Take a trip away this October. Check out our recommendations for what to do, where to go and what to eat in some of Cayman’s favorite overseas destinations.

New Orleans, Lousiana

Culture: It is the month of All Hallow’s Eve. Make like Anne Rice’s Vampire Lestat in the once-flooded city and kick off a trip with a wander around the beautiful tombs of St. Louis Cemetary. Creole grandees such as the voodoo priestess Marie Laveau are laid to rest in this oldest existing cemetary in the city.


Shopping: Exodus Goods in the French Quarter features indie fashion and lifestyle brands, as well as local fragrances and graphic print clutches. Instant hipster status.

Food: There’s no substitute for a real New Orleans po’ boy and Parkway Bakery and Tavern is known for the best. Get it fried or risk looking like a tourist or, much worse, a vegan.

Cocktails: The Old Absinthe House in the French Quarter serves the eponymous liquor in out-of-the-box ways. Try the Absinthe Frappé for a frozen take on the classic.

Must Do This Month: During the summer, one of New Orleans’s greatest treasures Audubon Park, located in Uptown, is a favorite spot for recreation and picnics. Visit “the Levee,” a spot locals visit to lay out and picnic by the Mississippi River. See online for directions.


Cambridge, Massachusetts

cambridge-massCulture: In the city of bright minds, the prestigious campus of the Massachusetts Institute of Technology (M.I.T.) is Mecca. Stop in the Mark Epstein Innovation Gallery, a space designed to celebrate the quirky culture of the school with robots and holograms.

Shopping: If you want to blend in with the locals, you should be carrying a tome of either the classic or trending variety. Revolution Books is a hole-in-the-wall shop run by the Revolutionary Communist Party selling a wide variety of both.

Food: The prepsters all brunch and the more eclectic, the better. Chinese-style tapas fits the bill at East by Northeast, where crispy pork belly and kale dumplings with carrot puree are on the menu.

cambridge-mass-mitCocktails: For serious mood lighting and classic cocktails, visit Cuchi Cuchi. Order the Pendennis Club Cocktail, a mix of gin, apricot brandy, lime juice and Peychauds bitters.

Must Do This Month: Take a short drive outside the city to Salem and celebrate Halloween in the town famous for its 1692 witch trials, which saw the execution of several locals under suspicion of practicing witchcraft. See online for information.



Madrid, Spain

Culture: At the epicenter of Spain, Madrid’s elegant boulevards and manicured parks make for a stylish getaway. Treat yourself to the extensive collection of European art at the Prado Museum with works by Goya, Velázquez and other Spanish masters.

Shopping: Invest in beautiful handmade leather at the shops at La Portegna, where purses, travel slippers, iPod covers and laptop skins are fashioned from the finest materials by local crasftmen.

Food: At Sala de Despiece, a personal waiter will take you on a flavor tour, showing you how to make fresh tapas dishes like porterhouse roll-ups with thin slices of raw steak, flakes of sea salt, fresh crushed tomatoes and truffle sauce.

Cocktails: With culture, architecture and climate creating the perfect trifecta, Madrid is the place for rooftop cocktails. The Penthouse at the ME Hotel and the Urban Hotel both boast beautiful views of the city.

Must Do This Month: Take advantage of beautiful weather with an “art crawl.” Start off at CaixaForum Madrid and end at La Fábrica Gallery with a delicious café con leche and fresh tostadas at the on-site café. See online for details.



Singapore, Southeast Asia

Culture: This thriving financial hub combines the best of the East and West. Rent a single-speed French city bike on Robertson Quay and tour the city’s own Chinatown, circa-1820, where the red and gold Tooth Relic Temple of Buddha makes for a perfect photo opportunity.

Shopping: While you are in Chinatown, take a stroll down to the Maxwell Road Hawker Centre, a partially open-air market where an eclectic array of crafts from Asia and India awaits. The fabric stalls in Little India are particularly dazzling.

Food: Singapore is home to some of Southeast Asia’s best street food, so explore at your will. Tian Tian Chicken in Hawker Centre is famous for its version of Hainanese chicken rice, a local favorite.

Cocktails: Long Bar at Raffles Hotel is your next stop. As the birthplace of the famous Singapore Sling, this hotel is a historical hot spot for celebrities like Ernest Hemingway and still draws travelers from across the world.

Must Do This Month: Take in the city from atop the Singapore Flywheel, one of the world’s largest observation wheels. See a stunning view of Marina Bay, with just a glimpse of neighboring Malaysia and Indonesia. Visit www.singaporeflyer.com for details



Toronto, Ontario

Culture: Unlike many city destinations, Toronto’s multi-cultural atmosphere is still alive and thriving. Stroll Kensington, where shops filled with Mandarin and Cantonese speakers sell books, gourmet coffee and vintage records.

Shopping: Toronto is a multi-cultural shopping hub, known for attracting indie creative brands. Visit The Future of Frances Watson where the vintage-inspired one pieces and classic denim never go out of style.

Food: The Foxley Bistro may be tiny but chef Tom Thai brings big flavor. Try their wild ceviche selection, including Arctic char with apples and ginger or sample sea bass with Asian greens and white truffles.

Cocktails: Go eccentric with your drink and head to Northwood for one of the most creative menus in the city. Think tea-infused cocktails, such as the Lady Grey Sour, a combination of Earl Grey, Rye, citrus and black pepper

Must Do This Month: This fall, The Art Gallery of Ontario will host “Mystical Landscapes: Masterpieces from Monet, Van Gogh and more,” exploring the mystical experiences of 36 artists including Claude Monet, Paul Gauguin, Vincent van Gogh, Wassily Kandinsky and Georgia O’Keefe. Visit www.ago.net for details.