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This 5-day Florida Keys itinerary has been carefully constructed to ensure the best possible visit. It includes all of the best places to eat, sleep, and visit.
We traveled to the Florida Keys in September 2022 and worked hand-in-hand with Florida Keys & Key West Tourism to create this travel guide.
In it, you will find honest reviews and recommendations, as well as tips and advice for arranging your vacation.
After reading, be sure to leave us any questions or feedback in the comments section!
Disclosure: In order to keep providing you with free content, this post likely contains affiliate links. If you make a booking or purchase through one of these links we earn a small commission at no extra cost to you. So a HUGE thank you to you if you click one of these links 🙂
Visitors will begin their 5-day Florida Keys vacation in either Miami or Key West (where the two nearest airports are).
We constructed this itinerary to begin by flying into Miami and end by flying out of Key West. This tends to be the most time and cost-effective method of visiting. If you’ve not already booked your flights, we recommend checking prices on Skyscanner to find the best option for you.
Do not worry if you are flying in and out of the same place! You can still follow the itinerary basically as written, though you may need to reverse the order or allow an extra half day for driving.
While there are plenty of cabs and ride-share services in Key West, the best way to get around the Florida Keys is by renting a car.
Car rentals to/from Miami are actually extremely reasonable, available as low as $30/ day!
Car rentals to/from Key West begin a bit higher at $50+ per day.
The roads in the Florida Keys are very safe and easy to drive.
🚗 Pro Tip: The gas in Key West is very expensive ($1/gallon more than in Key Largo!)
Click here or on the image above to open our 5 Day Florida Keys Itinerary Google Maps in a new tab.
Stretching from the southern tip of Florida, the Florida Keys are a small cluster of islands. The longest drive from Key West to Key Largo is around 2 hours (98 miles), and from Key Largo to Miami is around 1h15m (67 miles).
This itinerary follows a Miami to Key West route. We recommend arriving the night before you wish to begin, if possible, to allow yourself to rest and get over any jet lag.
Recommendations on your day of arrival are covered here before diving into the daily itinerary.
The drive from Miami to Key Largo is less than 2 hours, so it is achievable even on the day of your arrival.
If you are coming in from a long way away, however, it may be best to book a cheap night in Miami and get some rest before making the short drive down in the morning.
There is plenty of very affordable accommodation options near the Miami airport that are typically much cheaper than what you will find in the Keys.
If you are not flying out of Key West as recommended, you will either need to allow time for the long drive back to Miami (about 3.5 hours) or drive straight to Key West and follow this itinerary in reverse, ending in Key Largo instead.
If you have instead landed in Key West and are flying out of Miami, you will want to simply follow this itinerary in the reverse order!
If you are flying both in and out of Key West, however, you have the option of driving out to Key Largo on the day of arrival. In this case, you can follow our perfect 5-day itinerary for the Florida Keys exactly as is!
The first day of your visit to the Florida Keys should be spent enjoying the quiet, beautiful Key Largo.
Key Largo was our favorite of the Florida Keys. It had everything we needed to stock up on to begin our vacation and did not come with the logistical obstacles of travel that the city of Key West does.
If your idea of the perfect vacation is a quiet beach with a beverage and the possibility of dolphin and manatee sightings, Key Largo will be your favorite too. If you are more interested in activities, nightlife, and a vibrant city, you will likely prefer Key West.
John Pennekamp Coral Reef State Park was the first underwater park in the US and is the premier destination in Key Largo.
This park is best known for the diving and snorkeling opportunities it provides. The most famous destination is the Christ of the Abyss statue which you can only get to via a snorkel tour.
Even if you feel like staying dry, John Pennekamp is absolutely worth a visit. The beaches are beautiful and full facilities are available. You can also take a glass-bottom boat tour to witness the beauty of the underwater world without getting wet!
Be aware that there are some resident saltwater crocodiles and encounters are common. It is worth noting that there have been no deaths or incidents between man and croc here, but they can be unsettling and caution should be taken.
There are many snorkel tours to John Pennekamp to choose from, including those run by private companies and those available to book directly through the state park. Those run by private companies are typically longer and include entry to the park and snorkel gear rental. If you book directly through the state park, consider bringing your own snorkel gear to save money.
Mrs. Mac’s Kitchen is the most popular lunch spot in Key Largo and an absolute local favorite.
