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Key West Trip Planner

If you’ve landed here, you’re probably planning to drive the Overseas Highway between Miami and Key West. And let me tell you it’s amazing. Imagine the top down on the convertible, sparkling water on either side, stopping for a quick snorkel at the many beaches followed by a delicious seafood lunch.

Ready to go? Well here are all the ins and outs on how to plan the perfect day trip, weekend getaway, or multi-day vacation – and our recommendations when creating your itinerary.


How To Get Here

By Car

Because the Florida Keys are a series of islands, the only way to reach them is to drive over a magnificent highway pieced together by dozens of bridges. It feels, at times, as though you are floating over the water en route to the end of the Earth. The only road connecting the Florida Keys, US 1, is also known as the Overseas Highway. Once you’re on it, it’s an astounding 42 bridges and 113 miles to the southernmost tip of Key West. It’ll be like no other road you’ve driven. 

Part of the adventure is stopping at the various “keys” along the way. A key is an island made from coral deposits. The first key you’ll reach is Key Largo just 60 miles from Miami International Airport. From there, you’ll reach Islamorada, followed by Marathon and then the awe-inspiring Seven Mile Bridge floating above turquoise waters, Big Pine Key and the Lower Keys.  At the end of the road, you’ll reach the legendary Key West, the southernmost point in the continental United States. As you make your way down the Florida Keys, take time to explore the individual keys as each has its own character, attractions and seaside adventures. 

Miami is the closest major city to access the Florida Keys with Fort Lauderdale, 20 minutes north of Miami, as the second closest.

By Plane


Miami International Airport is the closest airport to access the Florida Keys, making it a 162-mile, 3-hour-and-20-minute drive to Key West. With more than 80 airlines and 1,000 flights in and out of there a day, Miami International is one of the busiest airports in the country. There’s a full-service rental car area on site, making it easy to land, pick up your rental car, and hit the road. You’ll start out of the airport by taking Fl 836 west, also known as the Dolphin Expressway, which is an electronic toll road. From there you’ll merge onto the Turnpike before reaching US 1 south, the iconic road to the Florida Keys. 

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Fort Lauderdale

Here’s a budget tip. Sometimes, you can find cheaper flights in and out of Fort Lauderdale-Hollywood International Airport, which has 700 daily flights but feels far less crowded and chaotic than its sister airport to the south. It’s only a 20-minute drive, pending traffic, between the two airports – so if you find a better deal flying into Fort Lauderdale, buy it. 

Fort Lauderdale has a full-service rental car area just a few minutes walk from baggage claim, making it a breeze to get your bags and load them into your car. Take I-595 west toward Port Everglades/Hollywood/Dania Beach, eventually merging onto Florida’s Turnpike before driving on Highway 821 to US 1 south. It’s 187 miles and 3 hours and 40 minutes to Key West.

By Train

The Brightline

A devastating hurricane in 1935 put an end to train service to the Florida Keys, but you can take a local train to Miami where you’ll start your journey to the Keys. Florida’s Brightline, a yellow, privately-run train with beverage and snack service, runs from West Palm Beach to Miami. Disembark at the slick Miami station and walk a few minutes to the Tri-Rail station to board a train that runs into the Miami International Airport. From there, head to the rental car area. Sometime in 2023, the line will be completed from Orlando International Airport to Miami.


Alternatively, take the Tri-Rail, the public commuter train managed by South Florida Regional Transportation Service. It runs from Mangonia/45th Street north of Palm Beach to Miami with numerous stops along the way. It drops you off at the Fort Lauderdale-Hollywood International Airport or the Miami International Airport where you can rent a car.

Entrance Fees

Along the 125-mile stretch of Florida’s Keys, there are 10 state parks, some only accessible by water and others by land. They offer rare glimpses into the natural wonders of the Florida Keys from award-winning beaches to the only living coral reef in the United States. If you visit a state park, you’ll pay a modest entrance fee per vehicle. You’ll also pay an entrance fee to Dry Tortugas National Park. While some parking lots by beaches or in town are free, others are fee-based.

