Highlights of Portugal & the Azores: Lisbon, Coimbra, Douro Valley, Porto, São Miguel - 16 Days

Day 1: Arrive in Lisbon, Food Tour of Mouraria & Baixa

Welcome to the bustling capital of Portugal, Lisbon! Meet your driver at the airport for a transfer to your hotel. After refreshing, set off on a 3.5-hour food and culture tour across two of the city's neighborhoods, starting in the Moorish district, Mouraria, the birthplace of Lisbon's soulful fado music. Wander down the narrow streets to local markets and popular eateries to sample a variety of small plates called petiscos, the Portuguese version of tapas. Then, wash everything down with samplings of local wine.

Leave room for more grazing as you continue to the downtown core, Baixa, known for its grand squares and elegant architecture. Make multiple stops at local haunts to try food like pastéis de bacalhau, deep-fried codfish cakes, or bifana, a spiced pork sandwich. End your evening with a sweet treat of pastel de nata, an egg custard tart that originated in Lisbon. When you're full, return to the hotel to rest after a delicious first day.

Day 2: Historical Tour of Lisbon, Free Afternoon to Explore the Capital

After breakfast, join a three-hour walking tour to learn about Lisbon's rich architectural and cultural history. Follow your guide through some of the city's oldest neighborhoods, like Alfama and Mouraria, and hear about the impact the devastating 7.7-magnitude earthquake had on the city in 1755 CE. Discover how the earthquake inspired architects to design seismic-resistant buildings visible in the downtown district of Baixa. Visit Parque das Naçōes next, a redeveloped waterfront area incorporating historic and futuristic designs to create a mix of cultural, recreational, and residential facilities.

When you're done exploring the park, the rest of the day is yours to spend as you wish. You can visit the UNESCO-listed Mosteiro dos Jerónimos, a 16th-century monastery built to commemorate Vasco da Gama's world-first ocean voyage to India. Admire the intricate facade adorned with maritime motifs before entering to discover the church within that holds the tombs of notable figures, such as Vasco da Gama and Luís de Camões, considered Portugal's greatest poet. In the evening, walk to the Belém riverfront to enjoy fresh seafood at one of the restaurants overlooking the water.

Day 3: Day Trip to Sintra, Cascais & Estoril

Leave the city behind for the day as your driver whisks you 30 minutes west to the picturesque hilltop town of Sintra. Start your guided tour at the 19th-century Monserrate Palace in Parque Natural de Sintra-Cascais. Admire the exterior, which blends Romantic, Gothic, and Indian architectural styles, then stroll along the winding paths of the surrounding park past exotic ferns, colorful flowerbeds, and over 1,000 species of trees. Explore the opulent halls lined with vibrant tiles and intricate details inside the palace before continuing to Cabo da Roca, the westernmost point of continental Europe.

Gaze over the Atlantic Ocean, then walk to nearby Guincho Beach, a surfer's paradise. Relax on the golden sands or try surfing or windsurfing if there's time. Once you've worked up an appetite, sit down for lunch in the coastal town of Cascais, where you can try fresh seafood dishes at one of the restaurants along the charming waterfront. End your full-day tour at another iconic coastal town, Estoril, famous for having one of the largest casinos in Europe. Place a bet to test your luck, or admire the casino's extravagant interior until it's time to return to your hotel in Lisbon.

Day 4: Explore Lisbon's Markets, Enjoy Dinner With a Local Family

Mingle with the locals and pick up an authentic souvenir by spending your morning exploring the city's markets. Check out Mercado de Santa Clara first, whose narrow alleys are lined with stalls full of antiques, vintage items, and secondhand goods. The market is only held on Tuesdays and Saturdays, so if you're visiting another day, head to the Mercado de Alvalade instead, which is only closed on Sundays. Browse the variety of locally sourced produce, aromatic spices, and traditional delicacies before stopping at the 19th-century Mercado da Ribeira, better known as Time Out Market.

Browse this modernized landmark's handmade goods or sample local delights, then in the evening, meet the Lisbon family who's welcoming you into their home for an authentic Portuguese meal. While your host prepares three courses, chat with them about their daily lives and how they differ from your own. Then, when dinner is ready, sit down to enjoy the meal paired with a selection of Portuguese wines. After dessert, graciously bid farewell to your hosts and return to your hotel. 

Day 5: Drive to Coimbra via Tomar & Obidos

Say goodbye to Lisbon today as you pick up your rental car and drive two hours north to Coimbra, the former capital of Portugal, nestled on the Mondego River. On the way, stop in the medieval town of Tomar, home to the UNESCO-listed Convento de Cristo, a 12th-century Knights Templar stronghold. Explore the sprawling complex and wander the vast cloisters, chapels, and courtyards. Visit the round church in the center to admire its Roman and Gothic-style architecture, then continue the drive, making another stop in the town of Óbidos.