This quaint restaurant has been serving the Florida Keys delicious food longer than nearly any other establishment, opening in 1947 as one of the few places to eat in all of the Keys.
Mrs. Mac’s Kitchen is a nearly-perennial winner of local People’s Choice Awards and is a must-visit while staying in Key Largo.
🐟 Pro Tip: Mrs. Mac’s Kitchen is closed on Sundays!
Kona Kai is an experience unto itself. This incredible resort provides an all-in-one staycation destination that may well have you scrapping your plans to spend more time at home base.
The harbor at Kona Kai provides a calm water break, perfect for exploring by paddle board or kayak… both of which the hotel provides for free!
The westerly views over the water provide an incredible scene for enjoying sunset and visitors can expect to see dolphins and potentially manatees right from the beach.
Our stay at Kona Kai was one of the most memorable of our extended travel lives. We cannot recommend this place highly enough!
🛌 Pro Tip: If available, try to get a water-view suite! They feature full kitchens and unbelievable views to wake up to.
Finish your day by enjoying delicious local cuisine with an unbeatable ocean view at Calusa restaurant at Baker’s Cay Resort.
Calusa serves all the Southern Florida favorites, primarily locally-caught seafood with a Caribbean influence, but they also prepared one of the finest filet mignons we have ever tasted.
Beyond the food, views, and service, what we loved about Calusa was that it felt elegant and upscale without feeling formal or pretentious.
That and the Jerk Prawns… you have to try the jerk prawns!
Day 2 of your 5-day Florida Keys itinerary involves enjoying the paradise you find yourself in.
This could mean waking up to a glorious sunrise or sleeping in until brunch – whichever you prefer!
We have left the morning open by design. If you have followed our advice and stayed at Kona Kai, this is a perfect opportunity to go for a paddle and enjoy a tranquil morning on the water.
The Key Largo Conch House is another local favorite and an excellent place to fuel up for the day.
This historic house is one of the oldest in the Keys and has been serving large portions of local fare for over half a century.
Prices are reasonable, portions are ample, and flavor is true.
🍽 Pro Tip: You have to try the Key Lime Pancakes!
Beyond the tropical climate and amazing food, the incredible snorkeling and diving available in the Florida Keys is the primary motivator for many visits.
Of the many places you can choose to explore underwater, few if any offer as impressive a coral garden as the Upper Keys National Sanctuary.
What lurks below the crystal clear water is a world of colorful, thriving marine life and vegetation. On our visit, we encountered nurse sharks, stingrays, puffer fish, and lots of tropical fish.
The only way to experience the Upper Keys National Sanctuary (without your own boat) is via tour.
We went with Horizon Divers and highly recommend them. The captain and crew were exceptionally friendly, helpful, and very patient with some of the inexperienced snorkelers aboard. Additionally, they are Blue Star certified by Florida Keys National Marine Sanctuary, which recognizes their commitment to promoting responsible and sustainable tours.
The “water table dinner” at Sol by the Sea is the perfect way to spend your final night in Key Largo and promises to be one of the most unforgettable meals of your life!
Sol by the Sea restaurant actually arranges a table and service IN the water. Imagine dining while fish swim about and the sun sets magically over the very water you are eating in.
“But what about the food?” you may be asking. Rest assured, they have that covered. Sol by the Sea serves some of the best food you will have anywhere in Florida, specializing in local favorites such as seafood, key lime food and cocktails, and catch of the day.
Our sunset dinner in the water was one of the most unique dining experiences we have ever experienced. This is definitely one you will not want to miss!
After spending a couple of days enjoying Key Largo, it is time to head west.
You will end your day in Key West, but not before traveling through the other primary Keys. Along the way are some of our favorite places in Southern Florida.
The drive time from Key Largo to Key West is about 2 hours, so plan accordingly and be sure to get a reasonably early start to your day so you don’t have to rush or miss anything special on your way!
A tour of the Turtle Hospital in Marathon is a must on your way to Key West. This incredible place rescues and rehabilitates hundreds of endangered turtles every year.
By taking a tour of the hospital, not only will you get up close to lots of turtles from hatchlings to fully grown adults, but you will also be helping to support their amazing work. The tours last approximately 1.5 hours and run every half hour from 9am-4pm.
We learned so much during our visit and loved being able to feed the resident turtles at the end of our tour.
Pigeon Key is a small but stunning little island just outside of Marathon. It is only accessible by walking, cycling, or taking the Pigeon Key Trolley 2-mile down the old bridge which stops just after reaching the key.
