Love Winter or Leave It Behind with These Vacation Itineraries

by Andrea Guthman

Planning a winter vacation? Whether you seek snow or a tropical paradise, we’ve got you covered.

Windy City & Wisconsin Charm

Named the best big city in the U.S. for seven straight years by Conde Nast Traveler, Chicago combines friendly Midwesterners with impressive architecture, world-class museums, and a thriving theater and comedy club scene. And don’t forget shopping along the Magnificent Mile.

Take a break from sightseeing by warming up at a restaurant with a fireplace, like Chicago Winery, in the bustling River North neighborhood. Ask for a table by the fire, and afterwards step inside their tasting room to sample their locally made wines. Of course, you can’t leave Chicago without indulging in deep dish pizza. Why not have it 103 floors up?! At the top of the Willis Tower (still known by many as Sears Tower) you can enjoy a Chicago classic while being stunned by jaw-dropping city views at Skydeck Chicago. This once-in-a-lifetime experience is only offered on Thursday and Friday nights at 10pm.

Foodies will get their fill of award-winning cuisine during Chicago Restaurant Week, which is actually more than two weeks of deeply discounted opportunities to experience the city’s culinary scene. It’s always held at the end of January and beginning of February.

One last must-do for a winter Windy City visit? An old factory in the West Loop’s been remarkably transformed into a luxurious, ancient Roman-style bathhouse. Soaring ceilings, exposed wood beams, and twinkling lights from candles set the scene for a serene escape from the city’s excitement at Aire Ancient Baths.

Just over an hour from the bright lights of Chicago lies Lake Geneva, Wisconsin, a small town that seems straight out of a Norman Rockwell painting. Tourists descend on downtown shops and restaurants in the summer, but the town has plenty to do in winter as well. Time your visit to coincide with Lake Geneva’s Winterfest, the first week of February, so you can observe one of the country’s biggest snow sculpting competitions.

Make Grand Geneva Resort & Spa your home base. It has a modest ski hill with three chair lifts, perfect for beginners. Grand Geneva Resort also has access to five miles of wooded trails for cross-country skiing and offers ski rentals. Kids will love overnighting at Grand Geneva’s family-friendly Timber Ridge Lodge and Waterpark for indoor aquatic fun while adults can schedule some me time with a treatment at the spa.

Chilling Out in Cancun and Cozumel

If your idea of winter bliss is toes in the sand and a drink in your hand, Mexico’s oceanfront all-inclusives are a great tropical escape. Plenty of quick flights to Cancun make it an easy choice.  Fairmont Mayakoba in Playa del Carmen, 45 minutes south of Cancun’s airport, makes for a good home base. It’s a luxurious property with five pools, including one with a water slide, surrounded by jungle and a white sand beach. Take a cooking class to learn how to make the resort chef’s recipes. If you’re really feeling adventurous, sign up for a sampling of edible insects. Dried grasshoppers, maguey worms, ant eggs, and escamoles (larvae from the chicatana ant). These insects are considered a delicacy in Mexico!

When you’re ready to explore, take a day trip to the ancient Mayan ruins in Tulum or visit a nearby cenote. These are essentially caves containing water, where the ceiling has collapsed, so it resembles a sinkhole. There are thousands of cenotes throughout the Yucatan Peninsula. Fairmont Mayakoba can even arrange for you to experience an underground classical concert in a cenote, offered a few times throughout the year.

Playa del Carmen is also home to the ferry port that takes you to the island of Cozumel, an inexpensive 45-minute trip. The bright colors and mariachi bands make the ferry port a fun experience. Try to get a seat on one of the outside decks to take in the gorgeous crystal-blue ocean views during the ride.

Cozumel’s pretty much about one thing, the ocean. If you’ve ever wanted to learn to scuba dive, stay at a resort like Iberostar Cozumel with a dive shop on property. Take an on-line course before you travel, and you can get your scuba certification in as little two days while on vacation. Not ready for the deep dive? Try snorkeling right off the beach. Simple rooms are surrounded by serene tropical gardens with flamingoes and parrots, making it feel like paradise. Families will appreciate the kids club and a pool just for children, in addition to two other pools. Nightly shows and daily activities keep everyone entertained. And if you want to go exploring off property, it’s easy to rent a jeep from the car rental agency inside the hotel.