Step off Portugal's well-trodden tourist path with this luxury, weeklong road trip. Drive from Lisbon to the unspoiled Alentejo region, where you'll soar over the ancient city of Évora in a hot-air balloon, stargaze in Alqueva Dark Sky Reserve, and explore the region's wineries and cork forests by private Jeep. The road trip continues to Comporta on the sparkling Atlantic coast for a boat trip in Arrábida Marine Reserve and horseback riding along deserted, white-sand beaches.


  • Discover Alentejo's wineries and cork forests on a private Jeep safari
  • Spend an evening stargazing in Alqueva Dark Sky Reserve
  • Float over the UNESCO-listed town of Évora in a hot-air balloon
  • Charter a luxury boat to explore the Arrábida Marine Reserve
  • Ride through Comporta's wild forests and beaches on horseback

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon, Scenic Drive to the Alentejo Alentejo
Day 2 Alentejo Jeep Tour with Winery Visit Alentejo
Day 3 Hot-Air Balloon Over Évora, Dark Sky Reserve Stargazing Alentejo
Day 4 Drive to Comporta, Explore the Hotel & Beach Town Comporta
Day 5 Arrábida Marine Reserve Boat Trip Comporta
Day 6 Horseback Riding with Picnic Lunch Comporta
Day 7 Drive to Lisbon, Depart   

Detailed Itinerary

Day 1: Arrive in Lisbon, Scenic Drive to the Alentejo

Drive from Lisbon to the Alentejo, passing quaint towns like Monsaraz

Welcome to Portugal! Touch down in the vibrant capital of Lisbon, which is full of winding cobbled streets traversed by yellow trams, with historic towers, Baroque palaces, and atmospheric monasteries. Pick up your rental car to begin your self-drive adventure, heading 1.5 hours east into the Alentejo, Portugal's largest region. 

Alentejo's fertile landscape is carpeted with vineyards, cork plantations, olive groves, and wheat fields. Among the rural splendor, you'll find medieval towns like Monsaraz, surrounded by imposing walls and topped with a castle. São Lourenço do Barrocal, your chic 5-star 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 2: Alentejo Jeep Tour with Winery Visit

Discover the secrets of cork production on your Alentejo Jeep safari

Uncover the rural 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 3: Hot-Air Balloon Over Évora, Dark Sky Reserve Stargazing

Spot distant planets and constellations in Alqueva Dark Sky Reserve

Start 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.

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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 its 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 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 4: Drive to Comporta, Explore the Hotel & Beach Town

Drive to Portugal's Atlantic coast for some beach time

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 region is privately owned by the Espirito Santos family and protected by a nature reserve on the Sado Estuary, home to over 200 bird species, 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 5-star 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 high ceilings, 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 a heated pool 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 5: Arrábida Marine Reserve Boat Trip

Sail the crystal clear waters of Arrábida Marine Reserve

Explore Comporta's idyllic coastline today on a private boat trip. 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 6: Horseback Riding with Picnic Lunch

Ride from rice fields and forests to the Atlantic coast with a private guide

Saddle up for today's private horseback tour of Comporta's windswept beaches and remote countryside trails, complete with a picnic lunch. 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 feast on Portuguese dishes made with produce grown in the resort's organic garden.

Day 7: Drive to Lisbon, Depart 

Drive back to colorful Lisbon before catching your onward flight

Today, your luxury Portugal escape comes to an end. Enjoy a final one-hour drive north to Lisbon, where you'll drop off your rental car in time to board your homebound flight. Safe travels!

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Map of Off-the-Beaten-Path Luxury in Portugal: Alentejo & Comporta - 7 Days
Map of Off-the-Beaten-Path Luxury in Portugal: Alentejo & Comporta - 7 Days