Provincetown vs. Key West: Which City Has the Best Small-Town Charm?
Each week, Yahoo Travel pits rival destinations against each other to determine once and for all which place is the best. This week it’s Provincetown vs. Key West in a duel of vacation spots.
And just when I thought I couldn’t feel any more like Meryl Streep today, someone goes and asks me to choose between Provincetown, Mass., and Key West, Fla., two of the most charming, quaint, adorable, occasionally risqué, and gay towns on Earth. They are trailblazing communities, both artsy, both foodie havens, both idyllic communities where people go for vacation and end up staying a lifetime.
So here we go:
The Case for Provincetown
Provincetown, MA (Photo: Corbis Images)
In one corner, wearing cedar-gray shingles with rainbow-flag trim, you have Provincetown. This New England charmer is a small resort town on the tip of Cape Cod; small in stature but a true heavyweight in the lesbian, gay, bisexual, transgender community and an escape for artists, it is comprised of about 10 square miles of pure adorableness. Seriously.
Population: About 3,000
Anthony Bourdain (Photo: Corbis Images)
Famous Faces
Celebrity chef Anthony Bourdain, a whole bunch of writers like Michael Cunningham (The Hours) and Mary Oliver (Pulitzer Prize-winning poet.) Tennessee Williams was a famous longtime resident.
Small-Town Charm
Rows of cottages line the beaches in Provincetown (Photo: Getty Images)
When it comes to class and quaintness, the small-town charm of P-town gets the nod over Key West. With its rows of New England-style cottages, corner cafes, homemade ice cream shops, lobster shacks, and quaint, family-owned bookstores, this place is right out of a storybook. And while Key West has a lot of the same charm, it has a more southern, N’awlins feel to it, folksy with a drunkard’s edge, while P-town is pure Americana.
B&Bs
One of the bedrooms at the Salt House Inn (Photo: Salt House Inn)
There was a time not so long ago that many mainstream hotels weren’t very hospitable to gays. (Two gay men checking into a hotel in the ’60s and asking for a single bed would be met with odd stares and finger-pointing.) But did they complain? Maybe a little. And then they moved to Fort Lauderdale, Fla., Palm Springs, Calif., and Provincetown, Mass., and they opened their own hotels, with comfy beds and fresh-squeezed juice and tall fences so they could walk around naked. So there! And while hotels have become much more gay-friendly, these gay guesthouses are still popular in the community – and nowhere are they more chic than in P-town. The Salt House Inn is the best of the bunch, new and rustic and chic, run by a cute gay couple, one of whom has a strong culinary background and makes a homemade breakfast every morning. You can rent bikes, the inn always has snacks and hot coffee, and the rooms have vaulted ceilings and claw tubs.
Related: Wild West Smackdown: Montana vs. Wyoming
Watersports
Some sailing happens in Provincetown, but most of the action is in town (Photo: Corbis Images)
We’re talking surfing, scuba diving, and sunset sails. There’s some beach activity here, but most of P-town’s focus is on Commercial Street, the quaint shops, and bike-riding on the picture-perfect roads. The water is great for views and some sailing, but Key West takes this round, hands down.
Getting There
Provincetown is about a five hour drive from New York City (Photo: Getty Images)
From Logan International Airport in Boston, Provincetown is just a quick ride and a ferry (or even cooler, a small and wobbly plane ride) away. From New York City, it’s about a five-hour drive, no traffic, and it remains one of the easier secluded resort towns to get to. While Key West boasts that it’s only 90 miles from Cuba, it’s also a long and desolate (albeit beautiful) car ride away, or two flights, which can be a deterrent. I give the nod here to P-town.
The Art Scene
The artist Mark Rothko spent time in Provincetown (Photo: Corbis Images)
This one’s really a toss-up. Both places are escapes for writers, both host world-class literary gatherings and festivals, but we’re giving the edge to P-town for its theater scene, its artists-in-residence, and its proximity to artsy Boston. In 1916, the Boston Globe called it the oldest continuous art colony in the world. Back then, artists like Norman Rockwell and Mark Rothko had ties to Provincetown. Today, it’s defined by boutique galleries, designers, sculptures, knick-knack shops, bookstores, and a vibrant theater scene.
