Celebrate Portugal's great outdoors with this two-week itinerary that combines historic cities with natural wonders. Start by exploring Lisbon by tuk-tuk and venturing into the forested hills of Sintra, then learn about wine in Porto and take a tasting tour of the Douro Valley. The second half of your trip takes you to the Azorean island of São Miguel, where you'll sample local cuisine in Ponta Delgada, explore crater lakes and volcanoes by 4WD, and enjoy free time on the island's pristine beaches.


  • Take a culinary walking tour of Lisbon and zoom through the streets by tuk-tuk
  • Uncover 2,000 years of history as your guide leads you through Porto
  • Travel through the Douro Valley and get an introduction to Portuguese wine
  • Taste Azorean food and wines on the remote Atlantic island of São Miguel 
  • Hike to the island's crater lakes, volcanoes, and pristine beaches 

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon, Roots, Food & Cultural Walk Lisbon
Day 2 Guided Tuk-Tuk Tour, Lisbon's Markets & Fairs, Evening of Fado Lisbon
Day 3 Day Trip to Sintra, Cascais & Estoril Lisbon
Day 4 Free Day in Lisbon Lisbon
Day 5 Transfer to Porto via Coimbra Porto
Day 6 Porto Walking Tour, Explore Porto & Introduction to Portuguese Wines Porto
Day 7 Day Trip to the Douro Valley, Wine Tasting & River Cruise Porto
Day 8 Hike in Peneda-Gerês National Park Porto
Day 9 Fly to São Miguel Island, Azorean Food Experience & Ponta Delgada Tour São Miguel Island
Day 10 Sete Ciudades Jeep Adventure, Optional Sunset Boat Experience São Miguel Island
Day 11 Hike in Lagoa do Fogo or Volcanic Experience in the Furnas Valley São Miguel Island
Day 12 Discover São Miguel's Beaches São Miguel Island
Day 13 Fly to Lisbon, Free Afternoon Lisbon
Day 14 Depart Lisbon  

Detailed Itinerary

Day 1: Arrive in Lisbon, Roots, Food & Cultural Walk

Colorful houses in Libson center
Experience the explosion of color in Lisbon's center

Welcome to Portugal! Upon arrival at the airport in Lisbon, your driver will be waiting to transfer you to your hotel in the city center. Once settled in at your hotel, rest up for tonight's events.

This evening you'll explore two of Lisbon's most ancient neighborhoods on a small-group food tour: Mouraria and Alfama. As you stroll from the old alleys of the 12th century into the bustling modern-day city, take a trip through time. Soak up the laid-back vibes of each area and stop to sample authentic Portuguese dishes and snacks. Your guide will take you off the beaten path to learn how Mouraria became the birthplace of fado music and the most multicultural neighborhood in Lisbon. You'll enjoy six stops for tastings at local haunts, where you'll discover Portuguese cuisine and its influences. 

Day 2: Guided Tuk-Tuk Tour, Lisbon's Markets & Fairs, Evening of Fado

Guided Tuk-Tuk Tour
The tuk-tuk is the best way to explore the city

Explore the City of Seven Hills today by electric tuk-tuk. With your guide, you'll zip through the capital's modern and historic districts, from the neoclassical avenues of Baixa to the cobblestone alleys of the bohemian Bairro Alto. Discover the city's fascinating history and hidden corners along the way. Stop at stunning panoramic viewpoints like São Pedro de Alcântara, Parque Eduardo VII, Senhora do Monte, and Santa Luzia. Afterward, take off on your own to explore Lisbon's markets and fairs. Each market has an entirely different atmosphere, so visiting several will give you compelling insights into the city.

There's a market or fair to suit every taste, from local produce to vintage objects, traditional handicrafts or contemporary urban art. The best-known fair is the Feira da Ladra Flea Market in Campo de Santa Clara, where you can find vintage clothing and quirky antiques. There are also countless small markets, such as the Feira das Almas and the trendy Sunday market at LX Factory, where you can find vintage clothing and products made by young and upcoming craftspeople.

