How I Plan Vacation

With our trip to Austria, Slovenia, Croatia, and Montenegro in two weeks, our planning is nearly done. It seemed like a good time to explain the insane process we use to plan our trips.

The last few trips we took, including our car delivery in Germany and driving around Lake Como, as well as my wife’s birthday trip to Hong Kong and Singapore, had us scheduling our itineraries down to the hour. While this approach gave us a good idea of all the things we could possibly do, and we were largely able to accomplish it, when we had to skip something, take more time somewhere, or discovered something unforeseen, it didn’t give us flexibility and we would feel disappointed to miss something. Regardless, we had great trips.


For my upcoming 30th birthday trip, I didn’t want to feel this pressure. After deciding on South Eastern Europe based on Formula One schedules, Game of Thrones’s expanding presence in Croatia, and every travel article telling us how Croatia would soon be overrun by tourists and lose its charm, we decided to make a conscious effort to not plan to the minute. 

Our approach instead involved several components. First, find the best walking tours for each city. Second, compile a list of recommended restaurants from sites we trust as a possible menu of where we can go, but not get too attached to any one specific place. And lastly, Sprinkle in a few must do activities that we would work around.


For walking tours, we started with Google searches, but had trouble finding much in some of the smaller or less traveled cities like Rovinj and Ljubljana. We stumbled across the GPSMyCity site which offers free maps online and a paid option to download on your phone. In the past we would copy the locations into Google maps, but the hastle of doing this for several cities made the $5 cost of the downloaded maps in the app seem worthwhile. I bought the maps, not realizing that it was $5 per city, so only ended up with Dubrovnik. On to the next option. Instead, I started marking each location on the Nokia Here maps, a nice free option with downloads of entire countries on the phone. However, I soon discovered its POI database to be quite lacking, which is consequently why Google and Apple and spending millions to snatch up companies with decent ones as this is a big differentiator in the market. Finally we decided to again manually enter them all into Google maps. When you have something that works…


For restaurant recommendations, we started with our go to regulars. The New York Times “36 Hours In” series tends to have great recommendations, especially in Europe, so we began there. After cross referencing with Trip Advisor for price and rating, we eliminated a few. We supplemented the list with some of the top recommendations from Trip Advisor and some web searching for blogs. We also dug up the Indenpent’s 48 hours, how original, and added some of these though their recommendations were in general less well rated than the NYT ones. On review sites, I have found that Google Maps reviews are nearly non-existant outside of the US, which I am slowly improving, and that Yelp reviews can’t really be trusted as they are largely from Americans who are looking for large portions and price over quality. Service is also always a huge knock from people who don’t understand how different our service cultures are. In Europe, I primary trust Trip Advisor, though will often do some filtering out of American reviews, as the customer base is much more global than competitors. Lately I’ve found Four Square’s recommendations to be getting pretty good, so may try this while there as well.


The most exciting part of the planning is finding the “must-do” activities. Coming from a long line of sea-faring Danes (probably made up), I love boating. In the last five years, we’ve done a sunset sail around New York,  Ferry to Block Island, small cruise around Newport Harbor, rented a motor boat on Lake Como, and went deep sea fishing off of the Jersey Shore. When we discovered a sunset sail around Rovinj and the Adriatic coast, we signed up right away. The motor boat rental on Lake Como was one of the most memorable experiences of my life, so when we discovered a rental on Hvar and a top rated restaurant only accessible by boat, we knew we had to do this as well. We didn’t find a place to go horseback riding like we enjoyed in Napa and Bermuda, but did find the highly recommended hot air balloon company in Bled. And with Croatia’s wine being so highly recognized lately, we knew we needed a tour to a winery, so found one on Hvar for my birthday. 


To keep track of all of this insanity, we created a shared Evernote note where we could both add our findings. In total, including the walking tour decorations and restaurant blurbs, this ended up being 46 pages long. Yikes! Maybe we ended up being just as insane but in a different way. We’ll see how the trip goes!

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