Portugal – Laidback Luxury in Spring 2025

DAY 1: WELCOME TO LISBON

Lisbon, named one of the world’s 10 friendliest cities by Conde Nast Traveler, sprawls along the banks of the Tagus River estuary. Its name comes from the Phoenician meaning “enchanting port.” From the city’s hills, you can look toward the Atlantic where the Portuguese inaugurated the Age of Discovery. The low-lying areas of the city were rebuilt after the destructive Great Earthquake of 1755 but in recent times, Lisbon has come to life with a newfound energy. Travel writers are running out of superlatives to describe this once sleepy capital on the Atlantic coast, where history and tradition coalesce with contemporary chic and style.

You’ll enjoy free time this afternoon to rest from the journey. Wander through “our” part of town, Bairro Alto, filled with distinctive shops and an artistic vibe. Here you’ll find street musicians, art studios, high fashion stores and dozens of sunny cafes. We’ll end the evening with a cocktail and well-earned welcome dinner.

Lodging for the next 2 nights: Classic rooms at the Palacio Ludovice (or similar) a 5-star boutique hotel in the heart of historic Lisbon. A privileged location with sumptuous accommodation, an iconic gastronomic experience at Federico restaurant, curated wine tastings at the Porto Wine Institute and the luxurious grapevine wellness treatments at CAUDALIE come together to allow guests to discover Lisbon through the lens of a fine wine connoisseur. Drinks and dinner

DAY 2: GUIDED GALAVANT THROUGH TOWN

After a rich breakfast, meet your local guide to begin exploring Lisbon, one of the oldest capitals of Europe. Lisbon is a city of pastel colors and cobblestone streets, of vistas and monuments. Discover some of the most iconic neighborhoods, from Bairro Alto (where your hotel is located) to Chiado, with its sophisticated atmosphere and emblematic cafes such as the “Brasileira”. Contemplate the Rossio train station, with its beautiful façade, and walk around Baixa, the heart of the city. Rebuilt after the 1755 earthquake, Baixa enchants with its cobbled streets named after the artisans who traded in the area.

Finally, visit the Alfama district, the unmistakable soul of the capital city. Alfama is adorned with steep winding alleys, hidden landmark churches, echoes of tunes of fado music and stunning views of the Tagus River. It’s the Moors who shaped this district, although the earthquake brought down many of its classy Moorish mansions. The Arab influence is obvious here, with narrow streets, winding alleys, colorful houses, and endless stairs! End the morning with a visit to São Jorge Castle, formerly a Moorish citadel, whose location offers impressive panoramic views of Lisbon sprawling over the Tagus estuary.

Lunch on your own and free afternoon/evening. Might we suggest a Fado dinner? Breakfast

DAY 3: LISBON | ÉVORA | HERDADE DO SOBROSO
Check out and depart for Alentejo (Allen-tay’-jo), where the plains extend as far as the eye can see. Portugal’s largest region, covering a third of the country, simply mesmerizes. Think golden plains, rolling hillsides and lime-green vines. A rugged coastline, traditional whitewashed villages, marble towns and majestic medieval cities. This landscape combines with the sun, a proudly traditional people, and a slower pace of life.

Alentejo is also one of the main wine regions of Portugal. You’ll visit some of the best wineries, including one entirely covered in cork!  The visit here is full of history and passion – for Alentejo wines, for the terroir, for almost extinct grape varieties, for vineyards amongst cork oaks, for Portuguese gastronomy and for everything that makes life a daily celebration. Enjoy a wine-pairing lunch before continuing to Évora, the capital of Alentejo and one of Portugal’s most beautifully preserved medieval towns. Inside the 14th-century walls, Évora’s narrow, winding lanes lead to striking architectural works: an elaborate medieval cathedral and cloisters; the cinematic columns of the Roman Temple (near the intriguing Roman baths); and a picturesque town square, once the site of some rather gruesome episodes courtesy of the Inquisition. Continue to your secret wine retreat and home for the next two nights, Herdade do Sobroso. Breakfast, lunch with wine pairing and dinner

DAY 4 : THE GOOD LIFE
Sobroso’s fresh country breakfast is a highlight: everything is locally sourced and memorable. Life is peaceful here. Herdade roughly translates as homestead or large farm, and your late morning introduction to this exceptional one will be on board a 4×4 off-roader. You may very well spot deer, fallow deer, mouflons, boars, hares, several birds and endless flocks of mallards.  Herdade do Sobroso is set in a unique landscape full of heritage, including a cork oak forest and vineyards that produce very fine wine which you’ll discover today. 

