And if you’ve ever tried to snag flights, hotel rooms, or resort packages in November or December, you know last-minute planning is the fast track to frustration, sky-high prices, and limited choices. That’s why now, while the summer sun is still shining, is the time to start thinking about how you want to spend the season.

For many of my clients, holiday travel is no longer about squeezing everyone into one house with air mattresses in the living room. These days, families are scattered across cities, states, and even countries. Meeting somewhere new not only makes travel fairer for everyone, but it also turns the holiday into an adventure. And makes connecting with family feel even more special.

Connecting With Family This Holiday Season

Here are three of my most-requested holiday travel styles and why you should start planning your holiday vacation today.

Theme Park Magic While Connecting with Family

If your idea of holiday joy includes twinkling lights, festive music, and an atmosphere so full of excitement you can practically taste it, a theme park getaway might be for you. Picture this… Walking down Main Street, U.S.A. at a Disney Park, surrounded by garlands, towering Christmas trees, and the scent of fresh-baked holiday treats. Parades with dancing reindeer, nighttime fireworks, and seasonal shows add an extra layer of magic.

Universal Studios offers its own holiday flair. The Wizarding World of Harry Potter blanketed in festive décor and Grinchmas celebrations that will have the whole family laughing. Yes, the parks are busier this time of year. But the extended hours, special events, and once-a-year atmosphere make it worth it. Just remember, holiday theme park vacations sell out fast. So, August is the sweet spot to lock in your spot.

Check out which holiday towns are perfect for connecting with your family. 

Ski Slopes & Snowy Memories

For families who’d rather trade sandals for snow boots, a ski vacation offers the perfect mix of activity and cozy downtime. I work with partners who have a portfolio of breathtaking ski resorts across Europe. From charming chalets in the French Alps to mountainside retreats in Switzerland.

And with the resorts in Canada, you could be sipping hot cocoa by the fire one day and tasting fresh maple taffy made right on the snow the next.

These all-inclusive ski resorts often bundle ski passes, lessons, equipment, gourmet meals, and après-ski fun into one package. That means more time for connecting with family. Whether you’re gliding down the slopes together. Exploring local winter markets. Or simply gathering around a crackling fireplace with a board game. And no one has to wash dishes.

Luxury ski resorts in the US for your family vacation. 

Sun, Sand, & Stress-Free Days While Connecting with Family

Of course, maybe your perfect holiday escape involves zero snow and zero schedules. For many of my clients, the answer is a week at an all-inclusive beach resort. Imagine trading sleet for sunshine. Waking up to ocean views. And spending your days snorkeling, lounging by the pool, or indulging in spa treatments.

Holiday beach vacations often feature festive touches. Think gourmet Christmas dinners with tropical twists. Live entertainment under the stars. And even visits from Santa (in swim trunks). Whether you’re toasting with a glass of champagne on New Year’s Eve or watching your kids build sand “snowmen,” these trips deliver a completely different kind of holiday magic.

Check out these family friendly Thanksgiving travel tips! 

The Time to Plan is Now

Whether you dream of snow-dusted mountain towns, roller coasters and parades, or a beachside holiday brunch, the most important step is starting early. Flights fill quickly. The best resorts book months in advance. And prices only climb as the holidays approach.

If connecting with family is at the top of your wish list this season, I can help design a holiday trip that’s personal, stress-free, and exactly what your family needs. My job is to handle the details so you can focus on the fun and start making memories before you’ve even left home.

Let’s start planning now, so when the holidays arrive, you’re not stuck scrambling. You’re already packed, ready, and excited for the most meaningful gift of all. Time together.