Key West Florida Keys Tour Map

Where to Stay

There are a lot of choices along the Florida Keys for places to stay. From vintage roadside motels and vacation rentals to luxury resorts. But because this stretch of Florida is popular, you’ll want to book your lodging reservations in advance.

Three Areas to Consider Staying Along the Florida Keys

Key West offers a variety of experiences for visitors staying, from those who party and enjoy the nightlife and bars; to foodies  make their way around the number of restaurants, to those that enjoy it’s history and culture. The conch or cottage style houses with wrap around balconies painted in a variety of bright colors gives it a unique tropical feel. Key West is renowned for its welcoming and accepting attitude and is especially LGBTQ friendly.

Key Largo

While Key Largo is positioned at the start (or end) of the Overseas Highway, it’s a mecca for diving, snorkelling, fishing, boating and generally all water activities.


Stay in Marathon if you’re looking for attractions to incorporate into your vacation, the Turtle Hospital, the Theater of the Sea Park, or spotting deer at nearby Big Pine Key.

John Pennekamp Coral Reef State Park

Camping enthusiasts will find public campgrounds like the one at John Pennekamp Coral Reef State Park, as well as private campgrounds for travelers with tents or RVs. Camping is only permitted in designated sites. You can’t spend the night camping at a beach.

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When To Visit

You can visit the Florida Keys year-round, but there are a few factors to consider when planning your trip. December through May offers great warm temperatures and a bustling tourist scene filled with travelers relieved to escape the cold winter temperatures where they live. 

The months of June through November are typically hurricane season in Florida, with September commonly a hurricane magnet. Hurricane season is also the hottest time of the year, with temperatures well into the 90s and humidity as thick as Florida Key Lime Pie. The trade-off for weathering this time of year is you’ll most likely find lower hotel rates and fewer people.

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How Much Time Do You Need to Visit the Florida Keys

It’s possible to make it from Miami to Key West and back in one day, but that would mean spending nearly 7 hours in the car with little time to explore this beautiful area via flip flops and flippers. Most travelers spend at least two nights and two days in the Florida Keys. To really experience Margaritaville in all the ways Florida icon Jimmy Buffet sang about, plan on four days or more. 

With great snorkeling, glass-bottom boat tours and sunset happy hours, you don’t want to feel rushed to do it all.  Plus, you’ll want time to sample the local seafood and immerse yourself in the relaxed Florida Keys culture. You’ll find laidback locals, a zany sense of humor exhibited in colorful store signs and a cold margarita always a short stroll away.

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How to Avoid the Crowds

Most travelers visit the Florida Keys between December and April when the rest of North America and Europe is buried under snow. If you visit during this time frame, relish in everything high-season has to offer by making reservations way in advance. For instance, reserve your spot in advance on the glass-bottom boat tour. Arrive at a state park first thing in the morning and snag your table in front of the best sunset view 40 minutes before anyone else has left the beach. 

Low season in the Keys coincides with Florida’s hottest temperatures. Hurricane season runs from June through November, although September is when many hurricanes tend to hit the state. In exchange for enduring oppressive heat and a possible hurricane, you’ll find fewer people, lower lodging rates and more parking spots during this time.

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Things to See and Do

John Pennekamp Coral Reef State Park 

A state park gem, John Pennekamp Coral Reef State Park in Key Largo offers several small beaches with picnic areas, a visitor center with an aquarium, snorkeling over an underwater statue of Christ or remnants of a Spanish shipwreck just 100 feet from Cannon Beach, and glass-bottom catamaran tours. There is a modest state park entrance fee, as well as a fee for the boat tours. 

