Where To Stay

11 Things To Do On Your Next Key West Trip

A balcony overlooking Oceanside Marina from Stock Island's first hotel Ocean's Edge.
A balcony overlooking Oceanside Marina from Stock Island's first hotel Ocean's Edge.

Look—either you get Key West’s quirky, magical charms.

Or you don’t.

If you fall into the former camp, chances are you’re as madly in love with the island’s penchant for day drinking on Duval Street as you are riding bikes through quiet side streets lined with conch cottages and palm trees punctuated by bougainvillea. It’s equal parts sporting life and cultural hallowed ground with boundless offshore pleasures and a legacy as artist and writer haven.

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Oh yeah, and it’s always an unadulterated good time.

You’ve probably got the spots you hit on every visit, but read on to learn about the locals who are shaping the island into an ever-fascinating place to explore. From a new bookstore owned by Judy Blume to the gentrification of Stock Island (and, yes, plenty of new bars and restaurants), here’s where to go and what to do on your next trip to Key West.

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1. The New New

The interiors of the just opened Little Pearl restaurant on Olivia Street.

Thomas Quartararo and Kristen Onderdonk are having a good year. Within the span of about a month, the husband-wife duo, celebrated the one year anniversary of their much buzzed about Thirsty Mermaid restaurant (see #2 below), opened a second restaurant Little Pearl (305-204-4762) inside the former Seven Fish space on Olivia Street AND welcomed baby number two into the world.

Partnering once again with executive chef and Key West native Ryan Shapiro, Little Pearl is an intimate neighborhood restaurant open for dinner, serving refined and inventive preparations of fresh seafood.

Standout dishes include baked oysters, local snapper sautéed in guava beurre blanc and the impossible-to-resist Little Pearl lobster and crab pot pie. Carnivores will appreciate the kobe beef cheek ragu and 16-ounce bone-in ribeye.

632 Olivia St., Key West, FL

2. A Sidewalk Bistro Oyster Bar

Steamed Middleneck clams at Thirsty Mermaid. Nick Doll

And now for a little background on the Little Pearl team… New York transplant Tommy Quartararo first dove into the Key West culinary scene when he opened Blackfin Bistro in 2009 with a handful of partners. While no longer affiliated with the restaurant, he’s gone on to put the Midas touch on a handful of other restaurant ventures including Antonia’s for Italian and Thirsty Mermaid (305-204-4828), which opened in February 2016.

Inspired by the sidewalk cafes in New York City’s West Village, he’d always wanted to open a casual, yet sophisticated oyster bar—and that’s exactly what he’s created at Thirsty Mermaid. With picture windows looking out on Fleming Street and a subtle nautical theme inside, the restaurant turns out delectable small plates like crackling calamari, mac and cheese croquettes with truffle aioli and sautéed Bahamian conch with marinated artichokes. It’s a favorite amongst locals not only for the food, but also the buzzy, intimate bar.

521 Fleming St., Key West, FL

3. Judy Blume's Bookstore

The tropical moderne lines of Books & Books at the Studios of Key West.

There’s a Books & Books (305-320-0208) in Key West!

And what you may not realize until you set foot inside is that it’s owned by iconic young adult author Judy Blume. In partnership with Mitchell Kaplan and his famed Miami indie bookstore, the longtime Key West resident opened shop as a non-profit in February 2016 inside The Studios of Key West (TSKW) (305-296-0458) on Eaton Street. A cultural organization, home to artist studios, residencies and an exhibition gallery, TSKW is also where you’ll find reporter Nancy Klingener holding down the fort at WLRN’s “Southernmost news bureau.”

533 Eaton St., Key West, FL

4. Stock Island is Cool Now

A guest room at the brand new Ocean's Edge Hotel & Marina on Stock Island. SCcott Baker Photography

Stock Island, the sleepy key just north of Key West, is home to shipyards, marinas, shrimp boats and artist studios, as well as many multi-generational Keys and Cuban families. Considered a bastion of “old Key West,” it’s long been a destination for down-to-earth (and delicious) restaurants like Hogfish Bar & Grill (305-293-4041) and the more recently opened Pizzeria Roostica (305-296-4999). Now, it’s primed to woo travelers with the opening of its first hotel.

Ocean’s Edge Key West Hotel & Marina (305-809-8204), a luxurious resort, designed in a Key West vernacular townhouse style, opened in January 2017 boasting an al fresco restaurant overlooking six pools and the 111-slip Oceanside Marina. The Perry Hotel (305-296-1717) is slated to debut later this spring at Stock Island Marina with a modern, industrial aesthetic and a village concept that includes multiple dining venues and artist studios.

