Planning a Surprise Anniversary Trip

Tim’s been planning a surprise anniversary trip for me since the first year we were together—and this year marks the fourth surprise trip he’s planned. Year one? A romantic day trip around Hamburg. Year two? A weekend in Paris. Year three? Four days in Athens and Naxos. Year four? Five days in Sardinia. He laughingly says his goal is to plan one day more per year. As a Scorpio (and ok, a generally nosy person), I can typically work out a surprise well in advance of delivery. But Tim’s trips have always come as a complete surprise, and I have to admit, he’s a master. So of course, I had to ask him how manages to pull of such epic surprise trips every year. 

The mastermind on our Greek ferry.

Our Annual Surprise Anniversary Trip

Is it difficult to plan the trip? What is the trickiest part to plan?

TD: I wouldn’t call it difficult, but it can be challenging to keep it a surprise. Of course, when you plan a longer trip you have to plan vacation/take time off from work. If you just plan to go only for the weekend, you might even keep the entire trip as a surprise. This would be the most challenging option, since you have to make sure there are no other (important) things planned. Usually, we have the option that the significant other knows that there is some sort of surprise ahead.

What is your favorite part about surprising me?

TD: I mean there are people who plan everything in their life in detail and need to know their schedule for each day in the next month. Some people (in particular the Germans) like to discuss and plan things in the future. For those people, a surprise is a different challenge. I wouldn’t say surprising you is a smaller challenge—it is even a bigger one, since you love getting surprised and always get incredibly excited. That’s what makes it a fun challenge for me. The moment when I really achieved it to surprise you. I usually notice it, when you just smile and don’t say anything about it. That is the most beautiful part. The most fun part on the other hand is the guessing and intentional misleading what we do or what the destination is.

I usually notice it, when you just smile and don’t say anything about it. That is the most beautiful part.

What’s your favorite memory of one of our trips?

TD: I think my favorite, because most funny (for me), moment was the departure in the early morning from Hamburg airport to Paris. First of all, because you would have never guessed that we go to Paris. Second, it was great luck that next to our Paris Gate were the departures to Stockholm and Düsseldorf, both cities you were traveling to for work often that year. When I saw the departures after we passed security, I knew it would be awesome to see your face when we stood in line for Stockholm and/or Düsseldorf. 

Which surprise anniversary trip was your favorite and why?

TD: I actually don’t have the one favorite trip. Each of them had absolutely stunning moments, but if I would do them again, I would have some minor improvements for each trip:

2016: Hamburg

My highlight was to explore our neighborhood with the Kanu through the little rivers. But I packed the day with too many things, and we had to move the last stop on Sunday. I should have planned I’m advance 2 days.

2017: Paris

The best part of Paris was that you had no idea where we are going—so the surprise itself. The next time, I would esearch more special things to do. Especially when you have big cities like Paris as the surprise destination, the planning in advance is crucial regarding, tickets, reservations, etc. And also try to minimize the travel time and distance between the locations.

2018: Greece (Athens & Naxos)

I thought what was really cool was the surprise in the surprise. So arriving in Athens was not the final destination, even though I pretended it was. You didn’t expect that we would then take a ferry to Naxos. However, due to the long ferry rides and the day in Athens, one more day just at the beach would have made the trip more relaxing.

2019: Sardinia

The best thing about the trip was that it was completely suitable for our current mood. A totally low-key vacation with sunny weather, beautiful beaches, amazing food and wine, and some little adventures that supported switching off the work thoughts.

Curious about his tips for planning a surprise trip for the one(s) you love? Check them out here!