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Caffe degli Specchi has a wonderfully warm feeling inside, so it’s easy to feel comfortable sliding up to the bar and standing with the locals while you drink your morning cappuccino. Or, take your time enjoying your drink on the wooden porch out front while overlooking the crowds moving towards work in the small piazza below. Either way, the coffee here is rich and dark, so make sure you ask for ‘zucchero’ if you like yours slightly sweeter!

If you didn’t know before you dug into your meal, you might not realize that every item on Sage’s menu is vegan (a nice bonus for parents eating with kids). The jackfruit or tempeh tacos are so good many devoted carnivores choose to get their Mexican food fix here over local nonvegan Mexican joints. Sage also makes excellent vegan burgers, potato flautas, and salads filled with great crunchy textures and pops of flavor. Follow lunch or dinner with a slice of coconut cake or vegan birthday cake ice cream.

With its 26 suites, private beach, and two waterfront bars, Calabash Cove offers a boutique hotel alternative to the typical all-inclusive experience. Set a stone’s throw from the turquoise waves of Bonaire Bay, the sprawling, Balinese-inspired Water’s Edge cottages are the ones to book thanks to private plunge pools, outdoor rain showers, and patio hammocks positioned to highlight superb sunsets. The resort’s remote location ensures tranquility, as does the spa, which offers in-room treatments using ingredients sourced from St. Lucia’s floral and culinary bounty. That abundance is also on display in the Windsong restaurant, where local dishes get an elegant twist (octopus tempura, smoked coconut crème brûlée) in a terrace dining room with the ultimate ocean backdrop. Follow your meal with a brief walk down Calabash Cove’s small boardwalk and stop to spot shooting stars in the dark skies above.

There are a handful of appealing options in the West Loop, but the most exciting is the Hoxton Chicago, whose laid-back lobby is filled daily with locals and guests working, meeting, dining, drinking, or hanging out with a coffee. Part of the socially focused Hoxton hotel group that launched in London’s East End in 2006, this 182-room hotel has become the West Loop’s top rendezvous spot for meetings (unless you’re a member of nearby Soho House), but upstairs is just as enticing. We love “Flexy Time,” which allows guests to check in and out whatever time of day they like, so long as they book directly through the hotel website.

Hello, rooftop pool! Leave it to Chicagoans to remain optimistic that summer will be amazing, even if winter lasts well into May. The rooftop pool (open to restaurant as well as hotel guests), occupies a prime spot on one corner of Six Points, that crazy intersection where three major shopping streets cross paths. That means the regulars are a mixed bag, but all come in for a good time, whether that means for brunch in the newly redesigned Café Robey street-level restaurant, to drink until dawn at the poolside Cabana Club bar, or to sneak up to its new sister, the Up Room, at the top of the deco tower.

Mylopotas beach is a stretch of sunny beach lined with bars, restaurants, hotels, and a youthful party scene. Depending on the day or time of day this stretch of beach could be quite and lazy in the sun or have music and people dancing on cars. Either way Karma beach bar is a chill open air bar with pillow seating on the raised floor and hammocks hanging everywhere. The pizza is delicious and perfect for a light beach snack on a sunny day. They have a great drink menu including island cocktails and prosecco fruit mixers. We lounged our first day away in the hammocks here sipping on cool drinks.

This 7.5-mile round-trip walk has some of the most amazing coastal views in Sydney and is a great introduction to the city’s Eastern Suburbs. Starting from Icebergs pool in Bondi, the path hugs cornmeal-sand coves, natural seawater pools, a marine reserve (Gordons Bay) that’s great for snorkeling, and unique attractions from ancient Aboriginal rock art sites to the oceanview Waverley Cemetery. In late October, site-specific art installations pop up along the cliffs between Bondi and Tamarama beaches as part of the Sculpture by the Sea exhibition, one of the largest outdoor sculpture events in the world. Spring (September through November) is also an excellent time to see migrating southern right whales spouting in the sunset. Toast your trek with a drink at the Coogee Pavilion.

