Booking the Trip You Actually Want

The Case for Planning Early

With September right around the corner, you may feel that there’s still plenty of time left in 2025. But before the fall festivities and holiday traditions take over your calendar, let me encourage you to think ahead—way ahead.

If you’re considering a major trip in 2026, now is the time to start planning. Early booking isn’t just about peace of mind—it’s about securing the best pricing, availability, and experiences. Let’s break down what that looks like for cruising, custom Europe trips, and theme park vacations.

Cruising: Ocean, Luxury, and Yachting

Cruises are one of the few vacations you can book years in advance (SeaDream already has itineraries through 2028!). That may not be typical, but it proves a point: the earlier you book, the better your options.

Cruise pricing works on a tiered system—cabins start at lower rates, then climb as inventory fills. Sure, promotions pop up occasionally, but those aren’t guaranteed. And even if a promo surfaces later, we can often apply it to your existing booking. What can’t be changed? Getting stuck in an interior stateroom when you dreamed of a suite with a balcony.

Early booking means first pick of the best cabins, concierge-level perks, and access to small vessels that sell out quickly in the luxury and yachting space.

And if you book through me, you’ll also unlock extra perks through Travel Leaders Network’s Distinctive Voyages program. These sailings—on lines like Cunard, Celebrity, Regent Seven Seas, Princess, Oceania, Seabourn, and Explora—come with exclusive benefits like a complimentary shore event, a welcome reception, and sometimes even shipboard credit. My fellow foodies can dive into the Culinary Collection itineraries, designed with gastronomy in mind.

👉 Below is a quick teaser video – Ask me if you’d like the full catalog!

Custom Europe Trips

Europe is one of those destinations where waiting too long can cost you—literally.

Take one of my clients headed to Munich this year: we secured their hotel room in March for Oktoberfest. By July, the same room had more than doubled in price. Planning early isn’t just smart—it’s essential.

For boutique experiences, limited capacity is a major factor. Think châteaus in the French countryside, family-run villas in Italy, or restored castles in Germany. Those elevated stays don’t have endless availability—you’ll want to be choosing from the best, not what’s left over.

And it’s not just hotels. Tours and experiences often sell out, too. For example, tickets to the Anne Frank House open six weeks in advance and disappear quickly! Without a plan in place, you could fly all the way to Amsterdam and miss out on what matters most.

Let’s not forget about entry requirements. While most European countries don’t require short-stay visas for Americans, new regulations are tightening. The UK now requires an electronic travel authorization (ETA), and the Schengen Zone is expected to implement ETIAS by the end of 2026. It’s ideal to have someone watching the fine print so your dream trip isn’t spoiled by paperwork.

Frauenkirche in Nuremberg on a bright fall day
Nuremberg’s Frauenkirche in the old town

Disney & Universal Vacations

Closer to home, Disney and Universal trips are every bit as time-sensitive—especially if you’re planning around school breaks or holidays.

Think: summer vacation, Thanksgiving, Christmas and New Year’s, spring break, or even long weekends around national holidays. Add in special events like Mardi Gras, Mickey’s Not-So-Scary Halloween, EPCOT festivals, and holiday parades, and the crowds multiply fast.

Booking early doesn’t just secure your spot—it gives you better access to premium accommodations. Want a room overlooking Magic Kingdom’s fireworks? Or club-level service with extra perks? Those disappear quickly. And if a promo comes out later, we can often apply it to your existing reservation.

Another thing to keep in mind: the parks are constantly evolving. Rides close for refurbishment, new shows debut, and major openings (like Universal Orlando’s Epic Universe) draw huge crowds. Planning with plenty of lead time helps us build your trip around what’s open, new, and can’t-miss.

Cinderella's Castle in Magic Kingdom at night during Mickey's Very Merry Christmas Party
Cinderella’s Castle during Mickey’s Very Merry Christmas Party

To Wrap It Up

At the end of the day, planning early doesn’t just save money—it saves stress. It lets you focus on enjoying your time away, confident that you’ve got the best rooms, cabins, and experiences locked in.

That said, if your travel plans are sooner, don’t panic—I can still help. Last-minute cruise deals pop up, tickets to Europe are always possible, and Disney still sells park passes. It just means we’ll shift into “fast-track” mode to make it happen.

But if you’re dreaming bigger for 2026, now’s the perfect time to start. That way, when you’re raising a glass on New Year’s Eve, you’ll already know the adventures waiting for you in the year ahead.

Headshot of Joy

✨ Ready to start planning? Let’s talk about your 2026 trip today.

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