With so many marinas, a Stock Island stay is the perfect excuse to charter a boat. Try Key West native Shon Williams’ Fun in the Sun fleet (305-510-3523), offering everything from fishing to snorkeling to eco tours and boat rentals.

While on “the rock,” swing by COAST, an artist collective founded by longtime local and boat captain Billy Kearins, hosting concerts, events and studio tours.

5950 Peninsular Ave., Key West, FL

5. A Different Kind of Duval Crawl

The Key West Library's facade flanked by palms on Fleming Street.

The island’s rich literary history is stoked every January with Key West Literary Seminar‘s (305-293-9291) program of panel discussions, parties and author readings. Celebrating its 36th annual seminar in 2018, the theme is “Writers of the Caribbean.”

For new executive director Arlo Haskell, one of his missions is to bring more year round programming to the island. This is being realized with February’s introduction of Literary Walking Tours. Departing from the Key West Library on Fleming Street every Friday and Saturday, the 75-minute tour ($25) led by Sarah Thomas, will explore the former homes and favorite haunts of famous writers including Tennessee Williams, Shel Silverstein, Elizabeth Bishop and Robert Frost, as well as highlight tales of the island’s lesser-known literary talent.

700 Fleming St., Key West, FL

6. Take Center Stage

The newly lit marquee at Key West Theater.

Helmed by artistic directors Mike Marrero and Juliet Gray, Key West Theater (305-985-0433) opened its doors in 2015 inside a restored Baptist church on Eaton Street that was originally built in 1848. The performing arts venue has attracted a new caliber of entertainers with recent shows ranging from Broadway superstar Alan Cumming to comedian Jim Breuer. It also supports a thriving local theater scene staging original plays.

512 Eaton St., Key West, FL

7. Grilled Cheese Please

Key West's newest dive bar: Mary Ellen's.

The latest outpost by nightlife and dining impresarios Chris Shultz & Co. (The Porch, Two Cents, The Other Side), Mary Ellen’s (305-916-5816) is a dive bar on Appelrouth Lane inside what was once the island’s most notorious nightclub, Wax. In this iteration, there’s an extensive beer menu and a grilled cheese counter open late.

420 Appelrouth Lane, Key West, FL

8. Sail Away

A sunset sail with Schooner Hindu is good for the soul.

Take in Key West’s famous sunset in the most relaxing way with a dreamy sail aboard the historic Schooner Hindu (305-509-1771). Originally built in 1925, the beautiful wooden boat was restored in 2012 by the Rowan family who operate it today out of the Key West Bight Marina. Their sunset sails include wine pairings with artisanal cheese and charcuterie. Call ahead to reserve your spot and ensure the boat’s not in Provincetown where it often spends the summer season.

201 William Street, Key West, FL

9. Craft Beer Game

When in Key West, drink the Crazy Lady... and get crazy!

After more than five years in the making, the Waterfront Brewery (305-440-2270) opened its doors in 2015 inside the old Waterfront Market made unmistakable by the enormous Wyland mural painted on its warehouse-like facade. The vast, open-air space with views of the Historic Seaport serves a full menu of bar fare, from burgers to conch fritters. Start with a flight of their onsite brewed craft beers, like the Crazy Lady Honey Blonde, Key Lime Witness and Truman Double IPA.

201 William Street, Key West, FL

10. What's in a Name?

Keep it green and clean at the rebranded Date & Thyme on Fleming Street.

Originally called Help Yourself when it opened back in 2008, Charlie Wilson recently renamed her organic cafe on the corner of Fleming and Margaret Street to Date & Thyme (305-296-7766). Her ever-evolving health food concept boasts a juice bar and market in addition to the cafe. Come for breakfast and try the bagel with cashew cream cheese, avocado and tomato or the paleo plate with sautéed kale, grilled vegetables, pesto and eggs. The coffee menu is just as tempting as the juices with items like the yogi latte made with espresso, coconut milk, honey and chai tea.

829 Fleming St., Key West, FL

11. Key Largo Pitstop

Overnight in Key Largo, anyone?

There’s never been a better reason to make a pitstop in Key Largo on your way to Mile Marker 0 than with Playa Largo resort (305-853-1001), which opened in September 2016. Adding a touch of luxury to the uppermost Key as the first newly built resort in 20 years, Playa Largo boasts four food and drink venues, including a ceviche bar, steakhouse and casual seafood restaurant inside a reclaimed boathouse on one of the prettiest stretches of beach on Key Largo.

97450 Overseas Hwy, Key Largo, FL