How to Plan a Romantic Honeymoon in the Florida Keys

Here's how to plan a honeymoon in the Sunshine State full of sun, snorkeling, and stone crab.

An aerial view of the highway and ocean in the Florida Keys.

Artur Debat / Getty Images

"It’s the journey, not the destination." This phrase is often true, but in the case of the Florida Keys, a strong argument can be made for both the journey and the destination, given that getting there takes couples across one of the most scenic stretches of road in America. The 113-mile Overseas Highway connects the lush and long chain of islands across technicolor expanses of saltwater using 42 bridges, including the postcard star known as the Seven Mile Bridge. And once newlyweds have arrived, no matter which key was chosen as a base camp, they’ll be welcomed by more sun, sea, swaying palms, fresh seafood, and slices of citrusy pie.

“[With] stunning views of the Atlantic Ocean, Florida Bay, and the Gulf of Mexico on either side, driving the highway—sometimes called the highway that goes to sea— makes you feel as though you’ve set foot in the Caribbean and have access to a world of adventure and romance without needing a passport,” enthuses Stacey Mitchell, director of the Florida Keys and Key West Tourist Development Council. “The drive also encourages visitors to take life slower as there’s so much to see and do along the way.” 

When ticking off possible points of interest in the southernmost section of the American mainland, Mitchell mentions both the expected—pulling off to swim and snorkel, devouring just-caught shellfish at trusted roadside stands and marina restaurants, shipwreck diving,  sipping rum punches with spirits distilled nearby while the sun says goodnight—and the unique including volunteering on a coral restoration project, popping into the first and only breadfruit farm in the continental U.S., cycling the restored Old Seven Mile Bridge to Pigeon Key and getting a ride in President Harry S. Truman’s 1949 Lincoln limo at the vacation White House. By the time pairs reach the end of the line in Key West, they’ll be closer to Cuba than Miami and hopefully adjusted their internal clocks to island time.

A variety of stunning hotels and resorts, endless water sports pastimes, a lively nightlife scene, and a “year-round subtropical climate that rivals even the most popular island destinations” are more reasons Mitchell believes a road trip through the Florida Keys is the perfect choice for a dream honeymoon trip.

Meet the Expert

Stacey Mitchell is the director of the Florida Keys and Key West Tourist Development Council.

Planning Your Florida Keys Honeymoon

Beginning just south of Miami, the 125-mile-long chain of islands—roughly 1,700 of them—is divided into five main regions: Key Largo, Islamorada, Marathon/Middle Keys, Big Pine and the Lower Keys, and Key West, each with their own distinct personalities. For instance, the LGBTQ-friendly Key West feels like New Orleans’ French Quarter and a Jimmy Buffet song had a baby thanks to architecture, small-town vibes, literary history, and a party street with bars, restaurants, T-shirt shops, and mesmerizing people-watching. Mitchell adds, “Key Largo is home to some of the best snorkeling and diving opportunities in the U.S. Islamorada is the Sportfishing Capital of the World. Marathon is renowned for boating, large-scale resorts, and family-friendly attractions. The Lower Keys are the least people-populated and [are all about] the responsible use and preservation of the vast natural wonders found there.”

Once couples decide which key to stay on, they’ll need to figure out when to go. The best weather, the highest prices, and the biggest crowds are usually found from the Thanksgiving holiday through April. Summer tends to be cheaper as it’s hotter and stickier—though the Keys, especially the lower ones, are breezy and typically several degrees cooler than the rest of the Sunshine State. Hurricane season (June 1 through November 30) is still something to consider although the destination hasn’t been significantly impacted by a hurricane since 2017. The greatest potential for trip-ruining storms historically is from August through October.

