This 5-day trip is the ultimate cultural immersion into Portugal's up-and-coming capital, nicknamed 'The City of Seven Hills'. Let a local guide show you ancient ruins, cobbled alleyways, and hip neighborhoods—as well as the romantic UNESCO-listed village of Sintra surrounded by parks and gardens. Along with guided excursions, you'll have free time to explore on your own rounding out this fun adventure.


  • Kick off the trip with an evening culinary tour in Campo de Ourique
  • Stroll through Lisbon's bohemian neighborhoods like Alfama and Bairro Alto
  • Dine at a well-known Fado restaurant for an evening of live music
  • Visit Sintra's 16th-century monastery with breathtaking views
  • Walk the cliffs of Portugal's westernmost point overlooking the Atlantic

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon - Culinary Excursion Lisbon
Day 2 Half-Day Tour of Lisbon Lisbon
Day 3 Day-Trip to Sintra Lisbon
Day 4 Free Day in Lisbon Lisbon
Day 5 Depart Lisbon  

Detailed Itinerary

Day 1: Arrive in Lisbon - Culinary Excursion

Welcome to Lisbon!
Welcome to Lisbon!

Welcome to Portugal! Upon arrival at Lisbon's airport, you will be met by a driver who will transfer you to your hotel. Take some time to rest before you start exploring. 

When evening hits, you'll take part in a gourmet food tour in Lisbon—a great way to experience the city for the first time! Wear a good pair of walking shoes because you, along with your English-speaking guide, will meander through a series of authentic winding alleys tasting the incredible flavors of Portuguese gastronomy, especially in the neighborhood of Campo de Ourique—practically a city within the city—that sets the food culture and gastronomic trends of Lisbon.

Over the course of four hours, you will visit seven spots that brilliantly link tradition with modernity. Experience ways that locals have reinvented restaurant concepts, including a market and hotel school while getting a taste of culinary recipes that have become world-famous.

Day 2: Half-Day Tour of Lisbon

Statue at Praca do Comercio
Statue at Praca do Comercio

Today you'll get to discover Lisbon on a half-day tour visiting key sites and some well-kept secrets, exposing the city's unique atmosphere and authenticity. This will be a fun adventure as you travel around the city utilizing the yellow tram system broken up with relaxed strolls. Make sure to wear a good pair of walking shoes. 

The tour includes the following:

  • Praça do Comércio: the largest of Lisbon’s plazas
  • Baixa: the 'new city', built after the devastating  1755 earthquake
  • Praça da Figueira: Lisbon’s traditional market square
  • Rossio: the heart of downtown Lisbon
  • Iron Lift Viewpoint: a stellar 360º view over the downtown district
  • Largo do Carmo: the setting for the democratic revolution of 1974
  • Carmo ruins: the only Gothic monument of the city
  • St. Roque Church: a Baroque extravaganza
  • Bairro Alto: the lively bohemian district
  • Chiado: the city's most elegant shopping area
  • Portas do Sol: a breathtaking view over Alfama (the Old Town)

In the evening, you'll dine at one of the best Fado restaurants in Lisbon for traditional Portuguese cuisine interspersed with authentic singing and music.

Plan your trip to Portugal
Chat with a local specialist who can help organize your trip.

Day 3: Day-Trip to Sintra

Sintra's hilltop setting near Lisbon
Sintra's hilltop setting near Lisbon

After breakfast at your hotel in Lisbon, you will take an excursion to the nearby fairytale village of Sintra situated in the forested foothills near the capital.

This is one of the best ways to explore some of Portugal's best castles, historical mansions, and royal palaces. You'll quickly learn why Sintra—a UNESCO World Heritage Site since 1995—is considered one of the most beautiful, magical, and romantic places in Europe. 

During the tour, you will have a chance to see some of the most notable attractions, starting with a visit to the Royal Pena National Palace, built on the ruins of an old 16th-century monastery with breathtaking views. You'll later head to the quieter, lesser-visited area of Sintra (the west part of the village) for a chance to visit The Cork Convent of Capuchos—a stunning place, surrounded by nature, built 500 years ago for the Capuchin monks/friars.

Your last stop in the afternoon will be Cabo da Roca, Europe’s official 'westernmost point' situated on the coastal cliffs of Sintra. En route, you'll pass more historic mansions and palaces, so keep your camera close.

Following the tour, return to your hotel in Lisbon.

Day 4: Free Day in Lisbon

San Vicente Church of Lisbon
San Vicente Church of Lisbon

Today is a free day to enjoy one of Western Europe's most beautiful capitals any way you wish, perhaps taking advantage of anything you may have missed in previous days.

If you're ready to hit the streets on foot, make sure to wear some walking shoes to handle Lisbon's infamous hills, though luckily many attractions are located downtown, especially the areas of Baixa and Rossio. This is where you can find key city landmarks, as well as restaurants, shops, and the oldest bookstore in the world called Livraria Bertrand.

If you haven't explored them yet, make sure to check out the city's two oldest neighborhoods: Alfama and Graça. These narrow, winding streets ooze with Lisbon charm and are made for strolling and taking photos. Keep an eye out for shopkeepers selling authentic handicrafts.

To get a taste of residential Lisbon, head to the leafy area of Príncipe Real, home to charming restaurants, cafes, and boutique shops, as well as the city’s Botanic Gardens and Museum of Natural History and Science. For a spectacular view over the city and river, head to Miradouro de São Pedro de Alcântara, especially pretty at sunset.

Day 5: Depart Lisbon

Lisbon's historic Alfama district
Lisbon's historic Alfama district

It's time to say goodbye to Portugal! Depending on the time of your flight, squeeze in one more walk through the streets of Lisbon, perhaps picking up some last-minute souvenirs. At the designated time you will be picked up at your hotel and transferred to the airport for your departure onwards. Safe travels!


Map of Highlights of Lisbon & Sintra - 5 Days
Map of Highlights of Lisbon & Sintra - 5 Days