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One of my favorite sit-down dining experiences in the city, Zelai Txiki has a couple things going for it. One is a gigantic terrace that overlooks the entire city. On a summer evening there are only a few places I would rather be. Call ahead to try one of Zelai Txiki’s specialties: whole suckling roasted pig or suckling lamb. These are roasted in a wood-burning oven and are an experience that shouldn’t be missed.

Husband and wife Isamu and Tazuye Fujita opened up Tokyo Fish Market in 1963. Since 1971 it’s been an extended family affair and the fish market, grocery store and gift shop (two different buildings on San Pablo Avenue) are fabulous places to head for lunch or dinner options. You’ll truly feel like you’re stepping into Japan and you’ll be amazed at how affordable the food is. Head to Tokyo Fish Market and know that you and your stomach, will be impressed.

Nothing says Santorini like an aqua-blue infinity pool, and Katikies has three of them—all the better to take in westward-facing sunset views. Carved out of the cliff side 300 feet above the Aegean, the hotel’s public spaces are connected by a series of bridges and Escher-esque stairways as they descend from the town of Oia above it. Cube-shaped rooms and suites are minimalist but inviting, nearly every surface painted or clothed in calming white; all have verandas, while a few large suites have outdoor plunge pools or Jacuzzi tubs and alfresco seating areas. Upon check-in, guests are given cell phones to summon 24/7 service from anywhere on the property. They use them to order light snacks at the poolside bar and restaurant or make reservations for some of the best sushi on the island at the champagne bar, but the candlelit rooftop restaurant—serving Greek and Anatolian cuisine—is about as romantic as it gets.

Owned by Terry Kaljo—a former model and founder of the Contemporary Hotels collection of upscale rental homes and villas—the Medusa Boutique Hotel offers 18 unique accommodations in Darlinghurst, an eclectic area and the epicenter of Sydney’s gay community. The 19th-century home is filled with wacky touches, from red Alice in Wonderland–style carpeting that runs up the grand staircase to pastel-pink walls studded with maple leaves in the entryway. The midcentury-modern rooms—with their retro primary colors, geometric patterns, and vintage chaises longues—attract fashion, media, and design professionals looking to get beneath the surface of one of Sydney’s liveliest neighborhoods. But there’s still the opportunity to relax, as guests can settle in next to the fireplace in the lobby to read the newspaper, enjoy a complimentary pastry, or make new friends. Longtime staff members offer the kind of local knowledge and personal attention that keeps guests coming back.

This pink-marble waterfront edifice in Piazza San Marco dates back to the 14th century, when it was the residence and seat of government for the doges (rulers) of Venice. Today the ornate Byzantine- and Moorish-influenced Gothic Palazzo Ducale is a symbol of the city, and serves as a museum hosting some of Venice’s most important art, including the famous Bacchus, Venus, and Ariadne masterpiece by Tintoretto. It also runs the popular Secret Itinerary and Doge’s Palace Hidden Treasures tours. After you’re done, treat yourself to a glass of wine in the small on-site bistro, with windows looking onto the Grand Canal adjacent to the Bridge of Sighs.

171 years crafting hats is a long time. The family behind Casa Ponsol are maestros of adorning heads, although they have since branched out into men’s fashion as well. The Basque beret is ubiquitous, and if you find yourself pining for one this is the spot to stop.

Vinos Ezeiza is a store of a dying breed. A knowledgeable owner stands among dusty wine bottles, able to answer any question you might have about his collection. Headed out to a fiesta? Bring your wineskin and fill it by volume. Buying Rioja wine in bulk is the ultimate Basque shopping experience.

Hakei began as a single boutique, but in the last five years has expanded rapidly, even crossing Spanish borders. The secret to its success? Gorgeously simple leather bags, supremely gorgeous shoes that tend toward the suede-leather persuasion, and luxe, drapey, oh-so-soft clothing for women. The price is right, too.

Among the several art galleries along Main Road in Kalk Bay, Kalk Bay Modern displays a variety of art, jewelry, fabric, photography, and pottery from several different African countries, as well as an exciting collection of the works of South African aboriginal San artists.

