The Ultimate 2-Week Lisbon Itinerary: Luxury Travel, Hidden Gems, and Authentic Portuguese Eats

8 min readSep 9, 2024

Lisbon, Portugal’s sun-kissed capital, offers a perfect blend of old-world charm, modern luxury, rich history, and vibrant culture. Whether you’re exploring its maze of cobblestone streets, savoring local delicacies, or soaking up panoramic views from hilltop castles, this two-week itinerary will help you experience Lisbon in all its glory — while traveling in style without breaking the bank. From scoring deals on business-class flights to discovering the best places to stay and eat, I’ve got you covered.

Getting There: Flying to Lisbon in Style

Airport: Fly into Lisbon Humberto Delgado Airport (LIS), the main international gateway to Portugal, conveniently located just 7 kilometers from the city center.

How to Get Business Class Deals: To fly in luxury without paying a fortune, use Skyscanner to find the best deals on business-class flights. You can set up price alerts to notify you when fares drop, and Skyscanner allows you to search for flights by date flexibility, giving you the best chance of landing an affordable deal.

Pro Tip: Use your American Express Gold Card to book your flight and rack up 90K miles to use for future travel. After you’ve maxed out the benefits on the Gold card, switch to the American Express Platinum for an additional 150K points — perfect for future luxury getaways.

Where to Stay in Lisbon

Lisbon is known for its range of stylish hotels, from boutique stays in historic buildings to luxurious waterfront retreats. Here are three top recommendations:

Four Seasons Hotel Ritz Lisbon (Luxury): This 5-star hotel offers breathtaking views of the city, a rooftop running track, and a world-class spa. It’s a perfect choice for those looking for luxury and comfort, located just a 10-minute drive from the city center.
Pestana Palace Lisboa (Luxury): A member of the “Leading Hotels of the World,” Pestana Palace is set in a restored 19th-century palace with lush gardens. You’ll feel like royalty while staying here, and the outdoor pool is perfect for relaxing after a day of exploring.
The Lumiares Hotel & Spa (Boutique): Nestled in the trendy Bairro Alto neighborhood, this boutique hotel offers chic apartments and an onsite spa. It’s an excellent choice for those who want to combine modern luxury with the charm of Lisbon’s narrow, winding streets.

Day-by-Day Itinerary

Day 1–3: Getting Acquainted with Lisbon

Day 1: Arrival and Relaxation

Breakfast: Enjoy breakfast onboard your flight or at the hotel after arriving in Lisbon. Most luxury hotels, like the Four Seasons and Pestana Palace, offer a buffet breakfast with fresh local ingredients.
Morning: After settling in, start with a jet lag recovery massage at your hotel’s spa.
Afternoon: Stroll through Avenida da Liberdade, a tree-lined boulevard filled with luxury shops and cafes.
Dinner: Dine at Belcanto, a two-Michelin-starred restaurant known for its creative take on traditional Portuguese dishes.

Day 2: Exploring Lisbon’s Historic Heart

Breakfast: Begin your day with a breakfast spread at your hotel, including fresh fruit, pastries, and local specialties.
Morning: Head to Alfama, the oldest district in Lisbon, and visit São Jorge Castle. Explore its winding streets, stopping at Miradouro de Santa Luzia for panoramic views.
Lunch: Enjoy a traditional lunch at O Pitéu in Alfama, known for its bacalhau (salted cod) and octopus rice.
Afternoon: Visit the Lisbon Cathedral and then wander down to Baixa, Lisbon’s downtown district, where you can explore Praça do Comércio and Rossio Square.
Dinner: Have dinner at Cervejaria Ramiro, one of Lisbon’s most famous seafood restaurants, known for its tiger prawns and garlic butter clams.

Day 3: Discovering Belém

Breakfast: Enjoy a relaxing breakfast at your hotel.
Morning: Take a tram to the Belém district and visit the Jerónimos Monastery, a stunning example of Manueline architecture. Don’t miss the Belém Tower and Monument to the Discoveries.
Lunch: Stop by Pasteis de Belém to try the famous pastéis de nata (custard tarts) at the bakery that invented them.
Afternoon: Relax at Belém Cultural Centre, which often hosts art exhibitions and performances.
Dinner: Dine at Eleven, a Michelin-starred restaurant with views over Eduardo VII Park.

Day 4–6: Sintra and Cascais — Day Trips from Lisbon

Day 4: A Day in Sintra

Breakfast: Start the day early with breakfast at your hotel.
Morning: Take a 40-minute train ride from Rossio Station to Sintra, a UNESCO World Heritage site. Visit the magical Pena Palace with its vibrant colors and unique architecture.
Lunch: Have lunch at Tascantiga in Sintra, offering tapas and Portuguese favorites.
Afternoon: Explore the Quinta da Regaleira, known for its mystical gardens, secret tunnels, and the famous Initiation Well.
Dinner: Return to Lisbon for dinner at Solar dos Presuntos, a traditional Portuguese restaurant known for its seafood and rustic charm.

Day 5: Cascais Coastal Charm

Breakfast: Breakfast at the hotel.
Morning: Head to Cascais, a scenic 40-minute train ride from Lisbon. Walk along the beautiful Praia da Rainha beach, and visit the Boca do Inferno cliffs for dramatic ocean views.
Lunch: Enjoy lunch at Mar do Inferno, a seafood restaurant offering fresh catch with ocean views.
Afternoon: Relax on Guincho Beach, known for its golden sand and stunning dunes. You can rent a bike and ride along the coastal paths.
Dinner: Return to Lisbon and dine at Taberna da Rua das Flores, a small, cozy restaurant known for its modern take on Portuguese dishes.

