Overview

Meet your Trek Travel host at 11:00 AM in the hotel lobby in the cozy beach town of Cattolica, on the Romagna coast, overlooking the Adriatic Sea. After reviewing the week's plans, your host will fit you to your Trek bike for maximum comfort and performance. Then, embark on a fabulous introductory ride, starting with a gradual climb to Gabicce Monte and rolling along the scenic Via Panoramica. The ride continues inland through charming villages, ending at the magnificent Gradara Castle that towers over the valley below. We recommend you spend some time wandering through the cobbled streets of this perfectly preserved medieval fortress and perhaps enjoy a coffee with sea views. This evening, dine at the hotel or choose from our hand-selected local restaurant recommendations.

Overview

Following your morning’s cappuccino, saddle up and head out to the ancient Republic of San Marino, the fortified town characterized by three famous peaks that you can clearly see from the coast. Along the way, you'll be joined by incredible views of hills dotted with farms, grapes vines, and grains. The ascent up to San Marino is challenging but you'll be rewarded with views from its highest point. If you feel like adding more miles and elevation, the avid option is spectacular—a single road chiseled into the rock that winds all the way up to the village of San Leo, a place of outstanding cultural richness and natural beauty. Back at the hotel, enjoy the spa or head to the hotel's private beach to rest your climbing legs and unwind after your ride. Tonight, treat yourself to another meal of your choice at the hotel or in town. If you haven’t tried it yet, savor the piadina romagnola, a flatbread typical of the region, served with a selection of cheese and dry-cured meats; you just need to stop at one of the many kiosks around town and watch as they're made in the traditional, local style.

Overview

Another fantastic day awaits today, with rolling hills stretching as far as the eye can see. The first highlight of the ride is Tavullia, the birthplace of the legendary motorcycle World Champion Valentino Rossi. As you continue your ride, you'll ascend to Montegridolfo, a fortified village encircled by robust walls. The entrance, guarded by a tower with a medieval gateway, has been meticulously and fully restored. After a lunch stop at your leisure, continue pedaling towards the remarkable village of Mondaino, located on a hilltop in the middle of the Conca Valley. This lovely place is mostly known for its local fossa cheese. Don’t miss the opportunity to visit the pits carved out of the rock under the castle of Mondaino, where the cheese is aged. Shortly after this you'll encounter Saludecio, an elegant town with a maze of alleyways enclosed within monumental walls. From there, it will be a speedy stretch back to the hotel in Cattolica. The avid option will extend the loop to Urbino. This walled medieval hilltop village is one of the most important sites in Renaissance Italy and a UNESCO World Heritage Site.

Overview

Today's journey takes you through fortresses revealing the turbulent past of rival families—the Malatesta family from Rimini and Montefeltro family from Urbino. First, visit the Malatesta Castle of Montefiore, a towering giant in the greenery of Malatesta Seignory, serving as both a defensive bastion and summer home. Climb to the highest terrace for splendid views of the Apennines and Romagna coasts. Next, head to Montecolombo and Montescudo on the left bank of the Conca River, passing Albereto Castle. Ride through fields of vines and olive trees, scattered farmhouses, and ancient villages, reaching Coriano before returning to the hotel. On request, avid cyclists have the option to retrace the roads where Marco Pantani used to train, with special GPX tracks of Pantani’s favorite routes, including the legendary Monte Carpegna. Your Trek Travel host is available to shuttle you to these routes (for an additional fee). Tonight, toast an incredible self-guided bike tour through the rolling hills of Romagna, discovering a land of exceptional culture, culinary delights, and fabulous riding.

Overview

On this final day of your self-guided bike tour in Romagna, take the morning to sleep in and relax, savoring a long breakfast and enjoying a walk on the beach. Or choose a final spin before leaving your lovely beach town. You’ll have enough time to return to the hotel, shower, and change before you depart. Your Trek Travel host will meet you at 11:00 AM at the hotel to take your bike and say farewell, concluding your self-guided adventure.