Florida Keys Travel Guide: Must-Read Tips for First Time Visitors

Share this!:

When most travelers think of travel to the Florida Keys, a Jimmy Buffett song probably springs to mind. Lazy days, gorgeous white sand beaches, and colorful tropical drinks are definitely the stuff of a Keys vacation. Margaritaville indeed.

Despite its laid back vibe, a successful Florida Keys trip definitely requires a fair bit of planning. The learning curve for the Keys is surprisingly steep. There are a number of logistics to plan around to experience all the area has to offer, especially in a single visit.

My family spent a full week visiting the Florida Keys for a Thanksgiving vacation a few years ago. The Keys had been on our bucket list for awhile, but they are a long way from where we live in California. It took awhile to make a trip happen, and our plans to visit were delayed by the destruction wrought upon the Keys by Hurricane Irma in September 2017.

We learned a lot of tricks along the way and made a few mistakes, so I decided that a Florida keys travel guide for other newbies might be helpful to other travelers venturing to this destination for the first time too. Here is what other first time travelers – families as well as travelers without kids – to the Florida Keys need to know.

(Trips With Tykes uses affiliate links which means I may earn a small commission if you purchase through links in this post. See our full disclosure policy linked in the menu at the bottom of this site.)

Where are the Florida Keys?

I know the answer to this question may seem painfully obvious to many of you. When I was planning our own trip, however, I can’t tell you how many people I spoke to who didn’t really understand where the Keys were! Perhaps that’s because I live in California, and it’s not a place that many West Coasters are likely to visit.

Obviously, the Florida Keys are part of the state of Florida. They are an archipelago – a chain of islands – that start near the tip of Florida not far from Miami. The islands form a long curving arc south and west, dividing the Atlantic Ocean from the Gulf of Mexico. The southernmost inhabited island connected by road is Key West which is less than 100 miles from Cuba.

The famous Florida Keys “Overseas Highway” also known as Highway 1 connects the mainland to most of the inhabited Keys all the way to Key West. Highway 1 is one of the most popular drives on a Florida road trip, spanning 42 bridges.

Sub-Regions, Major Cities, & Layout of the Florida Keys

What many new visitors to the Florida Keys don’t understand is just how big of an area the Keys are. To drive all of Highway 1 from the mainland to Key West takes 2.5-3 hours. The Overseas Highway is mostly two lane, very dark at night, and highly trafficked during peak tourist periods. Don’t expect to seamlessly hop from one area to another without some effort.

If you plan to explore the entire region, you definitely need at least a week to do it justice. If you only have 2-3 days, I’d recommend picking a sub-region and sticking close to a single home base. Otherwise, you are simply going to be doing too much driving and missing out on the R&R that is the major reason to visit the area.

The Keys are comprised of many towns, roughly divided into the following three regions:

Upper Keys: Stretching from Key Largo into Islamorada, the Upper Keys is an area that can be most easily experienced as a day trip or weekend getaway from Miami and other South Florida destinations.

Middle Keys: The Middle Keys are separated from the Lower Keys by the famous 7 mile bridge and are decidedly less populated. My family stayed in this region, which was the area hardest hit by Hurricane Irma. The biggest city is Marathon, where there are a number of inexpensive but delicious restaurants and tour and dive operators.

Lower Keys: The lower keys start south of the 7 Mile Bridge in Big Pine Key. The hub of activity for the lower Keys is the city of Key West, the most inhabited city in the region.

What are the Best Airports for Flying to the Florida Keys?

Given their remote location at the very south of Florida, the Florida Keys aren’t within reasonable driving distance for many visitors. A lot of travelers need to fly in to experience a vacation there. The best airport choices for a Florida Keys trip are:

Key West International Airport (EYW): Key West Airport is the only airport with commercial service located within the Florida Keys. The airport is just 15-20 minutes from the main tourist areas of Key West and is served by Delta, American Airlines, United, JetBlue, Allegiant, and Silver Airways. Flights are limited and often very pricey so this may not be a viable option for many travelers. That said, service to EYW has expanded the last few years, so check routes again anew in 2023 if it has been a few years since you’ve investigated flight options. If you do fly into this airport, Uber and Lyft are alive and well in Key West (although not always reliable elsewhere in the Keys). So it’s possible to go without a car if your plans will keep you in only Key West.