Food
The Canteen (Photo: Canteen)
With classy joints like Victor’s on Bradford Street and the newish, more casual Canteen on Commercial, P-town has no shortage of dining options. Most flourish when serving up fresh seafood, and only one chain to speak of (We’re looking at you, Ben & Jerry’s!) But for inventiveness, variety, and soul, we give the nod to Key West.
The Case for Key West
So many choices in Key West, which one will you choose? (Photo: Corbis Images)
In the other corner, Key West, a tropical getaway that trumps Provincetown in one very important way: the weather. It’s always sunny here, even during the winter, when Provincetown is muted in snow and bare trees. Come December, Key West is gorgeous: 85 degrees every day, cool nights, and you can swim, snorkel, and sunbathe. It may be the perfect winter getaway.
Population: 25,550
Famous Faces
Cary Grant once called Key West home (Photo: Corbis Images)
Cary Grant and Ernest Hemingway are among the most famous residents to have ever lived here.
Food
Key lime pie is a signature dish and a must have while in Key West (Photo: Corbis Images)
Sure, it’s the Florida Keys, but this is still the South, which means the food is untouchable. From the indigenous Key lime and Creole-French cuisine to fresh seafood and barbecue, this small town is a culinary treasure. For the best Key lime pie, hit up Blue Heaven, or for breakfast and hot coffee, head right next door to Le Crêpe Café, with its classic French café décor. El Siboney is the last old-fashioned Cuban joint in town, If you’re looking for something a little haute, we rave about Café Marquesa,intimate with a dynamic menu and possibly the best date-night spot in town.
Watersports
Key West beaches are some of the best you’re likely to find (Photo: Corbis Images)
Key West wallops P-town on this one. In the summer, the turquoise water is crystal clear, offering some of the best snorkeling outside of Belize. The water is almost always good for a swim, and the sunset at night, that honey-amber starburst against a backdrop of sapphire blue dusk, is among the best anywhere in the world.
Related: Mexico Smackdown: Los Cabos vs. Cancún and Riviera Maya
Small-Town Charm
(Photo: Corbis Images)
Riding down Duval Street at dusk, looking around at the Victorian houses, the quaint storefronts, the coffee shops, and cafes, and in the distance, the tropical water, you might swear you were in a postcard. Key West’s charm is bountiful and stems from its tropical roots, its southern flare, and its small-town-ness. And while it’s spectacular, it has met its match with P-town. Nobody does small-town like New England.
Nightlife
P-town has its Tea Dances, its underwear parties, and even a clothing-optional guesthouse or two, but that’s no match for the mighty one-two punch of Key West’s gay scene. Come nightfall, the main drag of Duval Street is a tropical version of Bourbon Street, and we’re not talking about the Bourbon St. Pub, where gay boys dance in skimpy briefs or less and offer way overpriced lap dances. For a more tame institution, the Green Parrot is beloved as everyone’s favorite hole-in-the-wall, and the bars along the marina are great for a drink with a view.
The Art Scene
The Hemingway house (Photo: Corbis Images)
Just off Duval Street, the Hemingway Home stands as the town’s most famous museum and, along with a world-class literary festival in January, represents the rich literary history of Key West. But P-town is an artist’s colony on a different level of sophistication.
B&Bs
(Photo: Corbis Images)
Key West has its B&Bs, the Equator being the best of them, with spacious, cozy rooms and a lively pool and bar scene just a few blocks from the nightlife of Duval. But P-town is a B&B haven, and nothing in Key West is going to compare.
Getting There
A short 30 minute flight from Miami (Photo: Getty Images)
A flight into Miami and a 30-minute hopper to Key West sounds easy enough and is surely more convenient than the hours-long drive, but P-town is just a quick ferry from Boston. No contest here.
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