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  • Jennifer

Travel Serendipity: The unexpected and wonderful moments that make travel awesome

Updated: Jan 17, 2022

We spend lots of time planning our travels - places to go, things to see, local foods to eat. And while it's nice to know that we're maximizing our time on the road, some of the most amazing and unforgettable experiences we've had have been what we've come to call travel serendipity. These are the moments you can't plan or anticipate. They just happen...and that's what makes them all the more wonderful. They appear around the corner or up in the air, or you follow the sounds of something and discover you've stumbled upon a once in a lifetime experience. Here are some of our favorites.

1. Soriano nel Cimino, Pressione della Madonna della Misericordia

We'd picked the hilltop town of Soriano nel Cimino, Italy, for a simple, if practical reason: it was convenient. On our road trip from Bologna down to Rome, we decided to enjoy a few days in Tuscany and, after Montepulciano, Soriano nel Cimino was the perfect stopover before finishing in the capital city.

There was nothing mainstream about this fact, the only real "sight" to see was the castle built by Pope Nicolas Orsini as a defensive lookout. And look out it did, the view from the Cimini mountains was amazing, even if the town itself was piccolo (small), consisting of not more than a few narrow, meandering streets through a medieval village. Located where Lazio, Umbria and Tuscany meet, the place was secluded, to say the least. In fact, one of the only restaurants we found was in a cave...which was actually very cool.

But it was what we encountered on the way to that dinner one night that left us awestruck. We were walking down the stone street toward the restaurant when we realized everyone around us was heading in the same direction, and there were a bunch of people wearing what appeared to be ambulance or emergency worker uniforms. Odd! For a town this small, we knew that had to mean something was going on. It seemed that everyone was going to the Chiesa della Misericordia (Church of Mercy), the oldest church in Soriano, and when we followed them and stepped inside the church it was packed. The priest had just finished talking and people started piling out onto the piazza, so we joined them. Suddenly everyone started singing as several men emerged from the church holding a statue in the air. Watch what happened next in the video.

A procession of people holding candles formed a line in front of the church and the entire town started singing as they walked up the hill toward another church, following a path marked by large paper flowers and streamers hanging from windows and streetlamps. Everyone made their way through the dark street in candlelight while singing together. It was surreal and unexpected, and like being in another world. Witnessing this and actually being in the middle of such a ritual was truly a highlight of our trip.

2. A front yard barbeque in Anguilla

We always like to eat local, but a dinner we had in Anguilla took it to the next level. Anguilla is an island with no shortage of amazing, world-class restaurants, but one day we were on a walk around the residential area near our hotel and found a place we knew we had to try. B&D's Barbecue was literally in a local family's yard, complete with just a few plastic tables and chairs, and children's toys scattered around the lawn. This is a family-run place, with Bernice (the B in B&Ds) running the show.

When we arrived the entire family gave us a huge welcome, including the little kids that came over and sat with us while we decided what to eat. It was like hanging out at Bernice's family home...because we really were. The young children were absolutely adorable and pretty much kept us company the entire time we were there, which we didn't mind at all.

Everything was grilled to order. How did we know this? Because the actual grill was about fifteen feet away from us under a little tent, and we could see the fresh lobster, chicken, racks of ribs and lamb neatly lined up over the coals in the "coal keel" (coal kiln).

The place smelled so good! Apparently, we'd picked a spot loved by locals, and every few minutes someone would drive up in a car and run out to pick up some food to go. Our drinks were given to us from an ice-filled cooler, and when our meals arrived on paper plates our dinner was hot, and we were hungry! This was just about the most unusual dinner spot we've encountered and there's no way we could have planned to eat there if it wasn't for our chance encounter, in a random neighborhood we happened to come across. It made the whole night an even more memorable, and delicious, Anguillan experience.

