
Planning a road trip through the Florida Keys? Here’s a comprehensive 5-day itinerary that includes the best places to visit, highly recommended dining options, and must-see attractions. This guide will ensure you make the most of your trip, whether it’s your first time in this beautiful place or a repeat visit.
Day 1: Miami to Key Largo

Main Activities:
- John Pennekamp Coral Reef State Park: Your first stop on this Florida Keys itinerary. Enjoy a snorkel tour or glass-bottom boat ride to explore the vibrant marine life and tropical fish in the clear water. The park is a great spot for both beginners and experienced snorkelers.
- Sunset Cruise: Take a sunset sail to end your day with stunning views of the horizon. This is a perfect place to relax and enjoy the beautiful beaches and palm trees.
Meals:
- Breakfast: GreenStreet Café, Miami – A great way to start your day with their popular pancakes or omelets.
- Lunch: The Fish House, Key Largo – Known for its fresh seafood platters and conch chowder.
- Dinner: Snook’s Bayside Restaurant & Grand Tiki Bar – Enjoy fish tacos and key lime pie with a sunset view.
Overnight: Marriott Key Largo Bay Resort
- Amenities: Pool, spa, hot tub, and water activities.
- Cost: $200-$300 per night.
Additional Recommendations:
- Florida Keys Wild Bird Rehabilitation Center: A great place to see native birds and learn about conservation.
- Dagny Johnson Key Largo Hammock Botanical State Park: Explore nature trails and spot rare plant species.
- Biscayne National Park: If you have enough time, this nearby park offers boating, snorkeling, and diving opportunities.
Day 2: Key Largo to Islamorada

Main Activities:
- Theater of the Sea: Participate in marine mammal shows and interact with dolphins, sea lions, and stingrays. A great way to learn about marine life.
- Robbie’s Marina: Feed the tarpon, explore local art and craft stalls, and enjoy live music. A favorite spot for many visitors.
Meals:
- Breakfast: Doc’s Diner, Key Largo – Known for hearty breakfasts.
- Lunch: Lazy Days Restaurant, Islamorada – Offers seafood pasta and stunning ocean views.
- Dinner: Morada Bay Beach Café – Beachside dining with options like grilled fish and tropical salads.
Overnight: Amara Cay Resort or Cheeca Lodge & Spa
- Amenities: Beach access, pools, hot tub, and water sports.
- Cost: $200-$400 per night.
Additional Recommendations:
- History of Diving Museum: Discover the history of diving with exhibits from the early 1900s.
- Windley Key Fossil Reef Geological State Park: See exposed fossilized coral reef formations.
- Florida Keys Brewing Company: Stop by for a brewery tour and taste local craft beers.
- Food Trucks: Explore local food trucks for a casual dining experience.
Day 3: Islamorada to Marathon

Main Activities:
- Dolphin Research Center: Educational tours and dolphin encounters. Reserve in advance.
- Seven Mile Bridge: Drive the scenic Overseas Highway and stop for photos at the old Seven Mile Bridge.
- Bahia Honda State Park: Known for its white sandy beaches and clear water, it’s one of the best places to relax and enjoy the natural beauty.
Meals:
- Breakfast: Mangrove Mike’s Café, Islamorada – Try their breakfast burritos.
- Lunch: Keys Fisheries, Marathon – Famous for lobster Reuben sandwiches and stone crab claws.
- Dinner: The Island Fish Company – Enjoy fresh seafood and a laid-back atmosphere.
Overnight: Tranquility Bay Beach House Resort or Hawks Cay Resort
- Amenities: Family-friendly activities, waterfront views, pools, and hot tub.
- Cost: $200-$350 per night.
Additional Recommendations:
- Crane Point Hammock: Visit the nature center and historic site with nature trails.
- Turtle Hospital: Take a guided tour of this sea turtle rehabilitation center.
- Sombrero Beach: A great place for a picnic and some beach time.
Day 4: Marathon to Key West

Main Activities:
- Ernest Hemingway Home and Museum: Tour the historic home of the famous writer, located in Old Town Key West.
- Duval Street & Mallory Square: Explore shops, bars, and restaurants. Mallory Square hosts a nightly sunset celebration with street performers.
Meals:
- Breakfast: The Stuffed Pig, Marathon – Known for its hearty breakfast plates.
- Lunch: Blue Heaven, Key West – Famous for its banana pancakes and lobster Benedict.
- Dinner: Louie’s Backyard – Fine dining with ocean views.
Overnight: Southernmost Beach Resort or The Reach Key West
- Amenities: Beachfront accommodations, pools, and hot tub.
- Cost: $250-$400 per night.
Additional Recommendations:
- Southernmost Point Buoy: Snap a photo at this iconic marker.
- Harry S. Truman Little White House: Tour the winter White House of President Truman.
- Key West Butterfly and Nature Conservatory: Walk through a lush habitat filled with butterflies.
- Key West Shipwreck Treasure Museum: Learn about the island’s maritime history.
- Conch Train Tour: Take a narrated tour around Key West.
- Dry Tortugas National Park: A full day trip by ferry or seaplane for snorkeling and exploring Fort Jefferson.
- The Studios of Key West: Check out art exhibitions and cultural events.
Day 5: Key West Exploration and Return

Main Activities:
- Key West Lighthouse and Keeper’s Quarters Museum: Climb to the top for stunning views.
- Fort Zachary Taylor Historic State Park: Tour the historic fort and relax on the beach.
Meals:
- Breakfast: Sarabeth’s Key West – Known for pastries and traditional breakfast options.
- Lunch: Salute! On The Beach – Beachfront dining with seafood pasta and fresh salads.
- Dinner: Joe’s Stone Crab, Miami – End your trip with dinner at this Miami institution after returning.
Additional Recommendations:
- Key West Nature Preserve: Enjoy some additional nature and water sports activities like kayaking or paddleboarding.
- Stock Island: Visit for a quieter alternative to Key West with great restaurants and marinas.
- Smathers Beach: Known for its white sandy beaches and clear water.
Travel Tips:
- Best Time to Visit: The peak season is from December to April. This is the best time for good weather, but expect higher prices. For a quieter experience, consider visiting during the shoulder seasons (May to early June and September to November).
- Hurricane Season: Runs from June to November. Keep an eye on weather forecasts and plan accordingly.
- Car Rental: Renting a car is the best way to explore the Keys. Book your rental car in advance to get the best rates.
- Drive Time: Plan for longer drive times during peak season due to traffic.
- Grocery Stores: Stock up on essentials in larger towns like Key Largo or Marathon.
- Visitor Centers: Stop by local visitor centers for maps and additional recommendations.
This comprehensive Florida Keys itinerary ensures you experience the best of the Keys, from Miami to Key West, with a mix of adventure, relaxation, and cultural exploration. Enjoy your road trip through this beautiful part of the United States!
