Off-the-Beaten-Path Luxury in Portugal: Porto, Douro Valley, Alentejo, Comporta & Lisbon - 14 Days

Day 7: Scenic Drive to the Alentejo

Say goodbye to the Douro Valley this morning and drive five hours south into the Alentejo, Portugal's largest region, where fertile landscapes are carpeted with vineyards, cork plantations, olive groves, and wheat fields. Among the rural splendors, you'll find medieval towns like Monsaraz, which are surrounded by imposing walls and topped with a castle. São Lourenço do Barrocal, your chic hotel, lies in the shadow of Monsaraz, surrounded by unblemished countryside.

Spend the rest of the day relaxing at your hotel, a whitewashed former farmhouse that's been in the same family for over 200 years. The property has a selection of barns converted into luxurious rooms and cottages by renowned architect Eduardo Souto de Moura. Room highlights include traditional red floor tiles and wooden shutters combined with modern comforts like underfloor heating. 

Windows look out over the 1,927-acre (780 ha) estate, which you can explore on foot, bike, or horseback. Discover olive groves, vegetable gardens, a pool, and a vineyard where you can enjoy a wine-tasting session. Head to the spa for a decadent massage; try the signature Barrocal Purifying Massage, delivered with herbs grown on the estate. End the day with some farm-to-fork dining at the on-site restaurant. 

Day 8: Alentejo Jeep Tour with Winery Visit

Uncover the natural wonders of the Alentejo today on a private Jeep safari. Head out with a local guide to experience the beauty of the countryside, bumping through forests of cork and holm oak trees, where Iberian black pigs snuffle for acorns and farmers harvest cork. You'll learn the story of an English family that planted roots in the Alentejo in the 19th century and discover the secrets of olive oil and cork production. 

Continue to nearby vineyards, where you'll learn about the production process, from vine to bottle, and hear about how the Alentejo region's clay-lime soils and climate combine to produce award-winning varieties. Taste everything from syrah and Alicante Bouschet to Touriga Nacional and Aragonez. Return to your hotel afterward for a peaceful evening. 

Day 9: Hot-Air Balloon Over Évora, Dark Sky Reserve Stargazing

Begin the day with a private hot-air balloon flight over the city of Évora, which is encircled by 14th-century walls and protected by UNESCO for its well-preserved mix of Moorish architecture. Soak up bird's-eye views of Évora's ancient cobbled streets, looking out for the spires of the town's impressive 12th-century cathedral, then fly over the patchwork countryside, passing the archaeological site Cromeleque dos Almendres, a set of hulking megalithic monuments.

Spend a free afternoon at your hotel, lazing by the pool or rambling through the olive groves. Tonight, you'll embark upon a private stargazing trip in the Alqueva Dark Sky Reserve, the first reserve of this kind in the world. Your guide will teach you about the area's pristine skies—low light pollution in Alentejo means the region enjoys an average of 286 nights of clear sky a year. 

Start with a guided tour of the Dark Sky Reserve's astrophotography exhibition, then continue to the observatory in the village of Cumeada. Here, you'll have the chance to explore the celestial sphere with your naked eye, binoculars, and state-of-the-art telescopes. Let your guide point out twinkling constellations, distant planets, and the shiny smear of the Milky Way.

Day 10: Drive to Comporta, Explore the Hotel & Beach Town

This morning, take a scenic drive two hours east to the Atlantic coast, stopping to admire the Alqueva Dam, one of the largest artificial lakes in Europe. The final leg of the journey takes you through the Alentejo Litoral region to the beach town of Comporta. The surrounding area is a mass of dunes and beaches, fragrant forests of pine and cork trees, and irrigated rice fields that flourish in shades of green in the summer. 

Much of the area is privately owned by the Espirito Santos family and protected by a nature reserve on the Sado Estuary, where over 200 bird species flock, including flamingoes and Comporta's signature storks. This means the area has retained its natural peace and beauty, with few hotels and tourist crowds. You'll stay at the Sublime Comporta, which lies on 42 acres (17 ha) of forest and fields just minutes from the beach. 

Check into your room, which is made from wood and inspired by the traditional cabanas of local fishermen and farmers. Each has floor-to-ceiling windows and wooden decks, while villas feature fireplaces and a private pool. You'll find a further four pools spread around the estate, including one that's heated in the Sublime Spa, where you can enjoy a range of treatments. Indulge in the unique Our Land session, which includes a rice scrub and massage using handcrafted ceramic pots.

Day 11: Arrábida Marine Reserve Boat Trip

Explore Comporta's idyllic coastline today on a private boat. Join your skipper to sail along the Arrábida Marine Reserve, which stretches along the rugged Setúbal peninsula. Take in views of deserted golden beaches backed by wave-worn cliffs covered in rare Mediterranean plants, and look out for an array of seabirds as you sail.  

Your skipper will tailor the experience to your wishes, stopping at isolated coves where you can sunbathe, swim in azure waters, and have leisurely picnics. Drop anchor in supreme snorkeling spots where you can glimpse colorful fish and marine creatures. Sip cocktails as you sit on deck, zipping across the surface of the Atlantic. Back on land, return to your hotel for a restful evening. 

Day 12: Horseback Riding with Picnic Lunch

Saddle up for today's private horseback tour of Comporta's windswept beaches and remote countryside trails. Your guide will take you through fields of swaying rice and forests filled with towering pine forests, eventually crossing rolling dunes to the soft-sand beaches of the Atlantic coast. Canter across the honey-hued sands, hearing the waves crash against the shore. 

Spend the rest of the day as you please. Head into the village of Comporta to shop for souvenirs in its cobblestone streets, or take the complimentary hotel shuttle to Praia do Carvalhal for some relaxation. If you're still feeling active, take advantage of Sublime's yoga classes, tennis courts, and e-bikes. End the day with a meal at the on-site Sem Porta, where you can dine on Portuguese dishes made with produce grown in the resort's organic garden.

Day 13: Drive to Lisbon, Cooking Workshop or Michelin-Star Dinner

Leave Comporta this morning and embark on the hourlong drive to Lisbon, where you'll drop off your rental car and check into the hotel AlmaLusa Baixa/Chiado. Settle into one of the boutique rooms or suites in this 18th-century building, which offers everything from original fireplaces and flagstone floors to supreme city views. Spend the afternoon as you please, wandering the city's historic praças (squares), riding trams to eclectic neighborhoods, and sipping coffee in street-side cafés.

Tonight, enjoy a private cooking class where you'll learn to prepare a Portuguese meal, complete with both a fish and meat dish, followed by dessert. Alternatively, opt for an exclusive fine dining experience, where you'll have a meal prepared by a Michelin-starred chef in their culinary lab, who creates new recipes for award-winning restaurants. 

Day 14: Depart Lisbon

Today, your luxury Portugal escape comes to an end. A driver will take you to the airport in time to board your homebound flight. Safe travels!

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