A Weekend in Key West 

Water Sports, Intoxicating Libations, and a Historic Home 

It was 10 am. A bit of an early start for most Key West tourists still sleeping off the previous night out. But there we were, 500 feet in the sky, desperately hoping a sudden surge of wind didn’t knock us into the Gulf of Mexico. The distant shoreline with miniscule palm trees and sunburnt tourists crowding the pier suddenly seemed very far away as the line connected to our parasail reeled us farther out and up. Our only company was a blacktip shark lazily gliding directly below our dangling legs. 

Somewhere between thrilling and terrifying, parasailing ($69.95 at Sebago Watersports) is one of those prototypical Key West activities anyone can enjoy—as long as you don’t mind a small rush of adrenaline. For our part, we tried to experience Key West in every way possible—as adrenaline junkies, history buffs, and of course, as the tourists we were. 

The history of the island is nothing to scoff at. We got our first taste at The Grand Maloney, a historic home turned boutique hotel just a few blocks from Duval Street where we stayed two nights. The 1860s era home has gone through several renovations, most importantly after The Great Fire of Key West in 1886, when 50 acres of the island burned to the ground. The property was rebuilt with a tin roof and brick walls, aiming to be one of the most fire-resistant homes on the island. 

Hotel in Key West
The Grand Maloney, a historic home turned boutique hotel is on Caroline Street, a short walk from Duval Street
A Weekend in Key West 
A sitting nook off the lobby

The hotel, which feels more like an AirBNB, is owned by the Spottswood family, one of the Keys’ oldest families and owners of other hotels and properties in the surrounding area, including the Key West Marriott Beachside Hotel. While some of those properties offer a more traditional hotel experience, The Grand Maloney is Billy Spottswood’s unique brainchild. “The traditional hotel model is like focus groups — they want to build things that everyone likes, so that’s why they all look exactly the same. It’s like the same box,” he told us. “We want to make places that a lot of people love, not places that everyone likes.” With each of the six rooms uniquely themed and tropical- ly colored, The Grand Maloney feels like a microcosm of Key West itself — an island of its own decorated with sponges (a throw- back to the original owner’s sponging export business), shower tiles in colors so bright they stop just short of garish, and wallpaper featuring Miami Vice-styled palm fronds. 

The Grand Maloney is also located in one of the charming historic areas of the city, a few blocks in from the old waterfront but close enough for a stroll to Sloppy Joe’s (or, in the other direction, the Key West satellite of Books & Books). It was a longer walk to the Hemingway House ($17 for entry, cash only), and though we missed the guided tour we still managed to enjoy the grounds where the prolific writer penned some of his best works and where we had the chance to see some of the famous six-toed cats. 

Weekend in Key West - hotel
The “Blue Room” Bedroom suite at the Grand Maloney has retained a historic charm with a brick fireplace and bookshelves.

After Papa’s home, we abandoned attempts at historic edification, though there are plenty of opportunities here, from Audubon’s 1800s home to Mel Fisher’s treasure museum. Instead, after a brief rest, we stumbled upon Dante’s pool bar down by the City Marina. Sipping frozen strawberry daiquiris poolside, we watched parents play floating beer pong while their kids cavorted in the shallows. Advertisements featuring hydrating IVs were quite aptly placed by the bar. Next came a two-hour Sunset Sip n’ Sail cruise ($59.95, open bar included) on the Gulf, which had a similar atmosphere, although this time the cavorting youngsters were replaced by frolicking dolphins and drinkers, ages from 21 to 70. 

With eight generations of Key West knowledge, we entrusted our dinner plans to the Spottswoods, eating at the decadent Tavern N Town restaurant inside the family’s Marriott Key West, located at the north end of the island, right after the bridge from Stock Island. Tender and flavorful Australian Wagyu steak set to the tune of live piano music and an open kitchen made for the kind of fine dining experience you’d expect at a Coral Gables steakhouse. 

While Duval Street is a far cry from Miracle Mile, it makes for great people watching as the crowds churn up and down the island’s main tourist drag. We enjoyed our after-dinner stroll in search of more drinks, oftentimes running into the same people over again — also oftentimes in the same clothes they were wearing the night before. That’s the Key West experience: Bring a multi-use outfit consisting of swim trunks and a Hawaiian shirt and you won’t even need to stop off at your room to change between a jet ski ride and a brew at Hog’s Breath Saloon.  – By Kylie Wang and Carmen Fraga

The Grand Maloney – Key West

529 Caroline Street,

Tavern N Town – Key West

3841 N Roosevelt Blvd,