1. Portland, Oregon
Why Go: Beloved by creative types (singer Beth Ditto and filmmaker Gus Van Sant are longtime residents) who've spread a laid back vibe by osmosis, Portland is the perfect small city to chill out while staying tuned in.
What to do: Catch indie bands at the Wonder Ballroom (128 NE Russell St.; 503-284-8686; wonderballroom.com), and stroll around the Pearl District for boutique browsing-time your visit to the first Thursday of the month for art gallery openings and shop discounts. Portland's legendary food carts are fun for an al fresco lunch. If you love Thai, dinner at Pok Pok (3226 S.E. Division St.; 503-232-1387; pokpokpdx.com) is great value and totally authentic. And just when you thought it couldn't get any better, consider that downtown local transport is free.
Where to stay: The Ace Hotel (1022 S.W. Stark St.; 503-228-2277; acehotel.com/portland). Hipsters are drawn to this 79-room hotel (left) like moths to a flame. Think turntables in the rooms, utility and vintage styling, and complimentary bikes (grab 'em early). Rooms from $75.
Courtesy of Ace Hotel
2. Santa Fe, New Mexico
Why Go: When a tastemaker like Tom Ford calls Santa Fe home, you know there must be more going on than turquoise jewelry and red dust. From summer festivals and a thriving arts scene to hiking and biking for outdoorsy types, Santa Fe packs a lot into a small city.
What to Do: For food, keep things casual at the Guadalupe Café (422 Old Santa Fe Trail; 505-982-9762), an adobe building with a sweet patio where you can fill up on enchiladas, burritos, and tongue-blistering chile. The Railyard District is Santa Fe's happening neighborhood, with edgy galleries, shops and bars. Fashionistas might be interested in bagging a ticket for the world premiere of The Letter at Santa Fe Opera's Festival Season this summer (July 3 through August 29), to see Ford's first foray into costume design (www.santafeopera.org).
Where to stay: Inn on the Alameda (303 E. Alameda Street; 505-984-2121; innonthealameda.com). Tucked away in a garden behind a pueblo wall are 71 cute casita-style rooms and suites with kiva fireplaces and colorful Southwestern décor. Prices from $125.
Courtesy of The Santa Fe Opera House
3. Nashville, Tennessee
Why Go: Like a country star's Rhinestone nudie suit, timeless Nashville stays above all the what's hot and what's not nonsense.
What to Do: Music City is home to stars like Nicole Kidman and Jack White, whose wife, former supermodel Karen Elson, runs Venus and Mars: The Showroom (2009 Belmont Blvd.; myspace.com/venusandmarstheshowroom). This heavenly vintage boutique (left) selling men's and women's clothing. If vintage is your thing, Nashville is your place - the South district is also home to Local Honey (myspace.com/localhoneyvintage) and Savant Vintage Couture (myspace.com/savantvintage). It goes without saying that music should be on your agenda on a night out, mainly because you'll be hard pushed to find a bar that doesn't feature someone singing, strumming or both. The Mercy Lounge (1 Cannery Row; 615-251-3020; mercylounge.com) is a cool small venue to catch touring or live bands; grab a seat at the kitschy long bar and order a Yazoo. For eats, we like the rustic scene at Marche (1000 Main Street; 615-262-1111; www.marcheartisanfoods.com), where they keep things fresh, seasonal, and a bit cheaper than sister bistro and foodie's fave Margot just up the street.
Where to stay: Union Station (1001 Broadway; 615 726 1001; unionstationhotelnashville.com). This 125-room centrally located Victorian Hotel was once a train station, which makes for some very cool architectural features. Prices from $179
Courtesy of Venus & Mars
4. Washington, D.C.
Why Go: We admit the possibility of spotting First Lady and style icon-elect Michelle Obama grabbing take out from Good Stuff Eatery adds a certain appeal to D.C., but it always had its charms.