3. The joy of football (or soccer to us)

We arrived in Dubrovnik, Croatia in June when the weather was warm, sunny, and perfect for island hopping up the Dalmatian coast. What we didn't expect, though, was to arrive during the UEFA European Football Championship (or the UEFA Euro). And it was a big deal because Croatia had a really good chance of doing well. Our first night in the old city we joined a bunch of people at a local Irish bar to watch Croatia v. Scotland - and celebrate a win that had Croatia moving on. We were hooked! Now, we were not soccer fans, in fact we were baffled by some of the rules of the game we were watching (Why doesn't the game end when the time runs out? Why did it seem like players were constantly falling down as if they'd been mortally wounded, only to bounce up again a few minutes later ready to play?). But the excitement and national pride was contagious.

We continued to watch games no matter where we were...a plaza in the middle of Split where fans were cheering from the outdoor bars with screens set up to broadcast the games, to local sports bars and restaurants on islands along the way. Go Croatia!!

We screamed with every goal, groaned when the opposing team got ahead, and were in it to win it. When Croatia finally fell to Spain, we were deflated to have it all end. What was so cool about watching the games wasn't that we'd discovered how much fun European soccer could be, but rather how much fun it could be to join in with local fans to experience the highs and eventual lows of the national team (we even learned the players' names, and I came this-close to buying a Luke Modrić jersey). It was a crash course in football culture, a country's love for their team, and how, regardless of where you are from or the differences you have, there's nothing that makes you feel like you're all on the same team more than high-fiving strangers after a win.

4. Tis the season

We love the holiday season (well, one of us maybe more than the other). It's like a switch flips and everything is festive, with decorations and music that can't help but put a smile on your face (again, one of us may love the music more than the other). We were just coming off a trip to Germany - about the most festive holiday country going - when it was, once again, Joe's birthday.

After a week in Bavaria, a birthday celebration closer to home made sense, so a surprise trip was booked to the Mayflower Inn in Connecticut for some quiet and relaxation. This trip was all about doing nothing but enjoying the beautiful surroundings and coziness of our destination. Except...was that a jingle bell? It turned out that the day we arrived was also the day that the hotel was lighting up its 18-foot Christmas tree. The entire place was decorated in lights and ribbons and the fires were lit...and, to really bring home the holidays, they were having carolers, too!

That's how we found ourselves in the lobby counting down to the lighting of the most beautiful tree with the sounds of carols in the background (and the trays of champagne being served added to our holiday joy). Listen!

After the music and tree lighting, we enjoyed our champagne outside by a bonfire, which kept us warm on the cold December night under the stars. It was the most unexpected way to celebrate Joe's birthday, even if he had to share his happy birthday song with tunes about snowmen and silver bells.

5. Cars and more cars in the land of chocolate and fries

Did you know that it was actually the Belgians who invented French fries? Or that there's a museum with more than 300 automobiles in Parc du Cinquantenaire, and the neo-classical building commemorating the 50th anniversary of the Kingdom of Belgium? Neither did we, until our trip to Brussels.

Chocolate, the Christmas market, Flemish art, headquarters for the European Union, these were all things we expected to experience on our trip. But we had no idea that a stroll to check out the Cinquantenaire and its vast gardens and monuments would land us among a collection of automotive treasures. Since 1986, Autoworld, the Belgian National Automotive Museum, has housed the major part of Ghislain Mahy’s renowned classic car collection. There are cars from the late 19th century to the 1990s and every one of them is more beautiful and unique than the last - quirky sports cars sat next to Le Mans race legends, historic feats of automotive beauty, and concept cars that looked more like something the Jetsons would drive (fly?).

There were brands we'd never even heard of, Belgian cars, including Minerva, Germain, Imperia, Fondu, and limousines belonging to the Belgian Royal family. There were spacious classic luxury cars, sports cars and adorable little things that barely qualified as modes of transportation. Even for a car guy like Joe it was staggering both in the number of vehicles and the variety (A Spanish Pegaso? A Belgian FN 1300 Sport? An Alpine A110? A Talbot Lago?) in addition to the classics (Porsche 912 Coupe, BMW Isetta, Bugatti). Add in the stunning building housing this collection, and this was a gem we were thrilled to stumble upon. If you're ever in Brussels it is absolutely something that needs to be experienced to be believed.

