“On the island, time is measured in sunrises and sunsets, and worries dissolve into the vastness of the ocean.”
A road trip through the Florida Keys offers an unforgettable journey through some of the most scenic and vibrant landscapes in the United States. Starting in the lively city of Miami, you’ll cruise down the iconic Overseas Highway, crossing over stunning turquoise waters and enjoying panoramic views of the Atlantic Ocean and Gulf of Mexico. Along the way, you’ll explore charming islands like Key Largo, known for its crystal-clear waters and coral reefs, and Islamorada, the sport fishing capital of the world. Visit Marathon, a beautiful city in the middle of the Florida Keys, known for its stunning beaches, family-friendly atmosphere, and excellent water activities. The trip culminates in the laid-back, vibrant atmosphere of Key West, with its unique history, colorful streets, and spectacular sunsets. No Florida Keys road trip is complete without a visit to Smathers Beach, where you can relax on soft sand and soak up the sun. Get ready for a journey filled with adventure, relaxation, and breathtaking coastal beauty.
When to visit the Florida Keys:
March through May generally offers the best balance of good weather, fewer crowds, and reasonable prices. You’ll experience the Keys at their finest with sunny days, outdoor fun, and vibrant events, minus the peak-season prices and congestion.
If you prefer cooler weather and don’t mind higher prices, winter is a great time to enjoy the Keys. However, if you're traveling on a budget and can handle heat, fall offers lower rates and a more relaxed atmosphere, just be cautious about hurricanes.
Total Driving time from Miami to Smathers Beach is about 4 1/2 hours.
Day 1: Fly into Miami and begin your journey. If you would like to spend a couple of nights here, you can see my previous blog posts about Miami:
If you decide to skip Miami, continue south until you reach Key Largo.
Day 1-3: Key Largo
Key Largo, located at the northernmost tip of the Florida Keys, is a perfect destination for outdoor lovers, nature enthusiasts, and those seeking a relaxing escape. Known for its beautiful beaches, clear waters, and abundant marine life, Key Largo offers a variety of activities for visitors of all ages.
Where to stay in Key Largo:
Budget Pick: Drift Hotel
Meet the sandman by the sea in clean, bright, and comfortable guest rooms that beckon you to leave your worries behind and make the most of your Florida Keys vacation. Sandy shades and cool blues reminiscent of the stunning views just steps away invite you to immerse yourself in the experience, whether that involves kayaking through mangroves, snorkeling famed reefs, or simply staying in bed just a little longer.
Reefhouse Resort & Marina
4-Star hotel
Unwind in style in our chic waterfront accommodations. Each of our guestrooms and suites has been thoughtfully designed to reflect the coastal setting, with blue- and sand-colored accents, an abundance of natural light, and cozy fabrics in neutral, calming tones. Start and end your day on your private balcony, with spectacular views of the bay.
Set across 17 acres of tropical island overlooking picture-perfect Key Largo Bay, Reefhouse Resort & Marina is its own destination. Guests can take advantage of private beach access, a waterfront spa, a heated outdoor pool, and delicious on-site dining options, among other first-rate amenities. Slow down and bask in the seaside charm of the Florida Keys.
Baker's Cay Resort Key Largo
4-Star Hotel
The Baker's Cay Resort offers a tranquil beachside getaway in southern Key Largo. The facilities include two waterfall pools and beach hammocks. The hotel provides a wide range of water activities including diving, parasailing, catamaran sailing, and deep-sea fishing. Sit back and enjoy the waves on our private beach.
What to do and see in Key Largo:
1. John Pennekamp Coral Reef State Park
This is one of the most famous attractions in Key Largo, and for good reason. John Pennekamp Coral Reef State Park is the first underwater park in the U.S. and protects a portion of the Florida Reef, the third-largest coral reef in the world.
Activities:
Snorkeling and Scuba Diving: You can explore the reef by boat, snorkeling, or scuba diving. The waters are home to vibrant coral, schools of tropical fish, and even shipwrecks.
Glass-Bottom Boat Tours: If you're not into diving or snorkeling, a glass-bottom boat tour is a great way to view the marine life without getting wet.
