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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.

Don’t let Portland’s low-key, outdoorsy-hipster vibe fool you: the Heathman Hotel is as grown-up and refined as they come. Opened in 1927 as an expansion of one of the city’s grande dame hotels, the Heathman continues to set the standard for classic luxury in the City of Roses. Rather than rest on its laurels, though, the hotel has consistently upped the ante, collecting a museum-worthy array of modern art (including a handful of Warhols alongside works by acclaimed local artists), boasting one of the most impressive collections of autographed books in the world, and offering guests a choice of mattress in the sumptuous rooms. Indeed, so famously decadent and romantic is the Heathman, with its award-winning restaurant and almost-nightly live jazz in the bar, that it was used as the setting for several of the rendezvous in E.L. James’ infamous Fifty Shades of Grey—although, for most guests, the original crystal chandeliers and marble fireplaces inspire magic enough.

Eat dinner like a conquistador at Restaurante Sobrino de Botin. The combination of its central location off Plaza Mayor and its claim to be the “Oldest Restaurant in the World” makes it charming and fun for family and friends. Make sure to put in a reservation in advance and order a traditional dish. I particularly enjoyed the incredibly thin jamon because it was light and not oversalted.

Located in Buffalo’s booming Theatre District, Buffalo Proper is a great place to stop before or after a show. Guests can look forward to nearly 30 specialty cocktails, plus seasoned bartenders ready to mix all the classics. Favorites include the BFLO Bramble (vodka, blackberries, mint, lemon) and the Bare Knuckle Boxer (whiskey, lemon, honey, and strawberry), but there’s also beer and wine should cocktails not be your thing. While the two-story, lofted space is massive, it fills up quickly on weekends, so go early to secure your spot at the bar or one of the high-top tables. Then, put in an order for your favorite drink, along with elevated bar fare like Japanese-style fried chicken, white bean burgers, and grits with crème fraîche and cheddar.

With a nickname like the “Cave State,” Missouri certainly isn’t short on impressive caverns. Of the more than 6,000 across the state, however, Meramac Caverns is the largest—and stays open year-round for tours. Said to have been a hideout for the outlaw Jesse James in the 1870s, the seven-level, 4.6-mile-long natural wonder was purchased by Lester Dill in 1933 and opened as a tourist attraction in 1935. Today, visitors can take guided tram tours past the cave’s complex mineral formations, stopping at a “wine room” (named for its grape-like botryoids and accessed by a long stairwell). While exploring, keep your eyes peeled for the resident tricolored bats that call Meramac home.

Kenya‘s first board-game café. like many great spots in Nairobi, is hidden away—in this case, on the 8th floor of an office building. If anything, Bao Box’s location is actually a boon because the altitude offers fabulous city views, and its seemingly random location adds to the completely fun vibe of the place. Walls are stacked high with all the famous board games like Monopoly, Settlers of Catan… and some lesser-known gems including one bluntly named “Fact or Crap.” Whatever your board-game poison, here lies something for you. The decidedly non-corporate decor is funky and outdoorsy with blankets and colorful cushions on pallets. A simple menu of burgers, chips, beers, wines, and soft drinks will satisfy peckish players.

A Good Year, starring Russell Crowe and Marion Cotillard, was shot in Cucuron, just 35 miles north of Aix-en-Provence. While the medieval town hasn’t had many celebrity sightings since, it stills draws visitors with its exquisite Michelin-starred restaurant Le Petit Maison. Here, the weekly set menus—each available with wine pairings—come courtesy of chef Eric Sapet, who worked for 11 years in renowned Paris restaurants like the three-Michelin-starred Tour d’Argent. Ranging from wild shrimp bouillabaisse with chanterelle mushrooms to roast duck breast with peaches, his dishes are something to be savored, especially when enjoyed in La Petite Maison’s elegant dining room, which charms with old-fashioned woodwork, Renaissance tapestries, and period tiles.

