For the better part of twenty years, I was a teacher, first high school, then at the university level and I spent most of those summers as a European cycling tour guide. While I led trips all over Europe, the one trip I did more than any other was through the Loire Valley, which likely sees more tourists on bike than any other region in France and perhaps all of Europe. It provides beautiful landscapes, incredible architecture, endless history lessons, and some of the best food and wine in all of France.

But where to start? Here is one possible itinerary, that starts in perhaps the region’s wine capital, Sancerre.

Let’s get this out of the way: including Sancerre in any Loire Valley cycling itinerary is a big commitment for a few reasons. First, Sancerre does not have a train station, with the closest being on the opposite bank of the Loire, about 5 kilometers away from the center of town and involves climbing up a decent hill and train service to this tiny station is at best infrequent. There is another, larger station, Cosne-sur-Loire, with more frequent service and the ability to handle larger trains, but it is about 15 kilometers from Sancerre. Second, Sancerre is fairly adrift from what most people consider “the Loire Valley”, that is the series of spectacular medieval and Renaissance castles that pepper the landscape.

Having said all of that, if you are planning a cycling trip, you should want to climb some hills and pedal a few kilometers. And Sancerre is worth the visit. Aside from producing what I consider the best Sauvignon Blanc in the world (and it is not really close), the town itself is beautiful: the medieval old town, the majestic views of the Loire Valley, and its castle that dates from the 14th Century. It’s worth a day or two. So starting there makes sense.

Before we go any further, a quick note on a phenomenon that is unique to the Loire Valley: Château fatigue. It’s real. There are over 300 castles in the Loire Valley with about 100 open to the public. So you are going to need to pace yourself. My advice? Storm a few of the “big” castles and maybe a couple of the lesser-visited ones if you must, but even if you stick to a max of one a day, it will wear you down. Trust me.

From Sancerre head north to Orléans which offers bucolic views along the Loire River. The Loire Valley is mostly flat, but this leg is a good 100k (~65 mile) ride along the Loire à Vélo bike route (mostly well-marked but pretty simple: stay close to that big river you see)., with not many significant stops along the way. One possible detour, about halfway to Orléans is the Aqueduct de Briare, an engineering marvel built by a guy named Gustave Eiffel; yeah, that Eiffel.

For many, Orléans is the beginning of a tour of the Loire Valley; it’s easily accessible from Paris, has a rich history, and boasts the first of the many statues of Joan of Arc. Little Joannie looms large over the Loire, so you might want to brush up on your 100 Year War history as each town that Joan visited will have a statue marking the spot that she gave King Charles VII a good talking to.

Leaving Orléans and heading west, the next real stop is Blois roughly 65k (40mi) away to the west. Here is where we need to start making some choices with the first vineyards since Sancerre and a couple of “don’t miss” castles. Chambord might be the most famous château in the valley, a “tiny” hunting lodge that boasts an incredible double-helix staircase (wide enough for horses) and a rooftop with 65 chimneys. Then there is Cheverny, which is privately owned, but the first floor is open to the public. Last, there is Blois itself, with its own castle and charming town, so a ton to consider.

From Blois to Tours is another (mostly flat) 60k where castles abound, starting with the medieval Chaumont, then Amboise whose château is perhaps the best example of the Renaissance style, and a bit off the route, my favorite, Chenonceau. If you only visit one château in France, I would say it should be Chenonceau. Yes, I am including Versailles, but I am a hopeless romantic and Chenonceau is just stunning. Seriously. Back along the Loire, the white wines switch from Sauvignon to Chenin Blanc in Vouvray, where we can also see some incredible troglodyte homes high up in the limestone cliffs, then switches back to Sauvignon in Tours, a vibrant college town.

For the next leg, I would suggest leaving the Loire for a bit and head to Chinon, one of my favorite towns in France, and home to perhaps the best Cabernet Franc in France. It’s another 60k with another full plate of castles to consider; Villandry, famed for its gardens, Azay-le-Rideau with the first real “moat” thus far, another medieval structure in Langeais, and Ussé, which was apparently the inspiration for Walt Disney’s Cinderella and Charles Perrault’s Sleeping Beauty. The castle in Chinon is a ruin, but that fits in with the town’s medieval vibe and huge Joan statue.

The last leg is a big one, 80k (50mi) from Chinon to Angers with a couple of castles along the way, most notably in Saumur, also known for sparkling wine and a fascination with horses. There is also the Abbey at Fontevraud, a UNESCO world heritage site, which merits a visit. I have not spent a ton of time in Angers since I am usually rushing to catch a train, but it hosts a charming old town and another medieval castle, which, at this point, seems like a bit of overkill, but I told you: Château fatigue is a real thing.