People misread the American dream. It's not working
yourself dizzy till you retire in a house you spent 30 years paying off.
It's emailing your boss tomorrow to say you won't be in on
Monday, or ever again, because you’ve gone exploring. There's a reason
one of Google's favorite autofills after "quit my job and" is "travel
the world."
Getting the hell out never goes out of style. But
traveling -- like every other blasted thing in life -- requires money.
So we'll see you back at your desk on Monday after all.

San Juan, Puerto Rico
Travel time: A three- to five-hour nonstop flight from
major hubs like JFK, O’Hare, Dallas-Fort Worth, and Miami to the capital
city of San Juan will only set you back around $300 to $350 during low
season.
Why you'll love it: You don’t need a
passport to feel like you’ve stepped out of the country when you amble
through San Juan’s tangle of blue cobblestone streets, vibrantly painted
alleys, and Spanish colonial buildings draped with bougainvillea.
Mighty forts, grand old churches, and remarkable restaurants all host a
steady ebb and flow of tourists clambering off cruise ships for a few
hours. You, having booked a few nights, get to slow down a bit.
Carve your own trails in Old San Juan to stumble upon offbeat spots like Mi Pequeño, a local shop that makes and sells hand-painted reproductions of San Juan’s doors and building facades. Stop by Caribar
at Caribe Hilton, birthplace of the piña colada, and treat yourself to
some yummy nosh and cocktails. Explore the brilliant street art of the
Santurce neighborhood. Then day-trip: Among the best excursions are
Vieques’ bioluminescent bay; the adventure park of Toroverde, where
visitors can hop zip-lines -- some of the longest in the world -- over a
lush canopy of trees; and El Yunque, the only tropical rainforest in
the States. Well, sort of in the States. -- Michelle Rae Uy, Thrillist contributor

Whitehorse, Yukon Territory
Travel time: Fly into Whitehorse Airport (with a short
layover in Vancouver) on Air Canada or Air North, the only two airlines
that offer year-round service. Travel time varies from West Coast hubs
like LA, Portland, and Seattle, but you can get there in as little as
six hours. Considering you’ll be within driving range of the Arctic
Circle, it’s not bad for a Friday night flight. Book early to keep costs
as low as $450 (r/t Seattle).
Why you’ll love it: The Pacific
Crest Trail and Kilimanjaro may be next on your adventure to-do list,
but who’s got that kind of time? Instead, channel your inner Paul Bunyan
by exploring Canada’s least-populated territory, where spruce forests
and jagged mountain peaks have inspired intrepid travelers since the
Gold Rush. A stop at Braeburn Lodge is a must for the cinnamon bun
alone; it’s so big you’ll be snacking on it all weekend as you head
north to Tombstone Park where you’ll drop off the grid and be forced to
ponder life’s big questions.
You’ll have plenty of sunshine, too. During the
summer months, the “midnight sun” stays up until well after the witching
hour. So float down the mighty Yukon River on a white-water rafting
trip or chat up the friendly locals -- they’re all in bands, and will
low-key try to convince you to move here (they may be onto something).
Just don’t check the time, and your long weekend will feel like an
endless summer. -- Ryan MacDonald, Thrillist contributor

Hamilton, Bermuda
Travel time: Bermuda is an easy flight from the East
Coast: two hours from New York, DC, or Boston; about three from Miami or
Atlanta. Often you can get there for about $300.
Why you'll love it: Bermuda is a
weird bird. It’s not tropical, but it is warm and sunny and has pink
sand beaches and sunsets over the North Atlantic. It’s also close, both
geographically and culturally. Brits and Americans have been there since
the days of pirates (it’s still a playground for captains of finance and their offspring),
so you get gnarly old cannon-laden forts and a flourishing nightlife.
You can ride a jet ski into the Bermuda Triangle. You can visit The
Swizzle Inn for an iconic rum swizzle, and then seek out authentic local
fare in St. George’s or drop some cash at Marcus Samuelsson’s chic eatery Marcus’.
Or, save your dough -- even if you don’t want to
spend hedge-fund-manager dollars, you can enjoy the same beaches. Or
venture onto the bicycle trails, try a stand-up paddleboard, and walk
around Hamilton’s Downtown. It’s quaint, relaxing, and a shorter flight
home than some New Yorkers’ morning commutes. -- Emily Zemler, Thrillist contributor

London, England
Travel time: You’re pushing it for a three-day jaunt,
but it can be done from Boston (6.5 hours) or New York City (7-ish). Fly
out Thursday after work ready to nap. You’ll arrive Friday morning and
take the Heathrow Express straight into the city. Fly back Sunday night
and return stateside while it’s still Sunday, meaning you only need one
real day off for an incredible weekend in London. Off-season, you can
pull this stunt for under $400 in airfare.
Why you'll love it: If you’ve never
been before, get yourself to a double decker bus and breeze through the
sights: the British Museum, Buckingham Palace, Westminster Abbey, and
The Tower of London, or just toss the traditional guidebook vacation and
be a Londoner for a weekend.
Not only do Londoners order drinks in a better
accent than wherever you’re from, they are just undeniably more fun. Don
your best day-to-night outfit and set out to explore the stone streets
of Covent Gardens for boutique shopping, then pop into Soho’s posh
stores and Berwick Street Market for a bite and perhaps even venture out
to Brockley (pronounced broccoli) or Barnsbury to people watch and
drink your way around the up-and-coming neighborhoods like a local.
Because everything is so packed together throughout the city (which is
all connected by public transit), you can hit up impressive amounts of
pubs, shops, food stalls, restaurants, and even shows in a mere three
days. So fetch. -- Melissa Kravitz, Thrillist contributor

Antigua, Guatemala
Travel time: You can fly to Guatemala City in three
hours from Miami ($400), four from Dallas ($550), or around five from
New York ($400) or LA ($650). But don’t stop there. (Seriously, the
capital is polluted and kind of dangerous.) Hop an airport shuttle to
Antigua, the charming colonial town an hour away.
Why you'll love it: You’ll spend
the weekend getting off your butt and off your phone. Go bar hopping
through Antigua’s cobblestone streets after fueling up on legit street
food in Parque La Merced. Then burn off those tacos and beers with a
hike up one of the volcanoes surrounding the town. If one of them is
particularly active, join an overnight trip with OX Expeditions (~$100) where you’ll camp in view of exploding lava and hike to the peak at sunrise.
Or put on flip-flops and take a shuttle three hours
west to the shores of Lake Atitlán, which is so chilled out and pretty
that backpackers regularly get stuck here for months at a time. There
are about a dozen different lakeside towns to choose from: Panajachel,
San Pedro, and San Marcos are the most popular with travelers, but it’s
also worth visiting one of the more traditional Mayan pueblos to catch
indigenous villagers going about their everyday lives -- and maybe to
pick up a traditional multicolored blanket or two. It'll really tie your
lounge room together. -- Sarah Theeboom, Thrillist contributor

Quebec City, Quebec
Travel time: You can drive there from Boston in about
six hours. From the East Coast, it’s one connection through JFK; from
the Midwest, through Chicago. If you can get to either of those
airports, the flight is just a couple of hours.
Why you’ll love it: Quebec City is
the most French place I’ve ever been. And I’ve been to France. Not only
are the francophone people a cultural immersion that it’s hard to find
north of the border, the streets here look like the opening sequence to Beauty and the Beast.
Small, European buildings packed closely next to each other, where
bakeries alternate with cafes, brasseries, and bars making for a
completely walkable vacation. It’s also the only walled city north of
Mexico, and during the summer you can climb atop the rampart and do a
lap over the entire Old City. In the winter, it’s home to Carnaval de
Quebec, a sort of snowbound Mardi Gras where people jam the streets,
sub-freezing temperatures be damned. Quebec City is the most European
experience you can get in a weekend away from the States, and a city
unlike anything else you’ll find in North America. -- Matt Meltzer, Thrillist contributor

The British Virgin Islands
Travel time: From Miami, a nonstop flight to Tortola is
under three hours. But you can fly to St. Thomas in the USVI from New
York, Miami, Atlanta, Charlotte, and other major hubs in just a few
hours, and take a short, scenic ferry ride to any of the four islands.
If you leave work at noon to catch your first flight, you’ll be eating
dinner on a beach by sunset.
Why you’ll love it: The BVI is,
quite simply, the nicest destination in the Caribbean. Despite being a
British territory the islands are distinctly Caribbean, where small
fruit markets, windy roads with rickety cars, and slow-moving roti shops
abound. But because the people who frequent the BVI have money, the
infrastructure is better than you’ll find in most of the Caribbean. The
islands are nice, but it’s not a “you-can’t-sit-with-us” kind of
exclusivity one might find in St. Martin or St. Barts. Here yachtsman
pour into a ramshackle beach bar called Foxy’s on the island Jost Van
Dyke, sipping cheap beer on the white sand with no pretension. Jost is
also home to White Bay, one of the world’s most beautiful beaches that’s
also lined with cheap bars and no attitude. -- Matt Meltzer, Thrillist contributor

Mexico City, Mexico
Travel time: Direct flights from major airports will
get you into el DF quick: 2.5 hours from Dallas, three hours from Miami,
four hours from LA, five from NYC. Round-trip fare usually ranges from
$300-$500. Or go all On the Road with it: From San Antonio you’re a 16-hour drive away.
Why you'll love it: Anything feels
possible here. Spend an afternoon wandering the tree-lined streets of
super-trendy La Condesa or La Roma (like a Paris that rides the bus to
work), and sip artisanal coffee while eavesdropping on local slang (no mames guey!).
Get cultured in the Centro Historico, where grand colonial buildings
and churches tower over the electric, modern murals that line the
alleys. The top draft choices among the 150 museums in the city are the
stunning Museum of Anthropology and the Casa Azul of Frida Kahlo. Do ‘em
both.
At night, the city comes alive -- as will you, when
you sample pulque (a traditional, fermented agave drink, flavored with
strawberry or celery) and befriend the mariachi band busking on the
sidewalk. Get a midnight snack of the capital’s renowned tacos al
pastor, then stumble off to dance until the sunrise. Don’t forget a day
trip to the epic, pre-Hispanic city of Teotihuacan, where climbing the
steep steps of the ancient pyramids will leave you eager for a long
lunch in a restaurant in the desert: right next to a cactus farm. -- Laura Yan, Thrillist contributor

Lisbon, Portugal
Travel time: About 7 hours from the northeast or 8
hours from Miami. Boston is the sleeper deal here: New England has a
huge Portuguese population, and you can often find round-trip deals
between Logan and Lisbon in the $400s, rivaling the best New York
prices.
Why you’ll love it: Think of Lisbon
as a Barcelona that hasn’t been swarmed yet. It’s cheap, it’s
beautiful, and the food and wine are fantastic. You’ll want to spend
your evenings drinking and eating your way through the streets of Bairro
Alto on the northwest side of Lisbon’s Downtown, but make sure to take
day trips to both Belém and the panoramic views of the Atlantic Ocean in Sintra. (Belém is just a seaside tram ride away from Downtown Lisbon and it’s worth the ride just to get pastéis de Belém, the Portuguese egg custard pastry, where it was perfected back in 1837.) And yes, go see a Fado, ideally at A Baiuca
and preferably with a few bottles of Vinho Verde. Then catch a flight
home by noon Sunday: With the time change, you’ll be back in New York by
midnight, the perfect crime before showing up bleary but unbowed on
Monday morning. -- T.M. Brown, Thrillist contributor
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