Spend two weeks taking in the best of Portugal's scenery, history, food, and wine. This trip begins with three days in the Azores on the gorgeous green isle of São Miguel; discover the charming city of Ponta Delgada, sample local delicacies, go whale watching, and admire the island on a fantastic hike. You'll then head to Lisbon for two days of city life, followed by a string of beautiful towns and UNESCO World Heritage sites. End your stay with time in Porto and enjoy tasting flights of incredible Porto wine in the sweeping romance of the Douro Valley. 


  • Explore São Miguel island in the Azores
  • Whale watching in one of the world's best spots to see marine life
  • Enjoy a private guided tour of Lisbon
  • Visit stunning towns like Sintra, Évora, and Coimbra
  • Taste your way through Porto and the beautiful Douro Valley

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Ponta Delgada Ponta Delgada
Day 2 Culture & Food Tour Ponta Delgada
Day 3 Half-Day Whale Watch Excursion & Sete Cidades Hike Ponta Delgada
Day 4 Fly to Lisbon & Private Tour Lisbon
Day 5 Free Day in Lisbon Lisbon
Day 6 Day trip to Sintra, Cascais & Estoril Lisbon
Day 7 Transfer to Évora, Private Tour Évora
Day 8 Explore Évora & the Alentejo region Évora
Day 9 Drive to Coimbra, via Óbidos & Alcobaça Coimbra
Day 10 Guided Tour of Coimbra Coimbra
Day 11 Transfer to Porto, City Tour Porto
Day 12 Wine Tasting in the Douro Valley Douro Valley
Day 13 Full-Day Hiking in Peneda-Gerês National Park Braga
Day 14 Depart Porto  

Detailed Itinerary

Day 1: Arrive in Ponta Delgada

The striking landscape on São Miguel
São Miguel's striking landscape 

Welcome to Portugal! When you arrive on São Miguel, the "Green Island," you'll be transferred to your hotel in spectacular Ponta Delgada, the capital of the Azores. After you check in, take the rest of the day to relax and explore Ponta Delgada and its surroundings. There's much to discover depending on your interests and energy level. Amble through town, perhaps stopping at the striking and spiritually revered Convento de Nossa Senhora da Esperança, a 16th-century convent with an opulent Baroque altar.

You could wander the port and explore the Forte de São Bras, an imposing fortress erected in 1552 to guard the city, then stop for a bite and sink your teeth into the island's unique pineapples. If natural history's your thing, consider a self-guided tour of Museu Carlos Machado, the oldest museum in the Azores; dedicated to the 19th-century eponymous naturalist, the museum offers exhibits on geology, mineralogy, and an array of local flora and fauna classified and tagged by Machado himself.

If you're looking for adventure, explore the nearby caldera and emerald lakes on horseback, quad bike, or even by sailing through the sky on a paragliding flight. Or simply unwind after your travels with a relaxed stroll through the city's charming neighborhoods. Your specialist will also be happy to offer some recommendations for great places to dine tonight!

Day 2: Culture & Food Tour

The charming streets of Ponta Delgada
The charming streets of Ponta Delgada

Fuel up with a delicious breakfast, then get ready to learn about local culture and cuisine with the help of a private guide who will offer you a broader context of Ponta Delgada's importance in the Azores as well as the city's treasures. In classic Portuguese tradition, you'll discover through storytelling and food on a culinary exploration of the town.

Walk through downtown with your guide, exploring artisanal eateries and restaurants, highlights, and off-the-beaten-path gems in a  dynamic mix of sightseeing, delicious food, and great stories. You will enjoy a progressive menu—from timeless recipes to innovative modern cuisine — that includes the unique Azorean pineapple, physalis, blackberry jams, and seafood and organic meat delicacies. You'll finish your discovery with homemade desserts such as passionfruit bavaroise or green tea ice cream!

After ambling through town armed with recommendations from your guide or stop through any sights, you may have missed the day before. 

Day 3: Half-Day Whale Watch Excursion & Sete Cidades Hike

The incredible Lagoa do Fogo (Fire Lake)
The incredible Lagoa do Fogo (Fire Lake)

Today you'll enjoy an unsurpassed opportunity to see more than 20 different species of whales and dolphins on a thrilling half-day excursion on the high seas. The Azores are among the best whale watching destinations in the world, and after breakfast, you'll board a boat to spot these fantastic creatures. In spring and autumn, you'll be able to see some baleen whales, such as the blue, minke, sei, humpback, and fin whales. In the summer, you're more apt to see the sperm whale.