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Mallory Square

Looking for the most celebrated place to watch the sunset? Head to Mallory Square in Key West where the appropriately named “Sunset Celebration” party gets started every day of the year two hours before sunset. Watch street performers, listen to musicians, peruse boutiques, galleries and arts-and-crafts stands as the sun sets on Key West. The parking lot is expensive at the square, so it’s best to walk or park farther away. 

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Southernmost Point Buoy

Arrive early, go at sunset or prepare to line up for Key West’s most photographed spot.  The buoy roughly marks the southernmost point in the continental United States and the approximate 90 miles across the water to Cuba. Check the webcam for an idea of the crowds in real time.


Ernest Hemingway Home & Museum 

This historic gem with stunning grounds in Key West was author Ernest Hemingway’s home for nearly a decade during the 1930s. Buy a ticket for a 20 to 30-minute tour of the house and property. You’ll see a lot of cats while you’re there. Hemingway had more than 40 cats when he lived in Key West, one of which was a six-toed cat named Snow White. Today, the property is home to 60 six-toed cats, many descendants of the Nobel Prize winner’s clowder of cats. 

Jimmy Buffett’s Margaritaville 

If you’re looking for a cheeseburger in paradise, head to Jimmy Buffett’s Margaritaville, his first restaurant that opened in the 1980s, located at 500 Duval Street in Key West. Yes, it’s very touristy and it’s a chain restaurant, but for Parrotheads, this is a mecca.  

Pigeon Key

More than 100 years ago, this five-acre island two miles west of Marathon once served as the home base for railway workers who built and then operated the original Seven Mile Bridge. Their hard work was part of Henry Flagler’s successful and Herculean effort to create a railway system that extended from the mainland all the way to Key West. Unfortunately, a devastating 1935 hurricane destroyed the Keys’ railway system, putting an end to rail service to the Keys. 

Today, you can go on an hour-long guided historical tour of the island, which sits on the National Register of Historic Places. After touring the island’s fully restored buildings, which run on solar power, enjoy a picnic or snorkel off the shore. You can walk, run or bike to Pigeon Key on Old Seven Mile Bridge between 9am and 5pm, or take a train, which leaves from Pigeon Key Gift Shop at 2010 Overseas Hwy. 

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Lignumvitae Key Botanical State Park

Only accessible by boat, this state park off the coast of Islamorada enables you to catch a glimpse of what the Florida Keys looked like before they were developed for tourists. See a two-story stone home built in 1919, which houses a visitor center, and walk through a tropical forest that includes 1,500-year-old lignum vitae trees. Lignum vitae trees, once ubiquitous on the Upper Keys, have wood so dense and heavy that buildings built with it survived the 1906 San Francisco earthquake. 


Dry Tortugas National Park 

To see and snorkel in gorgeously clear waters and explore one of the most unique national parks in the United States, head to Dry Tortugas National Park off the coast of Key West. You’ll need to take a two-hour boat ride or a much faster seaplane to get here. This national park is spread across seven islands and surrounding coral reefs and is home to Fort Jefferson, one of the nation’s largest forts. 

It was built between 1846-75 to protect U.S. interests since it sits at the gateway to the Gulf of Mexico where shipping lanes from the Atlantic Ocean, the Gulf and the Caribbean intersect. You have to pay in cash a park entrance fee, which is included in your ferry ticket, for each person 16 years and over. If you take a seaplane, you can pay your entrance fee with cash when you arrive on the island.

Best Beaches

The Florida Keys are not known for the long, sandy beaches that line most of the east and west coasts of Florida. The Florida Keys are remnants of ancient coral reefs, and they have offshore reefs that prevent sand from gathering on the shores. Even so, you can still find a nice sandy beach to place your beach towel and relax. 

Smathers Beach 

Smathers Beach in Key West is popular for good reason. This sandy beach offers that classic Florida experience with swimming, jet ski rentals, volleyball nets and bathrooms. There is a fee for parking here. 

