8
Nights
3
Regions
4
Hotels
10 Years
Together
01

October 18, 2026

Sunday

Arrival — Lisbon to the Douro Valley

10:45 AM
Land at Lisbon Airport✓ Avis #22409792US6

Clear customs and collect the rental car.

12:00 PM
Drive to Six Senses Douro Valley

Scenic ~4 hour drive northeast through the heart of Portugal into the Douro wine country.

4:00 PM

Arrive and settle into our suite at this extraordinary hilltop retreat overlooking the river.

📍 Quinta de Vale Abraão, Samodães, 5100-758 Lamego, Portugal
6:00 PM
Local Wine TastingActivity

Introduction to the Douro's celebrated varietals — a perfect first evening in wine country.

7:30 PM

Michelin-recommended dinner at DOC, Chef Rui Paula's celebrated riverside restaurant in Folgosa — one of the Douro Valley's finest tables. Perched directly on the river with a stunning terrace, DOC blends contemporary technique with the chef's Trás-os-Montes roots, drawing on local produce and an exceptional Douro wine list. Tasting menus and à la carte available.

📍 Cais da Folgosa, Estrada Nacional 222, Folgosa, Portugal
02

October 19, 2026

Monday

Douro Valley — Explore, Tastings & Dinner

Morning
Breakfast & Explore the PropertyActivityBreakfast

Morning breakfast at the resort followed by time exploring the Six Senses estate — vineyards, gardens, and river views.

3:30 PM
Port Wine & Chocolates TastingActivity

Indulgent tasting of Port wines paired with artisan chocolates at the resort.

7:00 PM
The Vale de Abraão RestaurantDining

Dinner at the resort's intimate restaurant — relaxed and elegant.

03

October 20, 2026

Tuesday

Douro Valley — Hike, Port & Farewell Dinner

9:00 AM
Personal HikeActivity

Morning hike through the estate vineyards and surrounding hillsides.

12:30 PM
Portuguese Kitchen TableActivityLunch

90-minute immersive cooking experience at the resort — a hands-on introduction to the flavours and techniques of traditional Portuguese cuisine.

3:30 PM
Wine Tasting with CheesesActivity

Curated tasting of Douro Valley wines paired with local Portuguese cheeses at the resort.

7:00 PM
Cozinha do DouroDining

Final dinner at Six Senses — Cozinha do Douro celebrates the rustic flavours of the valley.

04

October 21, 2026

Wednesday

Into the Alentejo — São Lourenço do Barrocal

8:00 AM
Breakfast at Six SensesDiningBreakfast

Farewell breakfast before the drive south.

9:00 AM
Drive to São Lourenço do Barrocal

Scenic ~4 hour drive south through Portugal's interior into the heart of the Alentejo.

1:00 PM

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, Portugal
5:00 PM
Jeep Tour of the EstateActivity

Off-road exploration of the 780-hectare estate — cork oaks, olive groves, vineyards, and the Alqueva lake.

6:30 PM
Dinner at BarrocalDining

Dinner at the main restaurant — seasonal Alentejo cuisine anchored by the estate's own produce, wine, and olive oil.

05

October 22, 2026

Thursday

Alentejo — Olive Oil, Wine & Off-Property Dinner

11:30 AM
Olive Oil TastingActivity

Guided tasting of the estate's award-winning olive oils — a Barrocal signature experience.

4:00 PM
Vertical Wine TastingActivity

Vertical tasting of Barrocal wines across multiple vintages.

6:30 PM
Drive to Dinner

Short drive to Reguengos de Monsaraz.

7:00 PM
SAHIDADining

Contemporary Alentejo cuisine in a beautifully restored space in Reguengos de Monsaraz.

📍 R. José Fernandes Caeiro 5, 7200-175 Reguengos de Monsaraz, Portugal
06

October 23, 2026

Friday

Alentejo — Malhadinha Nova

Morning
Relax at BarrocalActivity

Final morning at the estate before heading south.

2:00 PM
Drive to Herdade da Malhadinha Nova

~1.5 hour drive south through the lower Alentejo plains.

3:30 PM

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, Portugal
7:00 PM
Casa do Alentejo — Casa VerdeDining

Dinner at Malhadinha Nova's fine dining restaurant — celebrated for its Alentejano tasting menus and exceptional estate wines.

07

October 24, 2026

Saturday

Malhadinha Nova — A Day on the Estate

Morning
Morning on the EstateActivity

Explore the vineyards, olive groves, and grounds at your own pace.

7:00 PM
Casa do Alentejo — Casa VerdeDining

Another evening at the estate restaurant.

08

October 25, 2026

Sunday

Lisbon — The Ivens

Morning
Morning at Malhadinha NovaActivity

Final morning in the Alentejo — breakfast and a walk through the vineyards.

2:00 PM
Drive to Lisbon

~2 hour drive west to Lisbon.

4:00 PM

Check in to The Ivens — a stylish boutique hotel in the heart of Lisbon's Chiado neighbourhood.

📍 Rua Ivens 10, 1200-226 Lisboa, Portugal
6:30 PM
Gastro Bar at the IvensDining

Evening cocktails and bites at the hotel's stylish gastro bar.

09

October 26, 2026

Monday

Lisbon — Last Day

Morning
Explore LisbonActivity

A final morning wandering Chiado, Bairro Alto, or the Alfama — trams, tiles, and pastéis de nata.

Afternoon
Fly Home

Return flight to Boston.