Excellent
Lisbon, Cascais & Sintra Itinerary: 1 Week in Portugal
7 Days
3 Stops
Private transfer
Plan your trip
Your tailor-made itinerary – No cost, no commitment
Excellent
From$1,765
per personAccommodations
Transportation
24/7 support
Activities
Meals
Tourlane App
Travel plan
Flights
Flexible cancellation policies
Trip curated by Roman Karin
ExpertPena Palace in Sintra works best with an early booking and a reverse visit direction: most visitors follow the main gate path to the palace facade, but entering from the upper terrace toward the Moorish Castle and working back down puts the Serra landscape in sequence first. The fado evening in Lisbon belongs on the first night rather than mid-stay; hearing the music before any monument visit means every subsequent walk through Alfama carries a soundtrack and a context that arrive the other way around as mere nostalgia. A practical note on Quinta da Regaleira: the initiatic wells are more theatrical in the afternoon when the tour groups thin and the spiral staircase descends into a dimmer light than the flat midday sun provides.
Pena Palace in Sintra works best with an early booking and a reverse visit direction: most visitors follow the main gate path to the palace facade, but entering from the upper terrace toward the Moorish Castle and working back down puts the Serra landscape in sequence first. The fado evening in Lisbon belongs on the first night rather than mid-stay; hearing the music before any monument visit means every subsequent walk through Alfama carries a soundtrack and a context that arrive the other way around as mere nostalgia. A practical note on Quinta da Regaleira: the initiatic wells are more theatrical in the afternoon when the tour groups thin and the spiral staircase descends into a dimmer light than the flat midday sun provides.
Recommended route
Customize at any time with an expert
Lisbon
Day 1 - 3
Lisbon, Portugal's hilly capital on the Tagus estuary, where the river meets the Atlantic Ocean, combines historic neighbourhoods, grand squares and waterfront districts with a lively contemporary atmosphere. A vibrant European capital, it is known for its distinctive yellow trams, tiled facades, winding streets and viewpoints overlooking the Tagus River. Travellers can explore the UNESCO-listed Jerónimos Monastery and Belém Tower, wander through the atmospheric lanes of Alfama, or ride Tram 28 through the city's historic quarters. Praça do Comércio and Rossio serve as lively gathering places, while the waterfront offers opportunities for dining and leisurely strolls. Lisbon also makes an excellent base for exploring nearby coastal scenery and cultural attractions, including Sintra. With its mild climate, rich maritime heritage and relaxed café culture, Lisbon offers a varied city break with plenty of character.
Portugal Boutique City Hotel
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.
Your activity
Lisbon by Night & Fado Show
Fado Lisbon by Night – Dinner & Panoramic City Tour
Experience the magic of Lisbon after dark and discover the true soul of the city through music, lights, and unforgettable views. This evening tour combines a panoramic drive by van/bus past Lisbon’s most iconic monuments with a traditional dinner accompanied by a live Fado performance.
The experience begins with a scenic night tour through the city by van/bus, offering illuminated views of landmarks such as Belém Tower, Jerónimos Monastery, and the Monument to the Discoveries. You will also cross the impressive 25 de Abril Bridge and enjoy views over both banks of the Tagus River, including the Cristo Rei statue.
After the panoramic tour, enjoy dinner at a traditional Portuguese restaurant while listening to live Fado. This unique musical expression, recognized as UNESCO Intangible Cultural Heritage, captures deep emotion and nostalgia. Fado is not just music—it is a feeling that must be experienced in silence and truly felt.
Highlights:
- Panoramic night tour of Lisbon by van/bus
- Views of Belém Tower, Jerónimos Monastery, Monument to the Discoveries
- Crossing the 25 de Abril Bridge with views of Cristo Rei
- Traditional dinner with live Fado show
Meeting Point:
Marquês de Pombal, Lisbon
Please check in 15 minutes before the scheduled departure time.