Don't forget to visit the local produce markets in the city. Start with the city's most significant traditional market, the daily Mercado da Ribeira, and then see the fashionable food hall Time Out Market next door. Be sure not to overeat because this evening, you'll head back into the Bairro Alto for a night at one of the city's best fado restaurants. Enjoy good food and an authentic atmosphere, with the melancholy tones of the fado music in the background for an unforgettable night in Lisbon.

Day 3: Day Trip to Sintra, Cascais & Estoril

Sintra's hilltop setting near Lisbon
Sintra's hilltop setting near Lisbon

UNESCO World Heritage-protected Sintra, with its romantic palaces, Moorish castle, and mystical forested hill, is Lisbon's best day trip. Explore the beautiful Palácio da Pena, a 19th-century romanticist palace that mixes Moorish and Portuguese late-Gothic architectural styles, with your guide. Next, enter Monserrate Palace to enjoy the beauty of the rugged and verdant Sintra-Cascais Natural Park before venturing toward the coast for a seafood lunch at a traditional restaurant on the beach.

Wind your way through the mountainous landscape toward the dramatic coastal cliffs of the Cabo de Roca, continental Europe's westernmost point. Continue along the ocean to Guincho Beach, an expansive stretch of golden sand that's popular with surfers, before reaching upmarket Cascais. This former fishing village is now a premier beach destination and was once the coastal playground of Portuguese royalty. Admire the many lavish mansions and historic manor homes in Cascais and Estoril before returning to the city. 

If you're looking for a more active day, you also have the option of embarking on a beautiful guided hike through Sintra, following a 6-mile (10 km) trail through the dense forest to reach the Palácio da Pena. 

Day 4: Free Day in Lisbon

Jeronimos Monastery
Don't miss a visit to the 16th-century Gothic-Manueline Jerónimos Monastery

Today is your last day in Lisbon, and you're free to explore at your own pace. If you didn't get a chance already, visit LX Factory, one of the city's most remarkable destinations, with street art galore and a host of restaurants, bars, and shops. Once an old unused cloth and textile factory, it's been transformed into a buzzing area of commerce in an eye-catching setting.

You could also your way to the National Azulejo Museum, located in an atmospheric 16th-century convent, and learn about the city's history through the colorful azulejos (Portuguese-style tiles). Afterward, visit the grand Jerónimos Monastery in picture-perfect Belém. This monastery was one of the few buildings to survive Lisbon's devastating 1775 earthquake. For art lovers, don't miss a visit to the fascinating Museu Calouste Gulbenkian, home to one of the world's most important private collections

Day 5: Transfer to Porto via Coimbra

A fountain Coimbra's city center
See the fountains along the Mondego River in Coimbra

After breakfast, meet your driver for the three-hour transfer north to Porto. About halfway through, you'll stop in Coimbra, where you'll have free time to explore and have lunch. This former medieval capital of Portugal is home to the country's oldest and most important university, the University of Coimbra, established in 1290. The city wears its weighty importance in Portuguese history with dignity and pride, witnessed by its multicolored collage of buildings that span nearly a millennium. The historic core cascades down a hillside to create a lovely setting along the east bank of the Mondego River.

After exploring Coimbra, you'll get back on the road and continue to Porto, where you'll check into your hotel. The remainder of the day is free for you to relax or start exploring this colorful 2,000-year-old city at your own pace. Head to the Ribeira neighborhood and wander past its famed, narrow, colorfully-tiled dockside houses, or get lost in the warren of winding of characterful streets behind the riverside.

Day 6: Porto Walking Tour, Introduction to Portuguese Wines

See Porto's key landmarks and learn about wine on today's guided tours

Today you'll embark on a memorable journey through the historic city of Porto with a local guide. Your adventure begins with a stroll along Boavista Avenue, one of the city's most important streets, and continues to Foz, home to some of the city's most revered museums and modern local treasures.

