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First Timer’s Guide to the Florida Keys

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This post is sponsored by Moon Travel Guides. All opinions are my own.

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

Florida Keys - Islamorada at the Moorings

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 last year visiting the Florida Keys for our Thanksgiving vacation. 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 newbies guide 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.

Florida Keys - Islamorada at the Moorings

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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 series 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 “Overseas Highway” also known as Highway 1 connects the mainland to most of the inhabited Keys all the way to Key West – one of the most popular drives on a Florida road trip.

Florida Keys - Islamorada at the Moorings
Roadtripping the Overseas Highway.

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 the major reason to visit the area.

Florida Keys - Hawks Cay Lagoon

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 hub of activity for the lower Keys is the city of Key West, the most inhabited city in the region.

Planning a trip to the Florida Keys? Travel tips and information for first time visitors to Key West, Key Largo, Marathon, Islamorada, and beyond. #floridakeys #keywest #florida

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, and Silver Airways. Flights are limited and often very pricey so this may not be a viable option for many travelers. If you do fly into this airport, Uber and Lyft are alive and well in Key West (although not elsewhere in the Keys) so it’s possible to go carless 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 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 (it’s 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.

Florida Keys - Fort Lauderdale Airport

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 cruise ship terminal is highly walkable to most of the major attractions in Key West so it’s a very easy cruise port to navigate for anyone, but especially families.

Even if you aren’t coming in via cruise ship, it’s smart to watch 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 city of Key West keeps a calendar several months in advance here.

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

Florida Keys - Hawks Cay Pool
There are a number of family-friendly resorts with amenities kids will love in the Keys.

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) 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.

We found on our visit in November 2018 that the Keys will still be living with the legacy of Irma for a long time to come. It’s important for visitors to realize that and be prepared. Many hotels and resorts still – as of May 2019 – are not fully rebuilt. Some that have reopened still don’t have the full range of restaurants and activities available.

Most important to note is the fact that the Keys are very short-staffed as a result of Irma. A huge percentage of the labor force left the Keys after the hurricane, never to return. Now, the lack of housing and its expense has prevented much of a new labor force from coming back. The effects on tourism are very real. Construction is proceeding more slowly than expected at resorts trying to rebuild. Resorts that are open are short-staffed, with a pretty green labor pool often commuting daily all the way from cities in South Florida.

We experienced the effect in a lot of ways on our vacation. When combined with the fact that the Keys are very much already on island time, the service lapses were noticeable, frequent, and frustrating. My husband and I normally very easygoing travel customers, and we were willing to – and did – extend a lot of grace under the extreme circumstances. But it’s something that visitors planning a trip to the Keys in the near future need to be aware of, especially as many resorts are charging full price without delivering full service. This was very much the situation at the resort we stayed in, Hawks Cay Resort, which I cannot recommend (yet) to other traveling families for that reason. Travelers demanding a certain standard of service and luxury might be better served in waiting a year or two to visit until the recovery is more complete. We were happy to support the region with our tourism dollars as it rebuilds, but definitely want to return to experience more in a few years time.

Tips & Tricks for First Time Visitors to the Florida Keys

1. Get a good guidebook: Even as a travel blogger who researches trips with online resources, my family still relies heavily on well-researched expert guidebooks in our travels. We took along a book from Moon Guides that proved extraordinarily helpful in our travel planning. Moon Guides just released the updated Moon South Florida & the Keys Road Trip: With Miami, Walt Disney World, Tampa & the Everglades, so definitely check it out if you have a Keys trip coming up!

Moon South Florida and the Keys Guide

2. 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. (And here is where the maps in that guidebook can come in handy too!)

3. Really do your resort research: As already mentioned, be sure the Keys resort you book is really fully operational and ready for visitors before spending your hard earned money. Read recent reviews on sites like TripAdvisor that can really give you a sense of the situation on the ground at a given time. Things are improving with each passing month, but it may be well into 2020 before a lot of places are fully back on their feet.

4. Pre-book excursions: Because of the impact of Irma, a lot of tour operators are short staffed. 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.

5. 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 (more on that below).

6. 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 and personal? (If you are new to national parks travel, check out my beginners guide to visiting national parks.)

Florida Keys - Everglades Alligator
Yes, that is an alligator behind us in the Everglades! We took the Shark Valley tram tour, which was a must-do.

What 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 activity highlights that we enjoyed that I’d recommend to other visitors:

Conch Train (Key West)

Florida Keys - Conch Train

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 Hemingway Museum to the Southernmost Point. Guides share a bit of history and humor as you see the city’s most famous stops.

Snorkeling & Scuba Diving with Hall’s Diving Center (Marathon)

Florida Keys - Halls Diving

My husband and I both scuba dive and we loved that this dive shop let us take turns diving while the other of us stayed on the surface and snorkeled with the kids. The crew was super-friendly and one of the most safety-oriented dive operators we’ve ever encountered on our travels. You can snorkel and dive with a lot of outfits in the Keys, but this is one we’d go out of our way to use again.

Morada Bay Beach Cafe (Islamorada)

Florida Keys - Morada Bay Cafe

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 seafood is to die for and definitely don’t miss the Key Lime pie.

Mallory Square Sunset Celebration (Key West)

Florida Keys - Islamorada at the Moorings

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)

Florida Keys - Key West Lagerheads

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 family travel bloggers I personally know and trust:

Travel tips for first time visitors to the Florida Keys. Where to fly, what to do in Key West and beyond, and how the area and its tourism is faring rebuilding after Hurricane Irma. #floridakeys #keywest #visitflorida

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Jim Mastin

Saturday 10th of December 2022

I just got back from the keys. Went all the way down to Key West. It was in November and was very beautiful. I would tell anyone that they should see it at least one. Love it.❤️


Monday 7th of February 2022

Thanks for the wonderful info. Our family will be in the Keys for a week in April. Looking for the best places to snorkel in the Keys. What Key has the best chance of seeing fish and healthy reefs? What company does a good job with kids 10 and 12, and a family of 7? We are staying in Key Largo. Marathon, Key West, and Homestead. Thank you again.


Tuesday 4th of May 2021

Is the weather still warm and able to swim in the ocean during Thanksgiving time?


Thursday 14th of January 2021

Thank you so much for sharing this. We have a trip with my family next week on Florida and I’m going to visit there. Thank you so much. You are the best!


Jen Price

Wednesday 9th of December 2020

Anyone have any nanny recommendations in the Keys? Thank you!