Wisconsin Winter Getaways: Best Spring Break Cruises & All-Inclusive Resorts for 2026
Hey there, fellow Wisconsinites!
If you’re anything like me, you’re ready to trade that snow shovel for a beach towel by the time January rolls around. And guess what? You’re not alone! Every winter, our team helps thousands of folks from Milwaukee to Madison (and everywhere in between) escape the cold and head south for a warm-weather spring break.
So, where are Wisconsinites flocking to next winter? Grab your sunglasses and let’s dive into some of the most popular and fabulous destinations, from adults-only and family-friendly Caribbean cruises to sun-soaked all-inclusive resorts in Mexico and the Caribbean.
All Aboard: Why Celebrity Cruises is a Midwest Favorite
Celebrity Cruises is a top pick for our upscale couples, active retirees, and empty nesters (we see you, Brookfield and Green Bay!) Think of it as modern luxury at sea—you’re cruising through the Caribbean in serious style, sipping cocktails on an Edge Series ship, dining on meals curated by Michelin-starred chefs, and soaking in the spa life.
If you’re based in Milwaukee, Madison, or the Fox Valley and you’ve been dreaming of a getaway that blends relaxation, sophistication, and adventure, Celebrity’s Caribbean itineraries are calling your name. Oh, and pro tip? These cruises offer wellness options galore, which are perfect for kicking off the new year on a high (and healthy!) note.
Punta Cana, Jamaica & Mexico: All-Inclusive Bliss
Not a cruise person? No problem. We’ve got you covered with all-inclusive resorts that cater to just about everyone—families, couples, large friend groups, and everyone in between.
Hyatt Inclusive Collection: Luxury for Every Lifestyle
Whether you’re traveling with your kids, your sweetheart, or your besties, the Hyatt Inclusive Collection (Ziva, Dreams, Secrets, and Impression) hits the sweet spot. Families love Ziva and Dreams for their endless kid-friendly fun, while couples can’t get enough of the romantic vibes at Secrets. And if you’re ready to splurge, the Impression by Secrets line is pure vacation goals.
With resorts in Mexico, Jamaica, and Punta Cana, you’re never far from white sand, turquoise water, and next-level service. If you’re from the Milwaukee suburbs, Eau Claire, or Hudson, this one should be on your radar.
Iberostar: Eco-Friendly and Family-Focused
Our guests from Racine, Kenosha, Appleton, and La Crosse love Iberostar for its balance of value and comfort. These resorts are super family-friendly, located right on the beach, and have a strong focus on sustainability. That means you can relax knowing your getaway is a little more green.
It’s a great pick for repeat travelers who want familiar service and beachfront bliss—without breaking the bank.
Riu Resorts: Budget-Friendly & Fun-Filled
Traveling with a big group or just love a lively atmosphere? Riu Hotels & Resorts bring the fun. With resorts in all your favorite beach destinations, Riu is all about entertainment, beachfront access, and affordable all-inclusive pricing. Perfect for folks from Wausau, Sheboygan, Fond du Lac, or the Milwaukee metro who want maximum sun without maxing out their wallet.
So, Where Will You Go This Winter?
Whether you’re cruising through the Caribbean with Celebrity or sipping margaritas beachside at a resort in Punta Cana, Mexico, or Jamaica, one thing’s for sure: winter is way better when you’re barefoot and sun-kissed.
Need help picking the perfect destination? That’s what we’re here for! Our Fox World Travel advisors know all the best spots (and hidden gems), and we’ll make sure your winter escape is easy, relaxing, and full of unforgettable memories.
Bonus! This July, we are offering triple discounts and exclusive savings just for you and guess what? The sale is happening NOW! Contact one of our advisors today and lock in the savings!
Let’s plan your perfect spring break—before the snow piles up again!
