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Experience the best of Lisbon and the Madeira Islands in this vacation that showcases the history, culture, and natural attractions of these two world-class destinations. Head out on a tour of the most popular sights of Lisbon in style, in a vintage VW Beetle car, because the journey is as important as the destination! Nothing beats the opportunity of witnessing a soulful Fado music performance accompanied by an authentic Portuguese dinner – a treat for all your senses. Visit the Portuguese Riviera, the playground of the rich and famous, known for its palaces, picturesque surroundings, and fancy resorts. Go back in time as you wander the streets of Evora, a UNESCO World Heritage Center recognized for its remarkably well-preserved town center. Madeira Island provides the perfect setting for some relaxation. Spend the day on sun-soaked beaches, enjoy outdoor picnics with the most scenic views, and drink in the spectacular surroundings of the island on peaceful boat rides. Savor the flavors of Madeira wines and feast on the freshest seafood – a sublime experience.

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Itinerary Summary

DayPlaceHighlightsHotel Options
1 - 5LisbonAlfama & Belem Areas, Tram 28, Saint George’s Castle & Jeronimos Monastery, Street art, SintraInspira Santa Marta Hotel, Pousada de Lisboa
5 - 9Madeira IslandFunchal, The Levadas, Mercado dos Lavradores, Porto Santo, Porto Moniz Natural PoolsCastanheiro Boutique Hotel, Quinta da Bela Vista
9 - 9LisbonAlfama & Belem Areas, Tram 28, Saint George’s Castle & Jeronimos Monastery, Street art, Sintra

Ideal For

  • Beaches
  • Heritage
  • Landscape
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Itinerary Details

Day 1 - 5

International Arrival

You will be transferred from Lisbon airport to your hotel in a private vehicle


4 Nights

Explore Lisbon, Portugal’s cosmopolitan capital that graces the Tagus estuary on the Atlantic coast. Covering seven hills and a natural harbor, this intimate city welcomes you with an inclusive culture and a spirit of exploration!

Included Activities

Personalized Tour of Lisbon in Vintage Car
Explore the popular attractions of Lisbon in style and comfort in a vintage VW Beetle car! Choose a morning or afternoon departure and settle in for some fun. Start out from your hotel and enjoy a guided tour without leaving the comfort of your iconic car. Learn all about the history and cultural heritage of this sprawling city from your expert guide. Get a unique perspective on famous sites and stop to capture stunning images of the landmarks that you encounter along the way. (Duration: Half Day; Starting Time: 1000/1400 hrs; Ending Time: 1300/1700 hrs; Private Activity & Transfers; Fitness Level: Easy. You will not go inside any of the attractions on this tour.)

Group Tour: Dinner and Fado Show in Lisbon
Immerse yourself in the rich folk traditions of Lisbon at this intimate dinner show. Make your way to a cozy restaurant in the historic neighborhood of Alfama. Settle down at your table and take in the elegant ambience of the space. Enjoy the best of Portuguese cuisine as you listen to a live performance of authentic Fado music by talented artists. Return to your hotel with cherished memories of a unique experience. (Duration: Half Day; Shared Activity; Dinner Included; Fitness Level: Easy.)

Personalized Tour of Sintra & Portuguese Riviera
Immerse yourself in the cultural and natural beauty of the Portuguese Riviera on this leisurely tour from Lisbon. Drive out to the beautiful Pena Palace that sits tucked into a dense forest amid dramatic granite boulders. Soak in the fairytale ambience of this 15th century hilltop edifice that looks down upon the resort town of Sintra. Explore the charming town and stop by the stately Quinta da Regaleira, a UNESCO-listed 20th century residence known for its mysterious symbolism and tunnels. Travel on to Cape Roca to enjoy panoramic views from the westernmost point of continental Europe. Pass by the famous surfing beach of Guincho to reach the idyllic holiday destination of Cascais. Discover the historical center of this erstwhile fishing town and walk down its streets dotted with restaurants and quaint storefronts. The upscale resort town of Estoril, once a favorite destination of European royals, makes for an ideal last stop before you head back. (Duration: Full Day; Starting Time: 1000 hrs; Ending Time: 1800 hrs; Private Activity & Transfers; Fitness Level: Easy. Please note that this activity involves some walking.)

Personalized Tour of Evora With Off-road Adventure
Discover the UNESCO-listed town of Evora on this enjoyable full day tour. Drive across the 25 de Abril Bridge to the well-preserved medieval town. Walk down the maze of cobblestoned paths with your expert guide, to the imposing Cathedral of San Francisco and the unique Chapel of Bones. The 2,000-year-old town is also home to a majestic Roman Temple, one of the best preserved on the Iberian Peninsula. Afterwards, make your way to the J M Fonseca winery for a closer look at the process of manufacturing the famous Muscatel wine and tasting sessions. Head to a cork factory on the outskirts of Evora for insights into cork processing techniques. You could take your pick of a jeep safari or buggy tour for an off-road adventure into the cork oak groves that dot the countryside. A visit to a traditional tile painting workshop and a tile painting class could also be included in your itinerary. On your way back to Lisbon, drive along the 10-mile long Vasco da Gama bridge. (Duration: Full Day; Starting Time: 1000 hrs; Ending Time: 1800 hrs; Private Activity & Transfers; Fitness Level: Easy. Please note that this activity involves some walking.)

