Discover the best of the Florida Keys on this four-day road-trip from Miami to Key West. You’ll drive along the scenic Overseas Highway to Key West and back, stopping along the way to snorkel, SUP, and soak up the sun.


  • Visit the remote Dry Tortugas National Park
  • Explore historic Key West
  • Snorkel North America's only living coral reef
  • Join the Sunset Celebration at Mallory Square in Key West

Brief Itinerary

Day Highlights Overnight
Day 1 Key Largo and Marathon Key Key West
Day 2 Explore Key West, Snorkeling and Sunset Adventure Key West
Day 3 Day Trip to Dry Tortugas National Park Key West
Day 4 Back to Miami with a stop in Islamorada  

Detailed Itinerary

Day 1: Key Largo and Marathon Key

A beach on Key Largo
A beach on Key Largo

You'll head south out of Miami on the Ronald Reagan Turnpike to US Highway 1 (also known as the Overseas Highway), one of the most scenic roadways in the country.

Another option is to take the quieter route along Card Sound Road, which connects the mainland with the top half of Key Largo. More off-the-beaten-path than the main highway, Card Sound Road is lined with mangroves and locals selling blue crabs and won't add any additional drive time to your trip.

After the short (60-minute) drive, you'll arrive in Key Largo and head to John Pennekamp State Park ($8 entry per vehicle). Located at Mile Marker 102.5 on the ocean side of the highway, here you’ll find the oldest underwater preserve in the continental US, home to one of the world's living coral reefs.

There are a number of ways to take in the beauty here - walk the trails through tropical hardwood forests, kayak or SUP through the mangrove swamps, snorkel over the Spiegel Grove shipwreck, or board a glass-bottom boat over the reef. If you have the necessary certification, you can even scuba dive.

If you’d prefer to stay on land, you can walk the trails (Wild Tamarind Trail is a short and easy loop, while the Mangrove Trail takes you on a boardwalk to an observation tower) or hang out on one of the park’s beaches. Cannon Beach is better for snorkeling close to shore, while Far Beach is great for swimming and offers more shade for relaxing under the palms. 

Stop for lunch at the Fish House (try the fish of the day matecumbe-style) before continuing your drive south along the Overseas Highway.

Continue south along US 1 for 60 minutes to Marathon Key for a mid-afternoon pit stop at the halfway point between Key Largo and Key West.

On the north end of Marathon Key sits the Dolphin Research Center (Mile Marker 59), where visitors can interact with and learn about the dolphins and sea lions that live there.

Further south on the island is the Turtle Hospital (Mile Marker 48.5), a rehabilitation center for injured turtles. You can sign-up for a tour of the hospital to learn about their flippered residents and have the opportunity to feed sea turtles.

If you’d prefer to stretch your legs outside, Sombrero Beach is a beautiful stretch of white sand just off US 1. Take a left at Mile Marker 50 on the Atlantic side and follow Sombrero Beach Road to the end, where you'll find free parking.

Afterward, hop back on US 1 heading south, and it’s not long before you’ll come to Seven Mile Bridge, which was one of the longest bridges in the world at the time of its completion in the 1980s. Savor the miles of glistening blue ocean on all sides. From Bahia Honda Key at the southern end of the bridge, its a little less than an hour's drive to Key West. 

Once you’ve reached the final destination of Key West, you should find somewhere to park your car for the weekend - you won’t need it for the rest of your time on the island. If you’re staying in the Old Town, most points of interest are walkable or easy to reach by bicycle, as the Old Town is less than 2 square miles. Walking also allows you to see more of the charming, colorful homes and lush tropical foliage. 

Walk over to Mallory Square if you’ve made it in time for the Sunset Celebration, which begins daily two hours before sunset. Here you’ll find arts exhibitors, street performers, and food carts. Once the sun dips below the horizon, walk over to Bagatelle for a delicious seafood dinner. Be sure to make a reservation, as their outdoor seating fills up quickly.

Total drive time: Approx. 4 hours, depending on traffic

Day 2: Explore Key West, Snorkeling and Sunset Adventure

Colorful houses on Duval Street
Colorful houses on Duval Street

The southernmost point of the continental US, the town of Key West is a charming island of colorful architecture, free-roaming roosters, and quirky residents. Explore this tropical paradise by land and sea to uncover the allure that's drawn artists, musicians, smugglers, and pirates to the island during its storied history. Start your day with a build-your-own omelette at Pepe’s Cafe, a local institution since 1909. 

Afterward, head to Fort Zachary Taylor Historic State Park ($2 admission for pedestrians). Here, you can lounge on the white sand beach, swim and snorkel off the shore, hike on the two short nature trails, or explore the historic fort, an important Union outpost in the Civil War. If you’d prefer to spend the morning exploring the city streets, make use of the city’s hop-on/hop-off trolley, a great way to see the four corners of the island and learn its history along the way.

If time allows, you should take a stroll through the Key West Butterfly and Nature Conservatory. Some butterfly species here are the size of your hand, and will land on your palm if you’re lucky! 

For lunch, don’t miss Eaton Street Seafood Market for tasty sandwiches made to order, and dine al fresco at one of their outdoor picnic tables. After lunch, take a break from the sunshine at the Ernest Hemingway Home & Museum for a glimpse of Key West life in the ‘30s. Included in the admission price is a short, guided 30-minute tour led by a local volunteer. Look for descendants of Hemingway’s six-toed cat that lounge around the premises in the dozens.

