First Time to the Florida Keys? Here’s What You Need to Know

Never been to the Florida Keys before? If you’re planning a trip to this idyllic island chain, you might want to know a few things before you go.

As an Orlando-area resident, I’ve lived in Florida for nearly 25 years, exploring the Sunshine State from coast to coast—including multiple trips to the Keys. To help streamline your first trip to the island chain, let me dispel a few myths about the Keys and provide some been-there-done-that tips. I also reached out to Ashley Serrate, representative for the Florida Keys & Key West Tourism Board, for some additional expert advice to ensure you get the most out of your visit to this iconic island chain.

Understand the Logistics

While you can fly into Key West International Airport at the southern end of the island chain and just catch a shuttle/taxi to your Key West hotel, you’d miss out on the amazing must-see sites throughout the Keys. Instead, consider flying into Miami or Fort Lauderdale, renting a car, and driving through the entire Keys. From Miami to Key Largo it’s about 1.5 hours, and then from Key Largo to Key West, expect a three-hour drive via one primary corridor—the Overseas Highway (a.k.a. U.S. Route 1). With stunning views across 42 bridges, the Overseas Highway makes a spectacular scenic road trip. If you plan to enjoy all the Keys, your best bet is to stay two or three nights in the Upper or Middle Keys (like Key Largo, Islamorada or Marathon) and then two or three nights in Key West. I’ve enjoyed some amazing stays at Reef House Marina (Key Largo), Hawk’s Cay (Duck Key), and Margaritaville Beach House (Key West). And if you fly into Miami or Fort Lauderdale, bookend your Keys visit with a fabulous stay at National Hotel (Miami’s South Beach).

Dreaming of Visiting the Dry Tortugas?

If this is on your Key West bucket list, know that it’s about 70 miles west of Key West and only accessible by a boat ride (a 2.5-hour journey) or a quicker sea plane flight. “There are only two ways to get to the Dry Tortugas—either via seaplane with Key West Seaplane Adventures or via The Yankee Freedom Ferry. Both book up months in advance as the park has limited occupancy so definitely book ahead of time!” advises Serrate.

Don’t Expect to Find Expansive Beaches.

As a 120-mile island chain, the Keys surprisingly lack large swathes of sand. That doesn’t mean incredible beaches don’t exist—they’re just fewer and smaller. While many resorts offer their own slice of sandy heaven if you stay on property, visitors to the Keys can still find beautiful spots to spread out a beach towel and splash in the surf. “The destination isn't known for traditional beaches because of the natural barrier reef found off the Atlantic coast,” Serrate says. “But there are still great beach spots to be found like Bahia Honda State Park and Sombrero Beach in Marathon. Quirky spots like Anne's Beach are also great.” Personally, I’ve also enjoyed the beaches at John Pennekamp State Park in Key Largo and the popular Smathers Beach in Key West. While they don’t rival sprawling beaches like New Smyrna or St. Pete, they do still offer those toes-in-the-sand opportunities.

Do Something In, On, or Under the Water.

This is not the time to stay on dry land the entire time. But you don’t need to own a boat or be a licensed SCUBA diver to enjoy the stunning turquoise waters of the Keys. If you don’t dive, go snorkeling to catch a glimpse of the incredible coral reef and marine life teeming in the clear waters. If you don't have a boating license, take a boat tour (think eco-tour or glass-bottom boat tour). Try something new, like SNUBA, stand-up paddle boarding, or kayaking. At the very least, take a sunset cruise to see the blaze of orange and crimson colors from the water as you watch the sun set into the Gulf of Mexico. Serrate also suggests looking into the Blue Star Operator program established by Florida Keys National Marine Sanctuary with input from local Keys dive and snorkel shop staff/owners and REEF Environmental Education Foundation. “This voluntary recognition program aims to reduce the impact of divers, snorkelers, and anglers on the Keys’ ecosystems,” she says.

Map Out Your Key West Must-Do’s.

There’s a lot to see in this compact part of the Keys. From historical sites and botanical gardens to museums and state parks, .the Conch Republic offers a smorgasbord of activities. Do your research ahead of time, starting with the website maintained by the Florida Keys & Key West Tourism Board. There’s a reason the Conch Train/Trolley tours are popular—they give you a great visual overview of the island’s iconic sites, allowing you to hop on and off throughout your journey. Know that most sites charge admission fees, ranging from $2.50+/person to enter state parks to $15-$25+/person to enter museums. To save money on some of the city's best activities and attractions, consider getting a Vacation Discount Booklet from The Key West Attractions Association. This 2022 booklet costs $54.99 (plus s+h) and contains buy-one-get-one-free discounts on top Key West tours, attractions, watersports, and even restaurants, racking up visitor savings up to $850. If you’ll be visiting next year, look for the Key West Attractions Association’ annual six-week-long Kids Free Florida Keys promotion every September following Labor Day through October.

Consider a State Park Pass

If you visit Florida often, want to visit multiple Keys state parks, and/or are traveling with a large family, it might make sense to buy a Florida State Park pass, even if you don’t live in Florida. (My husband and I bought a family annual pass for about $125, but individual passes are available, too.) A pass will allow you to visit any of the 10 state parks in the Florida Keys for free.

Beat the Crowds

There’s usually a line waiting to snap a picture in front of the iconic Southernmost Point buoy. If you can’t jump in line early in the morning, consider skipping the line entirely by standing on the wall about 30 feet in front of the “official photo spot” and snapping a selfie with the buoy in the background. And if you want to have dinner watching the sunset from some of the amazing on-the-water restaurants (like rooftop dining at Bistro 245 at Opal Key Resort & Marina), make reservations early to snag a table.

Eat (and Drink) Local

You won’t find too many chain restaurants in the Florida Keys, but you wouldn’t want to waste time eating at them anyway. Even if you’re not a big seafood fan, eat fresh-from-the-waters culinary delights like conch chowder, mahi mahi paninis, grilled lobster tail, and shrimp tacos. Nosh on key lime pie for dessert every day, just to compare which eatery makes it the best. Not into desserts? Try key lime mojitos, sauces, or even non-edible items like salt scrubs. Forget your go-to martinis and mass-produced beers. Instead, opt for hand-crafted tropical cocktails (think mango margaritas) and locally crafted beer (like the Sun Session IPA from Florida Keys Brewing Co). My all-time favorite beer? The to-die-for No Wake Zone Coconut Key Lime Ale from Islamorada Brewery & Distillery. Best. Beer. Ever.

Lower Expectations

Due to the pandemic, many of the performers who graced Mallory Square in Key West have either found other jobs or left the area. While the sunsets are still spectacular and the crowds still gather, you might not see as many jugglers, musicians, and other street performers when you visit. “Sunset Celebration at Mallory Square is still one of the signature experiences in Key West and well worth a visit,” says Serrate, noting the end of a beautiful day in the fabulous Florida Keys is always cause for celebration with locals and visitors alike.

Lisa Beach is an Orlando freelance writer who covers travel, food, lifestyle, and wellness. She’s been published in The New York Times, Conde Nast Traveler, Islands, USA Today, and dozens more. Check out her writer’s website at www.LisaBeachWrites.com.