Somewhere between the wedding and, say, year 25, the way couples want to celebrate their marriage tends to change. What feels right at year five — spontaneous, a little indulgent, still figuring each other out as travelers — is rarely the same thing that feels right at year thirty. Neither is better. They’re just different chapters.
If you’re trying to figure out how to mark your own milestone, or you’re the friend everyone asks for ideas, here’s how anniversary trips tend to evolve, and a few ways to think beyond “just book a nice hotel.”
The early years: 1st–10th anniversary
In the first decade, most couples are still building their travel rhythm together — figuring out if they’re beach people or city people, planners or wanderers. These early anniversaries are a great excuse to try something you didn’t do on the honeymoon, rather than repeat it.
A few directions that tend to work well here:
- A “we’ve never done this” trip: pick a style of travel you haven’t tried as a couple yet: a river cruise, a road trip with no fixed itinerary, an all-inclusive where neither of you has to plan a single meal.
- A return to “your place,” upgraded: going back to where you got engaged or married, but staying somewhere nicer than you could afford back then.
- A milestone-specific splurge: the 5th and 10th tend to be when couples are willing to spend a bit more than a typical weekend away, without it needing to be a full-blown “vow renewal” production.
The middle years: 15th–25th anniversary
This stretch is often when life is fullest with careers, kids, aging parents, which paradoxically makes travel more important, not less. Couples in this range often aren’t looking for a bigger trip so much as a trip that actually feels like just the two of them again.
This is also where formal vow renewals start to enter the conversation, though they’re far from required. What I see more often is something in between a big ceremony and a regular vacation:
- A “just us” trip with real distance from home: not necessarily far geographically, but far enough that it doesn’t feel like an extension of regular life.
- A destination with a private, meaningful moment built in: a sunset dinner, a vow renewal on a beach with no guests but the two of you, a return to a place that mattered early in the relationship.
- A milestone trip that includes family, then peels off into couple time: this comes up a lot around the 25th anniversary especially, where a couple wants their kids or close family involved in part of the celebration, then wants a few days that are just theirs.
The later years: 30th and beyond
By this stage, many couples have the time, means, and life experience to travel exactly the way they want, and that often means going further, going longer, or finally taking the trip they’ve talked about “someday” for years.
- The “someday” trip, finally taken: the Mediterranean, the safari, the round-the-world cruise segment. If it’s been a running joke or a shared dream for decades, a big-number anniversary is exactly the occasion to stop postponing it.
- A formal vow renewal, done the way they actually want: not a redo of the wedding, but a version of it shaped entirely by who they are now: smaller, bigger, more relaxed, more elaborate, wherever their taste has landed.
- Multigenerational milestone travel: bringing children (now adults) and even grandchildren along to mark the occasion together, often as a hybrid of family reunion and anniversary celebration.
There’s no wrong way to mark it, but it’s worth being intentional
The couples I talk to who feel best about their anniversary trips aren’t the ones who spent the most. They’re the ones who thought about what this particular year actually calls for, instead of defaulting to whatever’s easiest to book. A 5th anniversary and a 30th anniversary shouldn’t necessarily look the same, and they don’t have to.
If you’re coming up on a milestone and aren’t sure what shape it should take, that’s exactly the kind of thing worth talking through before you start looking at hotels.
Have a milestone anniversary coming up? Let’s figure out what this one should actually look like for you two.