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Fort Zachary Taylor Historic State Park Beach 

Known as “Fort Zach,” this beach in Key West that sits where the Gulf of Mexico meets the Atlantic Ocean delivers on beauty and fun. It’s a fantastic place to snorkel, fish, bike, as well as explore the historic fort on the property.

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Clarence S. Higgs Memorial Beach Park

Lesser known than Smathers Beach, this beach in Key West leans up against Fort West Martello, a historic fort. There’s a 400-foot pier here and a cafe, as well as a concession stand that rents umbrellas, chairs, and kayaks. When you need a break from the beach, tour the fort’s two acres of beautiful gardens. 

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Calusa Beach 

Bahia Honda State Park in Big Pine Key, 40 minutes north of Key West, boasts one of the best beaches in the area. Because of this, its parking lots can fill quickly, leading the park to limit entry. Get here early. Its white sand and clear turquoise waters are welcoming. There’s very little shade here, so bring a beach umbrella or rent one from the concession stand. You can rent kayaks, snorkeling equipment and beach chairs. There’s a fee to get into the park.

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Sombrero Beach 

Tucked in Marathon Key, this beautiful beach offers a serene scene on the Atlantic Ocean. And it’s not just popular among travelers. Loggerhead turtles lay eggs here from April through October. There’s shade and picnic pavilions, plus restrooms and volleyball courts.

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Awesome Experiences 


Because the Florida Keys are part of a 3,000-square-mile marine sanctuary, they are excellent for snorkeling. Dry Tortugas National Park, in particular,  may offer the best snorkeling in the Keys. Rent snorkeling gear or bring your own and explore the clear waters off the Keys. You can do a self-guided snorkel tour or sign up for a half-day or full-day snorkel tour. Look for parrotfish, yellowtail snapper, damselfish, angelfish, barracuda, and spiny lobster.

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From glass-bottom boats to sunset cruises on a catamaran, the Florida Keys offer a multitude of ways to get on the water. For those looking for more solitude on the water, you can rent kayaks and stand-up paddleboards from a number of shore-side businesses. Keep your eyes out for dolphins who will often make a guest appearance.

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Scuba Diving

With its clear waters filled with more than 6,000 marine species and a shipwreck trail lined with nine shipwrecks, the Florida Keys offer excellent scuba diving. In fact, the second-largest ship ever intentionally sunk to create an artificial reef sits 7 miles south of Key West. Resting under 165 feet of water is the 522-foot-long U.S. Navy ship General Hoyt S. Vandenburg. Beyond the Vandenburg, there are great diving locations in the upper, middle and lower Keys. 


If there is one thing you learn while visiting the Florida Keys, it’s that the locals love to celebrate island life. Head here for one of the Key’s rocking festivals. Among the many festivals is the Key Lime Festival that celebrates citrus and the Key’s famous dish – Key lime pie. Hemingway Days celebrate Key West’s most famous author Ernest Hemingway. Fantasy Fest has been serving fun to adults with costumes, parades and all-day-and-night parties since 1979. Reef Fest focuses on the importance of marine conservation. 

Spotting a Manatee

The best way to see a manatee while in Florida is to get out onto the water on a kayak with a local guide. They know the favourite mangrove hangouts and areas where they have been recently spotted. And a good guiding operation will ensure you enjoy this experience responsibly as they are a protected and endangered species.

Like us, manatees are attracted to Floridas warm water especially in the winter. And while there is no guarantees, here are some places to chance your luck on your own.

John Pennekamp State Park.  The marinas around Key West; Cow Key, Harrison Bight and Key West Bight.  Look around the boats, especially those cleaning with hoses, as the manatees can be attracted to the freshwater.

Family Fun Adventures

The Beach 

It may be helpful to know that the Florida Keys are better known for excellent snorkeling and scuba diving than for white sandy beaches. Coral reefs prevent sand and waves from sweeping up against the shores, which means there aren’t sandy beaches everywhere. However, they’re easy to find if you know where to go. 

