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When a couple embarks on a spontaneous road trip through Italy, they rediscover the joys of unplanned adventure.

Some of the best shopping in Chicago happens in thrift and vintage shops scattered all over the city. For thrift shoppers who want a full day of searching for treasure, Wolff’s Flea Market is guaranteed to turn up some great finds. Architectural scavengers will lose hours at Urban Remains and Salvage One whereas lovers of vintage Japanese toys and go-go boots should set their GPS coordinates for Hollywood Mirror. Happy thrifting!

This hotel is on our list of The 11 Best Hotels in Chicago.

Set directly across from the Art Institute of Chicago, this former members-only men’s gymnasium is now the Chicago Athletic Association, which is part of Hyatt’s Unbound Collection. Enter at street level off Michigan Avenue and walk toward the back to find a staircase that leads to the old swimming pool, now a venue for parties and pop-up concepts. Take the nearby elevator to the restaurant, Cindy’s, easily the best rooftop scene in the city, with highly Instagrammable terrace views overlooking Millennium Park, the swooping Frank Gehry–designed bandshell, and Anish Kapoor’s Cloud Gate (aka the Bean).

Park yourself in the second-floor lobby and hang with locals as they tap away on their laptops and sip lattes by the two oversize fireplaces. Walk through that expansive by Roman & Williams–designed room, where light beams in through ornate stained-glass windows, and you enter a warren of table games and darts, all festive and typically open to the public. There’s also the secret six-seat bar, the Milk Room, a relic of Prohibition, and the James Beard Award–winning Cherry Circle Room—a sexy, dark restaurant with a circulating martini cart and a meat-centric menu.

Upstairs in the 1893 landmark, 240 guest rooms reflect the building’s former life, with gym horses as foot beds, working fireplaces in some rooms, plasterwork ceilings, ornate carved wood wainscotting, and a clubby vibe. Some of the rooms are rather small, but the location is hard to beat, and the cozy, wintry ambiance makes it a popular (and fun) place to spend a weekend. And because the CAA keeps an eye on its water conservation, sources its food locally, and adheres to strict recycling standards, eco-conscious travelers can feel good sleeping here.

Anyone visiting Philadelphia who plans to include the Museum of Art and/or the Fairmount Water Works in their itinerary should consider taking a little extra time to stroll along nearby Boathouse Row. The adventurous who have a bit more time can consider renting bikes and riding the recreational path that runs alongside the banks of the Schuylkill River. Many of the historic boathouses date back to 1860, and the last house on the row at #15, Sedgeley Club, is Philadelphia’s only operating lighthouse, built in 1887. The Schuylkill River and rowing are inextricably linked and the first recorded regatta on the Schuylkill took place in 1835. There is a regatta scheduled nearly every weekend from March through November, and to view the races you’ll need to venture a little further north on Kelly Drive, past the Girard and Columbia Bridges. For anyone who’d like to view or photograph the iconic illuminated boathouses after dark, the closest viewpoints would be either of the elevated gazebos behind the Art Museum, or the riverfront gazebo adjacent to the Water Works complex.

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.

Young and poor, but frequent-flier-mile rich, my wife and I were able to go to Corsica for our first anniversary...Staying with friends always helps...They lived in Ajaccio, (birthplace of Napoléon Bonaparte), and at sunset one evening, they took us for a drive a couple of miles to the west of the city. Dotting the island’s coast are the distinctive Genoese towers, fortifications built during the 16th century, and here is the view from one of them, from La Tour de la Parata, perched on cliffs at what feels like the end of the world...Ahh, to be newly married and in the Mediterranean...

Tour these U.S. cities by kayak for a fresh perspective.

From shopping and sailing to Michelin stars and spas, the Midwest’s biggest city has it all.

To do: Meet the dinosaurs. Swim in the river. Gorge on ice cream.

Get a glimpse of the plugged-in future on these tours.

Not many people visit Lady Elliot Island, at the Great Barrier Reef’s southern tip. But a lot of people are trying to protect it.

Sample gourmet Ukrainian food, watch a comedy show with puppets, and catch an all-ages jazz show.

This city is practically made for touring, whether you want to pedal, paddle, or stroll.

Blues music came from Mississippi to Chicago during the Great Migration, as praised in the new Michael B. Jordan film and throughout the city today.