Highlights of Lisbon, Sintra & the Alentejo Plains

Overview

Welcome to Portugal. This curated five-day private itinerary has been thoughtfully designed to showcase the vibrant heritage of Lisbon, the romantic allure of Sintra and the Atlantic coast, and the sun-drenched plains and historic treasures of the Alentejo. Traveling in comfort with your dedicated private driver/guide, you will experience Portugal's rich culture, renowned gastronomy, and breathtaking landscapes at an enjoyable and refined pace.

Highlights

• Warm meet and greet at Lisbon Airport with private Mercedes-Benz transfer
• Gentle panoramic orientation drive along Lisbon's grand boulevards
• Scenic introduction to the Tagus riverfront and historic central quarters
• Comfortable hotel arrival with free time for dinner on your own
• Admire the Manueline architecture of Jeronimos Monastery and Belem Tower
• Taste traditional warm custard tarts at the renowned Pasteis de Belem
• Wander through the historic Alfama quarter with its winding alleys and vistas
• Take in sweeping panoramic city views from the top of Eduardo VII Park
• Visit the whimsical Pena Palace nestled high above the Sintra hills
• Stroll the cobblestone streets and artisan boutiques of Sintra village

Day by day

1. Day 1 — Arrival & Gentle Introduction to Lisbon
   Upon arrival at Lisbon Airport, meet your private driver/guide for a warm welcome and seamless transfer into the city. Enjoy a gentle panoramic introduction past Lisbon's grand tree-lined avenues and scenic riverside before checking in at your hotel, leaving the afternoon free to unwind at your leisure.
2. Day 2 — Lisbon Historic Highlights & Cultural Quarters
   Embark on an immersive full-day discovery of Lisbon's most iconic quarters. Admire the landmark monuments of historic Belem before exploring the traditional alleys of Alfama and the lively squares of Baixa and Chiado, with plenty of time to savor genuine local flavors.
3. Day 3 — Sintra, Cabo da Roca & the Cascais Coast
   Journey to the forested hills of Sintra to explore the vibrant Pena Palace and its romantic surrounding parklands. Continue past rugged Atlantic cliffs to Cabo da Roca and finish along the glamorous coastline of Cascais and Estoril before returning to Lisbon.
4. Day 4 — Historic Evora & Medieval Monsaraz Wine Day
   Journey into the sun-drenched Alentejo region to explore the UNESCO-listed historic center of Évora, discovering its rich tapestry of Roman heritage, charming cobbled lanes, and timeless medieval quarter. Continue across rolling golden plains to the fairy-tale clifftop village of Monsaraz, where whitewashed ramparts offer breathtaking panoramic views over the vast Alqueva lake. Complete this unforgettable immersion with an exclusive tasting of celebrated Alentejo wines at an esteemed local estate, savoring the authentic flavors and tranquil spirit of the countryside.
5. Day 5 — Departure Transfer to Lisbon Cruise Port
   Following breakfast and check-out at your hotel, your private driver will meet you for a smooth and comfortable departure transfer directly to the Lisbon cruise terminal in time for your embarkation.

What is included

• Private English-speaking driver-guide
• Black Mercedes-Benz vehicle (E-Class, V-Class, or Sprinter based on group size)
• All ground transport between cities and on tour days
• Door-to-door pickups and drop-offs at hotels and airports
• Bottled water and Wi-Fi in the vehicle
• Personalized planning by Portugal Magik travel designers

Not included

• Hotel accommodation (we recommend properties on request)
• Flights to and from Portugal
• Meals and drinks (suggestions provided by your driver)
• Museum and monument entrance fees
• Travel insurance

Who this trip suits

Travellers who prefer a private, fully planned Portugal journey with a driver-guide handling every transfer.

Frequently asked questions