Among some of the best beaches are Calusa Beach in Bahia Honda State Park between Big Pine Key and Marathon, Sombrero Beach in Marathon, Fort Zachary Taylor Historic State Park Beach in Key West and the popular Smathers Beach in Key West. 

John Pennekamp Coral Reef State Park

This state park in Key Largo is a great place for families. Spend time in the visitor center where a 30,000-gallon saltwater aquarium and a theater featuring nature videos bring to life the marine ecosystem of the Keys. Then go on a 2.5-hour glass-bottom boat tour aboard a catamaran that can fit 130 people. Afterwards, have a picnic and relax at Cannon Beach where you can snorkel to a historic Spanish shipwreck 100 feet from shore. 

Robbie’s Marina in Islamorada 

Lined with souvenir shops, a refreshing shaved-ice stand and a dock where you can feed tarpon, Robbie’s Marina is a great place to bring the kids for a uniquely Florida cultural stop. Buy a bucket of bait and feed the tarpon at the end of the dock. Don’t miss drinking a Trailer Trash Bloody Mary on the deck on the waterfront.  You can also book a snorkel outing, a sunset cruise or a boat ride to Lignumvitae Key Botanical State Park at the marina. 

The Turtle Hospital

If you have turtle lovers in your family, head to the Turtle Hospital, a non-profit that rescues and rehabilitates injured sea turtles in Marathon. It’s a working hospital housed in the former Hidden Harbor Motel. Educational programs run every 30 minutes. You’ll need reservations for a guided tour, which last 70-90 minutes and end with guests feeding the hospital’s permanent residents. 

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Key West Lighthouse

Beginning in 1848, this lighthouse provided a safe passage to hundreds of ships that passed by Key West. While technological advances led the U.S. Coast Guard to decommission the lighthouse in 1969, it’s open to the public to explore. Climb up 88 steps to see panoramic views of Key West. Then visit the restored lighthouse keepers’ quarters and learn about their lives. 

Big Betsy

Are you a fan of those kitschy roadside attractions? Then you’ll want to stop by at the Rain Barrel Artisans Village in Islamorada (Mile 86) and grab a photo with this giant lobster.  Named Betsy, she represents a spiny lobster (no claws, lots of legs) found locally and measures about 30 feet tall and 40 feet wide.  Wander the shops and galleries for arts, crafts, souvenirs, gifts, jewelry and places to eat.

Key Deer

The tiny endangered Key Deer are now found exclusively in the Florida Keys. They are good swimmers, perhaps allowing them to survive hurricanes like Irma. Today, vehicle collisions are the number one threat, so you’ll see slow driving zones to help protect them, especially around Big Pine Key. Where’s the best place to see the Key Deer? The Key Deer Preserve on Big Pine Key. Visit the Nature Center to find out about the latest sightings.

Best Sunset Spots

The Florida Keys are known for beautiful sunsets, and you’ll find numerous bars and restaurants situated to give guests the best views of the sun come evening time. State parks and local beaches also offer exceptional views.  

Mallory Square

This iconic destination is the place to see the sunset in Key West, if you’re looking to gather with hundreds of others who also want to celebrate the end of another day in Florida. Every evening of the year, the Sunset Celebrations kick off two hours before sunset. You’ll find live music performances, magicians, psychics and arts and crafts vendors lining the area. It’s cheapest to park farther away than in the square’s parking lot. 

Fort Zachary Taylor State Park 

This 54-acre National Historic Landmark on the southern end of Key West is a great place to watch the sunset. Home to a Civil War-era fort, Fort Zach beckons you to set up your lawn chair and watch the sun sink into the ocean. The Key West Shipping Channel abuts the west side of the park and is popular among fishermen. There’s a fee per vehicle to enter the state park. 

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Sunset Park Beach 

Lose some of the crowds and follow the locals to Sunset Park Beach in Marathon Key. You can sit in the sand or on a bench and watch the sun slowly slip beyond the horizon.

