How to Plan a Birthday Trip Itinerary for a Loved One

June 10, 2020 Updated: June 20, 2020

We emerged from the Churchill War Rooms, squinting in the sunlight as we left 1945 behind and entered present-day London. 

“That was amazing,” my husband said as he went over details of Churchill’s documents, the Map Room, and the Transatlantic Telephone Room disguised as a private toilet. “The best part was that I didn’t have to plan getting here at all.” 

He was right. Every year, for my husband’s birthday, I plan him a surprise trip as his gift. He gets to show up and enjoy a mini-vacation tailored specifically for him, no preparation required. 

map room churchill war rooms
The Map Room within the Churchill War Rooms in London. (Courtesy of IWM)

I think one of the best things about birthdays is that they give us a chance to celebrate the people we love and the reasons why we love them. My husband Andrew loves to travel. He is always up to go anywhere. However, he hates to plan. He gets stressed out by the details of accommodation and travel arrangements. The number of places to go and things to do can overwhelm him to the point where planning a trip feels more stressful than fun. 

A few years ago, I realized that one way I could celebrate him on his birthday was to take him somewhere he’s always wanted to go, but plan it all so he wouldn’t have to. I picked a secret destination I thought he would love, booked accommodations, and planned our itinerary. When his birthday finally arrived, I packed our bags in the car, handed him a hot coffee and a folder containing the location of his surprise destination: London.

I gave him details as the trip unfolded, so that each day and destination was a surprise. He would find out where we were going to eat as we headed there, where we were staying only as we walked up to the Airbnb. Andrew was able to enjoy a vacation tailored specifically to him without planning a bit of it, and I got to be the one to plan an exciting surprise. 

churchill war rooms
Britain’s leaders plotted the Allied route to victory during the Second World War from the Churchill War Rooms in London. (Courtesy of IWM)

The trip was so much fun that it’s become a yearly tradition for us. It’s a wonderful way to give an experience as a gift, and Andrew loves knowing at least once a year he won’t have to navigate car rentals or sift through hundreds of Airbnb options to get away.

If a birthday trip would make a great gift for someone you care about, here are a few tips to get your planning underway. 

Plan a trip around what they love. Andrew loves history, so every trip I’ve done has been a historical destination. We’ve traveled to the monuments in Washington, D.C., to the French and Indian War Fort Necessity near Pittsburgh, to Dwight D. Eisenhower’s home at Gettysburg.  Every trip we plan has some kind of historical element as the central theme. Does the person you’re planning for love a certain type of food, or music, or climate? Picking something they love makes the trip feel truly special. 

Write out an itinerary. One of the early birthday trips I planned for Andrew was a day trip to St. Malo, France, while we were staying with family in the English Channel Islands. I thought that we would just arrive on the ferry in the morning, walk around, and figure out what we wanted to do as we went. The combination of old, winding streets and our abysmal understanding of French made the city feel overwhelming, and we spent most of the morning just trying to orient ourselves. 

I’ve solved this problem by creating a thorough itinerary. These itineraries are flexible—meant to serve more as a guide than a hard timeline. I put together sights and activities that are close in proximity to one another, and a couple of restaurants to choose from. This way I can offer a few choices without feeling like there is too much to pick from. 

Add in personal, memorable surprises. Andrew has read almost every biography that exists about George Washington. When we went to D.C., I knew that we had to visit Washington’s home, Mount Vernon. We could have driven there, but I wanted to find a way to make our journey more memorable. I found the Potomac Riverboat Company, and realized we could travel via boat, almost straight from our Airbnb to Mount Vernon. It was such a fun, special surprise for Andrew. I also knew that he had never toured the Capitol, but I wanted him to have a personalized experience. I contacted a friend who worked for a congressman, and she gave Andrew and me a private, behind-the-scenes tour.

mount vernon dining room
The Dining Room at the Mount Vernon Mansion. (Courtesy of George Washington’s Mount Vernon)

As you think about how to plan a trip for someone you love, think about what extra things you could throw in that would really make the trip stand out.  

You don’t have to break the bank for it to be special. Some years, these birthday trips have taken up a significant amount of our yearly travel budget, but other years, I prefer to go smaller and stay closer to home. When we went to Pittsburgh last year, I cut costs by staying with friends rather than a hotel or Airbnb. One year, we visited a battlefield close to us Andrew had never seen, and I packed a picnic lunch of Andrew’s favorite food—Italian subs and chocolate chip cookies—to enjoy while reading about the battle’s history. 

Far more special than an elaborate trip is showing that you know and care about the person you’re planning for. Coming up with a few personalized ways to make the day or trip about the person you love will go a long way. 

I didn’t have to take my husband to the Churchill War Rooms for him to have a special birthday. But making the effort to plan such a surprise for him gave us both memories to enjoy for years to come. 

Rachael Dymski is an author, florist, and mom to two little girls. She is currently writing a novel about the German occupation of the Channel Islands and blogs on her website, RachaelDymski.com