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In 2011, one of Chicago’s most popular restaurants, Longman & Eagle, expanded into an inn with the creation of six rooms. The owners, two of whom run the music venue Empty Bottle, built and outfitted the whole place. Each of the rooms is different, but all are stylishly simple and feature details such as wood floors, exposed brick, original art work and site-specific installations by local artists, cassette players with mix tapes, well-curated minibars, and Aesop toiletries. For the noise averse, the hotel reminds potential guests that the rooms are located above “an occasionally raucous, whisky-fueled tavern.”

A popular hangout, Kits Beach—as the locals call it—faces English Bay, and in the summertime it buzzes with beach activities. Volleyball players and Frisbee tossers mingle with sun worshippers, windsurfers and skim boarders. For sand-free dips and swimming lessons, there’s a heated saltwater pool that’s open when weather permits. Also in the vicinity is the Boathouse Restaurant, which serves peel-and-eat shrimp, tasty chowders and fresh grilled fish on a patio with panoramic views.

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.

The ire of Mount Kilauea reforges the world before visitors’ eyes. Nicknamed “the World’s Only Drive-In Volcano,” it’s produced serious lava every day since 1983 with no signs of stopping. Pele—the fire goddess who lives here, according to Hawaiian lore—is on a roll. Occasionally the lava flows spill into the sea, releasing stunning plumes of steam. Don’t miss the petroglyphs, lava tube, lush rain forest, and more than 150 miles of trail, including the four-mile Kilauea Iki loop. The drive here from Kona or Kohala can take two and a half hours, a bit of a long day, so consider reserving accommodations in the town of Volcano. You’ll have plenty of time to explore this otherworldly landscape, and even see the lava glowing in the dark!

Declared one of the best clubs in the world by the Grey Goose–sponsored World’s Finest Clubs, Le Palace is everything you’d expect from the brand. Glitzy and glamorous from the moment you drive down Hivernage’s palm-fringed, villa-lined avenue to get there to sipping champagne at the mirrored bar. It’s the latest project of local entrepreneur Nouredine Fakir, who with this opening proves that he’s made it. Clubby, sophisticated, and peopled with international and Moroccan players on the see-and-be-seen circuit—formal evening attire is expected—Le Palace is a riddle of intimate lounges and dining rooms that ooze a nonchalantly laid-back sort of sophistication. Full-time deejays, cigar bars, a packed restaurant serving dishes such as the signature Crying Tiger steak ensure that once firmly ensconced within its gilded chamber, you too will feel like you’ve made it.

Rio lacks São Paulo’s strong Italian traditions. Perhaps that’s why some of Rio’s best pizza in fact comes from there—like Pizzaria Bráz, if you can judge by critics and mad-crazy crowds that pack into this spot on the Jardim Botânico district’s liveliest street. The pizzas start as a thin, wood-smoked dough and then are topped with mozzarella and a sauce made from a careful selection of tomatoes, and sometimes involve elaborate toppings that add up to capreses, the classic Braz, or even more daring recipes like those with wild-game cold cuts. Appetizers, too, keep ’em coming back (pão de linguiça, a divine sausage bread, for example); and you’re served a capital chopp at your table or even as you wait in line at the door.

Here you’ll find all manner of steaks and chops, sides and beverages, but if you’re looking for the ultimate Brazilian cut, ask for a picanha ao braseiro, a two-person portion, seared on both sides in its own juices (let them know if you need it more well-done). It comes with fried potatoes (best served à portuguesa, i.e., round and crunchy), broccoli-rice salad and farofa (manioc meal) plus bananas and a (you guessed it) fried egg. It’s the kind of celebration that calls for free-flowing beer. Even when you’re satiated, leave room for dessert: fried plantain and sweet-cream ice. Look around to see the line is as long as when you arrived—now it all makes sense.

The carefully curated inventory of this shop across from the Hotel le Sirenuse is pretty much perfect, starting with a line of signature scents, L’Eau d’Italia, which evokes the magic of Mediterranean summers. Among your sublime choices are drinking glasses with swirls of color, made by the famous Venetian glassblower, Carlo Moretti; plates handmade in Milan by the owner’s sister, Costanza Paravicini; sophisticated beach cover-ups, the chicest bikinis, and bespoke swim trunks. In short, beautiful things sold in a beautiful space in one of the most beautiful destinations in Italy: Be prepared to want every single item.

It is all about farm-to-table cuisine at Primo, where two-time James Beard Award–winning chef Melissa Kelly hangs both her toque and her garden shears. Behind the restaurant, in a Victorian house on the Rockland–Owls Head town line, are acres of pastures and organic gardens. Be sure to allow time to visit with the chicken and pigs, buzz by the beehives, ogle the greenhouses, and admire the produce, edible-flower, and tea gardens. Make reservations for the intimate and elegant Parlor dining rooms, or head to the upstairs Counter Room and Bar, where the menu highlights pizza, cheeses, and charcuterie, and tapas-size portions. The flavors are Mediterranean with a Maine accent. Don’t miss the house-made breads or desserts, either.