In addition to being a beautiful place to explore, Pigeon Key offers perhaps the best beachside snorkeling in the Florida Keys. Even without getting wet, you can peer down at turtles, rays, and tons of fish right off the dock.
As your day will be busy with driving, we recommend taking the Pigeon Key Trolley to the island and planning to spend a couple of hours there.
The roundtrip trolley ride costs $25 per adult. They leave each day at 10am, 12pm, and 2pm, and the return trolley is two hours later. You also have the option of walking or cycling over the old Seven Mile Bridge, however, you will still need to pay $15 to enter the island.
Regardless of how you arrive, you have the option to take a guided tour of the island or relax and enjoy it at your own leisure.
After all that turtle watching, commuting, and a trolley ride to Pigeon Key, you will likely be getting pretty hungry.
While there are not a ton of options in Marathon for eating, there are a few good ones and the beach bar at Isla Bella stands above the rest for vibes.
Head to the beach and recharge with a signature island cocktail and a light nosh. The menu is somewhat limited, but will have some good options to tide you over until your dinner in Key West.
The most important decision you will make when planning your Florida Keys itinerary is deciding where you are going to call home.
We stayed at Parrot Key Hotel and genuinely feel it is one of the best options in Key West for accommodation. Our “room” was more like a house, and the views were just unbelievable.
Among the endless list of features and amenities you can expect, the most notable is their shuttle services to downtown Key West and Smathers Beach (the best beach in the region). This means you can just walk to the front desk and not have to worry about parking and driving in the busy streets of downtown.
Parrot Key also has FOUR pools for their guests, one with a full bar and small restaurant.
Downtown Key West is a colorful, vibrant place that really comes alive at night.
For your first night in the area, we recommend a more casual option that lets you see and feel what Key West is all about.
First Flight Brewery is the perfect choice. Leave the collared shirts and heels behind and come as you are for hand-crafted beer and exceptional comfort food in a garden-like setting.
With so many upscale and more elegant meals on the itinerary, we truly appreciated the experience at First Flight. Live music could be enjoyed from the bar adjacent, but provided ample distance for us to chat and enjoy each others’ company.
There is just so much to see and do in Key West that you will need to be very discerning with how you spend your time.
Only you know what things interest you most! Rather than breaking down exactly which to see and when to see them, this section covers the best options with recommendations, photos, descriptions, and links to tour operators when relevant.
We will also cover our favorite restaurants and experiences to choose from for lunch and dinner.
Smather’s Beach is the premier beach in the Florida Keys.
This postcard-perfect beach features pristine white sand, towering palm trees, and clear water. It is exactly the beach you daydream about when booking tickets to Florida.
Key West may not have the oldest history, but it has preserved most of the early architecture and aesthetics which makes for a fun stroll around town.
Of course, it is equally popular as a party destination; especially world-famous Duval Street.
Duval Street is often compared to Bourbon Street of New Orleans, and even boasts a touch of Nola culture in some of its bars and pubs.
The downtown area is also where you will find the majority of the main tourist attractions in Key West.
The Key West Butterfly Conservancy is the absolute best thing to do in Key West!
Imagine walking through a magical trail as tranquil music echoes throughout and hundreds of butterflies and colorful birds swirl about… it is truly an enchanting experience.
We were expecting little more than something “neat” on our visit, but ended up falling head over heels for this place. Definitely include the Butterfly Conservancy on your Key West itinerary!
The Ernest Hemingway Home and Museum is one of the most iconic places in Key West. During the 1930s it was home to the famous writer and was where he wrote 70% of his work.
Today, it is a National Historic Landmark and home to over 60 cats, including many that are famed for having six-toes!
The grounds are beautiful and you can choose to take a guided tour or explore by yourself.
💵 Pro tip: Entry is cash only.
While the only “experience” in visiting the Southernmost Point in the US is waiting in a long line to say you’ve been there and take a photo, it continues to be perhaps the most popular activity in Key West.
To add a little experience to the wait, grab a Cuban coffee from the nearby cafe to enjoy while in line.
🌅 Pro tip: Visit early morning to avoid waiting in line.
The Conch Tour Train is one of the best ways to see all of the hot spots in Key West while learning the history of the colloquially-known “Conch Republic.”
The Key West Lighthouse & Keeper’s Quarters can be seen from the roadside, across from the Ernest Hemingway House.