Miami International (MIA): Many more visitors coming to visit the Keys start their trip at the major airport in Miami and rent a car to drive down the rest of the way. Miami to Key West is a 160 mile drive. Miami has a bit of a reputation for being a beast of an airport with long lines and challenging logistics (much like LAX and ATL), so be sure you leave plenty of time in your travel plans in both directions to deal with that.

Fort Lauderdale-Hollywood International Airport (FLL): Another very viable option for travelers to the Keys is Fort Lauderdale. FLL is a larger airport with plenty of service from many cities and on multiple airlines (its largest carriers are Spirit and JetBlue and it’s also a Southwest Airlines mini-hub). It’s ultimately logistically easier than Miami even though its location adds about 30 extra minutes to the drive time down to the Keys. We used FLL for our trip and found the process quite seamless in terms of lines, rental cars, and more.

What do I Need to Know about Visiting the Florida Keys by Cruise Ship?

A lot of visitors to the Keys arrive via cruise ship. In fact, that was how I visited myself for the first time pre-kids. Cruise ships dock exclusively in Key West, so you really will only have a chance to explore the city proper if you come in via ship. The three Key West cruise ship piers (Mallory Square, Pier B, and Outer Mile) are all highly walkable to most of the major attractions in Key West. It’s a very easy cruise port to navigate for anyone, but especially for families.

Even if you aren’t coming in via cruise ship, it’s smart to keep an eye on the cruise ship schedules into Key West. They can dramatically affect crowd levels. If you want to have a mellower experience on a Key West day, try to visit on a day when ships aren’t in port (hard to do in the winter high season but easier to do in spring/summer/fall). The check out the cruise calendar several months in advance here.

Are the Florida Keys a Good Destination to Visit with Kids?

Yes! The Florida Keys is an ideal family vacation destination. My family found a ton of kid-friendly things to do on our week there – so much so that we didn’t feel like we had enough time. We spent most of our time in the middle Keys where our resort (Hawks Cay Resort) was located, taking a day trip down to Key West to experience all the city had to offer there. We didn’t even get to see much of the Upper Keys and Key Largo in the time we had.

One thing to be aware of – Key West after dark definitely has its bachelor and bachelorette party adult party vibes. And some of the fanciest resorts of the Central Keys are definitely more couples getaway destinations. But the vast majority of things to do and see in the Keys are incredibly family-friendly. Just pick your home base carefully.

How Has Hurricane Irma Affected the Keys?

Hurricane Irma made a direct hit on the Florida Keys in September 2017, which understandably has dramatically reshaped the landscape and tourism to the Keys since. Key West mostly escaped without major damage, but the Middle Keys were especially hard hit. Many of the homes and resorts there were completely destroyed.

Rebuilding took a very long time, made all the more difficult by the fact that a large percentage of the labor force left the Keys in the immediate wake of the hurricane. The tourism industry took another blow during the pandemic closures of 2020. Many businesses closed during this period and the labor market was impacted yet again.

Thankfully, the area has emerged from this one-two punch stronger than ever. Interest in the Florida Keys has only grown, and the area is bustling once again. That said, demand sometimes exceed supply. This means prices are higher than ever, even while some business operators (resorts, restaurants, etc.) are still short staffed.

Visitors should be aware of these challenges, especially when combined with the fact that the Keys are very much already on island time. If you can embrace your inner Jimmy Buffett, you will likely have a blast. But if you demand impeccable luxury hotel level service, it’s going to be harder to be satisfied, even at resorts charging luxury level prices.

Best Things to Do in the Florida Keys

Because we were only in the area for a week, we didn’t even begin to comprehensively do everything the Keys have to offer. Here are the top activity highlights that we enjoyed that I’d recommend to other visitors:

Conch Train (Key West)

It’s touristy and expensive, but it’s worth it. The Conch train is a vehicle that takes you to various sites all around Key West, from the Ernest Hemingway Museum to the Southernmost Point of the United States. Guides share a bit of history and humor as you see the city’s most famous stops. You can ride it multiple times and hop on and off so you may be able to use it as both transportation and as an attraction.