  • Language: English
  • Currency: U.S. Dollar
  • When to Go: High season (and its commensurate prices) is Thanksgiving through April. Hurricane season runs from June 1 to November 30.  
  • How Much Time To Spend: It can make for a great long weekend for southern U.S. or east coast-based couples but to truly experience what the destination has to offer and spend several days on the water, a week to 10 days is optimal. 
  • Getting There: Most fly to Miami and drive Highway 1 in a rental car. Visitors can also fly directly from cities like Charlotte, Chicago, Atlanta, New York, and Houston to Key West International Airport. Charter service into Florida Keys Marathon International Airport is another option. 
  • Transportation: Rent a car if you want to move between keys. If you plan to hunker down in one place like Key West, you can get away with walking, taxis, buses, or rideshare. Many hotels offer complimentary bicycles.
  • Must-Pack: Flip-flops (the official footwear of the Keys), swimsuits, reef-safe sunscreen to protect your skin and the only living coral barrier reef in the continental US, gear for water sports of choice, a dry bag, an underwater camera, and $1 bills for a drag revue.

Where to Stay During Your Florida Keys Honeymoon

Whether you want to check into an intimate hotel on a private island or hole up at an adults-only, all-inclusive resort, there is a nice variety of accommodations in the Keys, with properties ranging from low-key to luxe. Here are our top romantic recommendations.

Little Palm Island Resort & Spa, Little Torch Key

Courtesy of Little Palm Island Resort & Spa

Little Palm Island

Castaway by seaplane or vintage wooden boat to this four-acre private island resort in the Lower Keys where some of the thatched roof bungalows feature indoor and outdoor soaking tubs, daybeds built for two on the deck, and exclusive sandy beaches with fire pits. Without TVs, room phones, or guests under 18, it’s easy to bliss out here, especially after a few umbrella drinks at the palapa bar, a swing in a hammock, and some sound therapy at the elegantly appointed spa.

Southernmost Beach Resort

Sitting at the crossroads of Duval Street and the Atlantic, this six-acre Key West charmer that was renovated in late 2021 offers two types of accommodation experiences—a classily updated mid-century motel with granite vanities, plush robes, and electric car chargers, and two guesthouses run like bed and breakfasts inside an 1885 Victorian and a residence from 1920. Even if you choose to stay in one of the historic homes, you can access Southernmost’s private beaches, spa, three pools, and alfresco yoga classes.

Bungalows Key Largo Resort

Courtesy of Bungalows Key Largo Resort 

Bungalows Key Largo

This all-inclusive, adults-only resort is tucked into a lush botanical garden and boasts more than 1000 feet of shoreline. If you get tired of relaxing in the sand, you can retire to the deep bath on your room’s private veranda, the outdoor shower, or the double pillowtop in the boudoir. Enhance your arrival with pre-arranged floral bouquets or a platter of chocolate-covered strawberries.

The Marquesa

Despite being close to the Duval Street crazy in the convenient heart of Old Town Key West, the contemporary compound housed in 19th-century conch houses is surprisingly chill whether you’re smelling the courtyard’s fragrant blooms, relaxing by one of the three pools or devouring miso-glazed grouper with dashi mushrooms and a cucumber mule from the onsite fine dine on your cozy balcony.

Cheeca Lodge & Spa

 Courtesy of Cheeca Lodge & Spa

Cheeca Lodge & Spa

Set on 27 colorful acres, this Islamorada resort with its Tahitian lagoon and waterfall, two pools, nine-hole golf course, retro fishing pier, and beachfront tiki lounge is so camera-ready that they’ve already appeared in numerous TV shows like Bloodline and Platinum Weddings as well as commercials and photo shoots for Ralph Lauren, Victoria’s Secret, and Anthropologie. And like a Hollywood A-lister, you can be waited on in your casita by an included butler or customize a yoga session with a private teacher.

Sunset Key Lodges

Another day, another property on a private island. Part of the Opal Collection, the coastal chic cottages with touches of nautical whimsy and kitchenettes come in one- to four-bedroom configurations. Enjoy the daily breakfast basket on the wrap-around porch with the wind in your hair before taking to the tennis courts, joining a round of beach volleyball, or trying out parasailing. Listen for the afternoon bell that signals the ice cream man is open for business.