Food You Have To Try

A trip to the Keys would be incomplete without sampling the fresh locally caught seafood. Enjoy the sweet meat of stone crab claws, the tasty spiny lobster, which is clawless, Key West pink shrimp, hogfish and the regionally famous conch fritters.

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If you happen to see Lionfish on the menu – try it.  It’s great for a number of reasons; it has a delicious white firm meat, is healthy with high omega 3 fatty acids and it is invasive. This predatory fish eats native fish which keep algae in check.  So you’ll be supporting local fisherman, and supporting a balanced coral reef.

Of course save room to finish your meal with a slice of Key lime pie, Florida’s most famous dessert.   Where’s the best Key Lime Pie in Florida?  Well I’m still sampling my way through…


Key West Packing List

Town Clothes: Attire in the Florida Keys is casual unless you’re headed to a fancy restaurant or resort. Pack a pair of shorts, t-shirts and a nice shirt for dinner and a skirt or dress, if you want to dress up for dinner. A long-sleeve shirt or sweatshirt is nice for cooler evenings when the ocean breeze picks up. Bring a rain jacket for stormy weather.

Beach Supplies: There are some beautiful beaches along the way if you want to go for a swim or snorkel so bring a swimsuit, towel, rash guard, beach chair, swim goggles and a snorkel set with fins. Beach chairs are handy also.

Footwear: Pack a pair of flip flops and a pair of running shoes, if you’re a jogger.

Daypack or Beach Bag: A comfortable pack or roomy beach bag will help you carry your towel, snorkel equipment, sunscreen and snacks.

Sun Protection: Cut down your exposure to the sun with a broad-brimmed hat, sunblock and sunglasses. Even on cloudy days, wearing sunscreen is important because of the reflection of the sun on the water.

Water Bottles: Always bring water. And make sure you drink it. Spending a lot of time in the sun dehydrates you.

Mosquito Repellent: Depending on the season and the year, mosquitos could be an unwanted guest on your outings.

Portable Phone Charger and Cable: If you’re taking pictures with your phone, running out of batteries may result in missed opportunities. A DC car charger is best, so that you can charge your phone while driving.

Plastic Bag: We always carry a plastic bag, so we can do our part and help keep the beaches and waterways clean. If you see some trash along the way, pick it up, drop it in the bag. When you get back to the parking lot, simply drop your bag in the recycling or trash bin and voila! You’ve helped keep the area beautiful for everyone who visits.

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Top Tips for Key West

  • Tolls: Be aware that the tour route includes toll roads. You can sign up for a Toll Program at sunpass.com, enquire with your rental agency for a transponder, or drive through and receive the toll by invoice with an additional admin fee.
  • Get Up Early: A great way to beat the crowds for breakfast, for a choice spot at the beach, for the best snorkeling and for a parking spot in town, is to get up early and be among the first to every place you want to go.
  • Book Ahead: The Florida Keys are popular, especially during the high season of December through March. Make advanced lodging reservations, and some attractions like the Turtle Hospital in Marathon require advanced reservations.. Also, if there is a special dinner spot you want to go to, make dinner reservations way in advance. Likewise, if you plan on going on any boat, snorkel or scuba diving tours, book them in advance, so that you don’t arrive only to find out the tour you wanted to go on is sold out.
  • Protect Yourself from the Elements: Make sure to have sunscreen, a hat, sunglasses, and water with you at all times. Pack a rain jacket in case it rains. And always have mosquito repellent with you just in case you visit a buggy venue.
  • Be Prepared to Pay for Parking: There are a number of paid parking lots in the Keys, be it in historic Key West, which is notoriously hard to find parking, or beachfront lots.
  • Park Entrance Fees: Be aware that the State Parks do charge small entrance fees.
  • Phone Charger: Bring a portable charger or power bank to keep your phone up and running all day long.