Whether you’re a returning guest or you’ve never been on an inGamba trip before, you may be wondering how our guides develop the routes that we ride. Here, we’re sharing what goes on behind the scenes!
Hosting the perfect cycling trip doesn’t start when the riders begin pedaling on Day 1. It starts months—sometimes years—earlier, as our inGamba guides and special guest guides start poring over maps, comparing notes on past rides, looking for ways to tweak routes to add that one extra climb, scenic vista, hidden gem of a coffee shop in a town of 150, or chance to whizz down a perfectly swooping descent. It’s about precision: A route that’s not so hard that it feels impossible, yet one that provides enough challenge that riders feel accomplished by the time they roll back to the hotel. Even after a ride route is established, it’s constantly revisited, as our guides are always riding in their regions, looking for the latest and greatest.
We know that many of our guests are coming back to the same spots year after year, revisiting favorite roads. And while we want to preserve the favorite moments—like the pastries and espressos served at the Agribar Eroica Café in Tuscany—we want to explore new roads so our guests are almost never repeating the same exact routes.
Whether we add a small portion of gravel that’s traveled by the pro peloton during the legendary Strade Bianche race or we sneak in one more killer climb to test the legs of the guests who want to go for a KOM on the trip, we’re always chasing a route that’s even one percent better than before.
We also change up routes to better customize trips for our riders: If you’re looking for a more leisurely day, Giorgio is more than happy to take that secret shortcut that he discovered on a scouting mission. Want a flat day after all of those hills? Manuel knows just the right spot. No matter what kind of trip you’re looking for, our guides know each destination so well that they can tailor any ride to your preferences.
But how do we start the planning process? Let’s go behind the scenes of one of the toughest rides that we’ve ever offered: When pro cycling legend Ted King joined us to ride the inaugural N2 three-day tour in Portugal in 2024, he knew there was planning to be done. The route was set in stone, since it would follow the Estrada Nacional 2, the country’s most iconic road, winding its way the entire length of the country from the ancient city of Chaves to Faro, on the balmy southern coast of the Algarve. King knew he’d have three days to complete it with the riders, and that the mileage and elevation would challenge even a veteran rider like himself. How would he ensure that the cyclists who showed up to ride with him and Laurens Ten Dam handle the terrain… and have a good time?
“That route—with seven hour days, double the usual distance done in inGamba ride days—reminded me a lot of being on the WorldTour,” King says. “That final day, were it not for the tailwind, we would probably have had an 11 hour day. As it was, we were out for seven and a half hours, covering 160 miles. And there were moments that did feel tedious—but that’s part of the challenge and it’s beautiful in its own way.”
“It’s really hard to lead a ride and to do it well,” says King. “You might think it’s relatively simple—just follow a route and you’re good to go—but there’s so much more to it than that. The second you have more than one person on a ride, you have at least two disparate speeds, abilities, and mindsets. And it’s not a linear problem. The more people you bring, the more those issues are exacerbated. A good route, a good guide—these are the things that make the difference, and they’re not easy to find.”
“To have a great route, it first needs to be a route that’s tough enough to feel like a challenge, but with enough elements of fun that it’s not a grind,” King adds. “There are practical considerations as well: It’s not just about a route that has the best scenery, it’s about which route has less traffic at which time of day and where it’s safe to ride two abreast without getting buzzed by cars, which route allows for easy regrouping possibilities, and which route offers a shortcut if some riders want to get home faster.”
“When I look for routes, I want to find spots where the riders can see something unique—I think there’s something very awe-inspiring about seeing a part nature like a really cool waterfall or a screaming, fast descent on the other side of that climb that you’ve achieved,” he says.
And of course, inGamba has gained a following for our Classics trips, led by famed former pro Adrie Van der Poel—who younger cycling fans may know as the father of multi-time world champion Mathieu Van der Poel. Adrie Van der Poel and Manuel Cardoso shepherded guests to the Tour of Flanders and Milan-San Remo, with even more on the calendar for 2026. If you ever wanted to go behind the scenes at a WorldTour-level event, there isn’t a guide in the world who can show you more of the best back roads in Flanders, the best viewing location at Paris-Roubaix, or can even recount how the races were won back in the day, from personal experience.
As a retired pro and one of inGamba’s lead guides, Cardoso is primarily responsible for developing routes in Portugal and Spain, most recently adding six-day base-building adventures in Calpe to the destination list. Calpe—a well-kept secret training ground for pro cyclists—boasts beautiful coastline and wicked climbs. You may spot a rider who’s been in the yellow jersey at the Tour de France piling his plate with scrambled eggs and oatmeal at the breakfast buffet at the hotel… or you may spot him later in the day, screaming down a vicious descent as you climb up.
“Each trip is different,” Cardoso says. “We’re always thinking about our returning guests, but also new guests and what they may be looking for. A trip like Calpe, we’re thinking about our guests who are looking for more serious riding, who want to work on accumulating some base fitness in the winter months. I’m thinking about beautiful routes for them, but also more challenging, longer days on the bike that will build their fitness.”
“I like a good challenge—that’s fun for me,” King adds. “I’m not saying you need to be on some gut-busting route where you’re at threshold the entire time, but I think in the sport we’re in, there’s some element of suffering that we like and look forward to—we want to work hard and reward ourselves on the other side of it.”
Cardoso also plans the slightly less intense routes around his home country of Portugal, where he not only knows the best roads to ride, he knows all the best hidden gems where riders can stop and take a break and indulge in the best Portuegese snacks and drinks. “I really like the countryside of Portugal—it’s very special to me because I’m in my home country.” he says. “It’s so quiet on the roads, and these trips feel like the perfect blend of relaxing riding while still challenging yourself on the bike.We ride into places that are the most authentic for the region.”
After nine seasons as a guide, Cardoso knows what guests are looking for, and spends his time in the offseason looking for new ways to improve routes, to surprise and delight riders. And like all of inGamba’s lead guides, he also has perfected the art of the mid-ride pivot. Someone needs to cut the ride short because jet lag has kicked in? No problem—he knows the fastest route home. Pouring rain? He’s got a cafe he loves just up the road. “We always know how to split in totally different groups and riding levels when needed, so that we provide a good experience no matter what speed you want to do,” he says. “We have guests who come out and want to go fast, be competitive—great. We have guests who want to stop to take pictures at a mountaintop—great. We love all the ways people can experience these routes.”