Kayaking and Canoeing: Rent a kayak or canoe and explore the mangroves and crystal-clear waters in the park.
2. Scuba Diving
Key Largo is known as the “Diving Capital of the World” for its incredible dive sites. The coral reefs and wrecks provide a variety of underwater experiences for both beginners and experienced divers.
Popular Dive Spots:
The Spiegel Grove: A massive 510-foot shipwreck that has become a popular dive site for both experienced divers and beginners.
Molasses Reef: Famous for its shallow water, vibrant corals, and large population of fish.
Christ of the Abyss: A submerged statue of Jesus Christ located in Key Largo's waters, often visited by divers.
3. Swim with Dolphins at Dolphins Plus
Dolphins Plus offers an interactive experience where you can swim with bottlenose dolphins. The facility provides both shallow-water and deep-water encounters.
Activities:
Dolphin Encounters: Get up close with dolphins, learn about their behavior, and even interact with them in the water.
Dolphin Trainer for a Day: If you’re looking for a more in-depth experience, you can spend the day learning how to train and care for dolphins.
4. Florida Keys Wild Bird Rehabilitation Center
If you're a bird lover, a visit to the Florida Keys Wild Bird Rehabilitation Center is a must. This nonprofit center works to rehabilitate injured or orphaned wild birds with the goal of returning them to their natural habitats.
Activities:
Wildlife Viewing: You can walk through the facility and see various species of native and migratory birds, including pelicans, herons, and egrets.
Volunteer Opportunities: If you’re interested in helping, the center offers volunteer programs to assist with bird care.
5. Visit the African Queen
The African Queen is a famous boat used in the 1951 movie of the same name, starring Humphrey Bogart and Katharine Hepburn. It’s now a historic landmark and offers a unique cruise experience.
Activities:
Cruise on the African Queen: Take a guided cruise along the canals of Key Largo aboard this vintage boat. It’s a fun and historic way to explore the area.
Historical Tours: Learn about the film and the boat’s role in cinematic history.
6. Kayaking and Paddleboarding
Key Largo’s calm, clear waters are perfect for kayaking and paddleboarding. You can rent equipment from local shops and explore the mangroves, sea grass beds, and shallow reefs.
Popular Spots:
Florida Bay: This shallow, protected bay is ideal for kayaking and paddleboarding, with calm waters and opportunities to see manatees, dolphins, and a variety of bird species.
Blackwater Sound: Known for its mangroves, it’s a scenic and peaceful spot to paddle.
7. Explore Everglades National Park (Near Key Largo)
Key Largo is located near the entrance to Everglades National Park, one of the most unique ecosystems in the U.S. The park is known for its wetlands, mangrove forests, and wildlife, including alligators, manatees, and a wide variety of bird species.
Activities:
Airboat Tours: Take a thrilling airboat ride through the Everglades, where you’ll zip through the wetlands and spot wildlife.
Wildlife Viewing and Hiking: Explore the park’s trails, go birdwatching, or take a ranger-led program to learn about the ecosystem.
8. Key Largo Hammocks State Botanical Site
The Key Largo Hammocks State Botanical Site is a 2,400-acre park filled with rare and endangered plants native to the Florida Keys. The site features hiking trails and offers opportunities to explore the natural landscape of the Keys.
Activities:
Nature Walks: Walk the trails and learn about the unique flora and fauna of the Florida Keys.
Wildlife Viewing: Spot native species, such as the endangered Key Largo woodrat and various birds.
9. Visit the Islander Watersports
For adventure seekers, Islander Watersports offers a range of water activities such as snorkeling, kayaking, and fishing tours.
Activities:
Snorkel Tours: Explore nearby coral reefs and see tropical fish, sea turtles, and rays.
Fishing Charters: Key Largo is a prime spot for deep-sea fishing, and local guides offer half-day or full-day fishing trips.
10. Key Largo Art Gallery
If you're interested in local art, visit one of the art galleries in Key Largo. Many feature works by local artists and offer unique pieces inspired by the beauty of the Keys.
Popular Spots:
Key Largo Art Gallery: A gallery showcasing paintings, sculptures, and photography that capture the essence of the Keys.
