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Welcome to YMMV Reviews. On this site I write outdoor gear reviews and chronicle my adventures along the way.

Rapha Retreat Italy

Rapha Retreat Italy

Cycling in Italy is about as good as it gets. The history and love for the bicycle is evident even for someone living thousands of miles away in the US. It is even more apparent if you can get to Italy. If you ever get a chance, I would highly recommend getting over to Italy to ride and a Rapha trip is a good way to do it. For us, we were looking for a memorable vacation to celebrate Melissa's birthday. We tend to like active vacations and I had been looking at a cycling vacation for a couple of years.

If you are not familiar with Rapha. They are a high-end cycling apparel company out of the United Kingdom. They were founded back in 2004 and have evolved into more than just a clothing company. They now are an online emporium of performance road wear, accessories, and publications. The brand includes physical retail locations, luxury travel, and a cycling club with global membership. Rapha has also been a sponsor for many cycling teams, including Team Sky on the Pro Tour from 2012-2016. We had been familiar with Rapha due to me reviewing for this site over the years. Their products were always top notch; so over time I had purchased a good amount on my own. We also had noticed that they run a segment of their business to provide luxury travel for cyclist to destination around the world. These trips blend epic locations, with nice accommodations and attentive service. They also have plenty of riding depending on the type of trip you choose.

Speaking of these trips, Rapha offers 7 different trip types at the time of this writing.

  • Randonèe: This is the signature Rapha Travel experience. They are a week-long point-to-point ride in cycling's classic territories. Randonèes are all about the riding, averaging 150k in length and 2,500m in climbing. Tough days with ample support so all you must do is think about the riding. They are rated a 4 out of 5 in difficulty.

  • Raid: A pure cycling adventure. These are designed for riders looking to go off the beaten track and exploring spectacular destinations and roads. These are like Randonèes with point-to-point itineraries, similar distances, but less hands-on support. They are also a 4 out of 5 in difficulty.

  • Ascent: These trips conquer a legendary col. They are an ideal four-day getaway to ride in iconic cycling regions and tackle a legendary climb. The trips are based in one location and are more suitable for a wide range of riders. Difficulty of these trips area 3 out of 5.

  • Retreat: These are trips where you can ride and recharge in stunning settings. A luxurious break where the emphasis is as much on unwinding and enjoying the stunning surroundings as it is on the cycling. These have an exclusive accommodation that is home base where daily trips into the region and culture take place. These trips are more flexible and thus rates a 2 out of 5 in difficulty.

  • Pro Team Camp: Your opportunity to train like the pros. Hard days on fabulous terrain with eating and relaxation at night. These trips include a coaching consultancy on hand to offer training and nutrition advice to help you achieve your goals. These trips rate a 3 out of 5 difficulty.

  • Cent Cols Challenge: Here is where it gets tough. One hundred cols in ten days. Yes, that is right. The ultimate cycling endurance feat. These take place across Europe, crisscrossing entire mountain ranges to combine big grand tour climbs with back-country gems. Each day is 8-10 hours in the saddle and are only for the strongest riders. These trips are a 5 out of 5 in difficulty.

  • Bespoke: Create your own trip. Rapha can help you curate your own epic cycling trip. They can help you create a trip of a lifetime.

Famous Vecchio Bridge in Florence

Famous Vecchio Bridge in Florence

Both Melissa's and my birthday are at the end of September, so we decided to do a Tuscany trip that would be during this time. This trip was a Retreat, which meant that it was both on the easier side of the Rapha scale, but also had one home base where we would stay for the week. Since this was more of a vacation then a training camp, and we were not nearly in the shape we needed to be in, so we thought a Retreat would be the best option. Neither of us had ever been to Italy before either, which was a plus. We decided we would also extend our trip on both sides to take in a bit more of the country as we had flown all the way over there. Our trip started in Florence before the Retreat and then went to Cinque Terre, Monaco, and Villefranche-sur-Mer, France before flying home. Not a bad way to celebrate our birthdays!