Hotel Options
RoomDeluxe Twin
RoomSuperior Room
Day 5 - 9

You will be transferred from your hotel to Lisbon airport in a private vehicle

Board your flight from Lisbon to Madeira Island (Flight duration: 2 hrs).

You will be transferred from Madeira airport to your hotel in a private vehicle

Madeira Island

4 Nights

Enjoy Madeira Island, a gorgeous Portuguese getaway located off the African coast in the Atlantic Ocean. Encompassing a mountainous volcanic archipelago, Madeira is a year-round destination with outdoor adventures and vibrant festivities.

Included Activities

Personalized Tour of Porto Santo
Discover the unique natural beauty and history of the golden island of Porto Santo. Drive from your hotel to the Funchal port and hop into a ferry boat. As you sail along the southern coast of Madeira, enjoy beautiful views of the steep coastline, and verdant mountains and hilltop houses with tiled roofs on the approaching island. Disembark on the “golden” sands and climb into a vehicle to drive around the island which is nearly eight million years older than Madeira! You can also visit the prismatic columns of the Facho and Castelo peaks. Your guide will share fascinating stories about the island, including the history behind its emblematic windmills and pirate attacks through the ages. Later, you will make your way to Casa Colombo, a Portuguese history museum which recreates the original house where the explorer Christopher Columbus lived. In the evening, relax on the white sands of the beach, enjoying the sound of waves and the tranquility before you sail back to Funchal. (Duration: 14 hrs; Time: 0730 hrs to 2130 hrs; Private Activity & Transfers; Fitness level: Moderate; Includes a driver guide and ferry admission. Please carry a bathing suit, windbreaker, sneaker, water and sunscreen.)

Personalized Caldeirao Verde Hike with a Barbecue Picnic
Hike through picturesque green landscapes, lagoons and waterfalls to Caldeirão Verde with a private guide. Begin in the Queimadas Forestry Park and follow the walkway of the Caldeirão Verde levada, an impressive aqueduct which was built in the 18th century in the Santana municipality. Pass through steep cliffs and mountains as you descend into the deep valley of the São Jorge brook. Take in spectacular views of the terrain in the interior of the island and walk through tunnels carved out of rock. Emerge out in front of the Caldeirão Verde Lake. Sit for a while and take in the beautiful vistas before you indulge in a delicious barbeque picnic lunch in the Laurissilva forest. Once you’ve had your fill, set out on your return trip back to the Park. (Duration: Half Day; Timings: 9:00 AM to 2:00 PM; Private Activity & Transfers; BBQ Lunch Included; Fitness Level: Moderate as it is a 12km hike; Please wear comfortable clothes, hiking boots/sneakers and a windbreaker jacket.)

Personalized Tour of Porto Moniz With Lava Rock Pools
Discover the outdoor attractions of the Funchal region on this enjoyable tour. Drive out to the fishing village of Camara de Lobos to sample the world famous Madeira wines. Stop by the Henriques and Henriques wine cellars, where you can taste your pick of excellent vino including ones dating back to the 19th century. Travel past the town of Sao Vicente to reach Porto Muniz, that sits by the sea. You could enjoy a traditional lunch with fresh seafood before heading to the natural volcanic pools for a leisurely dip. Afterwards, drive along a picturesque mountain road to reach the plateau of Paul da Serra, situated at an altitude of nearly 5,000 feet above sea level. Capture stunning images of the Madeira mountains and the scenic landscape as your expert guide shares details about the region’s history and geography. (Duration: Full Day; Starting Time: 0900/1000 hrs; Ending Time: 1700/1800 hrs; Private Activity & Transfers; Wine Tastings Included; Fitness Level: Easy. Please note that this activity involves some walking. Do bring along a swimsuit.)

Hotel Options
RoomTwin Garden View
Day 9 - 9

You will be transferred from your hotel to Madeira airport in a private vehicle

Board your flight from Madeira Island to Lisbon (Flight duration: 2 hrs).


0 Nights

Explore Lisbon, Portugal’s cosmopolitan capital that graces the Tagus estuary on the Atlantic coast. Covering seven hills and a natural harbor, this intimate city welcomes you with an inclusive culture and a spirit of exploration!

International Departure

 Price & Inclusions

  • Option 1 From $ 4,090 /person
  • Option 2 From $ 4,390 /person

Prices are in USD and exclude international flights. This trip price is based on low season rates for accommodation and other applicable services, and may change depending on availability, currency fluctuations and number of people traveling together. For high season prices, please contact us with your exact travel dates and preferences.

Price Includes

  • Accommodation and meals, as specified in the itinerary
  • Activities and excursions, as specified in the itinerary
  • Transportation services, as specified in the itinerary
  • Your Trip Coordinator: a 24/7 point of contact supporting you during your trip
  • Carbon emissions offsetting for your trip

Not Included

  • Entrance fees and meals, unless mentioned in the itinerary description
  • Tips and personal expenses
  • Visa and tourism fees
  • Travel, health and cancellation insurance
  • International airfare
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What our guests say about this trip

Minute by minute tracking of travel/hotel stay and resolving the issues before we even felt them by Ms. Elena Kondyla.

– Biswanath Sinha
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Portugal: Lisbon & Island Life

9 days $ 4,090 / person