4-day Florida Keys Itinerary

If you’ve never been to the Florida Keys, you’re in for a treat. The sunshine and blue ocean water is breathtakingly beautiful. The laid-back lifestyle of tourists and locals alike contribute to a relaxed vacation that’s anything but boring. This sample Florida Keys itinerary will provide you with an exciting and enjoyable vacation, and allow you to see much of what makes the Keys so special.

Marathon, Florida is one of the more convenient places to stay if you want to see a lot of the Florida Keys in a single trip. It’s located in the middle keys, just before you cross the 7-Mile Bridge.

There are lots of fun things to do and restaurants to try in Marathon itself, and its central location makes it convenient for half-day or full-day trips to others parts of the Keys. This Florida Keys itinerary assumes you will be staying in the central Keys, but it’s easy to adjust it if you want to stay further north or south. Just expect that on certain days you’ll be doing more driving.

This also assumes you have access to a car and will be driving down and back up from Miami.

Day 1: Drive Down from Miami to Marathon

Day 1 of our Florida Keys itinerary will give you your first glimpse of what makes the Florida Keys so amazing – the ocean. You’ve probably seen the ocean before, but perhaps never like this. In the keys, the water is incredibly blue. Beds of seagrass make darker areas, and lighter spots are often sandbars. The variation in colors is simply amazing.

The first day will include a good bit of time in the car, but it’s not too bad as long as you avoid Miami rush hour traffic. When you drive from Miami, you’ll head southwest to Florida City, the last real location on the Florida mainland before you get into the Keys. If you have time, Florida City is pretty fun too. Take time to stop by Robert is Here, which is the craziest “fruit stand” you’ll ever see in your life.

After that it’s just a short drive into the Keys. You’ll know you’ve arrived when you see the road barricades that are painted light blue…I always think they look like an old-fashioned waterslide. And just like that, you’re in Key Largo!


Now I do like Key Largo; John Pennecamp Coral State Park is especially nice for kayaking, snorkeling, etc. However, we’ll leave Pennecamp out of this schedule because there’s so much more to see in the Keys.

Keep driving through Key Largo until you see a bright yellow building on the side of the road. You’ve reached Harriett’s! If you’re hungry, stop for a meal, but if not, at least pull in and get some muffins to go. You will not regret this, ever; their muffins are amazing!

Florida Keys Brewing Company, Islamorada
Florida Keys Brewing Company, Islamorada

Florida Keys Brewing Company

After Harriet’s, continue on to Islamorada. If you’re a beer drinker like I am, you’ll want to make a stop at the Florida Keys Brewing Company in Islamorada. They create some excellent brews; I’m a particular fan of their Weedline Wheat, Tripel Tail, and Sunsessional IPA.

The brewery has this gorgeous sitting area outside, full of tropical plants and brightly-painted tables and chairs. It has a great beachy feel. Inside, everything is tie-dyed, from their merchandise to their epoxy bar top. I also have found their bartenders / cicerones to be knowledgeable and friendly.

Robbie’s of Islamorada

Pelicans and Tarpon at Robbie's
Pelicans and Tarpon at Robbie’s

Next stop: the iconic Robbie’s of Islamorada. No Florida Keys itinerary would be complete without it!

You’ll find this on the right side just past the Indian Key Channel bridge. Robbie’s is best known for its tarpon feeding docks. For a small entrance fee, you can walk out onto the docks, where squares in the middle are open except for netting, and the tarpon swim up to be fed.

If you want to feed them yourself, you can also purchase some food for them. I just enjoyed watching other people do it. There are lots of pelicans who come in to try and steal some of the food too. Even though the staff discourages them, they’re also a lot of fun to watch.

If you decide to stay in the area, there’s really a lot more to do at Robbie’s. You can sit on the beach, rent kayaks, go fishing, grab a drink or two at the bar, or eat a meal at the Hungry Tarpon. There are also lots of little stands with cute souvenirs to purchase and bring home.

Hotel Check-in

By this point you’re probably exhausted from all of this fun you’ve been having! So hop in the car and keep going until you get to Marathon. Its about 30 more minute of driving time. Marathon has lots of little hotels and AirBnbs. Last time there we stayed at the Fairfield Inn & Suites, and it was fine. Nothing amazing, but certain met expectations. (Usually we rent a home on nearby Big Pine Key, but COVID made that impossible this time.)

If you want a very quick dinner, there are a few fast food places. For real restaurants in the area, check out my restaurant guide to Marathon, FL.

Day 2: Beach and Boats

Most people who visit the Keys want to spend time on the beach or on the water, and this day of our Florida Keys itinerary will accommodate both. If you’re looking for fun and sun, both on and beside the water, then this may be your perfect day!