As we prepared for the trip, Rapha communicated with us about what to expect on the trip. They sent out a couple pamphlets; one on the region of Tuscany and the other with tips for getting ready to ride. As we were living in Chicago, we tried to prepare for the trip by getting out and riding the Lakefront Trail or taking Flywheel courses. However, if you know Chicago, the hill training was a bit lacking. We were hoping that all our riding in Colorado will help, but that may be a stretch. One thing that is cool about a Rapha Retreat is the bike hire they have. With the cost, Rapha will set you up on one of their fleet bikes for the week. These are high end bikes from whomever is their partner for the season. In years past it had been Pinarello, but this recently changed to Canyon, so we were on the Canyon Endurance CF bike with Shimano Ultegra components. To get setup you send over your fit specs on your current ride and the mechanics will get you the right frame size and set up the bike to your specs. You can even bring your own saddle with you if you would rather, or you can opt for one of theirs. I opted for theirs which was a Fizik Antares+ which is what I currently have on one of my bikes now. You do have to bring your pedals, this allows you to ride what you are used to, and they are much easier to pack than a bike.

It seems like forever from the time we decided to do the trip and when it finally came time to go. We flew into Florence and couple days early and explored the city on foot. The first thing I noticed upon arriving in Florence was that the Tuscany region was not flat. I knew that Tuscany had rolling hills, but maybe not to the extent that they went up and down. More on that later.

Day 1 - Florence pickup & Chianti shake out ride

The trip started on Saturday in Florence. Since we were already in town, we opted to get picked up at the local train station rather than the airport. When we arrived, we noticed the Rapha van right off. In Italy, most the cars are tiny so spotting a larger car is pretty easy. When we got over there and met James, he mentioned that our van was now full and to hop in. James was the leader for our trip, from the UK, he was not only a great cyclist, but also had a witty humor that added to the experience over the whole trip. In our van, we had two other couples other than ourselves. Funny as it was, one of the couples was from Chicago, IL like us and the other was from the Bay Area in California. As far as the trip goes, it was much more diverse than our van. We had a gentleman from Norway, a couple from France, two ladies from Australia, another couple from the US, a gentleman from Minnesota, and a gentleman from the UK. To help support this group we had James who I mentioned before, Johnny, a guide from the UK, Mattia, a guide & mechanic from Italy, Alison a guide from Canada/Italy, and Vicki a soigneur from the UK/France. If it does not come across from the rest of this writing, our group was awesome. Both the clients and the support.

Our Humble Accommodations

Our home base for the week was Il Borgo di Vèscine in the Chianti region of Tuscany. This place was just as you would expect when staying in the Tuscan countryside. Up on the hillside with views of the region. This is a 13th century Etruscan village, the ancient dwellings of which have been transformed into charming guest rooms. It has a restaurant, a cellar, and even a pool. All of which is postcard worthy as you can hopefully see from my pictures. When we arrived in the early afternoon, we got our rooms for the week. Melissa and I were up in one of the higher up rooms in the back of the property. It was a one bedroom, one bath unit with a small porch and views out over the rest of the hotel. The group was given instructions to explore a bit of the hotel and get our bikes set up for the week. Our mechanic Mattia had all the bikes already set up, we only had to get our pedals on, saddles (if needed) on, and then a quick spin to double check seat height. Along with these, Rapha also had Garmin units ready for us to use during the week already pre-loaded with the maps for each day.

As the rest of the group arrived, we all sat down for a short l meet and greet over food and to discuss the evening ride. Of the group, two of the ladies on the trip were not planning on riding all the days or at all.  So, the team went over some of the options for them as well. We saddled up for our first ride, a 24-mile loop that headed east from the hotel. The Il Borgo di Vèscine sits up at 600m on a ridgetop. Remember how I mentioned that the Tuscan region was hilly, this ride gave a true reminder on how hilly it is. The ride was to be a lollipop through Radda in Chianti and Gaole in Chianti. The latter being the home of the Eroica events. It is worth mentioning that the weather for the whole trip was just about perfect. Averaging 75-80 degrees with sunshine every day. This ride was no different. As we got our legs heading down into Radda in Chianti, we talked and got to know each other and the Italian drivers who for the most part were very respectful of cyclists. The roads there do not have much of a shoulder and are not very wide either. However, cycling is a large part of the region and the drivers on the road were very respectful as long as you followed the rules of the road. Otherwise they would give you a nice honk. =)

After getting through Radda in Chianti, we road some back roads along the ridge which has some good punchy climbs in it. One thing also to note, on the trip we did not give climbs adjectives like steep or long, rather we called them spicy or memorable or something of that nature. I truly think they would do this so we would not fear them but rather let our imagination just wonder. It was on these first climb that both Melissa and I wondered if we may have bitten off more than we could chew. It was very apparent that our hill climbing was a bit lacking and that Tuscany, while note having any big mountains, had plenty of hills with lots of sting in them. With the first climb and descent in we took a cappuccino break in Gaole in Chianti. One thing that we did everyday was take a Cappuccino break after getting some miles in our legs. This allowed us to regroup and experience a bit of the culture along the way. Since much of the ride thus far was downhill, we knew that the remainder would be climbing back up to the hotel. I must say that the remainder was not nearly as tough as the first climb. I think some of it was getting my legs going, but the break did me good. The first ride was 24 miles with 2,300 feet of climbing. Pretty solid for the first day.