Stroll along the town's cobblestone streets past whitewashed houses, surrounded by well-preserved 14th-century walls, to get to Castelo de Óbidos, a sentinel atop a hill. Enter through the historic gate and admire the blend of Moorish and medieval architectural elements. Discover the sturdy towers, climb the ramparts, and marvel at the panoramic vistas of the surrounding countryside. When you're ready, complete the drive to your hotel in Coimbra, where you can refresh before venturing out to Praça da República (Republic Square) to enjoy dinner at one of the outdoor terraces.

Day 6: Guided Tour of the University of Coimbra & the Historic Center

Spend a half day exploring Coimbra on a private tour, starting at the UNESCO-listed University of Coimbra, one of the oldest universities in the world. Visit the Baroque Joanina Library, home to over 300,000 ancient and modern books protected by its resident bats. Climb to the top of one of the library's towers for panoramic views of the city and the tranquil river. Continue with your guide to St. Michael's Chapel next door to see the intricate Manueline and Renaissance details, showcasing the era's craftsmanship.

Step inside to admire the stained glass windows and ornate wooden altarpiece, then head to the city's historic district to walk through the labyrinthine alleys. Look out for architectural gems like Sé Velha, a Romanesque cathedral dating back to the 12th century. Observe the intricate Gothic and Manueline elements carved into the altars and woodwork, then visit the Museu Nacional de Machado de Castro, housed in the former Episcopal Palace, to browse the collection of Roman artifacts, medieval sculptures, and art pieces before ending your tour and returning to your hotel to unwind.

Day 7: Drive to the Douro Valley, Explore the Lush Grape-Growing Region

Trade the city for the countryside today as you drive 1.5 hours inland to the lush Douro Valley—a fertile grape-growing region historically renowned for its fortified wines and, more recently, its fine table wines. After settling into your hotel, choose a hillside restaurant or a riverside eatery for lunch, then spend the rest of the day as you wish. You can hop aboard the historic Douro Railway, which winds through the valley's picturesque scenery. Sit back and relax as you pass by terraced vineyards, quaint villages, and ancient landmarks echoing back to antiquity when the Romans made wine on these very banks.

Then, visit the Douro Museum to browse the artifacts, interactive displays, and multimedia presentations detailing the region's history. Or, Immerse yourself in the charm and heritage of Pinhão's historic tiled railway station. Marvel at each intricately painted azulejo (tile) that tells a story, weaving together the region's rich history of viticulture. Journey through time as the station's tiled walls come alive with scenes of vineyards and snapshots of daily life, then sample local cuisine, like pork cutlets marinated in the region's famous port wine, at an elegant restaurant before returning to your hotel.

Day 8: Vineyard Tour, Cruise the Douro River

Today, you'll spend time in the famous wine-growing Douro Valley, visiting a local winery or two. Follow your guide through the terraced vineyards and traditional aging cellars, where you'll learn about the winemaking process, from grape cultivation to fermentation and aging. After gaining insights into the traditional techniques to craft each wine, sit down for a delicious meal at a traditional quinta (wine estate). Savor a selection of the estate's finest wines and, with each sip, experience the nuances of the region's terroir and the winemaker's skill.

Following lunch, explore the valley from the water on a boat trip down the meandering Douro River. Jump on board and cruise down the tranquil waterway surrounded by terraced hills adorned with rows of grapevines. Look out for charming villages and historic estates showcasing the region's rich winemaking history. After the two-hour cruise, your guide will transfer you back to your hotel to enjoy its amenities and relax for the rest of the evening.

Day 9: Drive to Porto, Vintage Car Tour, Explore at Leisure

Pack your bags this morning and drive 1.5 hours west to the historic city of Porto on the Douro River, where you'll return your rental car. Once you've settled into your hotel, explore the city in style in a vintage 1920s car on a three-hour guided tour. Choose between the fishing village of São Pedro da Afurada, with its cobblestone streets and vibrant houses adorned with fishing nets, or coastal Foz do Douro, with its trendy boutiques, elegant mansions, and inviting cafés. Whichever you choose, the tour ends at a port cellar for a guided tasting of the city's fortified wines. Saúde! Cheers!