Sombrero Beach, Marathon
Sombrero Beach, Marathon

Sombrero Beach

There are a number of beautiful beaches nearby. The prettiest one, by far, is Sombrero Beach. It is moderately crowded in the spring; I haven’t been in the summer so I’m not sure about that. But I’ve never had trouble parking, even if I did have to loop around 2-3 times.

There’s no entry cost or parking fees at Sombrero Beach, and the beach is both family- and dog-friendly. There are pavilions with grills if you’re inclined toward a cookout. To reserve a pavilion, visit the City’s website.

As you sit on the beach, look toward the southeast and you’ll see the Sombrero Key Lighthouse in the distance. The only other way to visit this Florida lighthouse is by taking a boat out to the nearby area. The lighthouse itself is not open to the public.

Rent a Jet Ski, Kayak, or Take a Boat Cruise

After a day at the beach, you may want to relax at your hotel or a local bar before you hit the water yourself. (Just be sure not to drink if you’re going to pilot a craft yourself!) For me, an hour back at the hotel was a nice way to get out of the sun and to rest before going out again for some time on the water. And the late afternoon or evening is the perfect time to be on the water. There is less glare to bother your eyes, and a lower (but not insignificant) change of sunburn.

Here, there are options for many tastes:

  1. Rent jet skis – A jet ski tour is lots of fun if you’re into speed and excitement. If you take the same route we did, you’ll get to ride around the island of Marathon and even under the Seven Mile Bridge! Now, in my experience, a jet ski “tour” isn’t really a tour, it’s more of a race… we were expected to go as fast as the jet skis allowed for the first half of the tour. It wasn’t really my thing, but my teenage daughter loved it and my husband did too.
  2. Rent kayaks – Next time, this is what we’ll do, because I will insist on something slower and more relaxing! If that’s your style too, a kayak sunset tour will give you beautiful views of the sun setting over the water, with a little less adrenaline (or in my case, panic) than you get on the jet skis.
  3. Sunset cruise – If you prefer to let someone else do the work, join a sunset cruise. You can go further out into the water, and many offer drinks as well. A rum runner on a beautiful boat is a great way to end the day!

Dinner Out in Marathon

After this day, you’re sure to be tired! If you don’t want to wait at a restaurant for a table, this would be a good evening to try Castaway Waterfront Restaurant and Sushi Bar, one of the few places that actually accepts reservations. So make that reservation in advance so you can relax and enjoy dinner with less of a wait. If you don’t mind waiting, then I would try Burdine’s or Island Fish Co. All three options provide excellent meals!

Day 3: Key West

Day 3 of this Florida Keys Itinerary puts you back on land. And get excited, because this is the day to see what Key West has to offer. If you’re staying on Marathon, it’s just slightly over an hour’s drive to the southernmost city of Key West, a town rich with character and history.

Getting Around Key West

There’s a lot to see in Key West, so be prepared for some walking. Most of the tourist sights are in Old Town, on the west side of the island. It’s about a 2 mile by 2 mile area, so it’s not unfeasible to walk among most of the places. If walking isn’t your thing, don’t worry, there are other options!

  1. Driving: Of course, you can drive to different places, but parking can be difficult during the busy months, and expensive too.
  2. Rent Bicycles or Mopeds: It’s quite popular to rent bicycles or mopeds, and you’ll find it easier to park those when you want to go into an attraction.
  3. Trolley: You can purchase a day pass to use the trolleys, which have different stops around the island. When you choose a trolley, make sure it goes near the places you want to visit.
  4. Hire a Rickshaw: Key West has people who offer bicycle-powered rickshaws, You can rent them like you do a taxi, to take you from one location to the next. This can also be a good filler if you use a trolley but find it doesn’t go to a certain location.
  5. Duval Loop Bus: This is a free bus that has 16 stops in popular locations. It’s probably your cheapest option, assuming you want to stay in the area of town it serves. Find out more here.

Key West Sightseeing

Hemingway Cat
Hemingway Cat

There are so many things to see in Key West! Animal lovers will enjoy Nancy Forrester’s Secret Garden, which is a parrot sanctuary. It offers education and enrichment activities. Or check out the Key West Butterfly and Nature Conservatory, which has butterfly species from all over the world.

History and literature buffs should visit The Hemingway House, which is really just amazing even if you couldn’t give a whit about Ernest Hemingway. The house and grounds are beautiful, and everywhere you’ll see the Hemingway cats – descendants of Papa Hemingway’s own pets – about half of which have a condition called polydactyly, meaning they have extra toes.

Grab a bite and a drink at one (or more!) of the historical Key West pubs: Sloppy Joe’s Bar, Captain Tony’s Saloon, or Hog’s Breath Saloon. Check out my Instagram post here for more about each one.

