Bolzano is easily accessible from all major gateways. When you arrive, prepare yourself to experience some language confusion! Despite Bolzano’s location in Italy’s Dolomite Mountains, much of the city speaks German, negating any useful phrases you may have memorized from the back of your Italian guide book. This mesh of Italian and Austrian cultures, however, serves the city well, especially in its architecture. Bolzano’s medieval center features a parade of churches displaying both Gothic and Romanesque influences. In addition, Bolzano is also the current home of Reinhold Messner, considered the world’s greatest mountain climber. His Messner Mountain Museum, perched atop a cliff in the Castle Sigmundskron, is worth visiting for the views alone.

Today will begin with a shuttle to the top of Resia Pass. Surrounded by snow-dusted peaks, this pass tops out at 1,500 meters (4,921 ft), making for a shockingly scenic start for the bike portion of your tour. A designated cycle lane will protect you from vehicle traffic while you wheel past Lake Resia. Formed in 1950 by a dam, the lake actually flooded several alpine villages. This area has become iconic for a clock tower that juts out from the lake — it belonged to one of the submerged communities. 

You’ll then cruise through the tiny village of Clusio and then into Glorenza (pronounced Glurns in German). Completely walled and full of charm, Glorenza has the distinction of being Italy’s smallest city. You’ll lodge at night in Silandro, a quaint village surrounded by orchards, all situated in the heart of the Val Venosta Valley. The center of town is dominated by a 97-meter (318 ft) high steeple tower, making it the focus of cameras, especially when set against the backdrop of the surrounding mountain valley.

Today’s ride wheels through green alpine valleys checkered with orchards and farms, while following the twisting path of the Adige River, Italy’s second longest. Along the way you’ll pass Castle Dornsberg, an imposing structure built in 1217. You’ll eventually pedal into Merano for the night. Framed by snowtopped peaks, some stretching as high 3,335 meters (11,000 ft), this popular resort town is known for its hiking in the summer and skiing in the winter. Over the years Merano has attracted many literary giants, including Ezra Pound and Franz Kafka.

Again following the meandering path of the Adige River, you’ll pedal south through the Etschtal Valley into Nalles (Nals in German), the most northerly village of the South Tyrolean Wine Road. Vineyards and orchards mesh with castles and fortresses, lending this small village of 1,600 a picturesque quality normally only seen in the glossy pages of Condé Nast. Then it’s into Andriano (Andrian in German), a small resort town with the oldest wine cooperative (1893) in the South Tyrol region. You’ll then return to Bolzano, the starting point of your tour.

After breakfast, depart at the time of your choice.