In our new series that focuses on the many people involved with inGamba, our Creative Director James Startt sat down with two of our returning guests, Jenny and Roger Brown. The two have organized two private trips this past year and are already planning their next one in 2026. The couple, along with their teenage son, joined us in Northern Portugal recently for a trip with Laura and Ted King, and we wanted to hear about their experiences—and what keeps them coming back to inGamba.
It all started in Tuscany 20 years ago. That’s when Jenny Brown graduated from medical school and decided to celebrate with her first bike trip around Tuscany with family and friends. But the memories of that trip became a slow burn, and over the years, the idea of returning with even more family and friends only grew. Her 50th birthday proved to be the impetus that made it happen.
“For years I have told Roger [her husband] that my dream was to do more bike vacations in Europe,” she says. “When our kids were younger it was difficult, but when I turned 50, suddenly it was feasible.”
Jenny first heard about inGamba through their neighbors in Vermont, Ted and Laura King. It is here where Jenny, an OBGYN physician with a Reproductive Endocrinology and Infertility specialty met Roger, a former US National Ski Team member, the son of Marylin Cochran Brown, a World Cup ski champion. Between skiing, swimming and cycling, sports have always been a central part of their lives. And in recent years, Jenny has focused increasingly on cycling, where in addition to the physical aspect, she also loves the sport’s social side.
From there, her desire to do a group cycling vacation only grew.
Eventually, she was ready to book the trip. “We opted to do a private trip simply because we wanted to take all of the spots and be just with our friends,” Jenny says mid-way through their second inGamba trip of 2025.
Find out more about booking a private trip with inGamba here!
Jenny says that initially they were just planning to do one trip of eight to 14 people. “When we started thinking about it, and about how many friends were actually a cycling couple, the group just got bigger,” she adds. “We got so excited about it that we couldn’t just nail it down to one trip, so we added a second trip.”
“We just loved the idea of doing a group vacation but around a central theme like cycling,” Roger added.
For their first trip, Jenny opted to do one of inGamba’s Chianti Classico weeks, as it called to mind her trip 20 years prior. But there were also other considerations: “While the roads in Tuscany can be challenging, they are still doable for people that are not serious cyclists,” she says. “And when I found out that inGamba had an e-bike option, that just opened it up to all of our dearest friends. The e-bikes allowed those friends to be able to enjoy something they would not normally be able to do.”
With the memories still resonating from their first trip in the spring, the Browns then focused on their second trip in northern Portugal, which promised new horizons, both in terms of the riding and the landscapes. “I wanted a place with challenging climbs and fun descents, but I also wanted to go to a new place,” Jenny added. “We had never been to Portugal before, so this was a whole new adventure.”
Nearly 15 of the Brown’s friends and family came along for the ride here in Portugal, a veritable peloton that included not only the Kings but the Brown’s oldest son, Charlie.
“I looked at other bike tours before deciding who we would work with, but with inGamba, there just wasn’t any piece missing,” Jenny said, referring to inGamba’s unique combination of a professional cycling experience with singular itineraries and accommodations.
“Everything is so authentic,” Roger said. “The hotels are so authentic. The guides are not just guides, but real professionals. The bikes are not just any bike, but they are the nicest bikes you can put together. The mechanics are not just doing the minimum, they are doing the maximum to make sure every bike is perfect. Some of us don’t even see the details, but if you are an experienced racer, you will see that attention to detail, and you will appreciate it. It’s real. And at the end of the day, the deep Portuguese hospitality that comes from everyone we spent time with was incredible—everyone wanted to make us feel special and welcome to their incredible country.”
“It is not just some white-glove service. It is real and from the heart,” Jenny is quick to point out, speaking about the attention to detail provided by the guides, soigneurs and mechanics. “You just feel so loved and supported. They are very intuitive and caring. They notice if you need a little boost on the ride. They notice if your wine glass needs to be filled. The soigneurs are always there to make sure your bottle is filled. The mechanics are always looking over your bike. The attention to detail is just so incredible. Oh my gosh!”
While the Brown’s trip was one of the larger trips of the year, the roads of northern Portugal proved ideal for this inGamba peloton, as they are known for low traffic levels, and on certain rides we could literally count the number of cars we passed. Along the roads, the group often split up, as often happens, but the three guides—led by Giro and Tour stage winner Sergio Paulinho and Tour of Portugal winner Rui Vinhas—always made sure that the groups came back together regularly.
“The guides are one of those intangible parts of the trip. They make it magical because they know everything about these roads,” Jenny said during the trip. “Look at today’s ride: There was a lot of climbing actually, but we all finished pretty much together because the guides were always there, setting a perfect pace, pulling you back to a group, you name it. I think there are some people that might wonder if they are fit enough for an inGamba trip, but I wouldn’t worry about that at all, because the guides are always there to pull you together.”
“The people that want to go fast don’t feel like they are pulled back either,” Roger insisted. “And yet no one feels left behind. It’s so great.”
As our week-long trip closed in on our final destination in Porto, the riding became more relaxed. Time for reflection, there was plenty.
“I was thinking today, ‘How do you put a price tag on something like this?’” Roger said as we sat outside at the historic Quinta de Pacheca winery in Lamego. “It’s hard to describe everything that goes into it. The whole day was so special. It is hard to describe what it is like until you have been there. I mean, seeing our son Charlie descending behind Sergio, this multiple Grand Tour stage winner… That is a pretty unique, privileged moment. And now we are sitting here in front of one of the oldest wineries. I remember one morning, I came out for the ride and all the bikes were perfectly lined up. But then Ted said, ‘Look at the crankarms and how they are all perfectly lined up.’ I was just amazed. I would never have noticed something like that, to be honest. But that is a real pro detail you find here. That’s why inGamba, meaning ‘in the know,’ is such a perfect name.”
Jenny, admittedly, could not identify any singular aspect of inGamba that sets it apart either. But she is already organizing the family’s next trip to Mont Ventoux and French Provence in 2026. And while she doesn’t yet know who exactly will be joining her, she knows she will be with friends.