The Gallery at the American Outdoors: Offers a collection of nature-inspired works, perfect for taking home a souvenir.
11. Sunset Watching
Key Largo offers stunning sunsets, and many visitors enjoy watching the sun dip below the horizon over the water.
Popular Spots:
Marker 88: A waterfront restaurant with great views of the sunset, perfect for dining while watching the sky change colors.
Caribbean Club: This historic spot is known for its laid-back atmosphere and excellent views of the sunset.
12. Key Largo Lighthouse Beach
This small but scenic beach offers a relaxing spot to enjoy the sun and the sea. It’s also home to a historic lighthouse that’s perfect for photos.
Activities:
Relax on the Beach: Enjoy the calm waters and sandy beach.
Lighthouse Photos: Take pictures of the historic lighthouse, a symbol of Key Largo’s maritime heritage.
Day 3-5: Islamorada
Islamorada is a beautiful village of islands located in the Florida Keys, known for its stunning turquoise waters, laid-back vibe, and incredible outdoor activities. It's made up of six islands: Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, Indian Key, and Lignumvitae Key.
Where to stay in Islamorada:
Budget Pick: Fisher Inn
3-Star Hotel
Fisher Inn Resort & Marina offers guests a modern, stylish, and comfortable place to stay while visiting Islamorada. Experience an authentic Florida Keys getaway and enjoy our bright accommodations featuring décor inspired by the Keys.
A beachside setting with palm trees, string lights, Adirondack chairs around a fire pit, and a view of the ocean under a clear blue sky.
Three Waters Resort & Marina
4-Star Hotel
Discover a paradise of endless possibility that redefines what it means to escape to the Keys. History and adventure weave effortlessly throughout 15 oceanfront acres, home to island-inspired rooms and suites, nine delicious culinary experiences, a world-class fishing fleet, and authentic, elevated service. Guests can enjoy Tiki Bar, Little Limon, Mercado Morada, Kokomo, Islamorada Pizza Co, Lucky Twist, Angler's Arcade, two beaches, a pool, watersports, resort activities, a marina, two retail destinations, our water taxi, and more.
Bungalows
4-Star Hotel
An island oasis for downtime and disconnecting, Bungalows Key Largo rewrites the rule book on inclusive getaways. Our intimate adults-only (ages 21+ only) resort sits within a botanical garden edged by 1000 feet of ocean shoreline, just a few miles from the warm waters of the Gulf Stream. We take care of all the details, because the time you’ll spend together is the greatest luxury of all.
Things to do and see in Islamorada:
Water Activities: Snorkeling, scuba diving, kayaking, paddleboarding, and world-class fishing. Islamorada is known as the “Sportfishing Capital of the World.”
Beaches and Parks: Check out Anne's Beach and Founders Park. While the Florida Keys aren't known for wide sandy beaches, these spots are great for swimming and picnics.
Museums and Attractions: Visit the History of Diving Museum and the Theater of the Sea, where you can swim with dolphins and sea lions.
Shopping and Dining: Quaint local shops and fantastic seafood restaurants. Try local specialties like conch fritters and Key Lime pie.
Sunsets and Nightlife: Enjoy live music at local bars and breathtaking sunsets at places like Lorelei Restaurant and Cabana Bar.
Day 5-7: Marathon
Marathon is a great destination for snorkeling, boating, fishing, and simply relaxing in a laid-back island setting.
Where to stay in Marathon:
Budget Pick: Banana Bay
3-Star Hotel
Uncover a tranquil escape at our resort in the Florida Keys located on the Gulf of Mexico. At Banana Bay Resort and Marina wake up each morning on 10 spacious acres set against the picturesque Gulf Coast in Marathon Florida. An intimate getaway and romantic oasis - Banana Bay features 59 guestrooms designed to evoke the tropical charm of our classic Florida beach town. Feel a sense of calm with decor featuring serene blue-crisp whites- pops of coral and dark woods throughout the resort. Enjoy unparalleled comfort and convenience with our variety of amenities including complimentary continental breakfast free Wi-Fi pet-friendly accommodations and more.