Jade Bar regularly tops the local “Best Of” lists for places to drink. It’s a modern, cocktail-focused bar with sips like the Old Fashioned Whiskey, bourbon, simple syrup, bitters and citrus oils, and the Honeydew Liverthump made from gin, fresh lemon and honeydew juice, and sliced cucumbers, among other things. It’s the kind of place where bartenders are called mixologists and it actually means something. For a drink with a view, take it outdoors to Edge, the fashion-forward patio bar that juts out just below Elements restaurant.

The mercury during summer afternoons can hit 34C (or around 95F). How to stay cool during the hottest time of the day (4-6pm)? Besides seeking shade or air-conditioning, Santiaguinos seek solace in a traditional drink called “mote con huesillos.” Huesillos, sun-dried peaches, are cooked with water and a touch of sugar. The liquid and fruit are chilled and served with a scoop of toothy golden barley. Mote con huesillo is sold by vendors throughout downtown. More than a drink, it’s a satisfying, healthy snack.

Tree-Guys Pizza Pub is a great place to stop in for a pie and a beer. With the usual array of pizza choices, there’s no shortage of great eats right at your fingertips. Connected to the pizzeria is Hi-Fi Lounge (the pub) where you can belly up to the bar on any given night and sample their daily drink specials. From draft beers, to Bloody Marys, to choice tequila, there’s no shortage of libations at this local watering hole. Come for some pizza, stay for some drinks—the Tree-Guys insist.

A 100-foot schooner based in Bequia, The Friendship Rose takes passengers on daylong cruises to Tobago Cays for snorkeling and swimming with sea turtles, or Mustique for beaching, bar hopping, and relaxing. Excursions include breakfast, lunch, afternoon tea, and drinks throughout the day, including beer, fruit punch, and soft drinks. Whether you opt for the marine park or the private island, the entire family is sure to enjoy the experience.

One of my highest recommendations for drinks is the Grand Hyatt Shanghai. The Grand Hyatt occupies the top 36 floors of the 88-story Jin Mao Tower in the Jetsons-looking Pudong district, so at sunset (or anytime) you have a stunning view (with no cover charge!) of all of Shanghai. There are lots of choices for eating and drinking in the Grand Hyatt. When I was there at sunset, nobody else was in the Cloud 9 sky lounge (which is like a night club with a 360-degree view from the 87th floor), so I went down to the 53rd-floor Lobby Lounge, which still seemed plenty high, and enjoyed the view and the cocktails there.

You can only drink two martinis at the hotel bar at Dukes Hotel in Mayfair. The bartenders won’t serve you any more—that’s how potent they are. This is the place to come in London if you secretly wish you were a member of a gentlemen’s club, and if you want a martini made with all the fanfare—the drinks trolley brought to your table, the bottle, straight from the freezer, shaken as you sit and watch. There are cheaper places to drink, that’s for sure, but do they have green leather armchairs and white-jacketed bartenders and portraits of distinguished 19th-century gentlemen looking at you approvingly from the walls? There’s also a cognac and cigar garden.

Belize’s liveliest time of the year comes in September, when the entire country celebrates independence for three entire weeks leading up to Sept. 21. The major towns and cities host various events, and a countrywide calendar is published on Sept. 1, allowing you to follow along with the fun wherever you might find yourself in Belize. The most popular events are a steel pan concert called Pan Yaad, held in Belize City, and two full-blown carnival parades. Belize City Carnival, with soca and Caribbean music blaring, is held in mid-September, while Orange Walk Carnival takes place on Independence Day and celebrates Mestizo heritage. Take advantage of low-season fares to get a unique culture-filled experience in Belize in September.

Barefoot Bar is a place that’s known for just that: bare feet. Located on the shores of the Caribbean Sea, Barefoot is a Placencia staple where locals and visitors mingle, drink, and eat great Belizean food. The bar is known for the lobster grilled cheese—a huge grilled cheese sandwich stuffed with catch-of-the-day lobster. Buy two: one to eat now, and another to bring home for later. Barefoot also makes perfectly crispy salbutes, which are a great tacolike light lunch to go with your $3 drink special.