What to Do: The Smithsonian Museums are free, as are Summer Fridays nights at the Hirshhorn Museum's Sculpture Garden (left), where you can kick back with a local crowd -and a bottle of wine - and enjoy the live jazz. Come evening, try the mezze at Zaytinya, a jumping spot run by Ferran Adria protégé José Andrés. H Street is home to the cooler bars and clubs, like Dr. Granville Moore's Brickyard (1238 H St. NE; 202-399-2546; granvillemoores.com) for a Belgian beer in cozy surroundings, and the Rock n Roll Hotel (1353 H St. NE; 202-388-7625; rockandrollhoteldc.com) for live music, a fun crowd, and inexpensive drinks. For shopping, Nana (1528 U St. NW, at N 15th St., 202-667-6955; store.nanadc.com) is a funky little boutique selling new and vintage clothing, and it won't break the bank if you succumb to temptation.
Where to stay: Donavan House (1155 14th Street N.W.; 202 737 1200; www.thompsonhotels.com). This luxe 193-room hotel has spacious rooms with a retro vibe and a sexy rooftop pool. Summer deal (July 5 through September 8), $499 for 2-night stay, plus $100 food credit.
5. Minneapolis, Minnesota
Why Go: Design gurus will appreciate the city's impressive architectural additions of late.
What to Do: Check out the work of starchitects like Herzog and de Meuron's expansion to the Walker Art Center (go Thursdays 5-9pm for free admission), Jean Nouvel's Guthrie Theater, and César Pelli's Central Library - even Frank Gehry made his mark here pre-Bilbao with the Weisman Art Museum. Then there's the natural wonder of all those lakes to sail on or walk around smack bang in the city. Just across from the Walker, the Minneapolis Sculpture Garden is fun, arty and free (725 Vineland Pl.; 612-375-7622; garden.walkerart.org/index.wac). Try Grand Avenue in St. Paul for cool independent stores, and for food it's got to be pasta and meatballs at 112 Eatery in the warehouse district (112 North Third Street; 612-343-7696; 112eatery.com), a foodie haunt minus the foodie prices. Come nighttime, take advantage of the rooftop bar at the trendy Chambers Hotel. If you're looking for a local scene, you'll find it in the bars and clubs in the Northeast, 331 Club is 'always free - no cover!' (331 13th Ave.; 612-331-1746; 331.mn/home.php).
Where to stay: Hotel Ivy (1115 Second Ave. S.; 612-746-4600; starwoodhotels.com). The 136 plain but comfy rooms with spacious marble bathrooms in this 1930s building offer bang for your buck. Prices from $144.
6. Savannah, Georgia
Why Go: Consider that Savannah was far enough away from the media glare for Mandy Moore and Ryan Adams to get hitched in, yet hip enough for them to even consider, and you'll start to get what this place is all about.
What to Do: There's a thriving arts scene, helped in no small way by Savannah's College of Art and Design (left). And on that note, ShopSCAD (340 Bull St.; 912-525-5180; shopscadonline.com) is the place to go for one-off pieces - artwork, clothes, jewelry - by past and present students. Adventurous types prepared to leave the historic downtown can eat well and frugally at Desposito's crabshack (1 Macceo Dr.; 912-897-9963) on the edge of town. Come evening, watch the sun go down over the islands and marshes at the Bonna Bella Yacht Club (2740 Livingston Ave.; 912-352-3133; bonnabellayachtclub.com). Just try to ignore that you're drinking out of a plastic cup.
Where to stay: Marshall House (123 E Broughton St.; 912-644-7896; marshallhouse.com). A 65-room historic hotel right in the heart of the action, with wrought iron balconies and cool rockers. From $119 (special summer rate June through August).
7. Asheville, North Carolina
Why Go: Asheville is a surprisingly bohemian mountain town nestling between the Blue Ridge and Smoky Mountains.
What to Do: Location alone means active types will be kept occupied hiking the Great Smoky Mountains National Park and kayaking and whitewater rafting on the Nantahala River. If you prefer to keep your feet dry, check out the galleries in the River Arts District that's grown along the French Broad River. The historic downtown has Art Deco buildings and a quirky selection of shops, including a restored Woolworth's with a splendid 1950s Soda Fountain. Tupelo Honey Café is a bustling little bistro with its own organic garden out back, serving a modern take on Southern cuisine (12 College St.; 828-255-4863; tupelohoneycafe.com). There's a roll call of musicians from these parts, from Nina Simone to Ryan Adams, so catch some live music too. Root Bar No.1 (1410 Tunnel Rd.; 828-299-7597) is an authentic small venue, while the Orange Peel (101 Biltmore Avenue; www.theorangepeel.net) is larger, much respected rock club.
