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If you find yourself on Middle Caicos, don’t miss one of the most dramatic shorelines on the islands, along Mudjin Harbor. The three-mile-long stretch has tall limestone cliffs that drop directly into the water, interspersed by sandy coves. The ocean here is often too rough for swimming or snorkeling, but there are excellent walking trails, including the historic Crossing Place Trail that provides great views of the coastline. Mudjin Harbor also has two large sea caves that you can explore from the beach.

The Chicago River and Lake Michigan are two of the city’s greatest assets, and there’s no better way to experience both than with an architectural boat tour. While there are plenty of reliable options around, go with First Lady Cruises, which calls upon expert docents provided by the Chicago Architecture Foundation to reveal extensive history, culture, and style insights (for example, how the design of Willis Tower was based on cigarettes, or how the Monadnock Building on Jackson Boulevard was fabricated with 100 different shapes of brick). Book anytime between May and November for these rides, which run every day of the week and last 90 minutes.

I love visiting big iconic bridges during the sunset. Trips at dusk to the Golden Gate Bridge and the Brooklyn Bridge have resulted in spectacular photographs of the urban landscape. The Sydney Harbour Bridge was another great experience! The bridge is accessible by foot or by bike and is surrounded by some of the biggest attractions in Sydney. More adventurous types might opt for the Bridge Climb Tour (http://www.bridgeclimb.com/) where participants get to scale the summit of the 134-meter arch for panoramic views of the city. And yes, they offer a Twilight Tour near sunset (and a dawn tour at sunrise). We were content walking across the bridge on the pedestrian walkway. It was a brisk spring evening in Sydney, and we didn’t envy the tourists climbing the bridge overhead. The views from the bridge are stunning in every direction, and it is a magnificent vantage point to see the Sydney Opera House and the Central Business District.

This French-style bistro is a perennial favorite for locals, who come here for breakfast, brunch, dinner, or just drinks. The menu has a Scandinavian focus with some international offerings—hence regular dishes like catch of the day and a hearty fish soup can be found alongside high-quality steaks, club sandwiches, and moules marinières. Lunch specials keep the place busy during the week, and the weekend brunches are a big draw too. The bar’s offerings are equally balanced, with a range of beers, wines, and cocktails as well as fresh smoothies. Pleasant service, a classic, upmarket interior, and a generally convivial atmosphere conspire to make this bistro a great all-rounder.

The longest beach on Little Exuma is a stunning stretch of powder-white sand that is officially called Pelican Beach but more commonly called Tropic of Cancer Beach because it sits directly on the Tropic of Cancer latitude line—the dividing line between the subtropics and the tropics. This navigational line is marked on the pavement atop the stairs leading to the beach. Even without it, the beach would be well worth a visit—it’s often empty of visitors, and the calm turquoise waters and gently sloping, white-sand seafloor make it a great place to swim and sunbathe.

The Marine Room faces the Pacific Ocean and is the only place in San Diego where you can eat great food in a cozy atmosphere while the surf pounds the glass. Don’t even bother coming here unless it’s during high tide. When you visit San Diego- just check the tide charts and then call the Marine Room to reserve your breakfast spot during high tide. They do an elaborate buffet and I was actually impressed at the quality of food. There’s something for everyone. The set up is buffet style, but the food is definitely not! From wild caught salmon to pastries to breakfast meats- there’s something for everyone. Recommended: Definitely check the restaurant website before reserving your seat. And definitely reserve a seat!

When Charleston’s Blind Tiger opened in the late 1980s—long after Prohibition ended—its name, a phrase synonymous with “speakeasy,” lent the Broad Street bar a delightfully naughty air. Not that the joint needs more atmosphere. The building, which dates back to 1803, has the vibe of an old Irish bar, with big front windows, dark wood, the damp smell of years of spilled beer. But walk through the doors in back and you’ll find a tree-shaded, sun-dappled patio full of architectural ruins and kitted out with a few firepits for cool evenings. That handy backyard bar means you can stay in the fresh air and not venture inside for refills. Alas, the blissful al fresco scene is slightly marred by the inclusion of a television over the bar. (With college football enjoying nearly the same status of religion in the Holy City, only the fanciest cocktail bars can avoid having the game on in these parts).

Some find this narrow, neon-lit French Quarter street appealing, others appalling. But it’s worth a stroll either way. It’s as if all the sins of mankind and then some were rounded up and corralled here—tawdry strip shows, cheap and potent drinks, the coveting of neighbors’ wives, petty larceny, big-ass beers, bad cover bands, and so on. (Bad cover bands were not technically mentioned in the Old Testament, but to many they’re the street’s most shameful sin.) The heart of the party zone stretches eight blocks from Iberville Street to St. Philip Street, with the thickest concentration of bars on the Iberville end. New Orleans allows alcoholic drinks outside, as long as they’re in plastic cups, or “go-cups"—meaning you can roam the length of Bourbon Street with your beer or hurricane in hand.

