Best Surprise Trip Ever!

Best Surprise Vacation Trip


Color me surprised, even flabbergasted–my husband managed to pull off a surprise trip that is our very first couple's trip in our nearly 12 years as parents. The first I heard about it was the day before Thanksgiving, when we were having lunch and talking about our Thanksgiving preparations for the following day, when close friends of ours were coming over to celebrate.

G: “So, let's say, hypothetically, that I was going to surprise you with going somewhere. How much advance notice do you think you'd need?”

Me: “Well, it depends on whether any weekdays are involved, since I need to plan for work…”

G: “So say there's just 1 work day you'd miss.”

Me: “I'd need 2 weeks. Especially during busy times like now, in the lead-up to the festive season.”

G: [Gulping nervously] “Ah, well–too late, we're leaving tomorrow night.”

H: “What! Leaving where?!” My heart was racing. I'm so used to planning all of my work travel and our family travel that the thought of Greg planning an entire trip for us was both exhilarating and unnerving. “And are all of us going?”

Long story short, Greg had planned a long weekend for just the two of us in Europe, and our friends had very generously agreed to look after our son, who's the same age as their kid, for three nights. And our son both agreed to the plan, and was excellent at keeping a secret–I had no idea until Greg told me the day before.

“I was debating whether to try to keep it a secret until Thanksgiving Day,” Greg told me later, “but you were so busy with both work and prepping for Thanksgiving I started to get nervous about it.”

I was relieved he didn't wait any longer than he did, because, as much as I love surprises, I wouldn't have wanted to find out mere hours before we were supposed to leave for the airport.

I realize this is already after Thanksgiving, but I have so much to be thankful for:

  • An incredible husband who not only planned an amazingly romantic trip, but one that also includes seeing friends in Europe that we rarely get to see. More importantly, he's my best friend. And on a daily basis he does so much to support me, my company, and our family.
  • A wonderful son who thoughtfully and without resentment supported my husband's surprise trip;
  • Amazing NYC friends who not only agreed to look after our son, but even house sit for us and who took the kids today to MoMA and one of their favorite NYC bookstores.
  • Our European friends who, without much notice, made time to get together with us during our brief visit.

Has your spouse or partner ever given you a surprise trip for just the two of you? If so, when did you find out about the surprise, and where did you go?

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8 Comments on "Best Surprise Trip Ever!"

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What a great surprise Hilary! Thanks for sharing.
Cheers John & Nathan

Hilary Stockton

Still amazed and touched by my husband’s surprise, and that he and our friends kept the secret for weeks!


How wonderful, Hilary! The only surprise trip I ever got was our honeymoon! I’d been to Hawaii 3 times and was totally under its spell so, knowing how I loved it, he surprised me (although I managed to find out beforehand). His fondness for travel faded over the years but he did surprise with a car twice.

Hilary Stockton

What a wonderful honeymoon surprise to return to Hawaii, even if you did find out a bit beforehand! I think many husbands aren’t that keen on planning that far in advance, so it’s really very special when they do.

I have planned and executed two surprise trips for my wife. They were gifts to show her just how special she is to me (in addition to the day-to-day stuff I try to do). The first was a trip to NYC where she didn’t discover the destination until we were at the airport where I handed her her boarding pass. She didn’t find out we were flying anything other than economy until we got on board and she sat down in Mint – our first time flying in the front of the plane. We stayed at both the St. Regis… Read more »
Hilary Stockton

Nicholas, what wonderful surprise trips for your wife! Thrilled to hear you enjoyed NYC, including JetBlue Mint–it’s our favorite domestic U.S. business class as well. And Paris makes for a very special surprise trip–sounds like you made some incredible memories. Your wife is very lucky!


Very sweet. You are blessed.

Hilary Stockton

I do feel very grateful for my husband, but also for our son and our friends who helped him make this surprise possible.