Day 6: Lisbon’s Non-Touristy Hidden Gems

Breakfast: Have breakfast at your hotel to start the day energized.
Morning: Visit LX Factory, a former industrial complex turned into a trendy hotspot for art, food, and boutiques. Explore the local artisan shops and street art.
Lunch: Grab lunch at Rio Maravilha inside LX Factory, with great views of the 25th April Bridge.
Afternoon: Discover the Calouste Gulbenkian Museum, a hidden gem with an incredible collection of European and Asian art.
Dinner: Have a late dinner at Time Out Market, a gourmet food hall where you can sample the best from Lisbon’s top chefs and restaurants.

Day 7–9: Lisbon’s Modern Side and the Coast

Day 7: Parque das Nações

Breakfast: Start with breakfast at your hotel.
Morning: Visit Parque das Nações, Lisbon’s modern district. Explore the Oceanário de Lisboa, one of the largest aquariums in the world.
Lunch: Have lunch at D’Bacalhau, a restaurant specializing in all things cod.
Afternoon: Walk along the Tagus River and take the cable car for panoramic views of the Vasco da Gama Bridge.
Dinner: Head to Feitoria for a Michelin-starred dinner with an emphasis on modern Portuguese cuisine.

Day 8: Lisbon for Families — A Day at Lisbon Zoo

Breakfast: Enjoy breakfast at your hotel before heading out.
Morning & Afternoon: Spend the day at Lisbon Zoo, where you can see animals from around the world. The zoo has a cable car that gives you a bird’s-eye view of the park.
Lunch: Have a casual lunch at the zoo’s restaurant or bring a picnic.
Dinner: After your day at the zoo, return to the city and dine at Pharmacia, a restaurant offering playful, pharmaceutical-inspired décor and delicious petiscos (Portuguese tapas).

Day 9: Relaxing Spa Day

Breakfast: Start the day with a leisurely breakfast.
Morning & Afternoon: Treat yourself to a spa day at your hotel or book a luxury treatment at The Ritz Spa at the Four Seasons. Enjoy massages, facials, and relaxation time in the sauna and steam rooms.
Dinner: After a day of relaxation, dine at A Cevicheria, a modern restaurant serving creative ceviches with a Portuguese twist.

Day 10–12: Day Trips and Neighborhood Exploration

Day 10: Day Trip to Évora

Breakfast: Start with breakfast at your hotel.
Morning: Take a 1.5-hour drive to Évora, a beautiful town in the Alentejo region known for its Roman ruins and medieval charm.
Lunch: Have lunch at Taberna Típica Quarta-Feira, a cozy restaurant serving local Alentejo dishes.
Afternoon: Explore the Capela dos Ossos (Chapel of Bones) and the Roman Temple before heading back to Lisbon.
Dinner: Dine at Jncquoi Avenida, a stylish spot blending Portuguese and international cuisine.

Day 11: Exploring Lisbon’s Neighborhoods

Breakfast: Have breakfast at your hotel before venturing out.
Morning: Start with a visit to the charming Principe Real neighborhood. Browse through local boutiques, art galleries, and stop by Embaixada, a unique shopping gallery in a neo-Moorish palace.
Lunch: Grab lunch at Café de São Bento, famous for its Portuguese steaks.
Afternoon: Explore the vibrant Bairro Alto district, known for its nightlife and historic charm.
Dinner: End the day with dinner at 100 Maneiras, a chic, modern restaurant with a unique tasting menu.

Day 12: Secret Lisbon Spots

Breakfast: Start with breakfast at the hotel.
Morning: Explore Estrela Garden, a peaceful and lesser-known park in Lisbon. Walk over to the Basilica da Estrela, a hidden architectural gem.
Lunch: Try Chapitô à Mesa, a quirky restaurant located in a circus school with incredible views over Lisbon.
Afternoon: Discover Museu da Marioneta, a puppet museum that’s a fun, offbeat cultural experience.
Dinner: For your final evening in Lisbon, dine at Ramiro for some of the best seafood in the city.

Day 13–14: Family Fun at Lisbon and Final Shopping

Day 13: Lisbon’s Hidden Family Fun

Breakfast: Breakfast at the hotel before heading out.
Morning: Spend the day at KidZania, an interactive city where kids can role-play as professionals in various occupations.
Lunch: Have a casual lunch at the food court inside the Dolce Vita Tejo Shopping Mall, where KidZania is located.
Afternoon: Head back to central Lisbon for some final shopping in Chiado and Baixa.
Dinner: End the day at Mini Bar, a trendy restaurant from Michelin-starred chef José Avillez that offers creative dishes in a casual setting.

Day 14: Final Day of Relaxation

Breakfast: Enjoy your last breakfast at the hotel.
Morning: Take a leisurely walk through Jardim da Estrela or visit any spots you may have missed.
Lunch: Have lunch at Cantinho do Avillez, another favorite from José Avillez, offering modern Portuguese cuisine.
Afternoon: Spend your final afternoon relaxing or grabbing some last-minute souvenirs at Rua Augusta.
Dinner: For your farewell dinner, dine at Alma, another Michelin-starred restaurant, for an unforgettable culinary experience before heading back home.

Final Thoughts

Lisbon offers the perfect combination of history, culture, luxury, and modernity. From exploring hidden gems to enjoying world-class cuisine, this two-week itinerary gives you the perfect mix of sightseeing, relaxation, and authentic experiences. With smart booking tips — like using Skyscanner to find business-class deals and staying covered with Nomad Health Insurance by SafetyWing — you can enjoy affordable luxury while immersing yourself in everything Lisbon has to offer.

Until next time here’s to smooth skies, good company, a journey full of happy memories. I’m your Travel Hack Guide to affordable luxury tips. Catch you later. Peace

Travel Hack Guy

ZachusTravel.com & YouTube.com/zachustravel