On your whale watching tour, see if you can spot some of these behaviors: 

  • Blowing: a sound made when expelling air through the blow-hole, accompanied by a spout of condensed water
  • Breaching: the whale leaps from the water and falls back with a resounding slap
  • Lobtailing:  the whale loudly slaps its fluke on the water
  • Spy hopping: the whale lifts its head vertically out of the water, enabling it to see above the waterline

In the afternoon, you'll return to land for a spectacular hike of São Miguel, a land of lakes nestled in vast volcanic craters. The most iconic caldera lies in Sete Cidades, a place filled with legends and myths. Gaze out onto the landscape from the gorgeous Vista do Rei Lookout; from there, in noble contemplation, you can see two twin lakes, the Green and the Blue, paired together by a bridge.

Farther on your trail, you'll be treated to the wild jewel-toned splendor of Lagoa do Fogo (Fire Lake), a large lake surrounded by extravagant, lush vegetation amid the Furnas Valley, which lives up to its nickname of Vale Formoso (Beautiful Valley). You may also be able to hike out to other fantastic viewpoints and lakes in the Serra Devassa and in the central part of the island: the Canário, Santiago, Éguas, and Congro Lakes will all reward you with pristine beauty and quiet tranquility.

After a full day of exploring the island of São Miguel, head back into town and enjoy the evening tasting delicious Azorean cuisine.

Day 4: Fly to Lisbon & Private Tour

The red roofs of Lisbon
The red roofs of Lisbon

This morning, you'll transfer to the airport for your flight to Lisbon, one of Europe's fastest-changing and trendiest capitals. Upon arrival, check into your hotel, then prepare to hit the city's streets for a day of exploration. Your private guide will pick you up from your hotel to show you the highlights as well as some great gems off-the-beaten-track.

Your first stop is the beautiful area of Belém, an ode to the superb age of the Portuguese Discoveries—the numerous territories and maritime routes discovered by the Portuguese during the 15th and 16th centuries. Here you'll visit Belém Tower and the Monument to the Discoveries, followed by the magnificent Jerónimos Monastery, considered one of the most stunning monuments of Portugal.

Next, it's off to the dynamic Alfama district, home of traditional Fado music and charming, twisting streets that wind up to an imposing castle on one of the city's highest hills. With whitewashed houses, flower-laden balconies, and red-tiled roofs, Alfama is a perfect mix of historic landmarks and quaint residences. You will also discover one of the most important squares in the city and the famous Liberdade Avenue. Make sure to taste the delicious and sweet Pastel de Belém, a traditional pastry found here.

At the end of the visit, your guide will return you to your hotel. Take some time to relax after your tour, then head back out for dinner; consider choosing between some of the city's best Fado restaurants for a memorable evening of traditional cuisine and music.

Day 5: Free Day in Lisbon

San Vicente Church of Lisbon
San Vicente Church in Lisbon

Take today to enjoy one of Western Europe's most beautiful capitals any way you wish, perhaps taking advantage of anything you may have missed the day before. If you're ready to hit the streets on foot, make sure to wear some walking shoes to handle Lisbon's infamous hills; luckily, many attractions are located downtown, especially the areas of Baixa and Rossio. This is where you can find key city landmarks, as well as restaurants, shops, and the oldest bookstore in the world: Livraria Bertrand.

Make sure to check out the city's two oldest neighborhoods: Alfama and Graça. These narrow, winding streets ooze with Lisbon charm and are made for strolling and taking photos. Keep an eye out for shopkeepers selling authentic handicrafts. To get a taste of residential Lisbon, head to the leafy area of Príncipe Real, home to charming restaurants, cafés, and boutique shops, as well as the city's Botanic Gardens and Museum of Natural History and Science. For a spectacular view over the city and river, make your way to Miradouro de São Pedro de Alcântara, which is especially pretty at sunset.

Plan your trip to Portugal
Chat with a local specialist who can help organize your trip.

Day 6: Day trip to Sintra, Cascais & Estoril

Pena Palace
Pena Palace

Head out of Lisbon for an incredible day trip to a trio of picturesque locales. The area surrounding Lisbon offers an incredible variety of architecture and scenery, from fairy tale palaces to romantic towns and breathtaking viewpoints. Today's guided excursion is the ideal way to experience some of these attractions.