Winery Visit

Each afternoon when we got back to our hotel the Rapha team would have us rack our bikes where they would clean them up, recharge our Garmin's, and store them for the night to be out and ready the next day. We would also have a bunch of prepackaged as well as homemade recovery goodies ready for us. This way we could recover and be ready for the next day. After being given time to clean up we would meet back at the restaurant and have dinner and discuss the week ahead. Each day we had a planned ride. The location was picked not only due to the lush accommodations, but also since it had good routes out in each direction so we could flavor a different area of Tuscany each day. Rapha would support us on the bike with 2-3 guides a day as well as with a van or two depending on the day. The non-riders of the day could either join us in the vans or had other activities planned as well if they were so inclined. These included shopping and cooking lessons. This being a Retreat, the focus was cycling, but not just. During the week, we had events planned to visit a winery, check out some towns, and have an evening in Sienna. They wanted us to see both the cycling of the region as well as the culture. From coffee stops to excellent food, it all was meticulously crafted for us.

Day 2 - San Gigimnamo Loop

Day two was our big day. Our ride was another lollipop, this time heading to the east. Our big attraction was having lunch in Sam Gigimnano, a hill town encircled by walls from the 13th century. As the town was on a hill, you could pretty much see it from the break. All morning we could see where we were going. We got off to an early start after an upscale continental breakfast. The ride would start by descending for 18k into Poggibonsi where we would take a cappuccino break. While it was a long descent, it was not steep enough to not pedal, of course we also knew that we would later be climbing this same hill back up, bummer. From Poggibonsi we would meander through the valley in a not so direct route before climbing up to the town of San Gimignano. While not a long climb, I must say these hills were spicy. See what I did there? The sections would have gradients easily in the double digits. Apart from these short sections I must say I felt much stronger than the day before which made me feel good. Once we arrived at the town, we had about 45 minutes to wander before meeting up for lunch. The town of Sam Gimignano was just what I would have expected for an old Italian town. It had tight alleyways, made entirely of stone, and was beautiful. The main walkway was lines with shops and was only accessible by foot, no cars. One interesting thing about San Gigimnano is that it has multiple torture museums and the town is small. We wandered around town taking some pictures and then met up at a local pizza place for lunch. After lunch, we headed back out, descending back down to the valley floor. Melissa who is not a big fan of descending decided to ride in the van until the bottom which let me be a bit more aggressive than I had been thus far. Being a good husband, I try to stay with her on the descents for the most part. Now I was free to ride and even passed one section that said 20% which I know Melissa is glad she skipped. I even got a bit too excited in placed and may have slid a bit around a turn or two.

To San Gigimnamo on the hill.

After Melissa got back on the bike, we meandered a little through the valley before happening on a small backroad climb to a small group of homes on a hill. We were informed that this climb would be memorable, not a good thing when it comes to effort. To add insult to injury, Mattia, one of the guides, passed us all climbing while doing a wheelie. Pretty cool but humbling as well. The climb itself was memorable and after a short break we continued along the ridge and then descending back into Poggibonsi for our last fun of the day. The 18k climb back up to Castelina in Chianti where we had a gelato stop planned. Let me take a break from the riding to mention that gelato is awesome, especially in Italy, and even more so after an 18k climb. Highly recommended. The climb itself was not too bad. I hung back with Melissa and one of the ladies from Australia to support and get support to the top. What goes down must come up, but I would prefer not to. The ride all in was 62 miles in length with 5,407 feet off climbing. Nothing crazy, but about 5,390 feet more climbing than a typical ride in Chicago. That evening was like the first where we would have some time to clean up before meeting for dinner. The only difference would be how tired we all were from the first big day. I think we all slept well that night.

