This year we spent Easter going back to familial roots, and enjoying entirely too much wine and food along the way. How we planned this trip is a pretty good example of the unconventional way we go about our travelling. I would like to say that we were making our life-long dreams come true with a romantic weekend in Venice (which is partially true), though in reality this trip was a spur of the moment booking - seven months in advance.
Allow me to explain.
It all started when I was groggily waking up one weekend in late August and was mindlessly scrolling through my news feed on my phone. I came across a flight deal on @TheFlightDeal that had just been posted for Air Canada business class from select cities in the US to select cities in Europe starting at around $1,000USD roundtrip. That is business class at near economy prices, and too good of a deal to pass up. I quite literally jumped out of bed to grab my laptop and begin the search to see if the deal was still live (deals like this one disappear very quickly as everyone wants to take advantage of it) and if I could find an itinerary that we could fit into our schedule. Unfortunately, there were no deals out of Chicago, but they were plentiful out of Boston. We weren’t really planning to book any long trips that morning, but the thing is when you find a deal this good you have to book it fast. We settled on booking flights for late March, which would coincide with Easter where we could potentially meet up with Bettina’s family while in Europe. I began my search around those dates and found a few itineraries that might work to Amsterdam, Rome, and a few other cities in Europe. All options were restricted by having to leave on a Tuesday, and with a minimum 7 day stay in Europe. Once we found flights that worked I typed all of our information in as quickly as I could and we were able to successfully book business class from Boston to Amsterdam, return, with a short layover in Toronto both ways. At $1,020 each for a lieflat seat and as much as we could eat and drink, we were not complaining.
It wasn’t until a few months later that we solidified the rest of the trip and coordinated with Bettina’s family. We were going to meet them in Venice for two days before driving to the Dolomite mountain range, which is about 2 hours north, to spend Easter relaxing in the town where Bettina’s mom spent every summer of her childhood. As we were arriving in Europe a few days before they were able to meet us in Italy, we decided to add on a short side-trip to Belgium, which believe it or not, Bettina had never been to. We were able to secure pretty good flight prices this far in advance flying from Brussels to Venice and returning to Amsterdam.
We still had one problem to solve though. How would we possibly get to Boston? Given that it’s a U.S. destination and a major city, it was the perfect use of our Southwest Companion Pass. We again were able to get a reasonable price on flights by booking far in advance. We also planned to head there a few days before our international flights and tagged on a New England road trip for good measure. Here is what our final itinerary looked like:
Late in January, we received an update from Air Canada. Updates usually mean the flight itinerary changed and we were worried this change would disrupt our complicated trip. The good news was our flights from Toronto to Amsterdam had been updated from an older Airbus A330 to their brand new Boeing 787-9 Dreamliner. The bad news: Our originally booked flights had been cancelled and the auto-booked itinerary was completely messed up and illogical. With a call to Air Canada to resolve, we learned that our originally scheduled flight from Toronto to Amsterdam was cancelled on Tuesday, but we could alternatively fly the same itinerary, just one day earlier. An extra day in Europe for no charge? Yes please!
What we ended up flying:
Not for the faint hearted if you don’t enjoy flying – but that’s not a problem for us. As our return connection in Boston was unprotected (i.e. two separate tickets on two separate airlines – if the first flight is delayed and you miss the second, you don’t get reimbursed for your flight or rescheduled, tough luck) we had booked a fairly comfortable 4 hours buffer. However, Southwest decided to add a little fun to the mix in late February by rescheduling their last flight of the day from Boston to Chicago two hours earlier, and giving us just 2 hours to make our unprotected connection, at the mercy of weather delays, normal delays, running time between terminals, and security lines. Despite 45 minutes of weather delays on the actual flight day, we made our connection without issue! If we were travelling with checked luggage, it might have been another story, but we always try to travel with carry-ons only (see Bettina’s post here on making it work).
In March, a few weeks before the trip, when people inevitably began asking us where our next trip was it was a bit difficult to decide how to respond. “Venice” was the go-to answer. Sometimes that’s just easier to say, and also helps to avoid the looks we get when saying “Boston, Burlington, Portland, Amsterdam, Brussels, Bruges, Venice, and the Dolomites.”
We felt like we really lucked out being able to book these flights! We were not only looking forward to the destination but the entire journey as well. Bettina usually dreads the flight back home, however she can’t wait to get on the plane if our flight home is in business class.