Tranquility Bay Beach Resort
4-Star Hotel
Tranquility Bay is a place like no other. Nestled in the heart of the Florida Keys- it is a place for families and couples to relax together and reconnect in the privacy of a standalone beach house. Dive into a world of adventure without leaving the resort and discover unbeatable water-based activities directly from the beach. Or take things a little slower as you relax on the powder-soft sands of a 2.5-acre private beach. Cool off from the tropical temperatures in one of three sparkling swimming pools, which includes a relaxation pool just for adults and a family lagoon pool. Or sit back with a refreshing cocktail in-hand as you watch a famous Florida Keys sunset from TJs Tiki Bar on the Gulf of Mexico. The award-winning Butterfly Cafe is not to be missed either--especially the key lime pie. Whether you choose an elegant and private two- or three-bedroom beach house overlooking the turquoise waters of the Gulf of Mexico. Or discover an intimate single-level guestroom with no noisy hallways or shared spaces... just tranquility. Located 90 miles south of Miami and 45 miles north of Key West- a million miles away has never been this close.
Isla Bella Beach Resort & Spa
4-Star Hotel
At the threshold of the iconic Seven Mile Bridge lies Isla Bella Beach Resort the crown jewel of the Florida Keys. The resort sits on 1 mile of waterfront sandy beach. Guest can enjoy 5 oceanfront swimming pools and take part in daily activities including Bocce ball court and giant chess boards, beach yoga, biking, cornhole and stargazing. Book a fishing charter with Two Conchs Fishing Charters or hop on a paddleboard kayak or jet ski tour. The resort offers multiple room types including oceanfront one- or two-bedroom guestrooms and suites. All accommodations include a balcony, outdoor living area that is perfect for watching the sunrise. Multiple dining options including Mahina, a modern Polynesian Restaurant featuring a coastal culinary experience using local fresh ingredients, the beach bar for poolside food and beverage and the Marketplace cafe, which offers a variety of breakfast and lunch items. Visit the 4000 sq ft spa with 5 treatment rooms, a relaxation room with steam and a selection of services. Enjoy your daily workouts at the 24-hour 1000 Sq ft state of the art fitness center including Peloton. Host your event in the 4000 sq ft conference center for events from 25 to 300. The hotel is a 4-diamond resort and was voted number 14 Best Resort Hotels in Florida in 2021 by Travel and Leisure. Nearby attractions include Florida Keys Aquarium Encounters Crane Point Hammock Museum Dolphin Research Centre, The Turtle Hospital, Bahia Honda State Park, Curry Hammock State Park and Pigeon Key.
Things to do and see in Marathon:
Beaches and Parks:
Sombrero Beach: One of the best beaches in the Florida Keys, great for swimming, picnics, and watching the sunset.
Curry Hammock State Park: Ideal for kayaking, paddleboarding, hiking, and birdwatching.
Coco Plum Beach: A quieter, more natural beach with shallow waters and a peaceful vibe.
Aquatic Adventures:
Snorkeling and Diving: Visit Sombrero Reef for vibrant coral and marine life.
Fishing: Marathon is known for deep-sea fishing charters, particularly for sailfish, tarpon, and mahi-mahi.
Boating and Kayaking: Rent a boat or kayak to explore the clear waters and nearby islands.
Wildlife and Nature:
The Turtle Hospital: A rescue and rehabilitation center for sea turtles, offering educational tours.
Dolphin Research Center: Learn about and interact with dolphins and sea lions.
Florida Keys Aquarium Encounters: An interactive aquarium where you can snorkel with tropical fish or feed sharks.
Historical and Cultural Sites:
Pigeon Key: A small historic island accessible by ferry, once a work camp for the old Seven Mile Bridge.
Crane Point Hammock Museum and Nature Center: A 63-acre nature preserve with trails, a historic home, and a butterfly garden.
Dining and Nightlife:
Seafood Specialties: Enjoy fresh seafood at local favorites like The Island Fish Company, Lazy Days South, and Keys Fisheries, known for their lobster Reuben.
Sunset Dining: Sunset Grille & Raw Bar offers beautiful sunset views with a lively, casual atmosphere.
Nightlife: While more low-key than Key West, Marathon has local bars and live music venues, especially at waterfront restaurants.
