Private Portugal
A trip of conversations
This is Portugal the way locals experience it: unhurried, intimate, and full of quiet beauty. Instead of crowds and clichés, this trip takes you down sun-washed rural roads, into family-run wineries, historic towns, and villages where daily life unfolds with locals.
Alentejo — Where Time Slows and Tradition Speaks
Your journey begins in the Alentejo, Portugal’s vast golden heartland. It’s a region most travelers never reach, yet it holds some of the country’s most timeless landscapes. Here, cork forests stretch to the horizon, whitewashed villages glow in the afternoon sun, and the rhythm of life feels grounded in centuries of tradition.
Porto — Not the postcard version, but the soulful one
From the countryside, you move north to Porto, but not the Porto of riverfront crowds and souvenir shops. Instead, you’ll experience neighborhoods where locals gather in corner cafés, where grandmothers still shop at morning markets, and where the city’s storied connection to food and wine is woven into everyday life.
You’ll step inside traditional cellars to taste port from producers who’ve been perfecting their craft for generations, stroll quiet backstreets lined with tile-covered houses, and cross the river into Vila Nova de Gaia to see the Douro from a more authentic, less tourist-polished angle.
Porto isn’t just beautiful—it’s deeply, quietly charismatic.
Guimarães & the Northeast — Portugal’s Birthplace and Its Hidden Corners
Your final stop is the northeast, a region that most visitors skip entirely—but locals prize for its history, untouched landscapes, and strong cultural identity.
Guimarães, often called the “birthplace of Portugal,” is a living museum of medieval lanes, stone fortresses, and elegant plazas.
4th to 11th October 2026
8 places
8 nights boutique, beautiful hotels
perfect for art & history lovers, foodies, shoppers
$8,250 single occupancy
A spot on this trip may be reserved with a $1,000 non-refundable deposit, with the balance paid in full by June 15th, 2026
For a full itinerary& dates