Trying to find an expert Holiday Vacation Travel Agent in Milwaukee, WI, to help make your next trip smooth, special, and totally worth it? That’s what we’re here for at Me and The Mouse Travel. Whether it’s Universal, Disney, or something in between, we’ll plan it from start to finish.

Don’t wait—request your free quote and let our agents help you plan something unforgettable. Reach us at 1-855-764-2539 to speak with a Milwaukee, WI, holiday vacation travel agent.

Running out of time? Whether it’s Christmas week or a surprise New Year’s trip, we’ve made last-minute magic happen before—and we’ll do it again.

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Learn more directly from our travelers and their guestimonials.

Why Work with a Holiday Vacation Travel Agent?

If you’ve ever booked too late or picked the wrong week, you know how fast holiday plans can fall apart. That’s why families in Milwaukee, WI, trust Me and The Mouse Travel. Check out our Holiday Travel FAQ to get started.

We’re officially certified to plan Disney Cruise Line vacations and Universal Studios trips—taking the guesswork out of planning and adding more fun to the mix.

We’ve done the homework on peak crowds, price dips, and limited-time holiday deals, so your Milwaukee, WI, travel plans land right where they should—stress-free and full of magic.

Zero added fees. Full-service planning. Our holiday vacation help is completely free, with personalized guidance every step of the way.

Our agents have been there—and they share real advice, tips, and experiences on our travel blog.

What You Get When You Book with an Expert Milwaukee, WI, Holiday Travel Planner

  • Expert Advice: Get insider tips from real experiences—not reviews. Our holiday travel agents know how to help Milwaukee, WI families make the most of their trip.
  • Personalized Itineraries: We customize everything—flights, resorts, activities—to make your holiday trip seamless.
  • Time-Saving: Let us do the legwork so you can focus on the fun parts of the trip.
  • Exclusive Deals: Our partners give us exclusive rates you won’t find scrolling the web.
  • Stress-Free Planning: Skip the overwhelm—we manage the details from start to finish.
  • Last-Minute Help: Trip curveball? Our agents are ready to pivot with you.
  • 24/7 Backup: Travel support that sticks with you from planning to touchdown.

Our team helps families plan magical holidays to the places we know best—including Walt Disney World, Disney Cruise Line, and Universal Orlando. These are four of our most-requested styles of travel.

Milwaukee, WI, Holiday Travel Planners - Free Vacation Quotes

What Kind of Holiday Vacation Fits Your Family?

Some families want the magic of castle lights and character hugs. Others want beach breezes or holiday cruises. Our Milwaukee, WI, holiday vacation travel agents will help plan a trip that fits. Here are four of the top styles we book.

Parks

Seasonal overlays, themed entertainment, and a serious dose of magic—parks like Disney World, Disneyland, and Universal Orlando go all-in for the holidays. Ideal for families of any size.

Cruises

Themed shows, deck snow, and tree lightings—Very Merrytime Cruises with Disney Cruise Line turn the holidays into a floating celebration. We also plan seasonal trips with Royal Caribbean and Viking River Cruises.

Resorts

Prefer your holiday with more spa time and fewer lines? Aulani or Disney’s seasonal resorts offer plenty of cheer without the rush. Some cruise stops also bring that same resort-like escape to your itinerary.

  • Castaway Cay: A Disney-exclusive island with soft sand, calm water, and plenty of space to relax—plus a few magical extras like Dole Whip and themed cabanas.
  • Lookout Cay: A fresh take on island cruising—celebrating Bahamian culture, natural beauty, and limited-access excursions only Disney can offer.

Beaches

Rather sip something fruity under a palm tree? Sandals and Beaches Resorts deliver beachfront holiday cheer with none of the stress.

Want to spend the holidays exploring the world? We plan family cruise vacations to Grand Cayman, Mexico, and Europe where adventure meets comfort.

Which Holidays (and Milestones) Are Best for a Family Vacation?

Yes, holiday vacations are popular—and yes, they can be overwhelming. But we help families get it right every year with less stress and more magic. Trust Me and The Mouse Travel to help you plan your next getaway. Free quotes available.

Big celebrations, better weather, or just a break from routine—these travel windows are family favorites for a reason:

  • Thanksgiving: Want turkey without the dishes? A resort or cruise gives you the feast minus the cleanup.
  • Christmas: Holiday travel demand peaks here—early planning gives you the best shot at stress-free magic.
  • New Year’s: Sparkling skies and stress-free escapes make this a favorite for families ready to reset.
  • Spring Break: One of the smartest times to go—prices and crowds are still on your side.
  • Fall Break: Lower crowds and great weather make this a hidden gem for Disney or Universal vacations.
  • Graduations: Big moments deserve big rewards—think cruises, resorts, or park adventures.
  • Long weekends: Make the most of quick breaks with a park visit, beach stay, or resort getaway.

Think of this as your gentle push to make new memories—not just meals. Let’s plan something great.

Holiday Vacation FAQs

When should I start planning a holiday vacation?

Want to travel over the holidays? Plan ahead—6 to 12 months ahead, ideally. You’ll get the best picks for rooms, flights, and holiday extras like parades, parties, and character events.

Are the parks or cruises too crowded during the holidays?

They’re busy for a reason—holiday events are some of the best of the year. We’ll help you navigate the crowds with efficient plans and tips that make your trip feel like a breeze.

What should I pack for a holiday trip?

Pack for comfort, celebration, and a little sparkle. Bring a jacket, photo-ready outfits, and a few holiday items to make it feel special. We’ll send a personalized checklist to keep it stress-free.

Do cruises or resorts do anything special for the holidays?

You bet. Holiday sailings and resorts don’t just decorate—they transform. Expect themed menus, limited-time shows, and festive fun at every turn. We’ll help you land the experience your family’s after.

Is it worth traveling over Christmas or New Year’s?

While holiday vacations tend to be more expensive and crowded, they also deliver once-in-a-lifetime moments. If it’s on your wishlist, we’ll help you plan it right.

What if we want to celebrate the holidays while away from home?

From mini light displays to custom in-room décor, it’s easy to keep the holiday spirit alive on vacation. We’ll help you choose the best resort and festive add-ons for your family’s style.

Other trips and destination vacations we plan for Milwaukee travelers include:

These are just a few of the destinations our Milwaukee, WI, holiday travel agents help families explore every season.

Why Me and The Mouse? | Vacation Travel Agents for Milwaukee Families

Your next holiday trip starts here. Grab a free quote or send us a message to talk to our Milwaukee, WI, Holiday Vacation Travel Agents—or call us direct at 1-855-764-2539.