Hawk's Cay Resort

Courtesy of Hawks Cay Resort

Hawks Cay Resort

If you’re of the mind that bigger is better, this sprawling retreat on Duck Key with its five pools, saltwater lagoon, massive 7,000 square-foot spas and fitness center, full-service marina, paddleboard and kayak rentals, tennis complex, kids’ club, multiple restaurants, ballroom and a resident pod of bottlenose dolphins could be your ideal getaway. If you didn’t tire of picture taking at the wedding, sign up for a session with a professional photographer to preserve the happiness that stems from long walks on the beach and cabana naps.

Islamorada Resort Collection

Lots of changes are afoot at the four resorts that make up this longtime hospitality group—room redesigns, added dining and drinking choices including a pizzeria, a Central American-inspired food hall and a scoop shop, and a new retail space with everything you need to partake in the salt life. As a guest of one hotel—we’d recommend Amara Cay for lovers who want to set intentions in a private yoga practice, get massages with ocean views, or snuggle close on your personal lanai—you’ll have preferred access to the amenities and activities at all of them like the marina, bait and tackle and paint & sip events. Even if you choose to stay elsewhere, make sure to stop by the famous tiki bar as it was where the rum runner was invented.

Playa Largo Resort

Towering palms shade the 177-room beachfront hideaway from the sense-of-place experts at the Autograph Collection who have seamlessly blended Caribbean architecture, modern decor, and necessary tech. Whether you choose a suite, a bungalow, or the beach house, you’re never far from the sand, where you can splurge on a private dinner or a sexy chimenea experience complete with s’mores and stargazing, or the aquamarine surf.

A sea turtle spotted in the Florida Keys.

Stephen Frink / Getty Images

Things to Do During Your Florida Keys Honeymoon

There is no shortage of fun ways to spend your island time whether you’re a beach bum, history buff, foodie, sporty spice, wellness junkie, wildlife watcher, or drag show connoisseur—but according to Mitchell there is a very clear choice on which activity honeymooners should schedule first (and often). 

“Without question when someone comes to the Florida Keys, they should get out on the water immediately whether it’s through a fishing charter, snorkel excursion, or a sailing and kayaking or paddleboarding experience,” Mitchell says. “Offshore island picnics via chartered boat or seaplane are popular with couples looking for privacy, nature, great food, and bragging rights about what they did on their Florida Keys honeymoon.” 

Get Out on the Water

Key West Seaplane Charters takes couples to Dry Tortugas National Park 70 miles offshore. (A more pocketbook-friendly option to see the 19th-century fort and swim off its white beach is the Yankee Freedom ferry.) Learn to wakeboard, kiteboard, or efoil at the Lagoon on Grassy Key. The country’s first undersea park John Pennekamp Coral Reef State Park, which Mitchell refers to Key Largo’s “star attraction,” offers scuba diving, canoeing, snorkeling, and glass-bottom boat tours to see 70 types of coral, 600 species of fish, an occasional manatee and the Insta grid-worthy Christ of the Deep. 

View Local Wildlife

More wildlife viewing can be had on a private tour of narrow mangrove channels with KeyZ Charters, during a sandbar swim with Islander Girl, or atop a Big Pine Kayak in remote backcountry spots. Animal lovers should also pop into various rescue and preservation organizations including Florida Keys Wild Bird Rehabilitation Center in Key Largo, Mote Marine Laboratory’s Elizabeth Moore International Center for Coral Reef Research & Restoration on Summerland Key, Key West Butterfly & Nature Conservatory, and the Marathon Wild Bird Center, Dolphin Research Center and The Turtle Hospital in Marathon. Big Pine Key holds a national refuge for the endemic miniature Key deer.