Where to stay: Princess Anne Hotel (301 Chestnut St.; 828-258-0986; princessannehotel.com). There are 16 homey rooms in this central boutique hotel (left), formerly a historic boarding house. From $129.
8. Austin, Texas
Why Go: An oasis of hip in the Lone Heart State, Austin's music and Tex-Mex are equal staples. But while the bars, honky tonks and music festivals are the city's lifeblood, there's also the beautiful Hill Country for hiking and cycling (prepare to eat Lance Armstrong's dust if he's out training).
What to do: Cool down with a margarita and try to catch a breeze in the Lake Austin area, where Sandra Bullock owns a mansion. For shopping, South Congress Avenue is dotted with vintage clothes stores, antique wares and cowboy gear. Be there on the first Thursday of the month when the SoCo strip morphs into a street party, with late openings, food, drink and music. For something more substantial, try the classic Tex-Mex at Chuy's, it's where the Bush twins were busted a few years back for underage drinking, but don't let that stop you from ordering a second Texas Martini (1728 Barton Springs Rd.; 512 474 4452; chuys.com). Free trolleys, called 'Dillos, are a good way to get around the main neighborhoods.
Where to stay: Hotel San José (1316 S. Congress Ave.; 512 444 7322; sanjosehotel.com). This bungalow-style hotel has a cool location, happening courtyard bar, and 40 stylish rooms. Prices from $95.
9. Chicago, Illinois
Why Go: President Obama gave Chicago back some of its cool. And if that's one of the reasons why you're considering the Windy City this summer, you might want to join the free walking tour that includes the former Obama residence (leaves from Hyde Park Arts Center, Saturdays, June 6 through September 26).
What to Do:So many excellent museums, so little time - a must see is the Art Institute of Chicago (left), gratis on Thursdays, 5-8pm (111 S. Michigan Avenue, 312 443 3600; artic.edu/aic/). Spend some time at the Millennium Park, a green breathing space downtown (check out Jaume Plensa's Crown Fountain and Anish Kapoor's Cloud Gate). For edgier shopping and bars, the Bucktown/Wicker Park neighborhood is a good option. Have a drink at the speakeasy-styled Violet Hour (1520 N. Damen Ave.; 773-252-1500; theviolethour.com), where U2 held their launch party back in March. Eat at Urbanbelly (3053 N California Ave,; 773-583-0500; urbanbellychicago.com), you'll make friends at the communal tables, and the pan-asian dishes are affordable and unforgettable. While the city's mass transit system is super cheap, be aware that you can also hop on to the seasonal free trolleys.
Where to Stay: Hotel Felix (111 W. Huron St.; 312-447-3440; www.hotelfelixchicago.com). Newly reopened after an eco-friendly renovation, this 225-room property is sleek and modern on the inside, stylish 1920s on the outside. From $120.
10. Maui, Hawaii
Why Go: Never has Hawaii been so affordable for flights and accommodation. And never have you needed its white sands, crashing waves and general gorgeousness so much. Maui is the hip island that's attracted nature-lovin' souls like Woody Harrelson and good pal Owen Wilson.
What to Do: Hiking, diving, surfing, it's all here if you have the energy to get off your beach towel. For fun shopping, the Maui Swap Meet in Kahului (Kamehameha & Puunene Ave.; 808 877 3100) is a collection of stalls where you might just find a Hawaiian collectible dating back to the 1930s among the fresh veggies and kitschy tat ... if you're lucky. Eat at Mala Ocean Tavern (left; 1307 Front St.; 808-667-9394; malaoceantavern.com) for well-priced organic comfort food. And for an old school Hawaiian night out, enjoy a cocktail under the stars at Kaanapali Beach Hotel's tiki bar (2525 Kaanapali Parkway; 808-661-0011; kbhmaui.com).<
Where to stay: Paia Inn (93 Hana Highway; 808-579-6000; paiainn.com). Opened last year in the trendy North Shore town of Paia, this cool boutique has five cozy and colorful rooms. From $169.