Next, you'll head to the UNESCO-listed city center to admire an array of Romanesque, Gothic, Baroque, and neoclassical monuments and sites. Highlights include the São Bento Railway Station, Clerigos Tower, Church of St. Francis, Lello Bookshop, Sta. Catarina Street, Majestic Café, and Bolhão Market. After visiting the imposing Porto Cathedral with its grand silver altarpiece, your guide will lead you to the banks of the Douro River. Here, you can take in views of the iconic double-decker Dom Luís I Bridge

This evening, attend a wine tasting to discover the region's refreshing vinho verde wines, a lesser-known product of the neighboring Douro Valley wine country. Other varieties you'll sample include, barraida, a product of the heralded touriga nacional grape, and several of the rich and complex wines of the Alentejo. You'll leave this class with a new appreciation for Portuguese wines and a solid base to explore new grape varieties on your own.
Plan your trip to Portugal
Chat with a local specialist who can help organize your trip.

Day 7: Day Trip to the Douro Valley, Wine Tasting & River Cruise

Douro Valley
Discover the Douro Valley for an incredible wine-tasting experience

Your day begins with your private driver and guide whisking you away into the Douro Valley wine region. Here, you'll visit traditional wineries and learn about the intricate wine-making process and the region's history. Indulge in a wine tasting as you take in the breathtaking scenery of rolling hills and vineyards. Next, enjoy a traditional lunch at one of the valley's famous quintas (country estates). Savor local cuisine and wines as you immerse yourself in the authentic atmosphere of this idyllic setting. Your guide will share stories and insights into the local culture and history as you eat. 

After lunch, board a riverboat for an hour-long cruise down the tranquil Douro River. Relax as you admire the stunning views of the valley and the lush hills along the riverbanks. This tranquil river cruise offers a unique perspective on the picturesque landscape and provides a perfect opportunity for fantastic photos. As your day comes to an end, your guide will bring you back to Porto, where you can spend the evening at leisure in the city's lively Ribeira district. 

Day 8: Hike in Peneda-Gerês National Park

Enjoy the fresh air as you hike through Peneda-Gerês National Park

On your last day in Porto, you can explore the city at your own pace or take another day trip into the unspoiled countryside of northern Portugal with an adventurous hiking excursion to Peneda-Gerês National Park, one of the country's unspoiled areas of natural beauty. A driver will be waiting for you in a 4WD vehicle at your hotel to take you on a one-hour drive to the park. Once you arrive, you'll be led to secluded trails surrounded by gorgeous mountain landscapes. Follow one of the short and accessible trails to climb to scenic vistas, go wild swimming in crystal-clear lagoons, and discover hidden waterfalls. 

Day 9: Fly to São Miguel Island, Azorean Food Experience & Ponta Delgada Tour

Explore Ponta Delgada's landmarks as you taste local food and wine

Bid farewell to the mainland today as a driver takes you to the airport for your flight to São Miguel, the largest island in the Azores. Located roughly 1,000 miles (1,609 km) off Portugal's Atlantic coast, this archipelago of nine islands is known for its breathtaking natural beauty and distinctive landscapes of dormant volcanoes, lush greenery, and turquoise crater lakes. Upon arrival, pick up your rental car at the airport and head to your hotel in the island's capital of Ponta Delgada

As soon as you've settled in, discover some of the best drinks and bites in the Azores with a tour of the trendiest bars and eateries in town. This guided walk presents you with great locally-produced wines, delicious foods, and many compelling stories and the islands. You'll also have the opportunity to visit the local market, meet traders and sample their quality produce. Besides tasting fantastic food and drinks, you'll visit some of the city's landmarks, learn its history and discover areas off the beaten path. Get expert recommendations on where to go after the tour, including shops and things to do. 

Day 10: Sete Ciudades Jeep Adventure, Sunset Boat Experience

Sete Ciudades Jeep Adventure
You'll be in awe of the beauty at Sete Ciudades, one of the Seven Wonders of Portugal

Escape the usual tourist routes and add some adventure to your Azores holiday with an off-road excursion to Sete Cidades. Located on the west side of São Miguel, this remarkable area of natural beauty is considered one of the Seven Wonders of Portugal. Lush hillsides and volcanic craters rise between numerous tranquil lakes, each with its own distinctive character. Along today's 4WD trip, you'll stop at several viewpoints, such as Carvão and Vista da Princesa, where you can contemplate landscapes accessible only by foot or with a 4WD vehicle.