Enjoy free time this afternoon strolling or riding a bike through the vineyards or even kayaking on the little lake. Let yourself fall in love with the unique beauty of the unmistakable landscape of Herdade do Sobroso. Consider dinner out tonight at another lovely wine estate with a completely different feel. Breakfast and light lunch; wine tasting

DAY 5 : HEADING NORTH: MONSARAZ | REDONDO | TORRE DE PALMA 
After breakfast and check-out, head nearly to the Spanish border for a brief stop at the enchanting medieval village of hilltop Monsaraz, which dramatically overlooks the largest artificial lake in Europe. This small village of whitewashed and schist houses is truly an open-air museum. Next it’s north to Redondo for lunch at a typical restaurant, followed by a de rigueur visit to a family cork farm. Alentejo is the world’s largest producer of cork. Wandering through these strange forests of cork oaks, you’ll learn how the bark is harvested and how it’s being regulated today.

Late afternoon arrival at Torre de Palma Wine Hotel. A whitewashed oasis in the northern reaches of Alentejo, Torre de Palma was fashioned by a renowned Portuguese architect and interior designer.  Time to relax a bit before enjoying a country dinner paired with their quality wines. The resume of Chef Miguel Laffan boasts a Michelin star, but here at Palma Restaurant he strives not for haute cuisine, but to deliver local flavors in pure and simple form. Breakfast, lunch, dinner with wine pairing

DAY 6: COOKING AND AN EVENING SURPRISE AT TORRE DE PALMA

Enjoy a free morning, with breakfast at your leisure and time for a walk, swim in the indoor pool, spa treatment or even horseback riding (prior arrangement and additional cost). At midday, time for a fun Alentejo cooking experience, where you’ll learn (and eat!) local specialties. Torre de Palma is also a wine producer, focused on great quality and small production. Your afternoon will include a visit of their cellar, considered one of the most beautiful around by Conde Nast Traveler, followed by a tasting of wines and regional goodies in the outdoor lounge with a magical atmosphere specially prepared for you. Breakfast, cooking experience followed by lunch, wine tasting with snacks

DAY 7: TORRE DE PALMA | OBIDOS | AREIAS DO SEIXO
Alas, time to leave Alentejo for another haven of tranquility, the Portuguese Silver Coast. On the way, detour to Obidos, a medieval village surrounded by castle walls and characterized by bright white houses; while there, you must try “ginjinha” (cherry liqueur) — preferably in a tiny chocolate cup!. Lunch in a typical restaurant on the way to the final stop of your adventure, Areias do Seixo. This very special place is the embodiment of “laidback luxury”, which you’ll understand the moment you see it; and the vision will become more clear as your time here unfolds. We suggest catching their shuttle to funky little Noah Surf House, a sister property just a few minutes away, for a light and fresh oceanfront dinner tonight. Breakfast and lunch

DAY 8: AREIAS DO SEIXO
Picture a warm welcoming, sweetened by the freshly-baked-homemade cake and herbal tea from the garden. Think of olive trees inside bathrooms and landscaped roof tops, large windows to gaze at the sandy dunes and the staggering blue ocean. This place invites relaxation, so today is spent however you wish! We recommend the hotel SPA; a walk along the beach; grabbing a bike to check out the local scenery; enjoying one of their infusions (made from homegrown herbs) while reading a good book. There’s a reason the beaches here are called “natural wonders” and the expat community is beginning to arrive!

This evening there will be a special celebration of nature waiting for you. Under the starlight, surrounded by dunes and pine trees, enjoy your final night in a quite unique setting. Breakfast and dinner

DAY 9: TRANSFER TO LISBON AIRPORT

Departure for the Lisbon airport; where shall we go next? Breakfast

We strongly encourage you to purchase trip insurance, including “Cancel for Any Reason”, and Medjet, which will transfer you from a foreign hospital back to the US, no questions asked. Both are available through Adagio Travel.

A special treat on this trip: Stargazing in Alentejo, Wine Hotel Torre de Palma