Signature Series: Portugal

TO
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2 travelers

Sep 11 - 19, 2026

$23,150.00

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Your Advisor

Kathryn Moutray

Traveling JetSetter | Mediterranean Travel

FL SOT: ST15578

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kathryn@travelingjetsetter.com

314-833-0425

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Overview


Overview

Across sunlit plains and timeless villages, rural Portugal’s soul unfolds – rich in serenity, deep in tradition, alive with artistry

Rural Portugal endures in the Alentejo: in vineyard rows, in ancestral craft, in generous sunlight. Led by our hand-picked Signature Guide, start among Lisbon’s royal quarters and journey among the whitewashed villages of Arraiolos, Monsaraz, and Vila Viçosa. Deep discovery awaits. Meet artisans preserving tradition, taste biodynamic wines with their makers, and read the night skies with an astronomer. This is rural Portugal: graceful, unhurried, golden.

Venture to the very heart of each destination on our Signature Collection, where every journey is shaped by our unrivalled local connections and insider expertise. Step beyond the ordinary with private invitations, rare encounters, and experiences few will ever share. So when someone says, “I’ve been there,” you’ll simply smile, knowing you’ve experienced it differently.

Signature Day: Experience our distinctive Signature Day, choosing between included activities such as a horseback ride across the Alentejo plains, a tile workshop in an atelier, or a guided walk along Évora’s ancient aqueduct

Signature Stay: Enjoy timeless serenity at Convento do Espinheiro, a 15th-century monastery reimagined as a luxurious retreat of cloisters, gardens, and heritage

Signature Guide: Let your hand-picked Signature guide lead you to the country’s soul – sharing their home, heritage, and heart

🖋️ Signature Exclusive Inclusions

  • Elegant, hand-picked hotels and a Signature Stay in a 15th-century convent
  • All breakfasts, five lunches, and six dinners, capturing authentic Alentejano cuisine
  • Your preferred Signature Day experience, selected and prebooked ahead of travel
  • Named Signature Guide with outstanding knowledge and guest satisfaction
  • Complimentary transfers on arrival and departure, ensuring a smooth journey, plus comfortable private transport throughout
  • Gratuities for local support staff so every detail of your journey feels effortless

Day 1 · Fri, Sep 11 · St. Louis, MO, USA


Departure Flight

Day 2 · Sat, Sep 12 · Lisbon, Portugal


Welcome to Lisbon

Settle into Lisbon’s rhythm | Welcome reception in a historic convent Welcome to Lisbon, a city gilded by light where the scent of sweet pastries mingles with sea air. Settle into the Inspira Liberdade Boutique Hotel, a tranquil eco-conscious sanc...

Inspira Liberdade Boutique Hotel

This charming city hotel enjoys an exceptional location just a stone's throw away from Avenida da Liberdade. This means guests can get the most out of their stay in Lisbon, combining relaxation and well-being with the best of the cosmopolitan vibe...

Day 3 · Sun, Sep 13 · Arraiolos, Portugal


Arraiolos | João Tique Private Tasting

Trace Alentejo’s artistry | Join celebrated vintner João Tique for a private tasting Leaving Lisbon, we journey to Arraiolos to meet the women preserving Portugal’s hand-embroidered rug tradition. In their traditional atelier, every stitch reflect...

Convento do Espinheiro

Hotel This hotel is located about 4 km from the centre of Évora. Slippers are included. Bathrooms are equipped with a shower and a bathtub. A hairdryer, bathrobes and a telephone are available for daily use. Wheelchair-friendly rooms with wheelcha...

Day 4 · Mon, Sep 14 · Evora, Portugal


Évora

Step into living heritage | Private walk through UNESCO-listed Évora A private guided tour reveals Évora’s layered past: Roman temples, Gothic cathedrals, and exclusive access to sections of the Chapel of Bones built by Franciscan monks. Each ston...

Day 5 · Tue, Sep 15 · Monsaraz, Portugal


Vintage Boat w/Champagne on Lake Alqueva + Farm to table lunch

Follow the olive path | Cruise across Lake Alqueva in a private vintage boat Journey to Monsaraz, Alentejo’s most timeless medieval hilltop village. A guided visit of the castle offers panoramic views over Lake Alqueva before you descend through o...

Day 6 · Wed, Sep 16 · Estremoz, Portugal


Ducal Palace + Private Immersive Masterclass

Discover royal heritage | Create an Alentejano feast with chef Sofia Vila Viçosa opens its doors this morning for an exclusive tour of the Ducal Palace, a masterpiece of Renaissance grandeur. Later, we meet the Flores sisters in Estremoz, whose UN...

Day 7 · Thu, Sep 17 · Alentejo, Portugal


Signature Day Experience

Signature Day | Craft, ride or explore timeless Évora Today is your Signature Day, inviting you to connect with Alentejo’s quiet artistry and rhythm. You could: Ride horseback through golden countryside and holm oak forests, the gentle pace reveal...

Day 8 · Fri, Sep 18 · Vila de Frades, Portugal


Private Roman Ruins of São Cucufate, Wine Tasting & Farewell Dinner

Travel through the centuries | Honour the ancient winemaking tradition of ‘vinho de talha’ An archaeologist leads a private tour of the Roman ruins of São Cucufate, revealing millennia of human connection to the land. Signature Experience: Continu...

Day 9 · Sat, Sep 19 · St. Louis, MO, USA


Farewell to Portugal

Bid a fond farewell to Portugal Before taking your complimentary departure transfer to the airport, take a moment to linger in the quiet cloisters of Convento do Espinheiro. The week’s flavours, the friendships, and the golden landscapes of Alente...

Depart Portugal