Where To Stay

How to spend four days island hopping in the Florida Keys

Sunsets at Kona Kai in Key Largo are legendary.
Sunsets at Kona Kai in Key Largo are legendary.

The Florida Keys have officially been back in business to visitors since Oct. 1, 2017, just three weeks after Hurricane Irma made landfall in the Lower Keys. While the beloved island chain took a direct hit from the Category 4 hurricane and areas, especially in the Lower Keys and Islamorada, are still rebuilding, the Keys have largely rebounded and are as dreamy a destination as ever.

Read More: Five months after Hurricane Irma, how are the Florida Keys doing? 

Overall, 77 percent of lodging units are back online, all 10 state parks are open and almost all diving, fishing and boat charters are back in business. Now is the perfect time to rediscover the Keys and inject the area with some much needed tourism dollars.

Read on for our guide to the ultimate post-Irma road trip from Key West to Key Largo. It’s best enjoyed with at least one night at each destination, but you can easily tighten it up and tailor it to how long you’re able to getaway or stay longer at the islands that speak most to your soul.

Key West – Night 1


Marquesa guesthouse debuted an expansion to its property with the chic Marquesa 4-1-4 on Simonton Street.

Splurge:  Key West’s newest hotel opened Oct. 20 and is actually an addendum to the sophisticated Marquesa guesthouse on Fleming Street. Located just down Simonton, Marquesa 4-1-4 is a 17-guest room compound composed of three restored Victorian historic buildings with a central courtyard swimming pool. It’s all easy, breezy casual elegance and centrally located within a block of favorite spots like Judy Blume’s Books & Books at the Studios of Key West, the Key West Theater, Thirsty Mermaid cafe and Duval Street.

Save a Buck: Also located on Simonton Street on the corner of Caroline, Cypress House is a delightfully ramshackle bed and breakfast composed of 22 rooms across three conch cottages and mansions with spacious, modern guest rooms featuring original hardwood floors and paneled walls, as well as idyllic balconies to soak in Key West’s beauty.


Key West staple, The Green Parrot.

Rediscover Old Town. Take a walkabout or a bike ride through Old Town and rediscover the island’s laid-back charm on this route: Head up Duval Street and take a right on Petronia through Bahama Village. Stop for brunch or lunch beneath palm fronds and ship sails at Blue Heaven, snag a one-of-a-kind souvenir at Besame Mucho and then stroll down Southard towards Whitehead Street and the Green Parrot for day beers or bloody marys with freshly popped popcorn. Continue down Whitehead Street to Mallory Square and take in the sunset over conch fritters and mojitos from the waterfront kiosks.

Need more Key West inspo? Don’t skip these 11 things to do while you’re in town.

Stock Island – Night 2


The Perry Hotel in Stock Island boasts easy access to offshore pleasures.

Check into The Perry hotel located at the Stock Island Marina Village. The hotel’s stylish industrial design is inspired by its surroundings and was named one of the best designed hotels to open in 2016 by Architectural Digest. Their onsite restaurant Matt’s Stock Island Kitchen & Bar serves up some of the most sophisticated dining in town. Don’t skip the sumptuous grouper with cornbread gnudi or the the crab beignets.


Home to multi-generational working class families, fishermen, shrimpers and artists, many view Stock Island as a holdout of “old Key West” before the island became a popular tourist destination. If you want to get offshore, consider chartering a pontoon or fishing boat with Fun in the Sun Charters and enjoy all day access to the Key West Harbour Yacht Club.


Get a taste of Stock Island at Hogfish Bar & Grill for their famous hogfish sandwich and El Mocho (5708 Maloney Ave.) for a colada and the tastiest croquetas this side of Miami.

Islamorada – Night 3


The Moorings Beach 3
The tranquil beach at The Moorings Village in Islamorada. Sergio Jurado

Splurge: Islamorada’s oceanside took a thrashing from Irma, but the island’s most sought after resorts are finally starting to reopen. The Moorings Village and its 18 lush oceanfront acres with 18 cottages reopened on Jan. 15 and is as tranquil and dreamy a hideaway as ever. While away the afternoon in an oceanfront hammock swaying beneath palm trees, swim laps in the 25-meter pool or take a paddleboard or kayak for a spin.

Stock up your cottage’s kitchen with groceries from the nearby Trading Post or venture across the street to the property’s sister restaurants Morada Bay and Pierre’s, set on a beautifully landscaped stretch of beach overlooking the Florida Bay.

The swimming pool at Amara Cay Resort.

Save a Buck: Amara Cay re-opened in mid-December, welcoming guests back to its stylish digs outfitted in natural and organic tones and finishes. Rooms are chic and modern with floor-to-ceiling views of the tranquil bay.


For a sweet morning treat, swing by Bob’s Bunz and grab some of his signature freshly baked cinnamon bunz to go. My favorites are the bunz covered in cream cheese frosting and the sticky bunz topped with pecans.


Bad Boy Burrito

Islamorada’s Village Square is a little slice of al fresco heaven featuring a central boutique and gift shop, a plant and succulent shop and the Islamorada location of Key West’s own Bad Boy Burrito. Landscaped with sandy pathways, shady palms and plenty of outdoor seating, it’s a great place to linger and enjoy the ambiance.

Key Largo – Night 4


An aerial shot of Playa Largo’s 15 acre property on the Florida Bay
An aerial shot of Playa Largo’s 15 acre property on the Florida Bay

Splurge: Debuting as the first newly built resort in Key Largo in 20 years, Playa Largo provides an air of unprecedented luxury on this uppermost key. With a sprawling beach and poolscape overlooking Florida Bay and lush accommodations, it’s also home to three excellent dining options: Sol by the Sea for fresh seafood on the water, the upscale steakhouse La Marea and Las Olas for craft cocktails and ceviche.

Save a Buck: For a more intimate Key Largo experience, Kona Kai Resort is located just a mile north of Play Largo and is composed of 13 free-standing bungalows. The property features a swimming pool, small marina and dock jutting into the water making it an incredible place to take in the famous sunset. Kayaks, standup paddle boards and paddleboats are available for use at your leisure.


John Pennekamp Coral Reef State Park for an afternoon of hiking, snorkeling, kayaking or glass bottom boat adventures. The campgrounds here have also reopened if you’d like to sleep under the stars.


 Snooks Bayside Restaurant & Grand Tiki located at Mile Marker 99 before driving north and returning to the mainland.

How You Can Help

While visiting the Keys and your tourism dollars is a great way to help the local economy, there are still residents in dire need who are rebuilding their lives after Hurricane Irma. Local grassroots group Nourishing the Lower Keys prepares and delivers fresh, homemade meals to residents in need. Consider donating: gofundme.com/nourishFLkeys.