However, if you’re physically able, it is worth visiting to climb narrow spiral staircase to the top of the lighthouse and take in the views over the island.
The museum is small but provides an interesting glimpse into the life of the lighthouse keepers.
Built in 1890, the Truman Little White House first served as the naval station’s command headquarters during the Spanish-American War, WW1, and WW2.
It later became the winter home for President Truman and subsequent presidents.
Today, it continues to be a government building, in addition to a museum where you can take a guided tour to learn more.
One of the best ways to enjoy the Key West sunshine is by taking to the water.
From adrenaline-filled activities such as jet-skiing and parasailing to more energetic experiences such as kayaking, or a relaxing snorkel or sunset sail… Key West has it all!
If you can’t decide, many tour companies even offer full-day watersport packages so you can try multiple activities.
Just off the coast of Key West lives a resident pod of bottlenose dolphins.
Honest Eco takes visitors on a sustainable dolphin watch tour and snorkel aboard SQUID, the first electric passenger boat in the USA.
But it’s not just the boat and the wildlife that makes this tour special, the staff is truly exceptional. We were swept away by their enthusiasm and passion and learned so much from them.
Unfortunately, we visited on a rare day when the dolphins were playing hide and seek. However, we loved our time snorkeling and this trip was still an unbelievable experience and firm highlight.
Latitudes promises to be one of the most unique, memorable dinners of your life. That is not hyperbole, it is truly that special.
This Caribbean-inspired restaurant is located on a small, private island known appropriately as Sunset Key. To reach it, you will hop onto a ferry from Key West and take a short ride to a pristine, white sand beach.
Tiki torches and unbeatable sunset views surround beachside seating. Even on a busy night, the tables are arranged so that you forget anyone else is there.
Latitudes is the perfect place for a special occasion and/or to celebrate your final night in Key West. Every detail has been dialed in from the elegant service to the innovative menu; this is one you will not forget!
Matt’s Kitchen was one of our sneaky favorite meals in all of our time in the Keys. We visited on our last night, exhausted from so much sun and food and running around, and could not have been more impressed with everything.
Matt’s is not a fancy place, it is just a great one. It is located on a small harbor in a very quiet region of Stock Island just a short drive from Key West.
Sit by the fireplace and begin your evening with one of their incredible cocktails as the sun goes down. I recommend the Key Lime Pie martini, complete with crust-lined rim and absolutely perfectly flavored.
Pair it with some appetizers ranging from locally-sourced and expertly-prepared scallops to their signature duck wings. Both exceeded even our high expectations.
We ordered everything from apps to desserts and could barely move by the end, but enjoyed every single bite.
There are a few essentials that you will want to consider taking with you to the Florida Keys.
2-3 days is enough if you are only staying in Key West, but 5 days is the perfect amount of time for visiting the Florida Keys if you are planning on exploring everything from Key Largo to Key West.
5 days is the perfect amount of time for visiting the Florida Keys if you are planning on exploring Key Largo, Key West, and everything in between. A weekend would be sufficient for any ONE of the Florida Keys.
The major draw of the Florida Keys is the coral reef, fine dining, beaches, and of course the climate. Your Florida Keys itinerary should include at least a couple of trips to enjoy the reef via snorkel or dive tour, glass bottom boat, parasailing, and/or dolphin watch tour, as well as plenty of downtime for drinks on the beach.
Every month has its pros and cons for visiting the Florida Keys. Winter is peak season in Southern Florida as visitors flock to the region for its year-round sunshine. This is when you will find the best temperatures, but also struggle with availability and higher prices. Summer is the least popular, but also extremely hot and muggy. You also have to be prepared for tropical storms during the summer and shoulder seasons.
Key West has the prettiest beaches and most interesting town, and is generally considered the best of the Keys.
The best way to see the Florida Keys is by renting a car and dividing your time between Key Largo and Key West. The roads in the area are very driver-friendly and only about 2 hours of driving separate Key Largo and Key West, making everything explorable with day trips.
We truly hope you have found this guide for visiting the Florida Keys useful, informative, and inspiring.
Now we’d love to hear from you!
If there are any questions we have not answered, revisions we need to make, or other suggestions for improvement, please let us know in the comments below.
Likewise, if you have found it useful and want to leave some kind words, those are always appreciated.
Now grab some sunscreen and go prepare for the trip of a lifetime!
