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  • Vilano Beach, FL 32084, USA
    North Florida’s beaches hardly get the attention of those farther south or on the Gulf of Mexico. But there’s a lot to love about this laid-back surf community just north of St. Augustine’s busy historic district. The beach’s steep drop-off makes little waves jack up nicely, so Vilano is a favorite with surfers—especially on the incoming tide, when the waves are best. And Porpoise Point, on the southern end of the beach, is a great place to cast a line into the surf and fish. Facilities at the beach include parking, showers, pavilions that can be rented for gatherings, and picnic areas.
  • Donostia-San Sebastian, Gipuzkoa, Spain
    When someone tells me they’re traveling to Spain and looking for recommendations, San Sebastian (Donostia, in Basque) is my first thought for city destinations in the northern part of the country. It’s charming, beautiful, and steeped in history. Mount Urgull, the hill that stands on the right side of the bay, epitomizes all those characteristics in one easy to explore package. Mount Urgull is an easy walk from anywhere along the Promenade, and you can either walk up from Parte Vieja or walk around by the aquarium and the point to see views of the Bay of Biscay. I’ll recommend that you start with the second way and, coming back down, drop right into Parte Vieja. That way you get the best of both.
  • 60 South Shore Road, Paget PG 04, Bermuda
    Crashing waves serve as the soundtrack to your stay at Elbow Beach, situated on 50 lush acres along Bermuda’s rose-hued southern coast. Decorated with exposed beams, tiled floors, and neutral color schemes, the spacious cottage-style rooms are the portrait of coastal elegance—think coral-emblazoned throw pillows, wicker benches at the foot of the beds, and ocean or garden views through French doors. Polished-pebble paths lead the way to the spa, which offers treatments inspired by local ingredients, from a ginger-and-coconut scrub to a hibiscus bath. Grab a rum swizzle in the lounge, relax by the curving perimeter of the pool, or snorkel, swim, and kayak at the hotel’s private beach. You might also prefer to hit the pavement: Elbow Beach is mere minutes from the capital of Hamilton, Gibb’s Hill Lighthouse, and four 18-hole championship golf courses.
  • 1621 Polk St, San Francisco, CA 94109, United States
    There are plenty of fancy doughnut shops. You know the type, the ones that count bacon or basil in their ingredient list. But if you’re looking for an old-school bastion of fluorescent lights and pink boxes full of fried dough, this is the spot. A family-run joint that has supplied prework breakfast and postbar bingeing since the 1960s, Bob’s draws a crowd day and night for the fresh doughnuts made from scratch. Bob’s bakes all the nostalgic favorites: glazed, chocolate, sprinkles, sugar, and fresh apple fritters, and crumb-topped doughnuts. You might also notice a giant doughnut in the window. Like a dare, this doughy beast invites you to take Bob’s Big Donut Challenge. Finish the beast within three minutes, and you’ll get your money back plus a Bob’s Donuts T-shirt and bragging rights, not to mention an inevitable stomachache.
  • 420 E Hyman Ave, Aspen, CO 81611, USA
    Shopping is not only for humans in Aspen. Your dog should be spoiled with gifts too, especially if you left them at home for the trip. There is no better place for that than C.P. Paws. Look for their sandwich board sign on Hyman Avenue walking mall and walk down the alley. If your dog is with you they will generally sniff it out and lead the way. This is not your ordinary pet shop. Sure inside they have the toys, treats, coats, dog beds, leashes and collars but they have so much more. Get a hand painted dog bowl with your dog’s name or maybe you need a coffee mug with the breed of dog you have to let everyone know you love your pup. Everything is of a high quality and very stylish. Steve, the owner, and his faithful companion, Baxter, are there most days and will gladly help find the right accessories for your loved one. I bought a harness for my very lovable “Marley and Me” yellow lab that was pulling me everywhere and he helped me fit it to her and he even special ordered the perfect color. Your dog might forgive you for leaving them if you bring them back something good.
  • Shop #10, 26, Hope Rd, Kingston 10, Jamaica
    When in Kingston, make time for a stop at Devon House, a grand 1891 Georgian mansion that was built for George Stiebel, Jamaica‘s first non-white millionaire. The lovely upright house and its 11 surrounding acres are now protected as a National Heritage Site, but that doesn’t mean that there’s not fun to be had. The sprawling grounds include shops, restaurants, a bakery, and a popular ice-cream shop, I-Scream. House tours can be arranged, but the grounds, landscaped with stately palms and fountains, are the highlight—it’s a great spot to take a stroll, read, shop, or dine. The mansion and its manicured lawns are also used for weddings and lavish events.

  • 1500 Reynolds St, Key West, FL 33040, USA
    Key West doesn’t have many swimmable beaches, but this elegant 1920 oceanfront resort sits on the largest private one in town—an 1,100-square-foot strand punctuated with tall palms. While the shoreline itself is on a rocky shelf, a long dock extends out to the shallows for laps and snorkeling. Just off the beach, two large pools are set into green lawns and lush landscaping in front of the Spanish-style main building, which is on the National Register of Historic Places. The hotel’s wooden coffered ceilings, arched entryways, red-tile roofs, and other key architectural details recall the hotel’s glamorous heyday, while the clean, refreshed rooms are entirely modern, with sleek wood-framed beds, white linens and curtains, and ocean views. Children under 16 stay for free and babysitting is available for adults who want to take a break at the Spa al Mare, which has an open-air cabana right on the sand for al fresco massages and treatments.