Day 3 - Dudda Loop

Coming into the trip, Melissa had been battling a bit of neck pain which was aggravated from being on the bike. As day 3 was supposed to be a day with a couple good climbs and descents, Melissa decided to take the day off to attend the cooking class with a couple other ladies. Thus, we had a smaller group for the day. This time we headed north out of the hotel for a loop ride including Panzano in Chianti, Greve in Chianti, Dudda, Lucolena in Chianti, and Radda in Chianti. The ride was not very long in length, but it had some bite. We were either going up or down the whole time. With four thrilling descents and good climbs, I think this turned out to be the hardest day for me. The first descent and climb took up to the town of Panzano in Chianti. This little hilltop town was visible for most of the climb which made for an excellent carrot to chase. Once at the top we rendezvoused at a local butcher shop which had been in the family for hundreds of years. The Rapha team had set up for us to get a quick tour of the shop where they explained their history, philosophy, and let us sample some wine & bread. These are some of the things I really enjoyed being able to experience on the trip.

Dudda Pit Stop

With another decent, climb, and partial descent in the legs we rolled into Dudda, a small country hamlet that is part of Greve in Chianti. This hamlet had a small store with what appeared to be vacation villas scattered around. We stopped to have our daily cappuccino break and get ready for the largest climb of the day ahead. I must now say that even though I call these cappuccino breaks, there were more options then just coffee. As someone who is not a coffee drinker, I used these breaks to try all the different limonatas I could. Turns out there are several brands that make this sparkling lemon soda and honestly, they were all good. The third climb of the day was by far and away the hardest for me. I think the combination of the previous day, earlier climbs, heat, and difficulty of the climb made it grueling. The Baddiacia a Montemuro was 4.5 miles at 6% grade but it sure felt harder than that to me. With a small descent in there and a flatter section at the top, the rest was a bit steeper than the average. After a quick break at the top we continued to the town of Radda in Chianti for our lunch at La Vin'Osteria. I mention the name as it was the best Italian meal I have ever had!! An unassuming place next to the main road, it had a beautiful stone interior and the food was awesome. Maybe all the riding had something to do with it, but I would love to be eating that again for lunch today. We ordered family style for the whole group and that included bruschetta, a creamy pesto pasta, and a spicy red sauce gnocchi. Even though I knew I had to continue to ride, I could not help but eat a bit too much, it was that good. I do not think I was the only one, as the remaining couple miles were a bit of a slow roll uphill. Day 3 ended up being 35 miles with 4,500 feet of climbing.

Since we had a shorter ride, that afternoon the Rapha team had set up a tour of the Badia a Coltibuono hotel and wine cellars. It was really interesting getting to see how they age the wines in barrels and the families own collection dating back until the early 1900's. The hotel itself is an 11th century abbey that has been transformed. Attached is a historic church and has an idyllic setting in the back with manicured gardens surrounded by the wooded hills of the region.

Day 4 - Sienna outing

Day 4 was the day Melissa and I were looking forward to. I happened to be Melissa's birthday as well as the day we rode to Siena. Siena is a city steeped in history. A walled city that dates to AD 70 or more, the city is famous for its art, culture, and Palio horse race. For us the plan was to ride down through Radda in Chanti, Gaole in Chianti, and several other towns to the south to Siena. Along the ride, we had a planned picnic stop before riding into the city. The ride was going to be mostly flat to downhill which provided a nice break from the climbing the day before. On these flat roads, we were able to make good time. Getting into an echelon we could power along. We also came across several riders out preparing for the upcoming Eroica ride. Some of which joined in with our group for a couple miles at a time. Once we entered Siena, the Rapha team had rented two rooms in a local hotel for us to shower and clean up. This hotel was on the outskirts of the city and with our showers, we took the opportunity to lounge out on their outdoor patio overlooking the city.

Rapha Team

Once the whole team was cleaned up, we headed into the city where we had a private tour of the city arranged. It was by a local woman who not only had a passion for Siena, but also a passion for her district, the Rhino district. Siena is broken up into different districts within the city. These districts are who competes each July and August in the Palio horse race. Our guide made sure we understood two things during our tour, that the Rhino district was the best district and the Siena is better than Florence. It was cool to be able to walk around the city and get some of the history of the city and to go into some of the Rhino Districts gathering places. Siena was an interesting city with tight streets that went up and down the steep hill the city is perched on. The main Campo Square is a cool place to hang out. There are several restaurants around the edges and lots of people just sitting around enjoying the scenery. Melissa and I hit up one of the local gelato shops and enjoyed it within the square. Our group had a planned dinner at one of the local restaurants where we had a multi course meal and were able to celebrate Melissa's birthday. The Rapha team even surprised her with a birthday cake making for a birthday she will never forget.

