This year, plan—and pack—for the trip of a lifetime with insider advice and outfit inspo from travel expert and Cartogramme founder Ashlea Halpern.

Photo by: Thief&Bandit

So many countries, so little time off. When it comes to planning a vacation, the only thing more fun (and overwhelming) than deciding where to go is figuring out what to stuff in your suitcase. To help us make sense of it all, we turned to Ashlea Halpern, editor-at-large for AFAR Magazine and co-founder of Cartogramme, a cool new travel site devoted to art, culture, food and drink, vintage shopping, and all things awesome. Ashlea currently lives in Bangkok but has visited more than 50 countries. Last month she traveled to Laos; next month she’s considering Jordan or Western Australia. When asked which ports of call should be on every traveler’s radar right now, five spots rose to the top. Here, she explains why these destinations made the cut, what you should do when you get there, and what to pack for your great escape.
Clockwise, from left: Tropical midi skirt by Jojo Blanc, $162.54; crochet bikini top from Favorite Little Corner, $46; stained-glass monstera leaf necklace by here&now, $45

Honolulu, Hawaii

Why now: “The art and food scenes in the Hawaiian capital are exploding," Ashlea says. "The city’s first-ever contemporary art biennial is up through May 8. New murals were painted all over downtown as part of the recent POW! WOW! International art festival. On the food front, two Honolulu restaurants were just nominated for James Beard Awards: Senia in the Best New Restaurant category and Vino for Outstanding Wine Program.” Where to go: “Drop your bags at the stylish Surfjack Hotel near Waikiki Beach. The pool alone is Instagram gold, thanks to a huge 'Wish You Were Here' sign painted on the bottom by Matthew Tapia. Next, food—very important. Grab tables at Senia and Vino, but also try superstar chef Ed Kenney’s organically-driven Town or Kaimuki Superette, the loco moco at Koko Head Cafe, the traditional shave ice at Waiola Store, and a fresh-to-death poke bowl from Kahuku Superette. See what’s new at the Honolulu Museum of Art and Spalding House, or community creative hub The ARTS at Marks Garage. Oh, there’s also the fact that Honolulu is located on an island, Oahu, and Oahu is surrounded by ocean. You might want to carve out a little surf time, too.” What to pack: "Itsy-bitsy bikinis, big happy florals, floppy sun hats, button-down chambray shirts, tasseled necklaces, seersucker shorts, skater-punk sneakers, and lagoon green and flamingo pink everything."
Clockwise, from top: Crop-sleeve viscose top by Figura, $100; leather zip tote from Grace Gordon LDN, $254.83; mismatched wood earrings from Reason to Be Pretty, $38

Finland

Why now: “My crystal ball tells me this is the next—and probably last—Scandinavian country to be fetishized by US travelers. It also happens to be turning 100 this year. Helsinki is ground zero for the centennial partying: The city just hosted the World Figure Skating Championships and has 100 free events planned for June 12 (official Helsinki Day). About 500 miles north of the capital, near the Russian border, there is a new national park named Hossa, complete with sparkling lakes, towering forests, and unusual shamanistic cliff paintings. Plus, a slew of enticing accommodations in Lapland are making it easier than ever to see the elusive Northern Lights.” Where to go: “Start at the Helsinki Art Museum, which is staging a major exhibition on Finnish Modernism now through July 30. If you’ve got kids in town or just dig quirky illustration, look for the new Moomin Museum opening at Tampere Hall on June 17. The hippo-esque character is as beloved today as it was when Tove Jansson first drew it 72 years ago. Experiencing Finnish sauna culture is another must. There are two new spa complexes in Helsinki: Allas Sea Pool and Löyly, the latter designed by Avanto Architects. A big-deal luxury inn, St. George, opens this fall across from Old Church Park, but nothing beats a night of glamping in the Aurora Dome, an igloo-shaped tent perched on the banks of Lake Torassieppi.” What to pack: "Loose linens in a rainbow of neutral colors: beige, khaki, stormy gray, matte black, and navy blue. Dressing in minimalist fabrics means you can go wild with the accessories—to a point. Try mismatched statement earrings in wood or metal and classic bags in nonstandard hues."