Stop for a slice of Key lime pie at Kermit’s Key West Lime Shoppe on your way to the marina for your next adventure. The rest of the afternoon will be spent aboard a catamaran for some deep-sea snorkeling followed by a sunset at sea. The ship’s captain will take you out into deeper waters over North America’s only living coral reef. For two hours you’ll have the opportunity to snorkel in the crystal clear, turquoise waters over the reef. For the final hour at sea, you’ll be served rum punch to celebrate a fun day and ring in the sunset. The captain will return you to shore at 8 pm. If you’re traveling with young children, we recommend taking this excursion in the early morning, as you’ll share the ship with other families at that time.

Head to Southernmost Beach Cafe on the Atlantic end of Duval Street for a fresh seafood dinner.

Day 3: Day Trip to Dry Tortugas National Park

Aerial view of Fort Jefferson on Garden Key
Aerial view of Fort Jefferson on Garden Key

The Florida Keys come to an end about 67 miles west of Key West at the Dry Tortugas National Park, a remote 7-key archipelago. Only accessible by boat or seaplane, you must plan ahead if you want to see this amazing park, but it is well worth the trip. On Garden Key, you’ll find Fort Jefferson, the largest brick masonry structure in the Americas, which housed prisoners following the Civil War. 

Travel by seaplane is much faster (30-40 min), which allows you more freedom and offers an amazing aerial view over the ocean, islands, and reef. Keep in mind that you’ll have to bring your own food for the day, although they do provide water, a cooler, and snorkeling gear. However, we recommend that you take the ferry to reach the park, as the park entrance fee, breakfast, lunch, and snorkeling gear are included in the price. Do note that it will be an early morning - the ferry leaves at 8 am to allow a full day exploring the Dry Tortugas after the 2.25-hour journey to get there. This is a full-day trip, so be sure to bring some snacks as the boat does not return to Key West until after 5. 

You’ll arrive at Garden Key around 10 am. Most ferry-goers opt for the guided tour first thing off the boat, so we recommend you head straight to the beach. The shallow waters (5 - 15 ft) around Garden Key make for some really spectacular snorkeling - the park is home to 67,000 acres of coral reef under clear blue waters. 

You can snorkel off North & South Swim Beaches, but we recommend checking out South Swim Beach. Here, you can swim alongside the moat (no swimming is allowed inside the moat) that surrounds Fort Jefferson, where you’ll see an abundance of marine life. There is a sandbar land bridge that connects Garden Key to neighboring Bush Key at low tide, so check it out if you feel like exploring (keep in mind this is off-limits during tern nesting season Feb - Sep).

Ensure you head back to the ferry for lunch between 11 am and 1 pm. You can take your lunch to-go and enjoy it on the beach, but you’ll need to return your trash to the boat. 

After lunch, take a tour of the six-sided Fort Jefferson to learn about its storied history. You can take a guided tour (included in the price of your ferry ticket) to hear captivating stories about the fort and its remarkable history, but you can also take a self-guided tour using the helpful placards around the fort. There are three stories of the fort to explore and no shortage of incredible views. Be warned that there are no guide rails on the top level of the fort, so take extreme caution if you choose to walk this level.

All too soon, it’s time to head back to the ferry for the 2.25 hours trip back to Key West. The ferry deposits you back onshore at Key West just after 5 pm. If you’re super hungry, head straight to the Half Shell Raw Bar, a 5-minute walk from the dock. Conch Republic Seafood Company is another great place to eat dinner and catch the sunset if you walk just 5 minutes further.  For an upscale dinner with sunset views to match, head to Hot Tin Roof instead (after heading back to the hotel to change) for a Latin twist on traditional Key West fare. After dinner, walk down Duval Street for a taste of Key West’s active nightlife scene.

Day 4: Back to Miami with a stop in Islamorada

Seven Mile Bridge
Seven Mile Bridge

Before leaving Key West behind, be sure to have brunch at Blue Heaven, a quirky and authentic Key West favorite that's the perfect way to end your time here. Then start the 90-minute drive north on US 1 to Islamorada, the halfway point between Key West and Miami.

Stop at Robbie's Marina (on the left at Mile Marker 77.5) for a chance to feed a giant tarpon before reaching your next destination, Islamorada. Keep an eye out for the pelicans - they'll steal the bait right out of your hands! 

Often compared to Key West, Islamorada has all of the charm without the crowds. Stretch your legs and take a stroll through the 6-block corridor of the Morada Way Arts & Cultural District. Here you'll find galleries, shops, restaurants, and art studios along the only 'Main Street' between Miami and Key West. At the southern end of the MWACD, you’ll find the Green Turtle Inn, featured on the Food Network and famous for the Key lime pie, which is a great place to stop for lunch.  For those not driving (and of age), visit the beer garden at the Florida Keys Brewing Company for a tasting flight of local beers.  

If you’re not in a hurry to get back on the road, there are plenty of options for how to spend the rest of your afternoon. One way to explore the aquatic surroundings is by renting a Waverunner; you can zip around the high seas, cruise the mangrove tunnels, and motor out to smaller islands and the ‘secret’ sandbar off Whale Harbor, a local favorite (try to avoid the sandbar if you visit on the weekend, as this is when it is busiest).

If you'd prefer to spend the afternoon on dry land, head to Anne's Beach (parking at MM 73.4), voted as one of the Best Hidden Beaches of South Florida by Lonely Planet. The waters here are too shallow for swimming but are perfect for wading or strolling along the sands. From here, it’s only a 90-minute drive back up to the city along US 1.

Total drive time: Approx. 4 hours, depending on traffic