Winter Wanderlust for Chicagoans

Gray winter skies have you wondering why you live in Chicago? Me too. So instead of giving in to the urge of sweatpants and Netflix, I’ve been giving celebrating my winter wanderlust and planning a vacation. We tend to stay in Chicago for Spring Break and instead take a trip to soak up sunshine in the winter when the duldrums are hard to shake and the vacation prices are MUCH lower. Need some inspiration for your family’s winter wanderlust? Here are some of my family’s favorite Winter Wanderlust Locations for Chicagoans:

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Winter Wanderlust Option 1—San Diego

From the moment we stepped off the plane, my family and I soaked up the California way of life. Fish tacos and fresh sea air was just what we needed to shake our winter blues and seriously consider a family move to San Diego. Seriously. It was that fantastic.

What makes San Diego so special? The moderate weather makes it perfect for visiting any time of year, the environment encourages a healthy and active lifestyle for residents and tourists alike, and just about everything is family friendly.


Favorite things to do in San Diego:

Midway Museum (on a real life aircraft carrier!)

San Diego Zoo and Safari Park (discounts here)

La Jolla Seal Beach for observing and swimming depending on seal activity

Old Town for shopping and authentic Mexican cuisine


Where to Stay:

Coronado Home Rentals

Legoland Califronia Resort

Coronado Island Marriott Resort


Travel tips:

Book a direct flight and a car so that you can drive the scenic roads in and around San Diego, as well as travel to all of the different neighborhoods for meals, shopping, etc.


Winter Wanderlust Option 2—Turks and Caicos

Looking for a place to totally relax (even though your kids are there)? Then put Turks and Caicos on your winter vacation list. Grace Bay boasts the title of one of the most beautiful beaches in the world and it also has the third largest barrier reef systems to delight snorkelers and scuba divers. If you are looking for a relaxed and unplugged vacation, Turks and Caicos is perfect for your family.


Favorite things to do in Turks and Caicos:

Snorkeling or scuba diving at Smith’s Reef

Beach combing at off-the-radar Governor’s Beach

Nature Walks at Little Water Cay


Where to Stay:

Blue Haven Resort (all inclusive)

Ocean Club Resorts

Seven Stars Resort and Spa


Travel tips:

Book an American Airlines direct flight from Chicago and a mangrove tour for when you are visiting the islands!


Winter Wanderlust Option 3—Caribbean Disney Cruise

As I’ve shared on the blog before, my family isn’t really Disney crazy. But that changed once we enjoyed the STELLAR service on our Disney Cruise last winter. It was one of the best vacations we have ever taken because there were TONS of things to do, from raiding the ice cream machines to watching movies while floating in the pool and of course, the crown jewel…spending the day on Castaway Cay. Click here for my full review.


Favorite things to do on a Disney Cruise:

Character meet and greets

Poolside movies and games

Getting all decked out for Pirate Night

Castaway Cay, Disney’s private island


Where to Stay:

The boat. Duh. Spring for a room with a window (balconies are fantastic, too!) to ease any potential sea-sickness and enjoy the view while you cruise the Caribbean.


Travel Tips:

I can’t recommend a Disney cruise highly enough, especially if you book through a travel agent who can help you with complimentary “extra special touches” for your family.


Winter Wanderlust Option 4—Puerto Vallarta

Spoiler alert: My family and I haven’t visited Puerto Vallarta YET. We will be heading out next month on a family friendly adventure across the border and I cannot wait! I did learn a ton about what Puerto Vallarta has to offer thanks to the Puerto Vallarta tourism board and learned that it is a foodie destination and perfect for active families looking for some fun in the sun.


Favorite things to do in Puerto Vallarta:

Strolling El Malecon

Playa Los Muertos

Vallarta Food Tours

Whale Watching Tours


Where to Stay:

Hilton Puerto Vallarta (this is where we are staying next month!)

Marriott Puerto Vallarta Resort and Spa

The Club at Sheraton Buganvillias  


Travel tips:

Typically when we travel to Mexico we book through a resource such as Apple Vacations where everything is included. If you are looking for people to take care of the details while you sit back and enjoy, I highly recommend that route.

Be sure to check out my tips for navigating Chicago’s airports and my family travel checklist before you take off!

Bon Voyage!
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  1. Rachel says

    All of these sound amazing. We have done the San Diego trip and it was great. It was of course a heat wave in Chicago while we were there, but we still loved every second of it.

    • Amanda says

      I feel like renting your own car is always a better option when you are traveling with kids, too. That way the car can be home base for when the unexpected happens while out and about.

    • Amanda says

      Not gonna lie, the Disney cruise made me really happy, too. Everything was taken care of so mama actually got to relax!

    • Amanda says

      We just did a whale watching tour in Cape Cod last summer and it was incredible. I would love to try whale watching in a more tropical locale!

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