There’s something magical about spending the holidays somewhere warm. Imagine palm trees wrapped in twinkle lights, ocean waves rolling in like background music, and the scent of coconut sunscreen instead of pine needles. This year, my family is trading stockings for swimsuits and heading to Royalton Splash Punta Cana, An Autograph Collection All-Inclusive Resort & Casino in the Dominican Republic.

Our group is quite the mix. We have three adults and my mother-in-law. There is also one nineteen-year-old who is not quite a kid but not fully an adult either. We also have two children who probably can power the resort with their energy alone. It promises to be an adventure filled with laughter, a few eye rolls, plenty of sunscreen, and countless happy moments in between.

I’ve been deep in planning mode, checking passports, organizing packing lists, and mentally preparing for the juggling act that comes with traveling with multiple generations. I already know there will be moments of pure joy, a few challenges, and more than enough stories to share once we’re back home.

Here’s what I’m anticipating and how I’m hoping to make it special.

1. Traveling with Multiple Generations

This will be our first international trip with such a wide age range, which means I’m expecting equal parts sunshine, laughter, and “let’s all take a deep breath.”

My mother-in-law thinks she loves all the excitement with the music, the bustle, and the activities, but when the noise level rises or plans shift, she can get a little overwhelmed (and maybe just a touch cranky). My goal is to include her in moments she’ll love while making sure she has quiet spaces to unwind.

Royalton Splash has several pools, shaded lounge areas, and a laid-back coffee bar where I can already picture her sipping a cappuccino and people-watching while the rest of us zip down water slides. If she’s relaxed and content, the whole trip will run smoother. Trust me, this is the key.

2. The Tricky Nineteen-Year-Old Stage

Ah, the in-between phase. Too old for kids’ clubs, too young for the the cocktails. My goal is to make sure there’s still plenty for him to enjoy, including water slides, excursions, and maybe a little friendly competition on the beach.

My hope is that he finds that sweet spot between joining in the family fun and having his own downtime. With any luck, he’ll leave with both a tan and a few good memories that don’t involve me reminding him to put on sunscreen.

3. Christmas Away from Home

This will be our second Christmas away from home. Last year we spent the holiday on a Disney cruise, and it was pure magic. From Mickey in a Santa hat to carolers in the lobby, every detail felt straight out of a storybook. There was even hot cocoa served on deck while we watched fireworks under the stars.

This Christmas will have a new kind of sparkle at Royalton Splash. Picture warm breezes, waves in the background, and a tropical cocktail called “Santa’s Sunset.” To keep a little piece of home with us, I am bringing a few festive touches so the day feels both special and familiar.

Here are a few of my ideas:
• Mini stockings for everyone
• A few wrapped surprises for Christmas morning
• A playlist of our favorite holiday songs
• Maybe even matching swimsuits instead of pajamas

We’ll celebrate differently this year, but that’s the beauty of it. The holidays aren’t about where you are, but who you’re with and how you make the moment your own.

A Little Holiday Flashback

Last Christmas Eve on the cruise, my youngest insisted on leaving cookies for Santa… in the middle of the Caribbean. We set them out next to the mini Christmas tree we had managed to fit in our luggage with a note that said, “Dear Santa, we’re somewhere near the Bahamas.” The next morning, the cookies were gone, replaced with chocolate coins. To this day, she swears Santa found us at sea.

This year, I can’t wait to see what memories we’ll make under the palms instead of the pines.

As the trip gets closer, I feel a mix of excitement, curiosity, and that familiar pre-vacation buzz that comes from counting down the days to something special. Will it turn out to be the picture-perfect tropical Christmas I’m picturing, or a little chaotic, a little sandy, and perfectly imperfect in the best way? Probably both, and honestly, that sounds just right.

Either way, I’ll share all the details in Part Two: From Planning to Paradise: The Real Story of Our Tropical Christmas

✨ Let’s Chat About Holiday Travel

Have you ever celebrated Christmas away from home? Would you rather spend the holidays in cozy winter weather or somewhere sunny with your toes in the sand? Share your favorite holiday travel memories or tips for navigating multi-generational trips in the comments below. I’d love to hear from you.

And if you’re dreaming of your own holiday getaway, I’d love to help you plan it. Together, we can plan your perfect getaway filled with laughter, sunshine, and maybe a few chocolate coins from Santa too.

Because whether it’s palm trees or pine trees, the magic of the holidays is what we make of it.