Stop for a hike along the iconic Cumeeiras Trail, which follows the volcano's rim and offers stunning views from both sides. Continue to the charming local church and enjoy a cup of tea or coffee in the village located inside the crater. On the way back to Ponta Delgada, a trail around the lake's edge passes through a small peninsula shrouded in trees and flowers—giving you one last chance to capture the wilderness of this pristine landscape with your camera.

Later this evening, board a boat in Ponta Delgada and for a sunset cruise along the island's coastline, passing different volcanic structures such as caves, lava tubes, and the islet of São Roque. Smell the salt air, go for a swim, and feel the sun's warmth as it touches the horizon creating the most amazing shades of gold. As you return, you'll see the reflection of Ponta Delgada's lights as you reach the marina.

Day 11: Hike in Lagoa do Fogo or Volcanic Experience in Furnas Valley

Boardwalks wind through he fumaroles and hot springs of the Furnas Valley

Today, you'll have the option to hike to Lagoa do Fogo, one of the largest and most pristine of São Miguel's spectacular crater lakes. Your trip to the lake starts with a drive to Água D'Alto, on the south coast, where you'll set out on a hiking trail heading north. An uphill climb takes you to an altitude of nearly 1,968 feet (6,000 m) before leveling out onto a levada—an ancient drainage system that crosses the island and creates a perfect walking path for hikers. Catch your breath on this flat portion as you reach the lake's edge. Settle on the scenic south bank and enjoy a picnic lunch and a swim. 

The other option is to visit the Furnas Valley, a volcanic caldera that has lain dormant since 1630. It's one of São Miguel's most intriguing geothermal spots, where mud pots bubble and fumaroles steam amid the verdant landscape. You'll start with a circular, 1.5-hour walking trail of Pico do Ferro, which offers some of the best views of nearby Furnas Lake. From there, it's on to the Terra Nostra Botanical Garden―the oldest botanical garden in the Azores―where you can enjoy a dip in the thermal pools and natural Jacuzzis surrounded by the greenest scenery.

Your experience at Furnas won't be complete until you sit down to lunch to try the traditional dish of cozido, a stew famous for being cooked underground using geothermal heat, and the ananás (pineapple) for dessert. After lunch, you'll get to explore more of the valley's volcanic activity, like steam vents, fumaroles, and mineral water fountains that gush from the lava walls, before making a final stop at the Gorreana Tea Factory to enjoy a cup of delicious tea at the only tea plantation in Europe. 

Day 12: Discover São Miguel's Beaches

Agua Alto Beach
You won't want to drag yourself away from the beach today

Spend today exploring the plentiful praias (beaches) of São Miguel at your own pace. Head to Praia de Santa Bárbara for over half a mile (1 km) of soft sand and a great lunch spot at the nearby Tuka Tulá Bar. During the summer you can also attend nighttime concerts here. At Praia de Água D'Alto, you'll find a vast stretch of volcanic sand, clear water, and dramatic background cliffs—a combination that makes it one of the most popular beaches on the island.

If you want to swim, the sheltered Vila Franca do Campo Islet is a bather's paradise and a good snorkeling spot. At the same time, the oceans around Praia do Fogo remain naturally warmer due to nearby hot springs. For peace, Praia dos Moinhos can't be beaten. Praia dos Mosteiros, with its dark volcanic sand and towering rocks emerging from the sea, remains one of the best photo-ops on the island.

Day 13: Fly to Lisbon, Free Afternoon

Catch a few last glimpses of your Azorean paradise before today's flight
Savor your last few hours on the beach today before saying goodbye to the island. Drop your rental car at the airport and catch a flight back to the mainland, where you'll have the rest of the day free to spend however you wish.

Day 14: Depart Lisbon

Sunset over Lisbon's colorful Old Town 

It's time to bid farewell to Lisbon and Portugal! When the time comes, a driver will be waiting to take you to the airport to catch a flight to your final destination. Safe travels!

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Map of Portugal's Cities & Nature: Lisbon, Porto & São Miguel Island - 14 Days
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