Day 5 - Stradia Bianchi Loop

After a late night in Siena, we ended getting a bit later of a start on Day 5. Day 5 was going to be another harder day in the saddle and Melissa decided to take the day off due to her wrists and shoulders bothering her. The ride went to the southeast toward Gaole in Chianti and then climbed the highest hill in Tuscany, a 2,500 ft. hill with radio towers on top. The climb was tame compared to a couple others we had been on and before long we were taking a break at the top. The descent was a fun one where we eventually entered a small town where we stopped for our daily cappuccino break. What made the remainder of the day fun was that much of it was on the Stradia Bianchi, white roads of Tuscany. These roads along with the heat of the day made for a tough afternoon ride. The white roads have steeper climbs than you see on paved roads and have other obstacles like loose dirt and potholes to negotiate. After an especially spicy climb, we had a roadside picnic on top of one of the ridges. After lunch, we had plenty more miles along the white roads until we eventually popped out just below Radda in Chianti, ultimately doing a loop for the day. It was kind of bittersweet as we climbed up into town and then rode the ridge to the hotel for the last time. It had been a magical week of riding and was a bit sad knowing it was coming to an end. Day 5 ended up being 50 miles with 5,200 feet of climbing.

Ready to Ride

That night we enjoyed another great dinner at the hotel and relived some of the top moments of the trips. Depending on each group’s plans, some were leaving earlier than others so we said many of our goodbyes that evening. Melissa and I had train tickets to Cinque Terre the next day at 1 pm so we did not have to hurry out as early as some others. We could have breakfast with some of the team in the morning before we headed out. The group ultimately had so much fun together that we made informal plans to do it again in 2018 in the south of France.

Overall, the Rapha Retreat was incredible. Melissa and I thought it was an excellent mix of culture and riding. The service by the team was phenomenal with everything taken care of so you could relax, ride, and enjoy the experience. James, Johnny, Vicki, Mattia, and Alison were all fantastic. If you have ever thought about doing a cycling vacation, I would highly recommend do a Rapha trip. Especially the Tuscany trip. After several years of running this trip, they truly have everything dialed in. While the rest of our vacation was a lot of fun with some beautiful scenery, the Rapha Retreat was the highlight of our trip. We really hope we can make it to France in 2018!! As always, Your Mileage May Vary.

Gear Used (Only if Worthy of Mention)


  • Gregory Scout 65 Backpack - I have liked this pack thus far. Fit is solid with lots of storage solutions and easy to carry.

  • Rapha Lightweight Jersey - Lightweight and good fitting jersey. Great for the hot days. Even a touch of pink for Italy.

  • Rapha Lightweight Bib Shorts - Great bib shorts with a comfortable pad. I mentioned that I did not have much saddle time before the trip. Even so, I had no saddle issues on the whole trip and think my Rapha bibs with chamois cream are to thank.

  • Rapha Training Jersey - I like this jersey as it fits well, looks good and has good pockets. Might have been a bit heavier than I preferred for the hot days.

  • Rapha Training Bib Shorts - Comfortable bib shorts with a Team Sky Stripe. Like the Lightweight shorts above, these were comfortable for all day riding ion the warm temperatures.

  • Canyon Endurance CF Bike - My first time riding a Canyon bike. I was impressed by the quality of the ride and finish of this bike. Whether I was on smooth tarmac or a day on and off the Stradia Bianchi, the Canyon handled it well. We ran slightly wider tires and rim brakes. IT would have been nice to have disc brakes and an even wider tire for even more comfort. Even better is the price that this bike can be purchased for and they are coming to America in 2017!


  • Gregory Amber 60 Pack - Melissa liked the setup of the pack and all the storage solutions. Unfortunately, the size small was a little too small and the pack will ultimately be sold.

  • Canyon Endurance CF Bike - Melissa was also impressed with her Canyon. The Shimano Ultegra shifting was solid and the geometry even allowed Melissa to be comfortable on the bike which is important with a all the ups, downs, and turns.

2017 Chicago Marathon

2017 Chicago Marathon

2014 Bolder Boulder 10k

2014 Bolder Boulder 10k