Snorkeling & Scuba Diving (Multiple Locations)

My husband and I both scuba dive and we didn’t want to leave the Keys without seeing beneath the surface. We found a dive operator that let us take turns diving while the other of us stayed on the surface and snorkeled with the kids.

The amazing scuba operator we used sadly shuttered its doors for good, but there are a number of top notch dive operators all over the Keys. Some of the top snorkeling spots include: John Pennekamp Coral Reef State Park in Key Largo, Sombrero Reef near Marathon (where we dove), right off the beach in Key West at Fort Zachary Taylor Historic State Park, or in the Dry Tortugas.

If you have younger kids not ready to snorkel, consider doing a glass bottom boat tour as an alternative way to view marine life.

Morada Bay Beach Cafe (Islamorada)

This restaurant on the beach is affiliated with the resort where Netflix’s Bloodline was filmed, so my husband and I had to do a date night there. It’s kid-friendly as well, so feel free to bring the whole family. If you plan to have dinner there, arrive well before sunset to grab a table with a view. The fresh seafood is to die for and definitely don’t miss the Key Lime pie.

Mallory Square Sunset Celebration (Key West)

Every evening before sunset, street performers flock to Mallory Square in Key West and perform for the crowds right as the cruise ships are boarding for the evening.

Lagerheads Beach Bar (Key West)

While we were in Key West, we headed to Lagerheads for lunch. This open air restaurant is little more than a beach shack, but what makes it fun for families are the tables on the beach. Our kids played in the sand and surf with other kids while my husband and I enjoyed a margarita!

For even more in-depth recommendations of what to do (especially with kids) in the Florida Keys and all over the state of Florida, check out these guides from some fellow travel bloggers I personally know and trust:

• 26 Things to Do in Key West from Crazy Family Adventure
• 29 Perfect Things to Do in Key West for Every Type of Traveler from 365 Atlanta Traveler
• 49 Things to do in Florida from 365 Atlanta Traveler
• Planning a Florida Keys Road Trip from We3Travel
• Key West Girls Trip from Your Time to Fly

Tips & Tricks for First Time Visitors to the Florida Keys

1. Plan for cell dead spots: You are in the middle of an ocean. It might not surprise you that cell coverage can be spotty in various places in the Keys. Input directions into your cell phone before you leave the WiFi at your resort. (Maps in a guidebook can come in handy too!)
2. Really do your resort research: Given the volatility of the last several years, be sure the Keys resort you book is ready to deliver the travel experience you seek. Read recent reviews on sites like TripAdvisor that can really give you a sense of the situation on the ground at a given time.
3. Pre-book excursions: Because of increased interest in the Keys, a lot of tour operators have more demand than they have employees. If you want to scuba dive, snorkel, or do other similar excursions, I highly recommend booking ahead. If you wait to call until you get to the Keys, you may find many activities fully booked.
4. Have a parking strategy for Key West: Parking in the main part of Key West is a bit of a beast (and is pricey). If you are headed to the many attractions in Mallory Square on a day trip from elsewhere in the Keys, I recommend parking once and then using Uber or Lyft or the Conch Train to get around.
5. Combine the Keys with an Everglades trip: If you are flying into Miami or Fort Lauderdale, a Florida Keys trip can really be combined with a few other destinations. We decided to stay one night in Fort Lauderdale and spend the better part of a day in Everglades National Park before driving down to the Keys. It was a huge hit with both the kids and adults in our family – who can resist seeing alligators up close? (If you are new to national parks travel, check out my beginners guide to visiting national parks and be sure to know how to get a free national park pass if you have a 4th grader in the family!)

Disclosure: This post was originally published in partnership with by Moon Travel Guides. It has been updated independent of that relationship since that time. Check out Moon’s Florida Keys guidebook for more. As always, all opinions are my own.

Share this!: