Winter is coming, which means Portlanders are bracing for months of drizzle, cold, and gloom. That's why winter is also the perfect excuse for an inexpensive weekend adventure to somewhere warmer and sunnier, and we're thrilled to be partnering with Sun Country Airlines to make that attainable: over the course of 10 days, we're giving away 10 pairs of $100 vouchers ($200 in total value) towards flights to some great destinations.

To give you a better idea of your next weekend with Sun Country, we've highlighted a few spots where 10 lucky winners will have a chance to escape rain-drenched Portland for one glorious weekend with a friend:

Las Vegas

Las Vegas has flashy casinos, feather dressed showgirls and and an ageless Wayne Newton, but there's a whole lot more beyond the neon-haloed strip. In fact, with the recently opened Cannabition Art Museum, now is a better time than ever to visit. Touted as "the world's only immersive cannabis museum," Cannabition features interactive exhibits and art installations that celebrate the history of cannabis, such as a 24-foot bong and Hunter S. Thompson's personal 1973 Chevrolet Caprice, aka the "Red Shark," inspired by the book "Fear and Loathing in Las Vegas." Unfortunately, there's no consumption allowed at the museum. For a good party head over to the Fremont Street Experience, an outdoor street fair where you'll find free live music, restaurants, and Slotzilla, a 12-story slot machine-inspired zipline (Hint: it's cheaper if you ride before 6pm). Be sure to also check out the Las Vegas Arts District, known to locals as the 18b, where galleries and shops stay open late for a monthly block party every First Friday.


With its blissful white beaches and a climate that is better than any anti-anxiety medication , there's a reason why Hawaii is such a popular getaway. There is no end to activities, though we are partial to the torch lighting and hula show at Kuhio Beach, held every Tuesday, Thursday, and Saturday from 6:30-7:30pm (6-7pm November through January), and free beginner classes in lei making, hula, lauhala weaving, or ukulele playing at the Royal Hawaiian Center. For fresh local produce and other local treats, check out the KCC Farmers Market, held Tuesdays and Saturdays at the Kapiolani Community College Campus. The farmers market is located near Diamond Head, so you can grab some snacks and then hit the trail of this storied volcanic tuff cone. Want something more off the beaten path? Hit up Hawaii's Kaka'ako neighborhood, an artsy industrial district with eclectic eateries, craft beer, and artist studios. The neighborhood also hosts the POW! WOW! Festival every February, where artists from all over the world come together to deck the town's walls with huge colorful murals. And if you can plan ahead, make a reservation at Morio's Sushi Bistro, a tiny dive on King St that has developed a cult following.

San Francisco

SF is one of the great American cities that seems to be constantly reinventing itself. Currently, our favorite itinerary is to stroll through the historic Castro neighborhood, one of the first LGBTQ communities in the US, and visiting the GLBT Museum. The city is home to a number of great parks, but we suggest the the lesser known Land's End, where you'll find coastal hiking trails, a rock labyrinth, and the ruins of late 19th century Sutro Baths. San Francisco also has its own version of OMSI After Dark, and if you go on Thursday you can visit the California Academy of Sciences after hours (6-10pm) for adult-only access to exhibits, programs, and of course, food and booze. And try to make it to the Mission District and grab a flamed chicken at Pira Pica, the Portuguese fast casual restaurant that has become hotter than a ghost pepper. If you have time, take a ferry to Alcatraz Island. Once a federal penitentiary that housed Al Capone, it was also taken "hostage" by Native Americans for almost two years, and signs of their protests are still visible on the island, where you can get an extraordinary view of the city.


For a full-on desert experience where you'll find cacti that look like a scene out of a Looney Tunes episode, Phoenix is your place. The desert metropolis is known for its spa and golf resorts, however there's also some great opportunities for outdoor excursions, such as walking or biking around red buttes at Papago Park, or taking on the more challenging trek up Camelback Mountain. While exploring downtown Phoenix, we recommend a stroll through Roosevelt Row, a creative hub with award-winning galleries, local eateries, and boutiques. The city also hosts First Fridays Art Walk, where you can take a free trolley ride that connects to all the city's art districts. Come nightfall, you'll want to head over to Tempe, a quirky and vibrant college town just east of Phoenix where you'll find booze, food, and a great live music scene. Our fave restaurant? The Yard—a gastropub with ping pong

Want to make it out to any of these destinations? Enter to win vouchers below and make your winter escape!