Seeing the Big Island by air will have you sitting on the edge your seat anticipating what will turn up around the next mountain or valley. Waipio Valley, one of the most beautiful areas on the Island, is best seen from the air to really get a perspective of the area’s vast beauty. If staying on the ground is more your style, hit the trail and do some hiking through the Waipio area or make your way to the ocean and enjoy the sound of the surf.

Rick’s is probably the most touristy spot in all of Jamaica, but there’s a reason it’s listed in 1,000 Places to See Before You Die, so don’t miss experiencing it at least once. Get there around 4 p.m. to avoid the crush of tour bus traffic that happens closer to sunset, then order a couple of cocktails—Rick’s serves up a myriad of options—and stake your claim on a prime viewing spot for the sunset and cliff-diving. Local divers swing from trees and drop into the surf or plummet from the surrounding cliffs, some of which rise more than 30 feet above the sea. Even the occasional tourist will brave the jump into the water below. A reggae band adds to the animated vibe. Lest you feel like just another tourist sheep at the sunset very-happy hour, console yourself in knowing that locals enjoy it almost as much as visitors do.

The classic, late-morning Mexican breakfast (quite good for hangovers) is typically spicy, abundant, and sophisticated in ways quite distinct from the brunches that have become synonymous with the urban weekend—think solid, cold beer instead of innovative mimosa iterations. But for one of the town’s signature Mexican breakfasts, in one of its lushest courtyard gardens, try the Yucatecan fare at La Casa del Diezmo. And if you just can’t shake where you came from, the eggs Benedict at Lavanda prove to be artistic creations indeed, akin to lotus-flower sculptures.

Good breakfast spots are on the rise in San Pedro, but one of the most beloved places to grab a bite will always be Estel’s Dine by the Sea. Aside from its perfect beachfront location where you can eat with your toes in the sand, the food is pretty darn good as well. At Estel’s, you won’t find menus on the table; you must walk inside to check out the board. Don’t be surprised to find a crowd on the weekends, especially Sunday mornings. Just follow the smell of Charles Jr.’s famous BBQ specialties cooking on the grill, and you’ll understand why people are ordering plates of ribs first thing on Sunday! Aside from some impressive barbecue, Estel’s has a number of dishes that might leave you feeling the need to return once or twice more for breakfast. Personal recommendations include the Mayan Eggs, which is scrambled eggs with tomatoes, onions, bell peppers, and sausage, served with a side of refried beans and fry jacks, or try the breakfast burrito. Don’t forget the Marie Sharps hot sauce on top! Breakfast is served all day. Closed Tuesdays.

The roots of this Mediterranean Revival-style boutique hotel go back to 1914, when a local grocer created the tropically inspired property to house his visiting vendors. Nearly a century later in 2010, hotelier and style guru Liz Lambert added the place to her mini-empire, reviving the grounds that still feature magnolia, palm, and cypress trees planted by the original owner. Set on a quiet section of the River Walk near the museum corridor, the restored building (which is on the National Register of Historic Places) houses 27 guest rooms decorated in a designer-meets-flea market aesthetic, with bright pops of color and plenty of personality. All are pet-friendly, and feature stocked SMEG fridges, Red Flower bath amenities, custom serape bathrobes, and complimentary coffee and Wi-Fi; suites have sitting areas, terraces, or other perks. Room service comes from the in-house Ocho restaurant, but it’s better to head down and eat there in person to take in the cheery setting, river views, pan-Latin menus, and cocktails that highlight rum (as a nod to Havana) and tequila (an homage to San Antonio’s Mexican roots). A regular calendar of happy hours, musical performances, and cultural events round out life at this vibrant hotel.

Situated oceanfront on Collins Avenue in the shadow of The Setai (South Beach’s tallest and most expensive hotel), Townhouse is a humble Art Deco concrete building trimmed in red with two very cool venues hidden inside, a subterranean ramen lounge and a laidback rooftop bar. K. Ramen. Burger. Beer excels in all of its eponymous categories and also serves delightful poke bowls and chicken wings, while The Cape is a surprisingly rare rooftop perch in South Beach with a laidback bungalow atmosphere playing host to live music.