Southern Portugal


Experience the distinctive flair of southern Portugal across a landscape dotted with the ruins of ancient empires. Explore the cobbled lanes of Lisbon and the quirky architecture of Sintra; prepare traditional cuisine, visit medieval towns, and savor the star-filled night skies in the Alentejo region; and sail and hike along the cliffs and beaches of the Algarve.

Days: 13
Best time to visit: April-June, September-November
Ideal for: Couples

Trip Itinerary

Day 1 – Walking Tour of Lisbon

Arriving in Lisbon, settle into your hotel in the heart of the city. This afternoon, embark on a private walking tour starting along the elegant cobbled streets of the Baixa district. Head to the narrow lanes of the Alfama district and delve into the ancient history of the Visigoths and the Moors. Climb through the winding alleys to the Castle of St. Jorge, once a Moorish citadel, where you’ll have stunning views over the city and the Tagus River.


Day 2 – Sintra and Cascais Tour

Travel north from Lisbon on a guided tour of the UNESCO-listed region of Sintra, a landscape of forested hills, ornate castles, and lush vineyards. Begin the day with a visit to the Palace of Pena, the vibrant-hued, 19th-century romantic centerpiece of the Sintra hills. Next, explore one of Sintra’s most enthralling monuments, the Quinta da Regaleira, defined by its masterfully carved-stone designs. On your return journey to Lisbon, stop at the Atlantic beaches and cliffs of Boca do Inferno and Cabo da Roca.


Day 3 – Explore Lisbon

Spend today exploring Lisbon on your own. There are a number of quality museums like the National Museum of Ancient Art, the National Coach Museum—showcasing historical royal carriages—and the National Tile Museum, with its collection of decorative blue-painted ceramics. In the afternoon, take a scenic ferry ride for a unique perspective of both banks of the Tagus River.


Day 4 – Medieval Monuments in the Alentejo Region

Travel with your expert guide from Lisbon to Évora, a well-preserved medieval city with monuments stretching all the way back to the Romans. Tour the historic center of town, visit the magnificent 12th-century Cathedral of Évora, and stroll through the picturesque campus of the university. At lunchtime, savor the flavors of Alentejan cuisine by preparing your own meal under the guidance of a local chef, pairing simple yet elegant dishes with regional wines. In the late afternoon you’ll arrive at your hotel and have the remainder of the evening at your leisure.


Day 5 – Tastes & Traditions

Today, explore the agricultural and gastronomic traditions of the Alentejo region on a visit to a local Biological Production farm estate where they raise and grow almost the full spectrum of Mediterranean diet products. After learning about and sampling Alentejo specialties, head to the town of Alcaçovas to learn about the ancient culture of crafting cowbells. On the way back to your lodging, visit the mystical Neolithic stone formations Cromlech of the Almendres.


Day 6 – Wine & Cork

Take a journey into the world of sustainably produced wines and olive oils at Herdade do Esporão near the historical city of Reguengos de Monsaraz. Enjoy tastings of their wines and olive oils as well as a delicious lunch. In the afternoon, visit a cork factory and learn about the forests that put Alentejo on the map as the world’s largest cork producer. This evening with dinner, enjoy a performance of the region’s distinctive choral style, Cante Alentejano.


Day 7 – Trades & Stars

This morning, tour the workshop of one of the last traditional leather boot and shoemakers of region. In the afternoon, get your hands dirty in a traditional pottery workshop, and then enjoy an evening of fine cuisine and stargazing at the Dark Sky Alqueva center in Cumeada, near the Great Lake of the Alqueva. This area is a designated UNESCO Starlight Tourism Destination, where unpolluted skies and atmospheric conditions are ideal for seeing the stars.


Day 8 – Travel to the Algarve Region

Enjoy a relaxing morning after the late night under the stars, and then transfer to the Algarve region on the southern Atlantic coast of Portugal. Settle into your hotel on the coast near Galé and spend the day relaxing on the beach.


Day 9 – History of West Algarve

Meet your guide and driver this morning and embark on a full-day tour in the West Algarve. Visit the imposing 11th-century castle of Silves, once the Moorish provincial capital of this picturesque region, and then travel to Lagos to explore historical churches, ancient ramparts, and glimpses of Phoenician, Greek, and Roman influence.


Day 10 – Sailing Excursion

Drive to Lagos harbor in the morning for a private, half-day excursion on an elegant yacht, sailing along the majestic, rocky coast of the Algarve. Explore caves, seaside grottoes, and unique rock formations, stopping to swim in sandy coves. Head back to port in the afternoon with the remainder of the day to explore in Lagos or relax at your hotel.


Day 11 – Coastal Hiking

Today, head to Vila do Bispo, about an hour away, to join your private guide for a 3-hour hike along cliffs, ravines, and ancient rock formations. From the red sandstone cliffs of Telheiro Beach—set in rugged and majestic national parkland—you’ll follow the winding trails to Cape St. Vincent, on the southwestern tip of the country.


Day 12 – Return to Lisbon

After breakfast this morning, travel back to Lisbon. Settle into your hotel and enjoy the remainder of the day at your leisure.


Day 13 – Departure

Transfer to the airport for your international flight home.

Remarkable Journeys has partnered with Lost World Adventures to create this journey. We partnered with Lost World due to their well-mannered relationships with tour guides, hotellers, airlines, and ground management services in the region. In our opinion, they offer the best value and experience in the region.

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