but always features good food prepared with care and creative flavor combinations.
Sandy’s Cafe (Key West)
Locals swear that Sandy’s Cafe serves the best Cuban sandwich in Key West. This small, no-frills restaurant focuses on authentic Cuban cuisine at reasonable prices, making it a great spot for lunch.
Latitudes Restaurant (Sunset Key)
For a special occasion, consider taking the ferry to Sunset Key for dinner at Latitudes Restaurant. This upscale waterfront restaurant offers stunning sunset views and a refined menu featuring fresh seafood and creative preparations. It’s one of the most romantic dining spots in the Florida Keys and provides a different experience from the casual restaurants found throughout most of the islands.
Mrs. Mac’s Kitchen (Key Largo)
This casual Key Largo institution has been serving locals and tourists since 1976. The menu features comfort food, fresh seafood, and generous portions at reasonable prices. The walls are covered with dollar bills left by visitors over the years, creating a unique atmosphere.
First Flight Island Restaurant & Brewery (Key West)
Located at Key West International Airport, First Flight Island Restaurant & Brewery occupies a historic building that was the birthplace of Pan American Airways. The restaurant offers craft beers brewed on-site and a menu featuring pub favorites and fresh seafood. It’s a great place to grab lunch or dinner, particularly if you’re interested in aviation history.
Sloppy Joe’s (Key West)
One of the most famous bars in Key West, Sloppy Joe’s claims to have been Ernest Hemingway’s favorite watering hole. While the connection is debated by historians, the bar remains a popular spot for tourists looking to enjoy live music, cold drinks, and the lively atmosphere of Duval Street. The bar serves basic pub food and maintains a fun, energetic vibe throughout the day and night.
The Green Room Eco Bar (Key West)
This eco-conscious bar in Bahama Village offers craft cocktails, local beers, and a commitment to sustainability. The laid-back atmosphere and creative drinks make it a nice place to escape the crowds of Duval Street while still enjoying Key West nightlife.
The Fish House (Key West)
Located at the end of a marina, The Fish House specializes in ultra-fresh seafood served in a casual, waterfront setting. Watch the boats come and go while enjoying oysters, fish prepared different ways, and beautiful water views.
Holiday Isle Tiki Bar (Islamorada)
This legendary tiki bar in Islamorada claims to be the birthplace of the Rum Runner cocktail. The beachfront location, live music, and party atmosphere make it a favorite spot for those seeking a lively scene. The bar has been a Keys institution for decades and remains popular with both locals and visitors.
Practical Tips for Your Florida Keys Road Trip
Transportation and Getting Around
A rental car is essential for exploring the Florida Keys at your own pace. The Overseas Highway is the main route connecting all the islands, with mile markers (MM) used as the primary way to identify locations. Mile markers start at MM 0 in Key West and increase as you head north toward Miami. Addresses often reference the nearest mile marker to help visitors navigate.
Scooter rentals are popular in Key West for getting around Old Town without worrying about parking. Many hotels, including The Perry Hotel, offer scooter rentals on-site. However, a car is necessary for traveling between the different islands and exploring areas outside of Key West.
Parking in Key West
Parking in Old Town Key West can be challenging, especially during peak season. Many hotels offer parking, but spots in the historic district are limited. Consider parking in one of the paid lots and walking or using a scooter to explore. Some restaurants and attractions offer limited parking for patrons.
What to Pack
Pack light, breathable clothing suitable for hot, humid weather. Essential items include:
- Sunscreen (reef-safe formulas are recommended to protect coral reefs)
- Sunglasses and a hat
- Swimwear and beach cover-ups
- Water shoes for rocky beaches and water activities
- Light layers for air-conditioned restaurants and boats
- Insect repellent for evening activities
- Waterproof phone case for water activities
Reservations and Advance Planning
During peak season (December through April) and holidays, make reservations well in advance for:
- Hotels and waterfront resorts
- Popular restaurants
- Water sports activities including snorkeling tours, parasailing, and sunset sails
- Tours and specialty experiences
Hurricane Season Considerations
Hurricane season runs from June through November, with the highest risk typically in August and September. If traveling during this time, purchase travel insurance and monitor weather forecasts. While hurricanes don’t occur frequently, tropical storms can impact travel plans, and having flexibility in your itinerary is important.
Budget Considerations
The Florida Keys can be expensive, particularly in Key West and during peak season. Budget-conscious travelers should consider:
- Visiting during shoulder seasons for better prices on waterfront resorts and rental cars
- Eating at local favorites and food vendors rather than exclusively dining at upscale restaurants
- Booking water sports activities directly rather than through third parties
- Staying in Key Largo or the middle Keys, where accommodation is generally less expensive than Key West
Marine Life Etiquette
- When participating in snorkeling tours or visiting coral reefs:
- Follow all guidelines provided by tour operators
- Never touch or stand on coral
- Don’t feed fish or sea turtles
- Use reef-safe sunscreen to protect the marine environment
- Maintain a respectful distance from all marine life
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If you’re exploring more of Florida’s beautiful coastal destinations, check out this guide to things to do in Vero Beach for another laid-back beach getaway.
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