Housed on a 1,100-foot stretch of beachfront, Grace Bay Club is as stylishly current as it was in 1993, when it became the first luxury hotel to open on the then nearly empty sands of Grace Bay. From its original 21 rooms, the upscale property has grown to 82 suites, each of which features ocean views, a private veranda or patio, and chic interiors by renowned designer Thom Felicia. Guests can also look forward to superior service, including a personal concierge available day or night via a provided cell phone.

When hunger strikes, there’s the oceanfront Infiniti Restaurant & Raw Bar, which boasts sea-to-table fare and the longest bar in the Caribbean, as well as several other family-friendly venues, including The Grill. If it’s pampering you seek, make time to visit the spacious Anani Spa, where you’ll find six treatment rooms, including one just for couples. A spa tent is also available for beachfront massages.

Small enough to get around without being overwhelmed, the Musée d’Orsay is a favorite stop in Paris not just for its size but for its collection of Impressionist, Postimpressionist, and art nouveau art. Perfectly set in the center of the city, on the banks of the Seine, and opposite the Tuileries Gardens, the museum is housed in the former Gare d’Orsay, a railway station that was built for the Universal Exhibition of 1900—so the building itself could be seen as a work of art. The extraordinary collection spans art created in the period between 1848 and 1914.

This local institution has (miraculously) survived Mykonos’s transformation from 1970s boho-gay hideaway to glitzy playground of oligarchs and supermodels. There’s no website, no phone, not even a sign outside the tiny shack above Agios Sostis Beach, but the secret is out. Go early as the lunch queue starts forming long before the place opens around 12:30 p.m. Savor a free glass of rosé and conversations with strangers while you wait for a table, the aroma of pork chops sizzling on the grill stoking your hunger. (Mykonos cognoscenti get their teenagers or nannies to wait in line while they go for a swim.) Octopus, prawns, chicken, and chops are chargrilled to perfection, accompanied with zingy salads and baked feta, eggplant, and potatoes. Kiki’s closes when the food runs out, between 5 p.m. and 7 p.m.

Spend the night nestled under the Golden Gate Bridge in the most dignified of accommodations: the former living quarters of high-ranking officers in the U.S. Army. Cavallo Point is the result of the luxurious reimagining of a cluster of military lodges located within the Golden Gate National Recreation Area, just over the bridge in Marin County. Today, the 142-room hotel serves as a retreat for in-the-know travelers and locals looking for an easy, elevated escape from everyday city life. Original brick fireplaces and beamed ceilings mingle with modern finishes and furnishings, such as butter-soft leather sofas and whitewashed Adirondack chairs. The expansive grounds are meant to be explored on foot or bicycle. The Wellness Weekend package includes all meals, prepared with an emphasis on health at Murray Circle restaurant, morning yoga classes, guided hikes, a spa treatment, nightly wine receptions, and plenty of free moments to soak in the serene meditation pool—the very best kind of boot camp.

Built in the 1930s as a private villa, this boutique hotel was renovated in 2012, but still makes guests feel as if they’re staying in someone’s home. Perched on a steep hillside across the bay from the Old Town, it features stone terraces, vine-covered pergolas, and colorful gardens, all of which offer breathtaking vistas of the Adriatic and Dubrovnik’s signature tiled roofs. The 13 rooms—all but one with sea views—have high ceilings and arched windows lined with white shutters to soften the afternoon sun, while modern bathrooms come stocked with plush bathrobes and decadent Bulgari amenities. When not enjoying their daily delivery of fresh fruit or cookies, guests can head to the bathing platform at the bottom of the stone stairs, the outdoor pool at the neighboring Grand Villa Argentina, or the spa at the Hotel Excelsior.

Since 1862, fresh flowers and plants have arrived by barge from the Dutch countryside to Amsterdam. While this assemblage of flora still shows up daily, it comes by van, not boat, to the Bloemenmarkt, the world’s only floating flower market. Here, you can browse 15 fragrant stalls on houseboats permanently moored on the Singel. Now the best-known flower market in Holland, this colorful attraction is packed with tourists on sunny weekends. Still, it’s a great place to pick up Dutch tulip bulbs in a plethora of shades and varieties, as well as many other types of bulbs, seeds, cut blooms, and houseplants. Ship a bag of bulbs home, or grab a souvenir at one of several shops hawking T-shirts, mugs, clogs, Dutch cheese, and other fun and inexpensive gifts.