Lisbon Coast
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
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.
Cascais
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.
Pestana Cidadela Cascais Pousada & Art District
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.
From$1,765
per personAccommodations
Transportation
24/7 support
Activities
Meals
Tourlane App
Travel plan
Flights
Flexible cancellation policies
Why plan with an expert?
200+
Plan with professionals who are explorers themselves.
16+ hours of time saved
Our experts plan and book for you.
7+ Bookings managed
Everything is bundled in one place and perfectly planned.
6+ Transfers coordinated
For optimal transport and comfort.
Excellent
Why plan with an expert?
200+
Plan with professionals who are explorers themselves.
16+ hours of time saved
Our experts plan and book for you.
7+ Bookings managed
Everything is bundled in one place and perfectly planned.
6+ Transfers coordinated
For optimal transport and comfort.
Excellent
Itinerary inspiration
Three nights in Lisbon, two at the Penha Longa Resort above Sintra, and one in Cascais — seven days that cover Portugal's Atlantic coast in a sequence that moves from the urban and historical toward the increasingly coastal and natural. Staying near Sintra in the hills rather than making it a day trip from Lisbon changes the experience entirely: the Pena Palace at dawn before the coaches arrive, and the gardens of Quinta da Regaleira in the late afternoon when the light comes through the trees at the right angle, are things that a day-trip schedule rarely allows.
View less details
The Cabo da Roca section of the itinerary is often treated as a brief stop on the way between Sintra and Cascais. It deserves more than that. The westernmost point of continental Europe — the cliff edge, the lighthouse, the Atlantic in every direction — has a physical presence that a photograph doesn't capture and a visit of twenty minutes doesn't do justice. Give it an hour and go in the late afternoon when the light is coming from behind you over the ocean.
Day 1–3: Lisbon
Hotel: Portugal Boutique City Hotel
Three nights with the Alfama exploration, the Belém monuments and viewpoints, and the Lisbon by Night fado show. The fado in the Chiado is worth booking before you travel. The hotel's position in Chiado keeps the fado venues, the river, and the historic neighborhoods all within an easy walk.
Day 4–5: Sintra / Lisbon Coast
Hotel: Penha Longa Resort
Two nights at the Penha Longa Resort in its own grounds on the edge of the Sintra hills, with the Pena Palace, the Quinta da Regaleira, and the Cabo da Roca coastal viewpoints across the stay. The Pena Palace is best reached before 9 a.m. — the terracotta and yellow towers on the forested promontory, the views across to the Atlantic and back over the Tagus estuary, and the quiet of the grounds before the coaches arrive make the early start entirely worthwhile.
Day 6: Cascais
Hotel: Pestana Cidadela Cascais Pousada & Art District
One night at the Cidadela — a converted 17th-century citadel with views over the marina. Cascais' seafront market on Saturday mornings, the Boca do Inferno cliffs to the west, and the beach at Praia da Rainha below the town center fill the final day without effort. The private transfer to the airport on departure day closes the journey cleanly.
Why Tourlane?
Plan for free
Custom holiday packages and trips that fit your budget
Personalized for you
Itineraries built exactly to your needs
Private VIP guides
A personal English-speaking, native-European travel expert for every step
Peace-of-mind support
Full service assistance before, during, and after your trip
Custom Portugal trips
Tips for your 7 days in Lisbon, Cascais & Sintra itinerary
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.
Custom travel packages don’t have to be complicated
1
Dream it
Give us a few details like destination, travel preferences, and budget to receive a free personalized travel itinerary in minutes.
2
Customize it
In a one-on-one consultation, we pair you with an English-speaking, native-European travel expert to customize your trip even more, making it unique to you and providing in-depth knowledge on every destination.
3
Book it
Or better yet, we’ll book it for you. Every detail is covered by us and you’ll have dedicated guides with you every step of the way, so you can focus on the fun. No action needed — just enjoy the ride.