6. Mother Nature shows us who's boss in Lech, Austria

We skied over to Lech, Austria from St. Anton one day to explore. After lunch in the small town we clicked into our skis and were ready to explore the mountain. It was a stunning blue-bird sky when we'd skied over from St. Anton but a few clouds had started to cover the mountains and with every run the sky grew grayer and grayer and snow was falling faster and faster. It's so much fun skiing in the falling snow, we didn't think anything of continuing. Then, on our way up the mountain for another run, things got really dark.

Almost within minutes visibility went down to practically nothing. Suddenly we realized that it was also pretty quiet. We were on the lift up the mountain when it struck us that there were no skiers on the trail below our chair. We swiveled around to look down toward the bottom and realized why - we were the only two people on the chairlift and on the entire mountain. Seems like all the wiser skiers had decided to call it quits when the unexpected snowstorm hit, but there we were heading up for a run without a soul in sight. The lift operator had slowed the lift down to a snail's pace for safety reasons as the wind at the peak was now gusting to 50mph. It was almost creepy slowly making our way to the top with the chair blowing back and forth and no humans around - like a horror movie where all people disappear except the main characters who are about to have something crazy and horrible happen to them.

When we finally reached the top, it was deserted, just us and a driving snow that was falling harder than ever. The wind was blowing like mad (you can hear it in the video), but that only made it seem that much cooler. It wasn't a horror was the greatest thing ever! We had the entire mountain to ourselves and loved it. Never before had we been alone on 222 acres of pistes with the snow pouring down on us the entire way, and we never have again since that day. We yelled out loud on our way down, happily whooping and hollering into the vast nothingness with no one to hear us but us. It was awesome. Mother Nature had done us a serious solid.

7. Bonus: Civilian protests and government action

We were just leaving the Musée de l'Orangeri in Paris and were going to stroll along the Seine toward the Tuileries Garden.

Suddenly we realized that there were a lot of people walking down the street next to us and, further up, police were waiting for them. A parade? Exciting! All of the people were wearing yellow vests, some sort of safety measure, we decided. It was only when we realized that the police were in riot gear and there was nothing happy about the people in yellow vests that we knew this was no was a protest!

And it was looking like it was going to get pretty hairy.

We later learned, on the news, that this was part of the yellow vest movement, and they were French motorists from rural areas who were protesting the fuel taxes that French President Emmanuel Macron announced as part of his environmental policy strategy (under a 2008 French law, all motorists are required to keep a yellow vest in their vehicles and to wear in case of emergency). 136,000 protesters around the countries were out in full force on that history making day.

It reminded us of another time we inadvertently found ourselves in the middle of protesting citizens. In Barcelona we'd actually been right in the center of a protest by the Catalan independence movement. All day we'd seen cars and motorcycles driving around the city flying Catalan flags and honking their horns, so when we finally ran into the huge gathering of people and heard someone on a podium with a loudspeaker rallying up the crowd, we finally realized what all the action was about. We proceeded to fall into step with the swelling crowd as it marched down the street yelling "Viva Catalunya!" in support of making the Catalan region a sovereign entity that is not under Spanish rule. Some pretty heady stuff!

Fortunately, neither protest got out of hand, and we were able to experience local politics and issues impacting citizens of the countries and regions we were visiting. Not sure we'd want to be in the middle of anything more heated or volatile, but to be in the middle of history-making events was something we didn't plan for, and it was definitely unforgettable.

These are just a few of the travel serendipity moments we've had the good fortune to experience along the way. And no matter how much planning we do, how far in advance we lay out our trips and the things we'll do, or how prepared we think we are, there really is no substitute for the impromptu, unexpected experiences that come from going somewhere totally unfamiliar and just seeing what happens. There are no tips or shortcuts here, just encouragement to be open to what crosses your path along the way. It really is one of the best things about traveling.

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