Savoring Portugal: A Curated Two-Week Escape

Arrive in Lisbon and check into your centrally located hotel, with plenty of time to relax and settle in after the flight. Whether you stretch your legs with a walk around the neighborhood or grab a drink on the terrace, the rest of the day is yours. Use your hotel credit for an easy, early dinner—no planning required—making for a low-stress start to the adventure.

Start your first full day with a walking food tour through Lisbon’s most historic neighborhoods. In Alfama, you’ll wander narrow cobblestone streets and hear stories from centuries past while sampling local snacks like salted cod fritters and pastries. In Baixa, you’ll explore open plazas and elegant buildings. It’s part food crawl, part local immersion. Have dinner at Ramiro, a beloved no-frills seafood spot where garlic clams and cold beers are the order of the day.

Hop into a tuk-tuk and ride through Belém, Lisbon’s waterfront district known for its monuments and pastries. You’ll stop at Jerónimos Monastery, check out the Monument to the Discoveries, and grab a pastel de nata from the bakery that started it all. Tonight, enjoy a casual dinner paired with live Fado music—a signature Lisbon experience that blends local flavor with tradition.

Today’s excursion will take you into the heart of central Portugal. Begin in Fátima, an important pilgrimage site, where you’ll have time to walk the sanctuary grounds and visit the chapel. Enjoy lunch at Casa Platano before heading on to Nazaré, a cliffside coastal town famous for its massive waves and fishing traditions. Return to Lisbon for dinner at Trindade, a former monastery turned beer hall serving hearty Portuguese dishes.

Head into the hills to explore Sintra, a storybook town filled with palaces and gardens. Tour the bright and whimsical Pena Palace and stroll through its surrounding parklands. In the afternoon, continue to Cascais, a relaxed beach town with a great waterfront. Have lunch at Mar do Inferno, known for its fresh seafood and ocean views.

Start the day with a visit to a local market, where you’ll gather ingredients for a hands-on cooking class. With a local chef leading the way, you'll prep and cook a traditional Portuguese meal, then sit down to enjoy what you’ve made—with wine, of course. The rest of the day is yours to explore or unwind.

Pack a snack and hop on the train to the Algarve, Portugal’s southern coast known for its beaches and laid-back pace. The ride offers a relaxing glimpse of the countryside, with olive groves and rolling hills along the way. Once you arrive, check into your hotel and enjoy a free afternoon to hit the beach, the pool, or a seaside café.

Take a boat tour along the Algarve coast to see the famous Benagil Caves, where natural skylights shine into turquoise water. Then head inland to a local winery for a tasting and laid-back lunch. It’s a great mix of coastal adventure and countryside charm.

There’s no schedule today—just time to enjoy the Algarve at your own pace. Lounge at the beach, explore the coast, or treat yourself to a spa visit. This is the kind of day vacations are made for.

Take a short flight north to Porto, a colorful riverside city with tons of character. After settling in at your hotel, explore the Ribeira district or relax with a drink along the Douro. Have dinner at at Flow, a beautiful restaurant with a cool vibe and even better food.

Join a walking tour to see Porto’s highlights, from tiled churches to the famous Livraria Lello bookstore. In the afternoon, cross the river to Vila Nova de Gaia for a private port wine tasting in one of the city’s iconic cellars. Sip, learn, and take in the view.

Cruise through the Douro Valley by boat today, gliding past vineyard-covered hills and picturesque riverside villages. You’ll stop in Régua to visit the Douro Museum, which tells the story of the region’s wine culture and how barrels were once floated downriver before modern locks were added, then continue by boat to a small estate for a relaxed wine tasting and lunch with a view.

After two weeks of exploring, eating, and relaxing your way across Portugal, it’s time to head home. You’ll leave with great memories, a camera roll full of golden hour shots, and maybe a bottle of port tucked into your bag.