Try Your Hand at Fishing

If you prefer hooking instead of looking, head to Islamorada and book an expedition or two to reel in marlin, snapper, tarpon, wahoo, or sailfish. Mitchell says, “The Purple Isles are heralded for their angling diversity and feature the Keys’ largest fleet of offshore charter and shallow backcountry boats.”

Hit the Beach

While The Keys are more famous for warm crystalline waters than sandy spits at its edges, there are still several great beaches for sun worshippers to get their vitamin D fix including Anne’s Beach (heavily featured in the Netflix show Bloodline), Smathers Beach, Sombrero Beach and Calusa Beach in Bahia Honda State Park.

Catch Sunrise and Sunset

As one of the only places in the U.S. where you can view sunrise and sunset over different bodies of water, Mitchell strongly recommends catching a few of those spectacular solar shows. Join the crowd at the nightly gathering in Mallory Square complete with arts and crafts vendors, psychics, street performers, and food carts or if you prefer a more intimate setting, Mitchell recommends booking a Schooner Appledore sunset sail with champagne and light bites.

Can't-Miss Romantic Experience: For an even more private and romantic experience, hire your own luxury ride from Bluesail Yachting and watch the sun dip below the sea in an especially intimate and memorable setting.

Discover Local Culture and History

Sure, the call of the wild is strong in these parts but that doesn’t mean there aren’t opportunities for cultural appreciation. Key West has been home to many literary talents, most famously Ernest Hemingway and Tennessee Williams, both of whom are subjects of area museums. Hemingway’s museum is located at his home which is still occupied by six-toed descendants of the author’s cat Snow White. Combine culture, history, and snacks with a Key West Food Tour. There are several themed options including a Papa Hemingway one. Islamorada’s Morada Way Arts & Cultural District is a bustling six-block corridor filled with art galleries and studio spaces that hosts the Third Thursday Art Walk every month. Hop aboard a piece of old Hollywood history when you take a Port Largo Canal cruise aboard the African Queen, the iconic steam vessel used in the 1951 Humphrey Bogart-Katherine Hepburn classic. And that isn’t the only queen you catch as a trip to Key West isn’t complete without seeing some drag whether it comes in the form of bingo, brunch, karaoke, or full-blown cabarets at beloved institutions like 801 Bourbon Bar, Aquaplex, or La Te Da. This is such an integral part of the nightlife scene here that New Year’s Eve is celebrated with the drop of a live diva in a glittery red stiletto at midnight.

Schedule a Spa Day

To recover from active days and late nights, schedule some we-time at a spa. Spa Terre at Little Palm Island has some interesting treatments for couples including the heart chakra ritual and Madrugada, a sunrise water massage that takes place on a table in the ocean and utilizes seashells.

A slice of key lime pie in the Florida Keys.

Bill Boch / Getty Images

Places to Eat During Your Florida Keys Honeymoon

Given Keys’ geography, seafood is the obvious gastronomic play here. Especially because, Mitchell says, “the fresh fish found on restaurant menus throughout the Florida Keys was probably unloaded from the docks that morning.” Some restaurants and hotels including The Buzzard’s Roost in Key Largo and the beloved Stock Island dive, Hogfish Bar and Grill, will cook your personal catch of the day. 

Local aquatic delicacies not to be missed include Key West pink shrimp (considered sweeter than other species of shellfish), hogfish (the must-order at Chef Michael’s Islamorada), lionfish (an invasive species that is good for you, bad for the environment, and tasty as sushi or fish and chips), and stone crabs as the archipelago is Florida’s leading regional supplier of stone crabs. The season runs October 15 through May 15 annually and is a “sustainable, renewable resource” you can feel good about eating (with melted butter or a tangy mustard sauce) according to Mitchell. “Because nearly all of the crab’s meat is contained in its claws, they are the only parts of the animal that are harvested. Once a claw is removed, the crab is returned to the sea where the claw eventually regrows.” 

