Overview

Welcome to your cycling adventure spanning three countries in one week! Your guides will meet you at the main entrance of Trieste Centrale at 10:00 AM, then a brief shuttle takes you out of the city to the maritime villages near the border. In the Italian coastal town of Muggia, your bikes will be ready and waiting. After a personalized bike fit and a quick safety briefing, you’ll soon cross into Slovenia and roll along the Adriatic coastline, tracing seaside roads past Ankaran, Koper, and Izola. Much of the day follows the historic Parenzana Trail, a former railway turned dedicated cycling route. Leaving the trail, you’ll climb over the Piran peninsula before a rewarding descent into the resort town of Portorož. Settle in at Palace Portorož Hotel for the next two nights. This evening, the hotel welcomes you for dinner in its fine-dining restaurant, an ideal setting to gather, toast, and savor what’s ahead.

Overview

Today takes you into the hills above Portorož and into the Koper countryside, where quiet ridge roads wind through Slovenia’s Istria wine country. The terrain is a steady mix of climbs and rolling contours, with sweeping sightlines across vineyards and coastal hillsides. Along the way, your guides will share a bit of the region’s story and what grows here: Refošk, a bold local red with roots dating back to Roman times. After a breathtaking morning of climbs and curves, settle in for lunch at a local tavern and take in the panorama of the terrain you’ve just ridden. In the afternoon, choose between a few more punchy hills along the ridgeline or an easier return through the valley back to the hotel. This evening, we'll meet to head into nearby Piran together to explore its Venetian architecture and rich history with a private walking tour. Afterwards, enjoy a dinner of your choice at one of the many restaurants of the old town.

Overview

Say goodbye to Slovenia and hello to Croatia as you ride out of Portorož and cross the border. Today’s route follows sections of the scenic Istrian Wine Trail through rolling hills and coastal roads lined with vineyards full of Istria’s signature grapes—Malvazija and Teran—alongside other local varietals. Watch for the region’s distinctive red clay soils, and, with a bit of luck, you may even spot the Boškarin, the indigenous Istrian ox. By late morning, you’ll roll into Poreč, a historic seaside town home to the UNESCO-listed Euphrasian Basilica, renowned for its early Christian mosaics and Byzantine architecture. Spend time exploring the old town, then enjoy a relaxed lunch at one of our recommended spots. This afternoon, a shuttle brings everyone to San Canzian Village & Hotel. Tonight, gather for dinner at a favorite nearby restaurant and savor the flavors of the region.

Overview

Wake up in the quiet Istrian hills, then set out to explore a string of storybook villages and the region’s most prized ingredient: truffles. Your ride begins with a climb to Grožnjan, a hilltop town known for its creative spirit. Often referred to as the “artist town,” the tiny year-round population supports more than 20 art galleries and studios. From there, weave through Oprtalj’s stone streets toward the Motovun Forest. Here, a local truffle-hunting family introduces you to the “Gold of Istria” with a savory tasting lunch and cooking class. Afterward, opt for a scenic ride back to the hotel or hop in the shuttle to leave time to unwind. Riders looking for a little more time in the saddle can take the Avid option, adding an extra, winding climb back up to Grožnjan before returning. Dinner is on your own tonight, either at the hotel’s Luciano Restaurant or in nearby Buje, a short taxi ride from the hotel.

Overview

Start your day with the hotel’s fresh breakfast buffet, then set out with a descent into the Mirna Valley before your first climb of the day to Motovun, a beautifully preserved hilltop town known for its strategic perch and historic architecture. Enjoy a coffee with sweeping vistas, then return to the bikes and ride deeper into Istria’s farmland, passing vineyards and olive groves along quiet country roads. Midday brings a stop in Tinjan—often called the Municipality of Istrian ham—for lunch with a tasting of local prosciutto, a traditional specialty recognized with a protected European label of origin. Afterward, pedal back north across open countryside, crossing the Mirna river once more before the final climb back to San Canzian. Tonight, take a short shuttle to an inventive local restaurant to toast the week and enjoy one last Istrian feast.

Overview

The final morning is yours — rise early for a last spin through the quiet country roads of northern Croatia, or take your time over breakfast before saying goodbye. Guides will say farewell at 11:00 AM, with a private shuttle returning you to Trieste Central Station in approximately one hour, where frequent trains continue to Venice for those traveling onward.