Wedged deliciously between the Andes and the Pacific, Chile’s wine country pairs adventure with a splash (or two) of vino. Pedal coastal roads and valley lanes, taste world-class wines, enjoy chef-led meals and secret picnics, and sleep in unforgettable vineyard-side properties — including a night at the iconic Viña Vik. Perfect for travelers who want effortless logistics, refined local access, and a healthy appetite for discovery (and dessert).

Day 1 — Into the Casablanca Valley

Your adventure begins in Santiago, where we head west into the famed Casablanca Valley. After a private tasting at a local winery, set out on a leisurely ride through farmland and eucalyptus groves before reaching La Casona at Matetic Vineyards — a tranquil boutique hotel set amid rolling vines. Unwind by the pool before gathering for a farm-to-table dinner paired with Matetic’s award-winning wines.
Activity: Morning ride — 50 km / 31 mi

Day 2 — Vineyards, Valleys & Valparaíso

Today’s loop ride unfolds through the sun-dappled San Antonio Valley, framed by the distant Andes. Pause for a midday tasting and a fascinating horse-handling demonstration before heading to the colorful port city of Valparaíso. A private walking tour reveals its bohemian energy and hillside murals, before you return for another relaxing evening at your wine country hideaway.

Activity: Morning ride — 38 km / 24 mi.

Valparaíso

Day 3 | From Vineyards to the Pacific

Pedal westward as the landscape opens toward the coast, the Pacific glinting on one side and the mountains rising on the other. Stop for homemade empanadas at a seaside café before rolling into your oceanside hotel, where surfboards and serenity await. Savor the rhythm of the waves over a leisurely beachfront dinner. Check into the Hotel Surazo for a one night stay.

Activity: Morning ride | 49 km (31 mi.)

Day 4 | Across the Heart of Chile

Depart the coast and head inland on a spectacular ride toward the Andes, stopping for a secret picnic lunch with panoramic mountain views. Those seeking a challenge can extend to a full century ride before arriving at your next retreat—a tranquil hotel set deep in the vines. Tonight, enjoy a private, candlelit dinner at a nearby food and wine studio hosted by our local friends before an overnight at the Vibo Wine Lodge.

Activity: Century ride | 100 km (62 mi.)

Day 5 | Into the Apalta Valley

Cycle past Santa Cruz and into the Apalta Valley, Chile’s most prestigious winemaking region. Pause at a favorite estate for a tasting and leisurely lunch before continuing to the magnificent Viña Vik, a modern architectural masterpiece where art, wine, and hospitality blend seamlessly. Settle in for an exquisite dinner overlooking the vineyards.

Activity: Morning ride | 55 km (40 mi.)

Vina Vik

Day 6 | Exploring Millahue & Viña Vik

Ride through the serene Millahue Valley, where the landscape is dotted with sprawling estancias and wild beauty. After a tasting at the Vik estate, spend the afternoon exploring the property by foot, bike, or horseback. As the sun sets, gather for a special farewell celebration at this remarkable haven of wine and design.

Activity: Morning ride | 55 km (29 mi.)

Day 7 | Farewell to Chile

Enjoy a slow morning in the vineyards before one final lunch together, celebrating the week’s unforgettable rides, friendships, and flavors. Then, it’s adiós—for now—as you depart for Santiago and your onward journey.

Contact travel@admiraltravel.com for more information.

  • A $250 per person Admiral Travel booking fee will apply (VIPLane members complimentary).
  • All payments non-refundable. We highly recommend trip insurance and are happy to assist. Please inquire with your travel advisor.

PLEASE NOTE:

  • All payments made to or on behalf of Admiral Travel are non-refundable unless stated otherwise
  • Admiral Travel reserve the right to adjust the duration of their participation should any schedule conflicts arise.
  • Minimum numbers must be met in order for the ATI Hosts to host the journey. If minimum numbers are not met , our local partner will serve as the host for the duration of the journey.
  • Trips are offered well in advance to give ample time for your future planning.
  • Special global relationships that the Hiltons have formed over the years will allow you privileged access opportunities.
  • Tours, activities and special events subject to change.
  • Travel with like-minded individuals on these exclusive departures.