After breakfast at your hotel, you'll meet your guide, who will deliver you to your first stop: Sintra. This village —about 30 minutes by car from the capital—is a harmonic combination of history and fantasy, described as a "glorious Eden" by the 18th-century British poet Lord Byron. Your guide will give you plenty of information about the city's wonderful palaces, imposing monuments, and great eateries in the area; armed with these tips, explore Sintra on your own and have lunch amid the local splendor.

Your next stop is the Cabo da Roca, the westernmost point of not only Portugal but all of mainland Europe. Enjoy the gorgeous views across the Atlantic Ocean as waves crash onto the shore. As you head back to Lisbon, you'll visit the fishing harbor and tourist center of Cascais, the former summer residence of the Portuguese royal family, and nowadays an excellent spot for surfing. You'll also be able to visit the luxury entertainment town of Estoril, known for its casino (the largest in Europe) and beautiful gardens.

Once you return to Lisbon, you'll have the remainder of the day to enjoy the city in any way you like.

Day 7: Transfer to Évora, Private Tour

Évora's medieval architecture
Évora's medieval architecture

This morning after breakfast at your hotel, you'll be picked up for your private transfer to the small town of Évora, a tiny gem in the rural countryside of the Alentejo region. Enjoy lunch in town: dig into migas, a savory breadcrumb pudding infused with garlic, olive oil, herbs, and spices, all served alongside savory roasted meat. The local cheeses and bread are also world-class!

After, venture out on a private guided tour to discover the most impressive treasures of this UNESCO-recognized city. Your guide will cover Évora's main monuments, including the well-preserved ruins of the Templo Romano, as well as landmarks of the golden age of Portuguese maritime discoveries. This tour is especially perfect if you're interested in gaining an overview of the city's major events, which have always been linked to the most significant moments in Portuguese history.

In the evening, you'll have the free time to explore Évora's streets and dining scene on your own.

Day 8: Explore Évora & the Alentejo Region

An undulating vineyard in Alentejo
An undulating vineyard in Alentejo

Today you'll have a full-day excursion of the Alentejo region, where the pace of life slows amid the area's iconic golden plains. This sparsely populated yet vast swath of land between the Algarve region and Lisbon offers scenic rolling hills, olive groves, vineyards, and charming fortified towns with a number of walking trails, Neolithic monuments, rustic wineries, and cork production facilities.

Enjoy the slower rhythm here; residents in the Alentejo region are more traditional than in other parts of Portugal, something you'll see reflected in their home-cooked cuisine and beautiful handicrafts. Get to know the locals and their cultures today as you visit medieval villages, a cork forest, a winery, and Neolithic monuments. You'll also tuck into a delectable lunch at a traditional Alentejo cuisine restaurant before you head to Évora for the rest of the day.

A UNESCO-recognized city, Évora is filled with monuments, including those pertaining to the golden age of Portuguese maritime discoveries. You'll also find ancient ruins at the Templo Romano, gorgeous medieval landmarks, and a lively dining scene.

Day 9: Drive to Coimbra, via Óbidos & Alcobaça

Make a stop in historic Óbidos
Make a stop in historic Óbidos

After breakfast this morning, you'll make the two-hour drive to Coímbra, Portugal's medieval capital, featuring a beautifully-preserved old town and historic university. Along the way, you will make a few stops starting with adorable Óbidos. Surrounded by a classic crenelated wall, Óbidos' gorgeous historic center is a labyrinth of cobblestoned streets, and flower-bedecked, whitewashed houses livened up with dashes of vivid yellow and blue paint. Take a self-guided visit to this historic village and its stunning castle, which dates back almost a thousand years.

Stay in town to enjoy a traditional Portuguese lunch, then continue north to Alcobaça, a town with a charming enclave with a little river and bijou bridges, as well as the magnificent 12th-century Mosteiro de Santa Maria de Alcobaça—one of Portugal's most important UNESCO World Heritage Sites.

From here, continue the drive to Coimbra, where you'll have the evening to relax and wander the streets. Spend your evening serenaded by Fado, which has its origins in Coimbra, at one of the best places in the city.