Day 7-9: Key West
Key West is the southernmost point in the continental U.S., known for its vibrant nightlife, rich history, and stunning sunsets. It’s part of the Florida Keys archipelago and offers a unique blend of cultural influences, laid-back vibes, and beautiful tropical scenery.
Where to stay in Key West:
Budget Pick: The Gates Hotel Key West
4-Star Hotel
There’s a reason why the word “paradise” evokes images of white sand, swaying palm trees, gently rolling turquoise waves, and endless sunshine.
Dining at The Gates Hotel Key West is both relaxed and regionally inspired. From the convenience of the signature food truck The Blind Pig, to the energy of the outdoor bar Rum Row, the hotel offers imaginative cuisine, festive cocktails and good times — ensuring an unrivaled experience.
The Gates Hotel’s accommodations in Key West are inviting, comfortable, and close to all the best of the island.
Thr Reach Hotel
4-Star Hotel
Set on the only private natural sand beach in Key West, The Reach is an excellent base for water sports, including sailing, scuba diving, and snorkeling. Duval Street and the Southernmost Point are steps away, and The Ernest Hemingway Home and Museum is just a short walk.
Relax in our stylish rooms and suites with a nautical theme. All rooms feature their own balcony where you can enjoy your morning coffee and soak up the sun while enjoying beautiful views.
The signature restaurant, Four Marlins, offers award-winning cuisine and stunning ocean views. Indulge in fresh seafood, locally sourced ingredients, and an extensive selection of wines and thoughtfully crafted cocktails.
Little Palm Island Resort & Spa
5-Star Hotel
The most distinctive feature of the Florida Keys might be the Overseas Highway, the stretch of U.S. Route 1 that makes the trip from Miami to Key West into a routine car trip. But Little Palm Island is anything but routine. Guests arrive at the relatively ordinary Little Torch Key and transfer to a yacht named for Harry Truman for the final hop to an island that was one of the former president’s favorite haunts and is now the only private island resort in North America: Little Palm Island.
This four-acre island is home to a mere 30 suites, and a couple of rules — no guests under 18, no audible cell phones — serve to keep the atmosphere properly tranquil. The suites themselves are divided among a number of thatched-roof bungalows, some more secluded than others, but all more than private enough. The look is thoroughly classic, in the British West Indies mode, while the comforts are delightfully low-tech — indoor and outdoor showers, outdoor copper tubs, and no televisions anywhere.
Given the scale there’s no need for more than one restaurant; the Dining Room handles everything, though a private dinner anywhere on the island is not out of the question. In fact, Little Palm Island is the sort of place where exceptions are the norm — at this level, the greatest luxury is a staff that’s willing and able to find a way.
What to see and do in Key West:
Historical Attractions: Visit the Ernest Hemingway Home and Museum, Harry S. Truman Little White House, and the Key West Lighthouse.
Southernmost Point: Take a photo at the famous Southernmost Point buoy.
Duval Street: Stroll along this lively street known for its shops, restaurants, bars, and vibrant nightlife.
Sunset Celebration: Head to Mallory Square for the daily sunset celebration with street performers, local artisans, and live music.
Beaches and Water Activities: Relax at Smathers Beach or Fort Zachary Taylor Beach. Enjoy snorkeling, scuba diving, paddleboarding, sailing, and jet skiing.
Day Trips: Take a ferry or seaplane to Dry Tortugas National Park, known for its pristine waters, coral reefs, and historic Fort Jefferson.
Museums and Culture: Key West Shipwreck Museum, Mel Fisher Maritime Museum, and art galleries showcasing local talent.
Food and Nightlife:
Cuisine: Fresh seafood, Cuban-inspired dishes, and, of course, Key Lime pie. Don’t miss Blue Heaven, a local favorite for its laid-back atmosphere and delicious food.
Bars and Entertainment: Experience live music and eclectic vibes at bars like Sloppy Joe’s, Hog’s Breath Saloon, and The Green Parrot.
Make sure to make your way to Smathers Beach, the largest public beach in Key West, stretching about half a mile along the southern shore of the island. It’s a popular spot for both tourists and locals, known for its picturesque views, soft white sand, and calm turquoise waters.
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