  • 6757 Washington St, Yountville, CA 94599, USA
    In the Napa Valley—and in Yountville, in particular—most hotels err on the side of sophisticated luxury. Which makes the North Block Hotel’s quirky style such a breath of fresh air. With the look of a Mediterranean town’s cobbled street, complete with lemon trees and hand-painted tiles, one of Napa’s few modern boutique hotels also displays quirky pieces like The Big Book of Boobs in its lobby. It’s hard to pass through the lobby without having a friendly concierge hand you a glass of bubbly, and the umbrella-shaded “sidewalk” tables seem like places you’d actually while away the hours over bottles of good wine with good friends. The trendy restaurant channels a midcentury Italian cool that’s more Fellini than Michelangelo, unlike most Napa wineries’ inclinations, and the fact that it doesn’t have a Michelin star is actually a vote in its favor in sometimes stuffy, star-saturated Yountville. Of course, the spa is still as luxuriously pampering as any in wine country, and the understated rooms are as decked out with designer amenities as they ought to be—and you might actually be having enough fun to enjoy them.
  • Wilson Road, Punta Gorda, Belize
    Formerly Belcampo.

    Each of the 16 rooms at Copal Tree Lodge is a spacious villa-style suite set on the edge of the jungle, which gives a sense of privacy and peacefulness. Guests shouldn’t be surprised to see coatimundi, agouti, and other wildlife while showering in the spa-style bathrooms with their floor-to-ceiling windows. Tile floors, comfortable beds wrapped with gauzy mosquito nets, and private verandas are standard in every suite, as is Wi-Fi and complimentary laundry service, and the hotel has a pool and a restaurant/bar. The numerous outdoor activities include exploring Copal Tree Lodge’s chocolate trail and kayaking or canoeing on the Rio Grande River at the base of the property; various trips can be organized off-site, too. The hotel is closed from mid-September to late October.
  • 6-chōme-11-1 Roppongi, Minato City, Tōkyō-to 106-0032, Japan
    In recent years the construction of Roppongi Hills Mori Tower and Tokyo Midtown has made Roppongi a high end shopping destination. Tokyo Midtown and Mori Tower combine art and fashion. Tokyo Midtown tauts stores like Pleats Please Issey Miyake, Boss Orange and museums including 21_21 Design Sight and The Suntory Museum of Art. While Mori Tower has The Mori Art Museum, and designer shops including Alexander McQueen, Diane Von Furstenberg, and Kate Spade. Both complexes have a rich assortment of traditional Japanese restaurants and global cuisine. Sukiyabashi Jiro Sushi is the Roppongi Hills sushi restaurant run by the son of Takashi Jiro, Tokyo‘s famous sushi chef featured in Jiro Dreams of Sushi.
  • This unassuming two-story plaza has become a popular Friday- and Saturday-night hangout for 20- and 30-something locals. In addition to its shops, Plaza Paseo Cobá is home to several restaurants and bars with a trendy, bohemian vibe that’s far removed from the beach area’s bump and grind. Feast on artisanal Italian at indoor-outdoor Casa Sofia, or dance to live music at the Public Place.
  • 3 Vickers Street
    A bright space in Darwin’s Parap neighborhood, Nomad Art Gallery emphasizes limited-edition prints and collections produced by contemporary Australian Artists as well as Aboriginal art centers around Northern Australia. The focal point is cross-cultural collaborations between artists and master painters and etchers. In addition to the prints shown in exhibitions and sold online and through the shop, visitors can purchase textiles, books, and small sculptures.
  • Stortingsgata 28, 0161 Oslo, Norway
    Norway Designs is a haven for all designer buffs. There are several floors which specialize in different concepts; paper goods, object d’art, women’s wear and accessories, furniture, you name it, they’ve got it covered. The brands are mostly Norwegian and Scandinavian, and the shop has been promoting Scandinavian art and design since 1957. Looking for an artsy piece to bring back home? Look no further!
  • Via di S. Sebastiano, 6, 16123 Genova GE, Italy
    If you come to Genoa in late winter, you will have to deal with many cool and rainy days. BUT, you will get the privilege of shopping the amazing (i.e. 40/50% off) sales. So it’s a toss-up! If you are looking for women’s clothing, Lo Spaventarasseri has beautiful, artisan options in a lovely calm environment - perfect for trying clothing on after the holidays of overeating!
  • 23 Eagle St, North Adams, MA 01247, USA
    North Adams has many galleries, shops selling vintage items and plenty of restaurants. The street art popping up around every corner reminds you that many artists are at work in the warehouses that make up much of the city. The efforts to preserve this former mill town are evident on the brick walls of buildings where an international collection of artists have taken their brushes to the streets.