They say that three is a sacred number. Pythagoras, the famous Greek mathematician, deemed it the perfect number: strong, harmonious, wise. Throughout history, most good things — all memorable ones — come in threes.
Whether or not the two female travelers featured in our Fall issue consciously postulated on the meaning behind three, or whether good luck just graced them with a holy trinity, each planned and executed a dream European vacation around three diverse cities in one beautiful country. By dividing up their trip into three legs, each was able to see the scope of what the land had to offer. The history of a city, the splendor of a beach, the stillness of a pastoral countryside — three slices of one culture creating the perfect juicy experience.
Read about our first traveler, Amy, who went to Greece here. Our second traveler, Shannon, shares her story below:
Three Cities in Italy
In order to sustain Shannon Jenkin’s mental health amidst her high-profile career in finance, she relies on travel. “I work a lot of hours, so planning a big family trip with my kids helps me have balance — it keeps me motivated. You will never catch me without my Google Sheets, planning my next trip!” Shannon says.
Every other year, Shannon has planned an adventure with her husband and three grown children. While her trips began small and stateside, Shannon’s most recent excursion took her brood abroad on a two-week tour of Italy via planes, trains, automobiles, a chartered yacht, and e-bikes.
When travel reopened post-pandemic, Shannon discovered that she could fly her family to Europe for about the same cost as a beach vacation. An additional catalyst for the trip was the news that her oldest daughter was expecting, so Shannon wanted to do something grand. “I knew it might be the last big trip we took for a while. We had never been to Europe before; it was a blank slate. But, as I started researching, I discovered it wasn’t as expensive or as big of a deal to plan as I once thought,” Shannon says. Around Christmas, the family got together and voted from their short list of destinations: Greece, Spain, France, and Italy. As soon as Italy was deemed the winner, Shannon got to work with her planning sheets.
“We like variety — my daughters love cities, my husband likes history, my son loves adventure and the outdoors and despises the city — so we needed to blend the vacation. It’s either a blessing or a curse with our diverse tastes, but we all enjoy having unique experiences — we’re not the tourist-attraction type of family. Plus, two weeks in one location can get redundant really quick, so I decided to pepper in different landscapes.”
Shannon divided the trip into three separate legs that propelled the adventurous trip: Florence for traditional Italian cuisine, Renaissance architecture, and cultural immersion; the pristine mountain terrain and Germanic influence of the Dolomites (The Italian Alps) in the north; and the ancient history of Rome, one of the world’s most iconic and ancient cityscapes. In between these three-to-four night jaunts, the family squeezed in day trips to Venice, the Amalfi Coast, Cinque Terre — as well as dipped into Austria and cruised Capri on a chartered yacht.
Shannon opted to conduct most of the family’s ground travel via train in order to avoid the stress of schlepping so many bodies and bags across the country. Train rides were a great way to take in the scenery and bond — no one had to navigate or drive, and tickets were easy to acquire day-of.
Another bit of advice she swears by is the magic of an e-bike tour. Upon arrival at each destination, her family took a guided e-bike tour to become acclimated with the city at ground-level. Being on bike allowed everyone to glean the cities’ layouts, attractions, and local foodie areas. In Rome, the family took a sunrise e-bike tour of the city’s famous sights called “Wake Up Rome” and avoided the droves of people that line up outside by 9am each day, saving them time and money in expensive admittance fees. “My whole family was grumpy and not even speaking to each other because we were all so exhausted that morning. But once we were done and had seen the Vatican, the Colosseum, Trevi Fountain, you name it — all before 9, before the city even started waking up — we were all so glad we made that choice. We were in a cafe having breakfast and coffee when wall-to-wall people started lining up at the same places we were at hours ago by ourselves.”
The e-bike tour of the Dolomites took the family on a 40-mile, river-lined trek through the Alps and into Austria. “We would have never seen that on our own — it was incredible. There were bike-path-side restaurants along the way to the train station. We took a train back to our Airbnb, and it was everything I thought riding a train through the Alps would be. A 10/10 experience!”
Despite the months of planning, Shannon knows the gift of balance between tight and loose when it comes to travel. One day the family skipped the second tour of Cinque Terre that Shannon had planned, instead opting to lounge on the beach, eating and drinking — it ended up being one of everyone’s favorite experiences.
The Dolomites also stole the family’s hearts. The change in landscape brought on by the mountains, where the architecture morphs from Italian to Germanic, the air thins and cools, and everything begins to look like the setting of The Sound of Music. There, they rented an Airbnb on a working farm and were greeted with fresh baked bread, fruit, eggs, and milk from the farm each morning — just outside their door. The relaxing and simple way of life in the mountains was how the family wanted to end the trip — not with the bustle of Rome — so on the last day, they changed course and chartered a yacht in the Amalfi Coast. There, they enjoyed lunch in Capri before the trip’s end and return to life in the busy city. Now that is a winning family vacation — a trifecta of culture and memories for a lifetime!
By Megan M. Seckman | Photos submitted