Day 10: Guided Tour of Coimbra

Coimbre's historic core
Coimbre's historic core

After breakfast at your hotel, it's time for a guided tour of Coimbra, the medieval capital of Portugal, and the site of the country's greatest university: the University of Coimbra, founded 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. Observe how Coimbre's historic core cascades down a hillside creating a lovely setting along the east bank of the Río Mondego. Once you've experienced Coimbra with your guide, you'll have the rest of the day to continue discovering the city on your own.

Day 11: Transfer to Porto, City Tour

Depart Coimbre and head north to Porto
Depart Coimbre and head north to Porto

This morning you'll be picked up from your hotel in Coimbra for a 90-minute drive to Portugal's second-largest city: Porto. Once you arrive, it's time for a city excursion. Your guide will explain the rich history of Porto, also called Invicta (the Unbeaten City), with stories of heroes and battles as you make your way to the trendiest and most cultural area in town. Here you'll explore Boavista Avenue, one of the city's most storied streets, and Foz, home to some of the most important museums and modern local treasures.

Next, you'll head to the city center—a UNESCO World Heritage Site—to admire renowned Romanesque, Gothic, Baroque, and neoclassical monuments and sites, including the São Bento Railway StationClerigos TowerChurch of St. FrancisLello BookshopSta. Catarina StreetMajestic Café, and Bolhão Market, to name a few. After visiting the imposing Porto Cathedral with its superb silver altarpiece, you'll head to the banks of the immense Douro River with views of Ribeira Plaza and the Dom Luís I Bridge. Finish the excursion with a visit to one of the famous port houses before heading back to your hotel.

Take the rest of the evening to explore Porto's dining scene on your own (or ask your guide for suggestions before parting ways!)

Day 12: Wine Tasting in the Douro Valley

Tour some vineyards known for Port wine production
Tour local vineyards known for port wine production

After breakfast, you'll be picked for a full-day wine experience in the Douro Valley. Your excursion begins at a family-owned winery in the picturesque town of S. João da Pesqueira, located in a small subregion called Douro Superior. Upon arrival, one of the family members will lead you on a walking tour of their undulating vineyards over the Douro River, followed by an intimate wine tasting. This winery is part of a new movement of small family facilities that utilize over a century of experience with port wine here in the Douro region.

For lunch, take your pick between several options, including a charming restaurant in the mountainous town of Ervedosa serving traditional recipes that have been made in households across the region for hundreds of years. Your driver will then take you through the picturesque vineyards of a winery in the heart of Douro's Pinhão Valley. This innovative yet rustic winery was founded by Jorge Serôdio Borges and his wife, Sandra Tavares da Silva—two of the most celebrated winemakers in Portugal. Initially, the winery included a lone vineyard called Pintas, but it has gradually expanded to include additional properties, such as the magnificent Quinta da Manoella.

In the late afternoon, your driver will take you back to your hotel. Tonight, allow the tranquil sounds of nature to lull you to sleep here in the relaxing countryside.

Day 13: Full-Day Hiking in Peneda-Gerês National Park

A tranquil rushing stream within Peneda- Gerês National Park,
A rushing stream within Peneda- Gerês National Park,

Immerse yourself in Portugal's wild landscape on a full-day small-group tour of Peneda-Gerês National Park, where you can hike incredible mountains, admire local fauna and flora, drink in amazing viewpoints, and splash around in mesmerizing waterfalls.

The park will greet you on your drive with superb views of the lush mountains, turquoise waterways, and iconic bridges. You'll lead out on a mellow but gorgeous trek to see beautiful lagoons and the stunning Tahiti Waterfall. If you like, you can also go for a dip in the therapeutic (though cold!) waters. You'll also enjoy a traditional picnic lunch at Pedra Bella, one of Gerês' most iconic viewpoints, while you rest with the mountain at your feet and admire the unparalleled scenery.

After your excursion, you'll travel to the charming town of Braga, where you'll spend the night. Explore the city's streets as the sun sets and ask your specialist for a recommendation for a great restaurant in town for this evening's dinner!

Day 14: Depart Porto

Sunrise in Porto
Sunrise in Porto

It's time to say goodbye to Portugal! Depending on the time of your flight, you may be able to squeeze in one more walk through the streets of Porto or perhaps pick up some last-minute souvenirs. At the designated time, you'll be picked up at your hotel and transferred to the airport for your onward departure.

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