Thanks to a new direct flight from Orlando Sanford International Airport, you can close your laptop at noon, hop on a flight and be sipping a cocktail in Mallory Square at sunset – and, yes, take the kids!
Can it really be this easy?
We packed carry-ons, hopped out curbside at Orlando Sanford International Airport, breezed through short lines for security and buckled up for a 55-minute direct flight on Allegiant Air to Key West. Right on time, we touched down in the laid-back land of the Conch Republic, a warm sea breeze welcoming us.
Resorts and B&Bs are plentiful on this 5-square-mile island, but for location you can’t beat The Marker Resort, right on the Key West Historic Seaport and just three blocks from Duval Street, the island’s version of New Orleans’ Bourbon Street. Chilled bubbly and a friendly concierge start your weekend (ignore the Peloton bikes in the fitness center just off the lobby if you’re there for R&R). With spacious rooms, three saltwater swimming pools and myriad water sports steps away, it’s an ideal spot to land for a long weekend.
Museums and historic sites are plentiful, and you can walk or Uber most anywhere – the streets are busy with mopeds, bicycles, conch trains and cars, so cross carefully. There’s no lack of places to eat and things to do, but don’t try to take in every site. Relax. Walk the neighborhood streets at sunset and enjoy the living history in pastel bungalows and restored Victorian gems. Skip raucous Mallory Square one night and sit on the pier at Fort Zachary for a quiet sunset. Take a walking tour of the historic cemetery. Changes in latitude, changes in attitude. For more inspiration, visit our travel archives.
Where to stay
Great for families:
The Marker Key West Harbor Resort, 200 William St. 96 spacious rooms, 3 pools, restaurant and bar, great location on the waterfront. themarkerkeywest.com.
Casa Marina Key West, 1500 Reynolds St. A rambling Spanish Renaissance opened in 1920, conceived by railroad tycoon Henry Flagler, now a Waldorf Astoria Resort. Oceanfront with private beach with concierge, 2 pools, spa, restaurants, fitness center. casamarinaresort.com
Southernmost Beach Resort, 1319 Duval St. “Where Duval meets the Atlantic Ocean.” A quiet part of town with concierge, 3 pools, beach and tanning pier, bars and restaurant. southernmostbeachresort.com
The Reach Resort, 1435 Simonton St. Curio Collection by Hilton, the only private natural sand beach in Key West, poolside concierge, popular Four Marlins restaurant (order the grouper with crab rice and hot sauce butter). reachresort.com
Great for couples:
H2O Suites Hotel, 1212 Simonton St. Cozy, luxurious suites (some with plunge pools), 24/7 concierge—no kids allowed, must be 25 to check in. Private patios and balconies with beautiful gardens. h2osuites.com
Santa Maria Suite Resort, 1401 Simonton St. Wonderfully kitschy lobby and courtyard, but the suites are all beautifully renovated with full kitchens. 24/7 concierge and brand-new Milagro restaurant serving upscale local catch and steaks. santamariasuites.com
Eden House Resort, 1015 Fleming St. Built in 1924, the quirky, cute hotel now includes renovated conch houses, so there’s lots of choices for accommodations. Rooms are small, but the lush landscaping, tiki bar and pool are where you’ll spend the most time. Azur Restaurant open for brunch and dinner daily. edenhouse.com
Where to Eat
Half Shell Raw Bar, 231 Margaret St. Our top pick for a classic fried grouper sandwich, conch fritters, Gulf oysters and a cold rum drink. halfshellrawbar.com
4 Marlins at The Reach, 1435 Simon St. Quiet, pretty oceanfront setting, small plates like grilled spiny lobster with coconut red curry bisque and grouper with crab rice and hot sauce butter. And a delicious Key lime pie. reachresort.com
Matt’s Stock Island Kitchen & Bar, Perry Hotel, 7001 Shrimp Road. Uber to adjacent Stock Island to this chic resort at the Stock Island Marina for fresh catch, fried chicken, shrimp & grits. Our favorite was the grouper gnudi with crawfish thyme butter. mattsstockisland.com
Eaton Street Market, 801 Eaton St. Offers a solid selection of fresh local seafood – Royal Reds, Key West pinks, snowy grouper, golden tile and Florida lobster tails were in the case when we stopped by. Also limited supplies for cooking if you’ve got a kitchen. Menu of prepared seafood that you can eat at outdoor picnic tables. kwseafood.com
The Lobster Shack, 507 South St. There’s usually a line at this little spot for the Key West lobster roll and the shrimp roll. Pricey but the crowds don’t seem to mind. lobstershackkw.com
Fisherman’s Cafe, 205 Elizabeth St. Fresh catch changes daily and is served fried, blackened, or grilled as fish tacos or a sandwich. Counter service and a few stools for eating there, or take it to go. fishermandcafekeywest.com
5 Brothers Grocery and Sandwich Shop, 930 Southard St. Where the locals head for a high-test cortadito and pressed sandwiches on Cuban bread. Opens at 6 a.m. 5brotherskw.com
Cuban Coffee Queen (3 locations). If you can’t make it to 5 Brothers, this will do. Sandwiches on Cuban bread, salad, smoothies. cubancoffeequeen.com
El Siboney, 900 Catherine St. May be the best meal in all of Key West. Authentic, affordable and family-friendly (the kids loved the roast pork and chicharrons). The garlic shrimp was sublime, the tender yuca was the best we’ve tasted. elsiboneyrestaurant.com
