Escape to the Azores on this 11-day itinerary that combines a remote island getaway with some of mainland Portugal's essential cultural highlights. Start in the Atlantic archipelago for four days of whale watching, caving, and hiking in the otherworldly landscapes of São Miguel Island. Then it's time to switch gears and head back to the mainland, where sightseeing, food tours, and wine tasting are on the menu as you make your way north from Lisbon to Porto.


  • Discover the lush valleys, mountains, and coastlines of São Miguel Island
  • Embark on whale spotting and volcanic cave excursions
  • Discover Portuguese delicacies and authentic neighborhoods on a food tour of Lisbon
  • See Porto by boat with a cruise down the Douro River
  • Head to the Douro Valley for a day of port wine tasting

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon, Fly to Ponta Delgada São Miguel Island
Day 2 Whale & Dolphin Watching in the Azores São Miguel Island
Day 3 Adventure in Gruta do Carvão São Miguel Island
Day 4 Free Day in Ponta Delgada São Miguel Island
Day 5 Fly to Lisbon, Gourmet Lisbon Food Tour Lisbon
Day 6 Half-Day Tour of Lisbon Lisbon
Day 7 Day Trip to Sintra & Cascais Lisbon
Day 8 Transfer to Porto via Óbidos Porto
Day 9 Get to Know Porto, Canning Factory & Evening Cruise Porto
Day 10 Day Trip to the Douro Valley & River Cruise Porto
Day 11 Depart Porto  

Detailed Itinerary

Day 1: Arrive in Lisbon, Fly to Ponta Delgada

Viewpoint in Nordeste
Welcome to the Azores!

Welcome to Portugal! Upon arrival at Lisbon Airport, you'll connect with your flight to 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. Your destination is the Azores' largest city of Ponta Delgada, located on São Miguel Island, where you'll be met by your driver and transferred to your hotel to get settled in. 

Unwind after your travels with a relaxed stroll through the city's charming neighborhoods, then head to dinner at one of the city's many great restaurants—your specialist will also be happy to offer some recommendations!

Day 2: Whale & Dolphin Watching in the Azores

Dolphins off the coast of São Miguel Island

The Azores are among the best whale watching destinations in the world, with over 20 different species found in the archipelago's waters. After breakfast, you'll board a boat to spot these fantastic creatures alongside biologists and naturalist guides. Search for whales, dolphins, turtles, and more, discover the islands' scenic coastline and sandy beaches and take a tour around the islet of Vila Franca do Campo for a closer look at the volcanic marvel and its resident wildlife.

The rest of the day is free for you to explore the island at your own pace. For adventure seekers, Ponta Delgada acts as a base for exploring the rest of São Miguel Island. Within reach are a slew of outdoor activities and excursions in the lush Azores—truly a slice of heaven in the mid-Atlantic—including hiking, sailing, and horseback riding. Those who like to get in the water can also find countless surfing and scuba diving opportunities.

Day 3: Adventure in Gruta do Carvão

Blue sky views from the volcanic Gruta do Carvão 

Just outside the city, you'll find another of São Miguel's volcanic wonders—the caves of Gruta do Carvão. The largest lava tunnel on the island plows underground for more than a mile (1.6 km) and offers a fascinating look at the island's geology. Wander through the otherworldly tunnels and admire the dramatic natural formations—from stalactites and stalagmites to soaring galleries and columns. 

Afterward, the rest of the day will be free for you to head to the beach or discover more of the area's beautiful trails and walkways on foot. If you're looking for more adventure, explore the nearby caldera and emerald lakes on horseback, on a quad bike, or even by sailing through the sky on a paragliding flight.

Day 4: Free Day in Ponta Delgada

Ponta Delgada's Portas da Cidade (City Gates)

Today you'll have a free day to enjoy Ponta Delgada and São Miguel Island in any way you'd like! Despite being the most populous metropolis in the Azores archipelago, this is hardly a typical European city; in fact, Ponta Delgada retains a quiet, small-town charm with quaint cobbled streets, historic churches, pedestrian squares, and serene parks and gardens. You'll also find a lengthy seaside promenade, as well as some great restaurants and bars. If you get hungry along the way, stop for a bite and sink your teeth into the island's famous pineapples.

Don't miss a chance to see the City Gates—the 18th-century landmark that once acted as the island's first line of defense. Amble through town to see the striking Convento de Nossa Senhora da Esperança, a 16th-century convent with an opulent Baroque altar, or wander to the port and the imposing fortress of Forte de São Bras. 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 naturalist, the museum offers exhibits on geology, mineralogy, and an array of local flora and fauna.

Day 5: Fly to Lisbon, Gourmet Food Tour

Hop on one of Lisbon's iconic trams to start exploring
Plan your trip to Portugal
Chat with a local specialist who can help organize your trip.

This morning you'll bid the Azores farewell and catch a flight back to Lisbon. Upon arrival, you'll be greeted by your driver and transferred to your hotel in the city center. After checking in, you can unwind after your long journey or head out for a quick stroll. You'll find Lisbon to be an unheralded gem of a European capital. Hilly waterfront neighborhoods are dotted with grand plazas and pastel-colored buildings, many of which date back hundreds of years. Old cable cars lurch up winding cobbled roads, and medieval castles sit perched atop the highest points in the city.

