Tailor-made Lisbon and the South of Portugal trip

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Design your Lisbon and the South of Portugal trip to match your curiosity and taste. Choose a tailor-made route that trades crowds for local stories, arrange private tastings of regional cuisine, reserve time to wander hilltop palaces and quiet coastal coves, and set aside days to slow down on sunlit beaches.

Book local guides and unique stays to transform your Portugal trips into a personal discovery. Start planning now to turn inspiration into a crafted Portuguese experience.

Lisbon and the South of Portugal trip highlights

  • Historic Lisbon discoveries: Wander Alfama and Belém with a local guide for authentic stories and tailor-made routes.
  • Coastal Algarve beaches and villages: Discover secluded coves, charming fishing villages, and golden beaches.
  • Tailor-made food and wine experiences: Savor regional cuisine and boutique wines in family-run tavernas.
  • Scenic road trips and hidden spots: Drive through cork forests and cliff-top viewpoints.
  • Relaxation and boutique retreats: Unwind in boutique guesthouses, spa escapes, and sunset cruises tailored to your pace.
DayMorningAfternoonEvening
Day 1Arrival in Lisbon Leisurely historic-centre walk, sample pastéis de nata, hotel relaxation
Day 2Walking tour of Baixa, Alfama and Bairro Alto viewpoints Sunset cruise on Tagus River under 25th April Bridge
Day 3Stroll Sintra streets, visit Pena Palace, sample travesseiros and queijadasDrive to Cap da Roca; Guincho, Boca do Inferno, Cascais 
Day 4Lisbon to Évora  
Day 5 Hot air balloon over Evora 
Day 6 Alentejo discoveryRustic Alentejo tavern dinner
Day 7Évora to Mértola via Monsaraz and Vale do Guadiana  
Day 8Sunrise boat ride, island-hopping photo stops Personalized stargazing on calm waters
Day 9Stroll Mertola's winding streets; visit Islamic Museum; savour local restaurantsContinue to TaviraSavour local dishes in small authentic restaurants
Day 10 Private beach time, coastal walks, surf lessons, wellness treatment 
Day 11 Relaxation in the AlgarveSunset viewpoints
Day 12Savor pastel de nata, wander riverside promenade, photograph golden lightDeparture 

Places you'll visit

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Lisbon
LisbonLisbon
Evora
Evora
Tavira
Tavira-
Mertola
Mertola-
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Day01

Day 1: Arrival in Lisbon

Welcome to Portugal! Your private transfer brings you to Lisbon and the start of your Lisbon and the South of Portugal trip. Enjoy a warm check-in and personalized briefing from your travel designer for a tailor-made Portugal travel.

If time allows, take a leisurely walk through the historic center to catch the first city views, sample pastéis de nata, or relax at your hotel and enjoy amenities curated for your stay.

Lisbon
Day02

Day 2: Lisbon walking tour and Tagus cruise

Discover Lisbon on foot with a tailor-made walking tour that reveals Baixa, Alfama and Bairro Alto. Explore historic churches, castle walls and inviting squares, and climb to panoramic viewpoints for authentic city views.

End the day with a sunset cruise on the Tagus River, passing under the 25th of April Bridge, the Monument of the Discoveries and Belém with the statue of Christ the King.

Lisbon
Day03

Day 3: Enchanted Sintra and the beaches of Cascais and Estoril

Stroll Sintra's charming streets, discover local craft shops, and taste the famous travesseiros and queijadas. Visit the magical Pena Palace before lunch for panoramic views and fairy tale architecture. If you're wondering about the best time to visit Portugal, spring and early autumn offer mild weather and fewer crowds, ideal for exploring spots like Sintra.

Enjoy a seaside lunch, then drive to Cabo da Roca, the westernmost point of continental Europe. Pass Guincho Beach, famed for windsurfing, and the dramatic Boca do Inferno, returning along the scenic coast through Cascais and Estoril to Lisbon.

