Overview

Welcome to Japan! Your trip begins in Nara, where you’ll meet your guides at 10:30 AM at Noborioji Hotel Nara. After lunch, your guides will introduce you to your Trek bike with a personalized fit to ensure your comfort for the week, then cover safety tips and a route overview before heading out on your first scenic ride—and in Japan, that means remembering to ride on the left. You will wind along bike paths and back streets before passing the beautiful Todaiji Temple, one of many temples that we will visit on trip. Nara will be your home for the next three nights, just steps from Nara Park, where deer roam freely through the streets. This evening, gather for a warm welcome and trip overview at our social hour followed by an unforgettable dinner at the hotel restaurant, Le Bois.

Overview

Wake in Nara, a vibrant city that once served as Japan’s first permanent capital and remains a cultural center with UNESCO World Heritage sites, including historic temples and the former imperial palace grounds. After a freshly prepared breakfast, head out for a steady climb and quiet descent on rural backroads framed by rolling farmland. A small countryside temple offers a calm mid-ride stop before returning to the hotel. Lunch is back at the hotel, where a master sushi chef will guide a hands-on sushi-making experience. You’ll learn the techniques, try your hand at rolling, and enjoy additional dishes alongside the sushi you create. After a relaxed afternoon, we'll gather for dinner at a casual local restaurant.

Overview

Today you'll head out on your last ride around Nara. Get your legs ready because after a short warm-up, a sustained climb of four and a half miles winds through cedar forests and past centuries-old temples before reaching a broad plateau. At the top, flooded rice paddies stretch across the landscape, reflecting new seedlings in the water as frogs croak along the edges. Stop for a traditional lunch, including seasonal ingredients and noodles, rice-based donburi, or Japanese katsu curry. Back on the bike, a few small hills follow before a long descent back toward the city. Pass through Tenri, known for its distinctive modern Buddhist temples and the community that lives, studies, and worships there, then finish on quiet back streets lined with small gardens and traditional homes. This afternoon you're free to explore Nara’s historic center, including Tōdai-ji Temple—an impressive 8th-century landmark housing the world’s largest bronze statue of Buddha Vairocana. This evening enjoy a drink at the hotel's beautiful bar before heading out for dinner on your own at one of Nara’s many outstanding restaurants.

Overview

This morning you’ll roll out of Nara toward the edges of Kyoto, following quiet country lanes and gentle river paths. As rice paddies and forested stretches give way to the city’s outskirts, the route offers a natural transition from rural riding to Japan’s cultural heart. At the end of the ride, you’ll board the Shinkansen bullet train for a smooth, two-hour ride through the countryside toward Hakone while enjoying a traditional bento boxed lunch. After arrival at the Odawara Station, you will board a 30-minute shuttle to your hotel with views of the surrounding mountains. We will arrive at your luxurious accommodation in Hakone with some free time to enjoy the property before gathering for dinner, ending the day with warm hospitality in a serene mountain setting.

Overview

After breakfast, the day opens onto one of Japan's most celebrated rides—the Izu Skyline, a high ridgeline route that traces the spine of the peninsula. You’ll climb into long sightlines over rolling green hills, the Pacific coastline, and when conditions allow, Mount Fuji on the horizon—its near-perfect symmetry an unforgettable backdrop. A mix of steady climbs and flowing descents keeps the ride engaging and rewarding, with sea-breeze stretches adding to the rhythm of the day. Today's ride begins with a 30-minute shuttle to Motohakone, while the avid option offers a stout, 3-mile climb before joining the rest of the group. All riders end at Nakaizu Winery, set among endless vineyards with sweeping views, where a hearty lunch and glass of wine offer a well-earned break before a one-hour shuttle back to Hakone. Just before arriving back at the hotel, you'll have the opportunity to take the Hakone Ropeway—an aerial gondola that glides above the landscape—for wide-ranging panoramas and a closer look at the steaming volcanic terrain of Ōwakudani. Don't miss out on the famed black eggs that are known to add years to your life if you eat one. Then, back in your room, your private onsen offers a restorative natural hot spring soak after a day in the saddle. This evening, we'll gather for dinner over great conversation at the hotel.

Overview

Start the morning with a visit to the iconic Open-Air Museum minutes from our hotel. Set against Hakone’s mountain scenery, the Hakone Open-Air Museum was Japan’s first outdoor art museum and showcases more than 100 sculptures by masters such as Henry Moore and Rodin across its rolling lawns. Don’t miss the Picasso Pavilion, then rest your legs in the museum’s natural hot-spring foot bath. Then, enjoy an easygoing spin that captures the quiet beauty of this region as you wind along hillside roads to Odawara. Avid riders may choose to skip the museum to add on extra miles towards Lake Ashi before joining today's ride. You'll enjoy a lunch featuring local flavors before boarding the Shinkansen bullet train for a 30-minute ride to Tokyo. We'll arrive at Tokyo Station as calm landscapes give way to the city’s scale and energy. This evening, gather for a celebratory drink in a beautiful bar overlooking the city and farewell dinner to trade stories from the week. Then, if you're up for more, step out into Tokyo's neon nightlife.

Overview

On our final morning together, we’ll enjoy a walking tour from your guides in Asakusa—Tokyo's premier historic shitamachi, "low city", district. This neighborhood is famous for preserving the old-world atmosphere of Tokyo through traditional streets, classic food stalls, and the iconic 7th-century Sensō-ji Buddhist temple. This is just a short train ride from the hotel allowing flexibility to depart early if you have a flight to catch. After returning to the hotel around 11:00 AM, you’ll say your goodbyes to the guides and to an unforgettable week of cycling, culture, and connection. Departure is at your leisure before check-out at 12:00 PM.