Clockwise from top left: Turquoise chime earrings from Sarah Safavi Jewelry, $118; hand-dyed indigo bandana from APPRVL, $25; vintage Levis from Maeven Vintage, $148.75; leather tassel clutch from Tori Le Designs, $70.41

Colorado

Why now: “Colorado is one of my all-time favorite states—and I visited many when I embarked on a 9.5-month, 22,234-mile road trip across America last year. There are so many groovy, under-heralded mountain towns here, and, no, I’m not talking about Vail and Breckenridge. Flying into Denver or Grand Junction and driving in a big loop takes you through gorgeous national forests (Uncompahgre, San Juan, Gunnison, etc.) with winding roads and spectacular drop-offs. I recommend building your itinerary around million-dollar stops like Mesa Verde National Park and Colorado National Monument, but kicking it in small towns in between. And don’t forget to roll the windows down. You’ve never smelled air this clean.” Where to go: “Mancos, Montrose, Ouray, Dunton, Silt, Rifle, Crested Butte—if you’ve never heard of the towns you’re staying in, you’re on the right track. In Ridgway, tuck into creative farm-to-trailer plates from a Per Se alum at Eatery 66, rummage for colorful Pendleton blankets at Magpie Antiques, and bathe in a 'lobster pot' at the clothing-optional Orvis Hot Springs. Pick up hand-carved Native American beads at The Hogan Trading Post in Mancos and feed your face cream scones and savory hand pies at The Pie Maker Bakery in Cortez. Even tiny Minturn, way up in the Rocky Mountains, has The Blue Mini Urban Drive-In, the highest-altitude drive-in in the country! There’s always something special to discover here.” What to pack: “You’re in ranching country, so wide-brimmed hats, vintage denim, chunky silver and turquoise jewelry, and hand-tooled leather bags are the order of the day.”
Clockwise from top left: Leopard-print head wrap from Baby Okra Boutique, $15; leather tassel earrings from DDSLL Girls Store, $26; cotton maxi dress by Omi Woods, $198; beaded friendship bracelet from feltlikepaper, $19.50

Cape Town, South Africa

Why now: “The biggest news in the Mother City is the September 22 opening of the Zeitz Museum of Contemporary Art Africa, the world’s largest museum devoted to contemporary African art. It sits six floors beneath a grain elevator turned 28-room boutique hotel, The Silo. All things considered, it’s one of the biggest, most buzzed-about openings in African history.” Where to go: “Zeitz MOCAA, of course, but don’t stop there. Visit Durbanville’s Rust-en-Vrede Gallery + Clay Museum, housed in a converted 1840s jail, and book a multi-stop home gallery tour through Langa Township. The program is run by the not-for-profit Maboneng Township Arts Experience, which encourages local entrepreneurs to transform their personal homes into gallery spaces. Also essential: Book a half-day walking tour with art activist Juma Mkwela. He’ll take you through Woodstock or Khayalitsha, show you the best street art, introduce you to his (many, many) friends and neighbors, and join you for a sit-down lunch with a local family. Speaking of food and drink, a lot of ink has been spilled over the South African winelands. That’s all well and good, but gin is big here, too. Check out craft distilleries Hope on Hopkins and the Woodstock Gin Co., or get yourself a bonkers-progressive cocktail at Outrage of Modesty.” What to pack: "Eye-popping Dutch wax prints, funky beaded accessories, glamorous turbans, and mile-high wedges."
Clockwise from left: Cotton sun hat from Easy Living Hats, $89; waxed twill backpack from Artifact Bags, $265; sterling silver compass necklace from Metalicious, $159

Canada

Why now: “Our lovely neighbor to the north turns 150 this year and it’s throwing one heck of a party. Entrance fees to all national parks, including Jasper and Banff, are waived for 2017. Ottawa is hosting a bunch of sports and culture events, like Canada’s first Red Bull Global Rallycross and ‘Kontinuum,’ a trippy multimedia installation set up inside a future light-rail station. In Quebec, Montréal is pulling out all of the stops because it is turning 375. Literary festivals, jazz concerts, light shows in historic cathedrals: There are so many events going on, it boggles the mind.” Where to go: “Mistaken Point Ecological Reserve, a fossil-rich headland in Newfoundland, has just earned itself UNESCO World Heritage status. Toronto is landing a new Museum of Contemporary Art in its Lower Junction district, along with a flashy new food commissary from the team behind the Drake Hotel. (The bakery will be helmed by Jonas Grupiljonas, who studied with Chad Robertson of Tartine.) The Old Port of Montréal, meanwhile, just launched Village by the Locks, allowing guests to spend the night in a restored wooden boat, an old lock keeper’s cottage, or in a sustainably designed urban tent. Not to be outdone, Vancouver has all the beer and seafood nerds drooling with its weeks-old South American-style craft brewery and cevicheria, Andina Brewing Company. So, um, maybe the best plan here is to just buy a few trans-Canadian rail tickets and see it all?” What to pack: “For the parks, a vintage picnic basket, lightweight backpack, sturdy pair of hiking boots, and cozy flannel for chilly evenings. For the cities, high-waisted short shorts, strappy sandals, and a cute cell phone case, since you’re obviously going to be documenting everything.”
Still undecided about where to go? See more of Halpern’s top travel picks at Cartogramme or follow her adventures on Instagram at @ashleahalpern and @cartogramme.

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