October 18 – 26, 2026
Portugal
John · Lea
10th Anniversary
October 18, 2026
Sunday
Arrival — Lisbon to the Douro Valley
Clear customs and collect the rental car.
Scenic ~4 hour drive northeast through the heart of Portugal into the Douro wine country.
Arrive and settle into our suite at this extraordinary hilltop retreat overlooking the river.
📍 Quinta de Vale Abraão, Samodães, 5100-758 Lamego, PortugalTake in the terraced vineyards glowing in the late afternoon light.
Dinner at the resort's signature restaurant — contemporary Portuguese cuisine with panoramic Douro Valley views.
October 19, 2026
Monday
Douro Valley — Gardens, Wine & Dinner
Guided tour of the estate's organic gardens followed by a farm-to-table lunch celebrating the valley's harvest.
Private tasting of Douro Valley wines at the resort.
Dinner at the resort's intimate restaurant — relaxed and elegant.
October 20, 2026
Tuesday
Douro Valley — Hike, Port & Farewell Dinner
Morning hike through the estate vineyards and surrounding hillsides.
Lunch at the resort.
Guided walk through the estate with an immersive Port wine tasting experience.
Afternoon free time — spa, pool, or simply take in the views.
Final dinner at Six Senses — Cozinha do Douro celebrates the rustic flavours of the valley.
October 21, 2026
Wednesday
Into the Alentejo — São Lourenço do Barrocal
Farewell breakfast before the drive south.
Scenic ~4 hour drive south through Portugal's interior into the heart of the Alentejo.
Arrive at this extraordinary 780-hectare working estate — a restored 19th-century agricultural hamlet transformed into a singular hotel.
📍 Herdade do Barrocal, 7200-177 Monsaraz, PortugalOff-road exploration of the 780-hectare estate — cork oaks, olive groves, vineyards, and the Alqueva lake.
Dinner at the main restaurant — seasonal Alentejo cuisine anchored by the estate's own produce, wine, and olive oil.
October 22, 2026
Thursday
Alentejo — Olive Oil, Wine & Off-Property Dinner
Guided tasting of the estate's award-winning olive oils — a Barrocal signature experience.
Vertical tasting of Barrocal wines across multiple vintages.
Short drive to Reguengos de Monsaraz.
Contemporary Alentejo cuisine in a beautifully restored space in Reguengos de Monsaraz.
📍 R. José Fernandes Caeiro 5, 7200-175 Reguengos de Monsaraz, PortugalOctober 23, 2026
Friday
Alentejo — Malhadinha Nova
Final morning at the estate before heading south.
~1.5 hour drive south through the lower Alentejo plains.
Arrive at this family-run wine estate near Beja — elegant rooms, acclaimed wines, and one of the best restaurants in the Alentejo.
📍 Herdade da Malhadinha Nova, 7800-601 Albernoa, PortugalDinner at Malhadinha Nova's fine dining restaurant — celebrated for its Alentejano tasting menus and exceptional estate wines.
October 24, 2026
Saturday
Malhadinha Nova — A Day on the Estate
Explore the vineyards, olive groves, and grounds at your own pace.
Another evening at the estate restaurant.
October 25, 2026
Sunday
Lisbon — The Ivens
Final morning in the Alentejo — breakfast and a walk through the vineyards.
~2 hour drive west to Lisbon.
Check in to The Ivens — a stylish boutique hotel in the heart of Lisbon's Chiado neighbourhood.
📍 Rua Ivens 10, 1200-226 Lisboa, PortugalEvening cocktails and bites at the hotel's stylish gastro bar.
October 26, 2026
Monday
Lisbon — Last Day
A final morning wandering Chiado, Bairro Alto, or the Alfama — trams, tiles, and pastéis de nata.
Return flight to Boston.