Lisbon
Day04

Day 4: Lisbon to Évora

Leave Lisbon and cross the Alentejo plains to Évora, framed by cork oaks, olive groves, and vineyards. The walled city of white houses invites slow exploration and memorable monument visits.

Stroll narrow alleys, discover artisanal cork, ceramics, and copper, and tailor your day with local guides who reveal hidden workshops and tasting experiences for a truly authentic day.

Alentejo Region
Day05

Day 5: Hot air balloon over Evora

Rise above the plains of Alentejo on a hot air balloon flight from Evora. Drift in tranquil silence as the landscape transforms beneath you, tasting the serenity and light that shape this region. Perfect for photographers and calm seekers.

Alentejo
Sara

Tips from Sara

Portugal Travel Expert

quotes

Climb the roof of Évora Cathedral; it’s often overlooked, but the views over the city’s terracotta rooftops and surrounding plains are some of the best in Alentejo. Go just before sunset for the full effect.

Day06

Day 6: Discover Alentejo, Elvas

Explore Elvas, a star-shaped fortified town on the Spanish border. Walk fortifications classified by UNESCO, climb the bastions and soak up sweeping views, then enjoy rustic Alentejo cuisine in local taverns for an authentic taste of the region.

Return to Evora across the longest suspension bridge in the world, rising 175 meters above the Paiva River, for a dramatic photo stop.

Alentejo Region
Day07

Day 7: Estremoz

Discover Estremoz, the Alentejo “white city” with sunlit houses and centuries-old marble quarries. Walk through the castle, visit local markets and artisan workshops, and gain insights into marble craftsmanship.

Explore Roman and Muslim heritage, taste Alentejo wines and regional cuisine at family-run taverns, and spend the day soaking up relaxed village life and panoramic hilltop views.

Alentejo
Day08

Day 8: Évora to Mértola via Monsaraz and Vale do Guadiana

Begin your day at Alqueva Dam, Europe's largest artificial lake. Enjoy a sunrise boat ride, island hopping photo stops, and personalized stargazing on calm waters as part of a tailored experience for travelers seeking authentic immersion.

Wander medieval Monsaraz to discover its castle, narrow streets, and local wine. Continue to Vale do Guadiana Natural Park to hike river paths to Pulo do Lobo waterfall and the Vascão confluence, spotting birds and dramatic gorges.

Monsaraz
Day09

Day 9: Mertola to Tavira

Stroll Mertola's winding streets and feel its rich history, with human presence from Neolithic times through Phoenicians, Romans, Visigoths, and Moors. Visit Mertola's Islamic Museum, the largest in Europe for Islamic art, and savor local flavor in small, authentic restaurants serving unique regional dishes.

In the afternoon, continue to Tavira for the next chapter of your South Portugal tour, crafted for travelers seeking tailor-made, authentic experiences that blend discovery and relaxation.

Mertola
Day10

Day 10: Relaxation in the Algarve

Spend a tailor-made day in the Algarve, enjoying sun, sea, and authentic experiences: private beach time, coastal walks to hidden caves, seafood lunches in family-run taverns, optional surf lessons, or a wellness treatment to recharge.

Tavira
Day11

Day 11: Free day in the Algarve

Enjoy another free day in the Algarve tailored to your pace. Choose beach time on golden sands, a hidden cove swim, a coastal hike along dramatic cliffs, or a leisurely spa and seafood lunch in a fishing village.

Local guides can suggest private activities, guided town walks, and sunset viewpoints to make this day uniquely yours.

Tavira
Day12

Day 12: Departure

Thank you for joining our Lisbon and the South of Portugal: exploration and relaxation trip. Spend your final morning savoring a pastel de nata, wandering a riverside promenade, or photographing golden light before you go. Return your rental car at Faro airport with plenty of time for check-in.

As a tailored travel experience, we can arrange last-minute transfers, extensions, or bespoke recommendations. We hope your Portugal trip inspired you, and we look forward to welcoming you back.

Departure