Always leave room for the signature dessert—key lime pie. Long believed to have been invented in Key West by Aunt Sally, a cook who worked for millionaire William Curry in the mid-1800s, using the titular citrus that thrives in these parts, Mitchell says, “it’s the perfect end to a delicious seafood meal whether topped with meringue or whipped cream.” (Note: A recent James Beard Award-winning cookbook has challenged that origin story but that hasn’t stopped the annual Key Lime Festival.) The traditional version can be found in almost every professional kitchen along the Overseas Highway but some chefs have taken their rendition to the next level.

Blue Heaven

Seafood can be eaten around the clock. You can brunch on shrimp and grits and shrimp benedicts in the sail-shaded courtyard at the kooky Blue Heaven, a former bordello, billiard hall, and bar where Hemingway refereed bare-knuckle boxing matches in Key West’s Bahama Village.

Key Fisheries

Dig into stone crab soup and lobster Reubens at Keys Fisheries in Marathon for lunch.

Latitudes

Take a boat to Sunset Key for grouper tacos, coconut cracked conch, or snapper in key lime vin blanc at Latitudes, where you can simultaneously have your toes in the sand and get white tablecloth service while staring at the Gulf of Mexico.

Little Pearl

The sophisticated four-course tasting menu and wine pairing at Little Pearl will leave you with big city culinary scene feels especially if you add on classy bites like Siberian caviar, lobster corn dogs, and oysters.

5 Brothers

As in Miami, Cuban cuisine also reigns supreme and a juicy Cuban sandwich, ham croquettes, and mojo pulled pork bowls from 5 Brothers in Key West is a great way to give your palate a break from all of the fish feasts.

Cuban Coffee Queen

Need a quick pick me up? Strong café con leche and cortaditos await at three Key West locations of Cuban Coffee Queen. (It goes perfectly with the pan con guava.)

Island Fish Company

Island Fish Company in Marathon serves a deep-fried version that’s dusted with cinnamon sugar and finished with mango sauce.

Pierre's

A key lime tart is best enjoyed on the colonial veranda that looks out on a beach and bay at Pierre’s in Islamorada.

Lorelei Restaurant and Cabana Bar

Nearby at Lorelei Restaurant and Cabana Bar, diners can dig into a frozen KLP while listening to a live band.

Azure Restaurant

Start your day in Key West with slices wedged in between French toast and drizzled with berry compote at Azur Restaurant.

Budgeting for a Florida Keys Honeymoon

The palm-dotted paradise isn’t cheap but tends to be more affordable than similar-styled vacations on comparable Caribbean isles or Hawaii in terms of travel and lodging costs. For one, you won’t be leaving the country so there won’t be passport processing fees, visas, foreign driver’s licenses, Global Entry, or extra immunizations. Bonus: Water will be free at restaurants.

There are lots of strategies to bring a Florida Keys honeymoon under budget if necessary, starting with flying into Miami and driving instead of landing in the smaller Key West airport. (Those tickets are often double the price even if you live somewhere with direct flights to both airports. It’s even more if you have to connect first.) 

Accommodations will likely be the biggest expense to consider. But Mitchell promises that with more than 1,500 lodging venues plus hundreds of licensed vacation rentals peppered throughout the Keys, there’s bound to be one at “a price point that suits the needs of every budget” from a “$100-per-night independent bed and breakfasts to oceanfront hotel suites at over $1,000 per night for a truly luxe experience.”

Timing is also a key factor in cost. Rates for everything tend to be higher in winter and spring, on weekends and holidays versus weekdays, and when special events like Hemingway Days are happening in town. Those willing to endure the summer heat and humidity or risk their trip being upended by a hurricane can often score low-season deals on flights and hotels. The Key West Vacation Pass, which packages together various discounts on tour tickets, attraction and museum admissions, and restaurants including the aquarium, a ghost tour, and kayaking adventures for one price, is another way to save.

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