Acquaint yourself with Lisbon's culture through its traditional cuisine this evening with a gourmet food tour—a great way to experience the city for the first time! Wear a good pair of walking shoes because you, along with your guide, will meander through a series of authentic winding alleys tasting the incredible flavors of Portuguese gastronomy, particularly in the neighborhood of Campo de Ourique (practically a city within the city) that sets the food culture and culinary trends of Lisbon. 

Day 6: Half-Day Tour of Lisbon 

Statue at Praca do Comercio
A statue of King Joseph I at Lisbon's central Praça do Comercio

Today you'll discover Lisbon in-depth with a half-day tour of key sites and some well-kept secrets. Soak up the city's unique atmosphere and authenticity as you explore via the famous yellow tram system broken up with relaxed strolls. Make sure to wear a good pair of walking shoes!

Along the tour, you'll enjoy the lively bohemian district of Bairro Alto, visit the "new city" of Baixa built after the devastating 1755 earthquake, wander the traditional market square of Praça da Figueira, and climb to Portas do Sol for breathtaking views of the historic Alfama district.

Day 7: Day Trip to Sintra & Cascais

Pena Palace overlooking the forests of Sintra Cascais National Park

After breakfast, meet your driver for today's adventure in Sintra. Located just half an hour east of the city, this resort town in the Sintra Mountains is known for its forested hills, upscale villas, and Moorish palaces. Start with a visit to the Palacio Nacional da Pena (Pena Palace). This 19th-century romanticist castle mixes Moorish and Portuguese late-Gothic architectural styles with distinct features like gargoyles, ornate battlements, and colorful terraces. 

After touring the palace, you'll have a break for lunch, at which point you can also stroll through the historical village of Sintra and do some shopping and/or sightseeing. Then it's off to Sintra Cascais Natural Park. Some can't-miss locales in this area include the dramatic coastal cliffs of the Cabo de Roca, the wide and inviting Guincho Beach (a popular surf spot), and the glamorous towns of Cascais and Estoril. After a day of sightseeing, you'll return to Lisbon for the evening. 

Day 8: Transfer to Porto via Óbidos

Fortress walls surround the beautiful whitewashed village of Óbidos

After breakfast at your hotel, it's time to make the journey to Porto, Portugal's second-largest city. It won't be a direct route, though: about halfway through the drive, you'll make a morning stop in adorable Óbidos. Surrounded by a classic crenelated wall, this fortified village's historic center is a labyrinth of cobblestoned streets, riotous flowers, and whitewashed houses livened up with dashes of vivid yellow and blue paint.

Historically, Óbidos was recaptured from the Moors and presented to the Queen of Portugal on her wedding day—not once, but a long-lasting tradition that began with Queen Urraca in 1214 and continued until the 19th century. Take your time as you explore the historic center and its stunning castle, which dates back almost a thousand years. After lunch, you'll get back on the road and continue to Porto, where the remainder of the day is free for you to settle in and get your bearings in the city.

Day 9: Get to Know Porto, Canning Factory Tour & River Cruise

Let your guide should you the old town of Foz
Colorful houses in Porto's Foz neighborhood
Get to know more of Porto today with a half-day tour, where you'll learn about the city's history, heroes, and battles as you make your way through Boavista Avenue, one of Porto's most important streets, and Foz, home to revered museums and modern local treasures. Within the UNESCO-listed center, you'll find renowned Romanesque, Gothic, and Baroque monuments and sites, including the São Bento Railway Station, Clerigos Tower, the Church of St. Francis, Lello Bookshop, Sta. Catarina Street, Majestic Café, and Bolhão Market
After visiting the imposing Porto Cathedral with its superb silver altarpiece, finish the tour along the banks of the immense Douro River with views of Ribeira Plaza and the D. Luís Bridge. Later in the day, you have the option of visiting a small-scale canning factory, which produces Portugals' gourmet-quality tinned fish or seeing the city from a different vantage point with a scenic river cruise in a traditional rabelo wooden boat. This 50-minute excursion takes you between Porto and Vila Nova de Gaia to discover the beauty and tranquility of the Douro River up close.

Day 10: Day Trip to the Douro Valley & River Cruise

Cruise past vineyards on a traditional riverboat

 After breakfast in Porto, you will be picked up at your hotel for a full-day excursion into the mountains and valleys of the Douro Valley, one of the most beautiful wine regions in the world. Start the day at a notable local vineyard as you learn about the remarkable process of producing the valley's famous port wine. Enjoy a tasting, then continue to a local olive oil producer to learn about another of Douro's beloved products. 

At mid-day, you'll have lunch at a traditional Portuguese restaurant where there will be more time to learn about the area and ask your guide questions. Then it's time to hop aboard a riverboat for an hour-long cruise down the Douro River. Relax and admire the beautiful scenery of the valley and the rolling hills along the riverbanks. At the end of the day, your guide will return you to Porto, where you can spend the evening at leisure in the city's lively Ribeira area.

Day 11: Depart Porto

Enjoy a final morning along Porto's riverfront
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 transferred to the airport to catch your departing flight. Safe travels and boa viagem!

More Great 11-Day Portugal Itineraries

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Map of The Azores, Lisbon & Porto - 11 Days
Map of The Azores, Lisbon & Porto - 11 Days