Tuscany By the Sea Bike Tour

Meet your guides at the Pisa Centrale train station for a short transfer to the perched village of Montecatini Val di Cecina. Before we even hit the road, there are unbelievable views across the Cecina Valley—and after a bike fitting and safety briefing, we’ll ride out into the Tuscan countryside to chase them. Our route moves through pastures and forests, culminating in a climb that reaches a series of hill towns on the last ridge between us and the sea. Hilltop villages are common in this area along the Tuscan coast—known as the Maremma—and were originally designed to defend against pirates. In one such town, meet our friends Sara and Simone at their restaurant for a seasonal lunch with sea views. After, pedal into the Bolgheri wine region and check in at our lovely little relais at the heart of a working farm. We kick off our first dinner together the only way we know how: by uncorking a few of the Super Tuscans that make this part of Italy a standout in the wine world.

Meals: Lunch / Dinner
Destinations: Montecatini Val di Cecina, Guardistallo, Bibbona
Accomplished: 22 miles / 35 km, elevation gain: 1,486 feet / 453 meters
Longer Option: 27 miles / 44 km, elevation gain: 1,961 feet / 598 meters
Accommodations: Relais Sant’Elena

After breakfast on the hotel terrace, begin a loop ride that covers the full spectrum of local scenery. First, it’s tiny mountain hamlets like Canneto and Monteverdi, where we’ll stop for coffee with the locals. Densely forested valleys follow, eventually giving way to olive groves and vineyards of the coastal plain. Notably, we’ll pass through the hilltop town of Castagneto Carducci—renamed for Italy’s first Nobel Prizewinner in literature, Giosue Carducci, who spent his childhood here. A Mediterranean-style lunch is served at our friend’s farmhouse, followed by the remainder of the ride back into Bolgheri and ending at our hotel. Tonight we fill our cups with even more Tuscan wine at the Guado al Tasso estate, where dinner is paired with their exceptional Sassicaia and other top vintages.

Meals: Breakfast / Lunch / Dinner
Destinations: Monteverdi, Castagneto Carducci, Bolgheri
Accomplished: 31 miles / 50 km, elevation gain: 2,116 feet / 645 meters
Longer Option: 41 miles / 66 km, elevation gain: 2,768 feet / 844 meters
Accommodations: Relais Sant’Elena

The relais has been good to us, but it’s time head for the hills behind Castagneto Carducci. Today’s ride kicks off with a climb into the picturesque town of Sassetta, characterized by its chestnut stands and quarries of famous red marble. The highlight of the day is the glorious stretch of road between Sassetta and Suvereto, lined with wildflowers, cypress, and stone pines beneath the wide-open sky. Stop at a family farm for a picnic lunch featuring estate-grown wine and olive oil. From here, choose to transfer or ride the rest of the way to our next hotel, a boutique property built at a historic, family-owned villa. Catch a beautiful sunset on the Etruscan Coast during dinner—tomorrow, we too will move toward the Mediterranean bound for Elba island.

Meals: Breakfast / Lunch / Dinner
Destinations: Sassetta, Suvereto, Campiglia Marittima
Accomplished: 28 miles / 45 km, elevation gain: 2,070 feet / 631 meters
Longer Option: 37 miles / 60 km, elevation gain: 3,165 feet / 965 meters
Accommodations: Poggio ai Santi or Castello Bonaria

Many know Elba as the place synonymous with Napoleon’s white-collar exile, immortalized in the palindrome “able was I ere I saw Elba.” Emperor or not, Elba is hardly a hostile place to land, with its lush and scrubby peaks, powdery sand beaches, and inviting azure water. This morning we cross the straits by boat and arrive on island with our bikes ready to pedal down the coast to Porto Azzurro, where pretty pastel houses cluster around a tiny harbor. Dig a little deeper on a climb over the Passo del Monumento—the reward is a finish on the beaches of Biodola, our home for the next two nights. Take a triumphant dip in the sea and relax over lunch at our luxurious beachfront hotel. The rest of the day is yours to spend as you wish: visit Napoleon’s villa, tour any of the island’s historic fortresses, sprawl on the sand, or hit the spa. Come dinnertime, you’re free to dine on your own in one of Biodola’s many beachy restaurants.

Meals: Breakfast / Lunch
Destinations: Cavo, Porto Azzurro, Biodola
Accomplished: 30 miles / 48 km, elevation gain: 2,850 feet / 869 meters
Shorter Option: 22 miles / 36 km, elevation gain: 1,804 feet / 550 meters
Accommodations: Baia Bianca

We’ve saved the best for last: on our final day, we’ll complete Elba’s epic Giro dell’Isola—a circuit of the island entirely on panoramic coastal roads. Hug the cliffside as you drink in non-stop views until we come upon the port of Marciana Marina, peppered with terracotta-topped buildings. Challenge yourself with the climb into upper Marciana, then start smiling ear-to-ear as we curve along the other side of the island on scenic bends above Chiessi and round the Costa del Sole into Marina di Campo. A well-earned plate of seafood pasta is waiting for us, and it tastes almost as good as our triumphant ride. It’s a straight shot through the interior back to our hotel. Regroup for our celebratory farewell dinner this evening as the trip comes to a close on our quiet little bay.

Meals: Breakfast / Lunch / Dinner
Destinations: Marciana Marina, Pomonte, Campo di Marina
Accomplished: 38 miles / 56 km, elevation gain: 3,713 feet / 1,132 meters
Shorter Option: 29 miles / 47 km, elevation gain: 3,021 feet / 921 meters
Accommodations: Baia Bianca

Sleep in before a final dip in the sea or walk along the coast. Later in the morning we’ll head to Portoferraio, Elba’s main town, for a ferry back to Piombino on the mainland. We say our goodbyes at the Campiglia Marittima train station—from here, you can catch a train to Rome, Pisa, or Florence as you make your way to your next destination.

Meals: Breakfast
Destinations: Portoferraio, Piombino