How do you plan an anniversary trip that feels truly meaningful?
What makes an anniversary trip feel meaningful?
It's rarely the most famous restaurant or the most expensive suite. It's the feeling of being seen as a couple. When I design an anniversary journey, I ask about your story first: where you've traveled together, what you still talk about, what you never seem to have time for at home. Those answers shape everything else.
Should we go somewhere new or return somewhere special?
Both can be beautiful. A new place gives you a shared first, something that belongs only to the two of you. Returning to a meaningful place, like where you honeymooned, lets you see how far you've come. Sometimes the best answer is both: a return to somewhere you love, followed by somewhere neither of you has been.
How far ahead should we start planning?
The earlier the better, because an anniversary has a fixed date. Popular seasons, small ships, and the most beautiful rooms often book well in advance. That said, reach out whenever you're ready; I'll always tell you honestly what's possible.
How do you add special touches without it feeling staged?
The best touches feel effortless. A room with a view of the water instead of the parking lot. A dinner table timed for sunset. A private guide who tailors the day to your interests. A small surprise waiting when you return to your room. These are details I arrange quietly, so the moments simply unfold. And if part of the trip is a surprise for your partner, I'm very good at keeping secrets.
What about milestone anniversaries?
For a 10th, 25th, or 50th, many couples want to mark the moment more fully. Some choose a longer journey or a more indulgent stay. Others invite their children and grandchildren to celebrate with them, which turns the trip into a gift for the whole family. Either way, the pacing matters: a milestone should feel savored, not rushed.
Jen's take
Anniversaries are some of my favorite journeys to design. During one Rome and Amalfi Coast anniversary I designed, a strike hit while the couple was in Italy. We adjusted their train tickets behind the scenes and simply let them know, so they could keep enjoying their celebration instead of spending it on logistics. Right now, I'm designing a first-anniversary journey to Japan. Every one is different, because every couple's story is different, and that's exactly the point.
Last updated October 2026
Written by Jennifer Fichtner, ASTA Verified Travel Advisor® (VTA) Verify (opens VeriVacation in a new tab)