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It’s been more than two years since Hurricane Irma devastated part of the Florida Keys. The area has bounced back as it vowed it would, putting the Keys on our Where To Travel In 2020 list. Beautiful ocean views, conch fritters, and literary history await at this year-round picturesque destination.

Admittedly, I never understood the allure of the Florida Keys. There are more accessible and cheaper places to visit in Florida, and the lack of beaches has always been a deterrent. This fall, however, I found myself in need of a break from seasonal affective disorder and was finally convinced to give the Florida Keys a shot. Turns out fall in the Keys ended up being the perfect time to check it out, and I’ve already planned another visit for later in 2020!

Where To Go In The Florida Keys

The Keys span 125 miles from north to south and encompass many towns and villages along the way. Deciding where to stay and how to spend your time is up to you -- everything from sailing and diving to biking and bird watching is on the menu and just a taste of the range of activities waiting for you in the Keys.

The perfect destination in the Keys for your vacation will depend on what activities you’re after and when you intend to go. Here’s a guide to two of the most-loved Keys, based on my fall trip.

Aerial view of Islamorada.

Islamorada

Islamorada is the perfect Keys destination for a more laid-back vacation, with access to great restaurants and plenty of outdoor activities to keep you busy. It’s no secret why the picturesque area is so popular for weddings and honeymoons, but it’s also great for low-key family getaways, or a great place to recharge amongst nature and gorgeous sunsets. A little over seven square miles of postcard-worthy views await you in Islamorada, which is actually a collection of five smaller Keys.

Top Attractions In Islamorada

Fishing And Snorkeling

Islamorada is home to some of the best saltwater fishing in the world (really!). This closely grouped set of islets boasts reef and shipwreck fishing, plus nearby access to the Atlantic Gulf Stream. Whether you prefer trolling, deep-sea fishing, bottom fishing, or fly fishing, Islamorada offers year-round opportunities for casting off.

Not surprisingly, Islamorada is home to one of the world’s largest collection of professional offshore boats and many opportunities to fish with local fishing charters. If fishing isn’t your thing, the snorkeling is also some of the best in the country, and it’s easy to do almost anywhere in the waters around Islamorada.

Robbie’s of Islamorada

Whether you are driving through or staying nearby, Robbie’s of Islamorada (known by everyone as Robbie’s) should be on your list of places to see while in the Keys. Robbie’s is a destination all on its own: part local souvenir market, full restaurant and bar, plus a working marina complete with boat rentals and fishing charters. Even with all that and more, its most popular attraction is its world-famous tarpon feedings. Robbie’s allows patrons to hand-feed hungry tarpons with fish bait off their dock, which is home to a school of over 100 tarpons. A bucket of bait will set you back $4 and allow you access to the dock where the tarpons feed. Grab lunch and then head over to mix it up with the scavenging pelicans and hungry tarpons.

Where To Stay In Islamorada

Amara Cay Resort

As soon as you step foot into the lobby at Amara Cay Resort, you know relaxation is on the agenda for your vacation. Perfectly situated near Indian Key Historic State Park and in close proximity to some of the best restaurants in all of the Keys, Amara Cay was recently remodeled, undergoing a multimillion-dollar renovation in 2015. The results are nothing short of spectacular, with a private beach dotted with palm trees and hammocks and a zero-entry pool for sunbathing.

Adjacent to the pool are lawn games and the resort’s signature restaurant, Reelburger. The restaurant offers gourmet burgers, pastas, and fresh seafood, while the Tiki Bar welcomes guests with tropical cocktails and frozen drinks -- the pina coladas are not to be missed!

Beach in Key West, Florida.

Key West

Key West gets the most attention, and it’s a vibrant city with a laid-back party atmosphere. If that sounds like your kind of vacation, look no further than the area around Duval Street and make sure your lodging is within walking distance of this street, which is the lifeblood of Key West.

The Hemingway Home and Museum in Key West.

Top Attractions In Key West

Ernest Hemingway Home And Museum

Hemingway's home is perfectly preserved in the heart of Old Town Key West and open for visitors 7 days a week and 365 days a year. Once inside, tours are free with the cost of admission and depart from the front door every half hour. The tour guides are entertaining and tours definitely worth your time, maximizing anyone’s visit to casa Hemingway. Spend a morning at the Hemingway house for a step back in time profiling one of America’s most famous authors.

Key West Butterfly And Nature Conservatory

Visitors will find the Key West Butterfly and Nature Conservatory to be a unique attraction amongst the shops and restaurants of Duval Street. Inside the glass conservatory, visitors get the chance to walk amongst more than 50 species of butterflies and more than 20 species of exotic birds, including a pair of flamingos! Expect to spend an hour or so here, and don’t miss the gift shop for the chance to bring home a unique local souvenir.

Where To Stay In Key West

Downtown Key West is compact and easily walkable and/or bikeable. Some of the best lodging options to consider are those near Duval Street, Mallory Square, or, for a more relaxed vibe, the beach, and if you want a mix of nightlife, culture, and relaxation, there are many hotels in Key West that can offer the best of both worlds. Budget-minded travelers will find better options farther from downtown during high season for more reasonable rates.

The Southernmost Point Resort

This four-star resort is perfectly situated far enough off of Duval to be quiet and relaxing but close enough for a short walk to all the action. Aside from the near-perfect location, the resort boasts multiple pools, a fitness center and spa, two beaches (!), and a pier that is ideal for watching a famous Key West sunset (with libation in hand). The rooms are modern and comfortable with a hint of traditional Key West-inspired decor.

Aerial view of a highway along the Florida Keys.

Getting To The Keys

Unless you are heading to the Southernmost Point and staying solely in Key West (where there is an airport), flying into Miami (MIA) often makes the most sense. From there, rent a car and head south for one of America’s most scenic drives. The first stop in the Keys is Key Largo, which is roughly an hour and 15 minutes from the Miami International Airport and is the perfect first stop on a Florida Keys adventure.

The trip from Miami to the bottom of Key West is only three and a half hours, but is meant to be enjoyed slowly with many stops along the way. The other option is flying into the Florida Keys International Airport, which is conveniently located at the end of the southernmost Key.

When To Go To The Florida Keys

The busy season in the Keys starts mid-December and lasts through the end of March. The temps are perfect during this time, but the prices can be a little high. Summer is an affordable time to head down, and the majority of visitors are from Florida or the surrounding states. In the fall, once hurricane season is over, the weather is near perfection and the prices are reasonable.

Sunset over a beach in Key West.

Get Planning Your Keys Vacation!

The ideal way to soak up all the Keys has to offer is to maximize your vacation with a mix of both worlds. Start your trip in laid-back Islamorada to recharge your batteries, then head south to Key West for culture, a taste of nightlife, and great people watching. A week or long weekend in the Keys will leave you questioning why it took you so long to make the trek.

Regardless of where you choose to vacation in the Keys, the one thing that’s guaranteed is experiencing some of the best sunsets of your lifetime.

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