A labor of love from local brother-and-sister owners Joe and Catherine Bartolomei, this six-acre, farmhouse-style resort in Sonoma County’s Russian River Valley underwent an $8 million renovation in 2015, adding nine light-filled rooms with four-poster beds and fireplaces. The Spa at Farmhouse, modeled after a vintage stable, has double-height ceilings and pine doors for each of its four treatment rooms. The thoughtful details will win you over: a glass of wine at check-in, an attentive staff at the Michelin-starred restaurant, and fresh-baked cookies at turndown.

At the foot of the Rialto Bridge with fantastic views of the Grand Canal, Osteria Bancogiro sits under the archway of the Bancogiro (a bank founded in 1600) from which the tavern gets its name. Here, you’ll find a ground-floor wine bar serving carefully curated varietals by the glass and bottle, as well as stellar crostini cicheti choices like salumi and cheese, warm octopus and eggplant, and shrimp curry risotto. There are also blockbuster canal views from tables on the stone terrace in front. Upstairs, surrounded by brick walls and vaulted ceilings, the stylish dining room offers a full menu of intriguing, modern Venetian dishes, including cocoa fusilli with boar ragù and a flavorful sea bream fillet.

Surprisingly, great cocktails and an ocean breeze can be hard to find in San Diego, which makes JRDN at the Tower23 Hotel somewhat of an anomaly. It may be a scene—there are bouncers at the door, and the 70-foot-long wave wall would be more at home in Miami—but the wind-protected patio is practically on the boardwalk, offering great views of Crystal Pier and surfers catching waves. On warm evenings, drinks like the cava-based Raspberry Sparkler and the spicy chili-mango margarita make the experience even sweeter. JRDN’s happy hour (Mondays–Fridays, 4 p.m.–6 p.m.) offers discounted beer, wine and sake and coincides with the sunset for much of the year, making it a prime time to score a seat outside.

A quick bus ride from the city (or a refreshing end to the Bondi to Coogee Coastal Walk), Coogee Pavilion is one of the most happening beach bars in Sydney. The downstairs area is home to a wood-fired pizza oven, oyster bar, juice stall, and kids’ zone with giant Scrabble, pétanque, ping pong, and nautical books, while the breezy rooftop features four different bars, outfitted with love seats and wire-frame stools for taking in the breathtaking bay views. Aussie wines and beers plus fruity cocktails shaken with house-made juice pair with Mediterranean-themed tapas like chargrilled lamb chops and blistered Padrón peppers.

Mole Creek Karst National Park, along with the surrounding Tasmanian Wilderness World Heritage Area, offers subterranean streams and pools, plus at least 300 caves. At Marakoopa Cave, you’ll feel as though you’re in mother nature’s planetarium—the walls are lit up by Australia’s largest colony of glowworms. Caves like Honeycomb and Westmorland are best explored during a half- or full-day trip with Deb from Wild Cave Tours. Unlike most guides, she holds a PhD in speleology. But if one day is not enough, make it a wild caving weekend to progress from walking and wading to scrambling and squeezing through tight crevices. Local beer and wine await you at Mole Creek Guesthouse.

Located across the way from Half Moon Resort, Sugar Mill Restaurant is set on the grounds of an old plantation. Couples and small groups dine at candlelit tables either on a covered terrace or out on the lawn, and the splashing of the mill’s waterwheel and the chirping of crickets are an accompanying sound track to the top-notch service and Caribbean fusion menu. Order a bottle from the well-stocked wine cellar, visible as you enter the restaurant. For special occasions, a private table beside the waterwheel can be reserved. (In the mood for a lighter, slightly more casual meal? A tapas menu is available in the restaurant lounge.)

This is a peaceful spot to land when you want to soak up the tranquil breezes off the Chesapeake Bay. Head down south and enjoy a quaint stay in this hopeful little town still showing forth the glory of its historic roots. Grab a bicycle from the Hope & Glory Inn’s bike stand and head on over to their namesake vineyard. Taste a few of the delicious wines and dine at the Inn’s restaurant where the grub gives ‘country’ food a new meaning.

Before taking the train to Rome, we picked up a spread of antipasti at Peck, a vast and pristine food shop in Milan. In addition to a huge selection of cheeses, fruit, salumi, and bread, Peck sells prepared specialties like meatballs, potato croquettes, and caprese salad.