Frita’s Cuban Burgers, 425 Southard St. Cuban comfort food from a walk-up window just off Duval. The burger is a blend of beef and pork seasoned with Spanish spices, topped with julienned fried potato sticks on a Cuban bun. Add a fresh lemonade and relax in the funky courtyard. fritascubanburgers.com
Date & Thyme, 829 Fleming St. Organic café and market with wraps, smoothies, salads and fresh juices as well as fresh produce and a small selection of wholesome groceries. dateandthyme.com
When you’re tired of seafood and want a burger:
B.O.’s Fish Wagon, 801 Caroline St. It looks like a shack and roosters hop on the tables, but locals say it’s the best burger in town. We can vouch for the onion rings and cold beer. “B.O.” is Buddy Owens, the owner. bosfishwagon.com
Pepe’s, 806 Caroline St. Opened in 1909, the locals line up at this charming dive for brunch on the weekends – we tried the patty melt and can recommend. pepeskeywest.com
Blue Heaven, 729 Thomas St. It’s an almost-obligatory stop at this Key West shrine, but the veggie eggs Benedict were worth every calorie, ditto the pineapple pancakes. Go early, there’s usually a crowd, but you can walk across the street and order a Bloody Mary to tide you over. blueheavenkw.com
Moondog Cafe, 823 Whitehead St. Not strictly vegetarian, but a diverse menu with lots of vegetarian and gluten-free choices. Try the vegan lemon-blueberry quinoa pancakes or the chorizo omelet. And we loved their vegan Key lime tart. moondogcafe.com
For ice cream:
Flamingo Crossing, 1105 Duval St. Homemade ice cream with enchanting flavors like passion fruit, soursop, mango, lavender, guava, Cuban coffee – we made two trips. Cash only.
Mallory Square, 400 Wall St. It’s crowded, dirty and, well, you have to go at least once to sit on the seawall and watch the sunset, even if it is cloudy. Once the sun goes down, an odd assortment of jugglers, magicians, musicians, tarot card readers and artisans entertain.
Green Parrot Bar, 601 Whitehead St. After your mandatory stop at Sloppy Joe’s, head to Green Parrot where the locals go to listen to live music – there’s rich history with a backbeat of live music ever since the place opened in 1890 as a grocery store for Cuban and Bahamian immigrants. greenparrot.com
Fort Zachary Taylor Historic State Park, 601 Howard England Way Fort Zachary. If you prefer a quiet end to your day, take a detour from Mallory Square and head to “Fort Zach,” where you can take in the sunset without a crowd. fortzacharytaylor.com
Recommended spots we missed on Stock Island:
Roostica, 5620 MacDonald Ave. Our pal Sonal Dutt at People Magazine says it’s the best pizza in the Keys. roostica.com
Hogfish Bar & Grill 6810 Front St. “Hard to find, but it’s like the original joints of Key West back in the day,” says Chef Norman Van Aken. hogfishbar.com
Things to do when it’s too hot to be outside:
Conch Tour Train, 501 Front St. Take a ride on the bright yellow hop-on-hop-off trains, shuttling visitors around Old Town since 1958. Friendly tour guides point out notable spots. A great way to get the lay of the land and hear a little history. conchtourtrain.com
Mel Fisher Maritime Museum, 200 Greene St. Home to treasures from two shipwrecked Spanish galleons, it’s an enlightening stop if you enjoy history (not much to entertain kids). melfisher.org
Audubon House & Tropical Garden, 205 Whitehead St. If you’ve seen the Hemingway House, this jewel of a museum is a cool stop, and you can climb to the second floor to see how the wealthy Geiger family lived in the 1800s. The Audubon connection is a little sketchy (apparently, he visited in 1832), but prints of his artwork hang throughout. audubonhouse.org
Key West Shipwreck Treasure Museum, 1 Whitehead St. Fun way for kids to see artifacts from the wreck of the Isaac Allerton that sank off the keys in 1856. Climb the 65-foot lookout tower to ring a bell signaling that a wreck has been spotted (and take in beautiful views of the island). keywestshipwreck.com
Key West Butterfly & Nature Conservatory, 1316 Duval St. There’s just something delightful about a roomful of butterflies, pink flamingoes and classical music. keywestbutterfly.com
Key West Aquarium, 1 Whitehead St. Old-school entertainment at one of Key West’s oldest attractions, opened in 1934. Don’t expect high-tech, but kids can touch conch, starfish and other ocean critters, see a shark feeding and meet Spike, the Loggerhead sea turtle. www.keywestaquarium.com
On the water:
Honest Eco, 231 Margaret St. There are dozens of ways to get out on the water from jet skis to glass-bottom boats, sailboats and fishing charters. We spent the morning on the SQUID, Key West’s first electric-powered charter boat, fueled with a lithium ion battery. We spotted dolphins and snorkeled on a shallow reef with sponges, coral, stingrays and lots of tropical fish. www.honesteco.org
Fort Zachary Taylor Historic State Park beach, 601 Howard England Way. You can rent chairs and an umbrella as well as snorkels and fins. Spend a morning swimming and snorkeling, then grab a cold drink at the snack bar. fortzacharytaylor.com.
Dry Tortugas National Park. The sea planes book up fast for a spectacular 40-minute flight to Fort Jefferson, but it’s a must-do if you can reserve a spot and afford the half-day excursion ($361, $289 ages 12 and under). www.keywestseaplanecharters.com. There’s also a daily ferry ($190, $135 ages 4 to 16) that takes about two hours each way. Snorkel on the Florida Keys reef and explore the old fort. drytortugas.com