PAMROC REWINDS: Siblings Who Travel Together… and Survive the Group Chat Planning

Today, I’m looking back on some of my favorite travel memories with my brother, Jonathan—and let me tell you, every trip with him is a story. Our first cruise together was on the Sovereign of the Seas, and from that point on, we’ve been adventuring together through sunshine, salt air, and high-maintenance vacation demands.

Let’s be honest: I’m the planner. I handle the flights, the hotels, the excursions, the “what time should we be at the port” questions. Jonathan? He’s not the logistics guy. He’s the “Let me read 47 reviews before I agree to dinner” kind of guy. His role? Official vacation foodie and experience snob. He wants the best restaurant in town, the strongest coffee, the trendiest cocktail bar—and he wants to approve the vibe.

So while I’m booking the rooms and organizing the day, he’s making sure we’re not eating anywhere with less than 4.7 stars and a beautifully curated Instagram page. High-maintenance? A little. But also? That balance is what makes our trips unforgettable. I bring the structure, and he brings the flavor—literally and figuratively.

We’ve come a long way from that first cruise. Now our vacations are filled with hilarious travel moments, incredible meals, perfectly chosen spots, and of course, Jonathan’s running commentary on everything from bed firmness to bathroom tile. Every trip we take becomes a memory I treasure—planned to perfection (by me), and elevated with his extra flair.

Here’s to more unforgettable sibling escapes—meticulously planned, highly reviewed, and always filled with love and laughter.

—Pam

Want to see more? From wine tastings to resort lounging, we captured it all! Follow us at PamRoc Lifestyle on Facebook 🔵 and @PamRoc_Lifestyle on Instagram for all the island vibes, cocktail magic, dreamy hotel stays, and nonstop travel inspo.