7 Days
3 Stops
Private transfer
Your tailor-made itinerary – No cost, no commitment
Experience the cultural heart of Portugal with this 7-day itinerary through Lisbon, Cascais, and Sintra. Begin in Lisbon, where historic trams glide past tiled facades and panoramic viewpoints overlook the Tagus River. Explore Alfama’s winding streets, Belém’s monuments, and enjoy the haunting melodies of fado during an evening performance.More...
Day 1 - 3
The beautiful city of Lisbon lies draped across a string of seven hills on the western Iberian Peninsula and is the westernmost and oldest city in western Europe. Its long and tumultuous history has resulted in an aesthetic characterised by a haphazard combination of old and new; however, the aesthetic chaos of Lisbon only adds to its appeal and its undeniable charm. Bright yellow centenarian trams rattle their way up steep, tree-lined, cobbled streets; ornate ironwork balconies overrun with bougainvillaea sit above elegant outdoor cafes housed in ancient whitewashed, red-roofed stone houses; and a flurry of detailed mosaics decorate the sidewalks. Ancient statues adorn grand squares and hidden gardens. A diverse culinary scene, a plethora of fascinating museums, and numerous castles make it easy to see why Lisbon is one of Europe’s most misunderstood and underrated cities.
Portugal Boutique City Hotel is located in the heart of Lisbon, Portugal, with easy access to attractions such as the slopes of Castelo de São Jorge, Rossio Square and Igreja de São Roque. Accommodation consists of a variety of guest rooms and suites, each equipped with air conditioning, a hairdryer, a minibar, a safe and a flat-screen TV. Guests can enjoy delicious meals at any of the on-site restaurants and refreshing drinks at the hotel bar.
Experience an unforgettable evening. Admire the city's most important monuments at night. The intimacy of the fado house is the best way to enjoy this music. A typical Portuguese dinner will be served.
Day 4 - 5
The beautiful Lisbon Coast boasts a breathtaking stretch of golden beaches, dramatic cliffs and thriving seaside towns that rest languidly on the shores of the blue-green waters of gorgeous Portugal. Naturally, the country's illustrious capital, Lisbon, is an essential must-see, with its rich history, memorable Old Quarters, cobbled streets and picturesque period buildings. The turreted fairytale palaces of Sintra, the remote Convento dos Capuchos monastery, and the 12th-century walled town of Obidos are also unmissable highlights. Nature lovers will delight in exploring the forested slopes of Parque Natural da Arrábida and hiking at Parque Natural de Sintra-Cascais, where the trails carve through the craggy mountain range of Serra de Sintra. Other highlights include boat trips on the Sado Estuary, the spectacular caves at Grutas de Mira de Aire and the Berlengas Islands, which are rich in wild fauna and flora.
Penha Longa Resort is ideally nestled among the Sintra Mountains in a 220-hectare natural park in Lisbon, Portugal, near the Castelo dos Mouros, Cabo da Roca, and the Palacio de Monserrate. The resort has 204 well appointed and comfortably furnished rooms and suites equipped with air conditioning, balconies, living/sitting areas, ironing facilities, private bathrooms, hairdryers, mini-fridges, minibars, tea/coffee-making facilities, TVs, and workspaces. Additional accommodations include fully furnished apartments with kitchenettes, dining rooms, and living rooms. Guests can start the day with a complimentary breakfast on-site. Facilities and services include restaurants, bars, meeting/event facilities, a spa, a fitness centre, swimming pools, a game room, turndown services, daily housekeeping, a hair salon, an on-site laundromat, and Wi-Fi.
Day 6 - 7
Situated just 30 kilometres west of Lisbon, the coastal fishing town of Cascais - also a cosmopolitan suburb of Lisbon - is known as the region’s most popular holiday destination. Cascais provides the perfect setting for a day trip from Lisbon city. Once a favoured destination for Portugal’s nobility, today, the town features impressive 19th-century architecture and traditional Portuguese charm. It has everything from excellent restaurants, vibrant nightlife and world-class hotels blended with the traditional streets of the historic centre. Visitors can enjoy a wide selection of exciting activities, including surfing at Guincho Beach, soaking up the sun at the beautiful Carcavelos Beach, hiking the Serra de Sintra National Park hills and discovering the picturesque town of Sintra. Make sure to try the delicious, fresh seafood specialities: sea bass, calamari, and cod served with olives, bread and Portuguese wine.
Overlooking the sea and Cascais Marina, Pestana Cidadela Cascais Pousada & Art District is framed within the stately walls of the 16th-century Citadel of Cascais, a classified National Monument that was once the summer residence of the Portuguese royal family and is Europe's first hotel with an integrated Art District. The guest rooms and suites are modern, comfortable and well-appointed, equipped with air conditioning, Wi-Fi, TVs, coffee machines, hairdryers and private bathrooms. Guests can enjoy dining at the onsite restaurants serving delicious Mediterranean and signature cuisines and typical Portuguese specialities or relax with a refreshing drink from the bar. Additional amenities and services include a swimming pool, a spa, a fitness centre, concierge services and a 24-hour reception. The property is close to several beaches, parks, museums, shopping centres and the Estoril Casino.
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Spring (April–June) and fall (September–October) are the best months, with pleasant weather for Lisbon’s viewpoints, Sintra’s palaces, and Cascais’ beaches.
Hotels in Lisbon range $90–$150 per night for mid-range and $180–$250+ for boutique. Meals average $15–$25 in traditional restaurants and $50–$90 in fine dining. Entry fees include Pena Palace (~$15), Jerónimos Monastery (~$10), and Cabo da Roca tours. A one-week trip typically starts at around $1,100 per person.
Lisbon offers Alfama, Belém, and a fado evening. Sintra highlights Pena Palace, Quinta da Regaleira, and Cabo da Roca. Cascais features sandy beaches, the marina, and seafood restaurants. Activities include surfing at Guincho Beach, hiking in Serra de Sintra, and boat tours on the Tagus.
Book Pena Palace tickets in advance to avoid queues. Use trains for easy transfers from Lisbon to Sintra and Cascais. Comfortable shoes are essential for hilly streets and palace gardens, and evenings are best for enjoying traditional fado shows.
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Thanks to Thomas G.
Thanks to Thomas G. for listening so closely. He helped us plan our entire trip, tailoring everything to our requests. The Tourlane app is very well designed—all the travel documents and vouchers are updated and available offline. We had some flight changes, and customer service always responded quickly. Looking forward to planning our next trip!
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Top travel company—we’d book again anytime. My travel consultant was very friendly: I shared what we had in mind, and she planned the trip for us. She was also able to make adjustments when something didn’t quite fit—everything went perfectly. Afterwards, customer service took care of us and was quick to help. The trip itself was a dream. It’s also worth mentioning that we had a local guide we could message with any questions. Excellent support, and the Tourlane app was perfect—everything we needed right at hand on our phone. Many thanks to everyone who supported us on this trip.
She listened carefully to all my wishes and ideas, gave me excellent advice, and made everything happen. All my questions were answered, and I feel very well taken care of. Thank you so much!