And of course, get your picture taken at the Southernmost Point marker, at the corner of South and Whitehead streets. There will probably be a line of people waiting to do the same, so give yourself some extra time if you want to do this.

Sunset at Mallory Square, Key West
Sunset at Mallory Square, Key West

Finish the day by watching the sun set from Mallory Square, the iconic location to see a Key West sunset. Or to avoid those crowds, a sunset at Fort Zachary Taylor Sate Park is just as splendid.

Other attractions include Harry Truman’s “Little White House”, Fort Zachary Taylor (the actual fort as well as the surrounding state park), the Key West Aquarium, and the Key West Lighthouse, and the Key West Cemetery, which is known for tombstones with quirky engravings such as “I told you I was sick”!

Dinner in Key West

If you decide to stay for dinner, there are many options to choose from. Blue Heaven and Louie’s Backyard are two of my favorites. Both are well-known and popular, so try to get an advance reservation if you want to dine there.

Day 4: Big Pine Key, No Name Pub, and Saying Goodbye

For the purposes of this Florida Keys itinerary, we’re assuming 4 days including drive time to and from Miami. So day 4 is the day to say goodbye to the keys, but not before you spend some time on my favorite island, the laid-back town of Big Pine Key.

Approach to the Old 7 Mile Bridge
Approach to the Old 7 Mile Bridge

Walk the Old 7-Mile Bridge

A drive from Marathon to Big Pine Key will take you just under 30 minutes. It’s in the wrong direction if you’re leaving the Keys, but trust me, it’s worth it. Just after you cross over the 7-Mile Bridge, take a right into the parking lot. From there, you can walk part of the old 7-Mile Bridge, which will give you a beautiful birds-eye view of the bay.

When we walked it, we saw rays (not sure if they were sting rays or another species), many kinds of fish, a huge starfish, and even a cormorant, a type of bird that swims underwater and catches fish. Because the water is so clear, it was easy to watch the underwater species even though we were pretty high above them.

After walking the old bridge, continue southwest to Big Pine Key. This island is known for one thing, and that’s the Key deer!

Key Deer on Big Pine Key
Key Deer on Big Pine Key

Hang Out with the Key Deer

Key deer are a subspecies of the white-tailed deer found over most of the United States, but they’re like nothing you’ve ever seen before. That’s because they are the smallest subspecies, about the size of a medium-to-large dog! These beautiful creatures will charm the pants off of you, because they are just that cute! They tend to be unafraid of humans, because people tend to feed them – but please don’t. It’s illegal. However, you can take pictures of them, and sometimes with them, since they will generally come right up to you.

If you’re visiting during fall or early winter, you might even arrive in time for the rut. This is when the males compete with each other for the right to breed with the females. Imagine massive deer fighting each other with their huge antlers…and then miniaturize it! But for their size, they are no less fierce. The females stay pregnant for about 200 days, so if you visit in April, May, or June, you may even see spotted fawn!

One other thing to note: please drive carefully! Keep an eye on the road, and don’t go over the speed limit. Most key deer deaths occur when they are hit by cars, so be careful and don’t cause the death of one of these beautiful creatures. At night, slow down even further, because like all other deer, they will sometimes bolt out into the road.

Just drive around the island and you’re sure to spot one or more deer. Pull over anywhere that looks safe – a church or park parking lot is usually a good choice. Try to be respectful and don’t go into the locals’ yards to see deer. You’re sure to find them in a public location that won’t require you to trespass.

No Name Pub
No Name Pub

Lunch at No Name Pub

If you have trouble finding the deer, head to No Name Pub, because you’ll almost always find some there. Yep, that’s the name – and it’s name after the nearby island of No Name Key, which can be only reached by bridge from Big Pine Key. (Or by boat.) They have a good-sized parking lot, or you can park near the bridge to No Name Key itself. The pub is actually on Big Pine Key, however, and you’ll find it before the bridge to the island of the same name.

Dollar bills on the ceiling at No Name Pub
Dollar bills on the ceiling at No Name Pub

If you have time, grab lunch while you’re at No Name Pub. They have both indoor and outdoor seating, but to eat outside you’ll need to go through the interior. And the first thing you will notice is that the walls and ceiling are literally covered with one-dollar bills. Reports say that it’s over $90,000 taped up inside! They also offer pretty good pub food and a decent beer selection as well, as well as sangria. Make sure to purchase a shirt or hat on the way out! You may also see key deer around the pub itself.

I hope you’ve enjoyed this Florida Keys Itinerary and that it helps you plan your Florida vacation! From here, it’s time to drive out of the Keys and head back to Miami. Drive carefully and pack a little extra patience in case traffic leaving the islands is backed up. And remember: You can leave the Keys, but the Keys will never leave you!

Similar Posts

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.