Lanai, a sleepy, 140-square-mile former pineapple plantation, is suddenly in the spotlight. Following the island’s purchase by tech billionaire Larry Ellison in 2012, the bay-facing Four Seasons Resort Lanai underwent a multimillion-dollar overhaul that reduced the number of guest rooms from 286 to 213. The rooms shook off their dated look with mahogany floors and walls clad in slate and teak. Guests can dine at outposts of Nobu and Los Angeles–based Malibu Farm, take private flight lessons and horseback-riding excursions, or book one of the resort’s wellness-focused retreats.

Scrub Island is one place where being shipwrecked might actually be a good thing—pity that dockside boat slips abound. Located on a volcanic speck just 75 miles east of Puerto Rico, Scrub Island Resort is the ultimate tropical idyll, with a spa, marina, and three restaurants. Its 52 suites and villas sit on 230 pristine acres, complete with neutral, colonial–style interiors (think four-poster beds, marble baths with soaking tubs, and floral curtains) that intensify the ocean views. Charter a boat to explore hidden coves or test your nautical skills at the resort’s sailing school. You can always forget what you know once the time comes to lift anchor and head for the mainland.

For those who love a chicken tikka or a lamb rogan josh, Britain is a famously fulfilling destination, with some of the best Indian food you’ll find outside, well, India. The curryhouses on Brick Lane will ladle out masalas and rice until your belly’s ready to burst, but for a different take, try Dishoom, which operates in five different London locations (and Edinburgh) and specialises in the finger food of Mumbai’s Irani cafés: a fabulous array of grills and snacks, from the delicious lamb kebab to the moreish keema pav (minced lamb or chicken), served on a bun in an environment that recreates the décor of the colonial railways. If you can make it here for breakfast, the bacon naan roll or the spicy scrambled eggs are the perfect way to set up your day.

Though Belize is replete with Maya sites, including some spectacular archaeological examples that are open to the public, Chan Chich may well be the only hotel in the country that can claim to sit atop a known former Maya site. In the late 1980s, owner Barry Bowen sought and received permission from the country’s Department of Archaeology to build on the site, whose plaza was beyond repair. No doubt guests are surrounded by the spirits of ancient Maya as well as actual artifacts that remain hidden in the soil around the lodge. Accommodations are individual casitas and cabanas decorated with local art, fresh tropical flowers, and simple but sturdy furnishings. The hotel is part of the historic 130,000-acre Gallon Jug Estate, which is, among other things, a private nature preserve. Guests enjoy wildlife spotting on the property, whose staff has kept a running list of the bird species seen here: the current count tops 350 types.

You might hear Long Street before you see it—this bustling artery is the heart of Cape Town, home to some of the city’s most popular restaurants, bars, and boutiques, all within a few blocks’ radius of the Grand Daddy Hotel. Built in 1895, this landmark building has been transformed into one of the city’s quirkier havens, though it somehow manages to walk the fine line between campy and classy. It’s a spot that’s beloved by tourists and locals alike (don’t be surprised to stumble onto a local fashion shoot in the gilded Daddy Cool bar).

Behind the stately gray exterior lies a whimsical world: snuggle into crisp white sheets in one of the 26 colorful rooms or suites, or settle into a stylishly appointed Airstream in the rooftop trailer park. And speaking of the rooftop: there’s no better place to take in the view of Table Mountain presiding over the city.

The largest and most storied of the Sydney Harbour islands, Cockatoo was once an Aboriginal fishing ground, a naval shipyard, a girls’ reform school, and a gruesome prison. Today, it offers fascinating walking tours, a casual café, and a number of events such as the Biennale of Sydney. When most visitors line up in the evening to catch the ferry home, those staying on the island are just setting off on a leisurely sunset stroll. They can watch the city light up from what feels like another world and then retreat to their campsite, canvas “glamping” tent, heritage home, or modern apartment until they wake up to birds and boats the next morning.

For many, Thessaloniki is a happy alternative to the chaos of Athens. Although it’s home to just under 400,000 people, it’s the second largest city in Greece. There’s a large student population here, and so you’ll find the city busy with cafes, pubs, clubs, and restaurants. Of noteworthy mention is the iconic White Tower, built in the Byzantine period and still standing guard over the waterfront. There are a number of other Byzantine monuments around as well, including the churches of Acheiropoietos and the Heptapyrgion castle. The Old Town is worth exploring as well, which has a classically Macedonian feel to it.