After lunch, spend the afternoon exploring Porto at your leisure. Marvel at views of the double-decked Dom Luís I Bridge from the UNESCO-listed Ribeira area with its colorful dockside houses on the Douro River. Amble through the maze of winding streets behind, or immerse yourself in history at the Sé do Porto, an impressive cathedral showcasing a blend of Romanesque and Gothic architecture.

Day 10: Ceramic Tile-Painting Workshop, Wine Tasting at Sandeman Cellar 

On your last morning in Porto, immerse yourself in the city's rich culture by painting your own azulejos. These traditionally decorated Portuguese tiles typically adorn buildings, depicting historical events, religious scenes, or detailed patterns. Learn about the rich history and intricate painting process, then create your own colorful design. Whether you're a novice or an experienced artist, express your creativity during the two-hour workshop and craft a personalized souvenir to take home. Afterward, find a cozy tasca (casual bar restaurant) overlooking the river for lunch and watch the boats go by.

In the evening, cross the Dom Luís I Bridge to Sandeman Cellar in Vila Nova de Gaia, where the resident wine expert will guide you through their vast collection of wine aging in oak barrels, some for over 200 years. Learn about the company's rich history and winemaking traditions, then wander through the cellars' cool and dimly lit chambers, with the distinct aroma of port wine filling the air. The tour's highlight awaits you in the tasting room, where you'll sample three of Sandeman's finest wines, including an elegant tawny, a velvet ruby, and a crisp white.

Day 11: Fly to São Miguel, Discover the Island's Pristine Beaches

Say goodbye to mainland Portugal today as you head to the airport for a 2.5-hour flight to São Miguel, the biggest island in the Azores archipelago. Meet your driver at the airport for a transfer to your hotel, where you can refresh before venturing out to explore the area on your own. Plenty of beaches are scattered across the island, so you could spend the entire day hopping from one to another. An excellent place to start is Praia de São Roque, close to the capital city of Ponta Delgada, where you can admire the verdant hills while soaking up the sun on the sand.

When you're ready, continue to nearby Praia das Milicias for more tranquility. The calm waters here make it the perfect place for a refreshing swim. Then, end your self-guided beach-hopping tour at Praia do Populo, whose western-facing location offers the ideal spot to see the sunset over the water. Watch as the sky transforms into warm oranges and reds while the ocean reflects nature's spectacle. In the evening, stroll through the 18th-century arches of Portas da Cidade to enter Ponta Delgada's historic center, where you'll find plenty of local and international restaurants for dinner.

Day 12: 4WD Adventure to Sete Ciudades

Go off-road today on a 4WD adventure to Sete Cidades, a village on the island's west side known for its lush hillsides, volcanic craters, and tranquil lakes. Start the 40-minute drive from Ponta Delgada, stopping at Pico do Carvão for panoramic views of the lush greenery and the vast Atlantic Ocean. Continue to another iconic viewpoint, Vista do Rei, to see the Lagoa das Sete Cidades, twin blue and green lakes nestled within a volcanic crater. After taking in the view, head to the four-mile-long (6.4 km) Cumeeiras Trail to trek along the volcano's rim.

Follow the path through towering forests and open meadows, stopping at several viewpoints along the trail to see the glittering lakes. When you finally reach the village, stop for a snack and a cup of coffee or tea in the central square. If you have energy to spare, stroll through the charming streets to admire the local churches and markets. On your way back to Ponta Delgada, stop for a short, 40-minute hike around the lake's edge, passing through a small peninsula shrouded in trees and flowers for one last look at the pristine landscape. 

Day 13: Food Tour Across Ponta Delgada 

Immerse yourself in the island's rich culinary culture today on a 3.5-hour food tour to some of the best local bars, markets, and eateries in Ponta Delgada. Follow your guide along the cobblestone streets, stopping for a tempting array of Azorean specialties, from the iconic cozido das furnas, a stew slow-cooked in volcanic steam, to succulent seafood, including the freshest octopus and grilled limpets straight from the Atlantic. Alongside these savory delights, indulge in the island's renowned cheeses, such as queijo da ilha, paired with sweet jams made from tropical fruits. 

Pass historic landmarks along the way and learn about the island's rich history from your guide, then meander through traditional markets, like Mercado da Graça, where you'll engage with local vendors, learn about their agricultural practices and fishing methods, and sample artisanal products you can take home. Then, follow all the delicious food with locally produced wines and end the tour with a sweet treat of bolo lêvedo, a sweet bread or muffin originating on the island.

Day 14: Full-Day Tour of Furnas & Parque Terra Nostra

Delve into the heart of the island's geothermal activity today in Furnas, a charming town renowned for its natural hot springs. After the 40-minute 4WD drive, stretch your legs on a 2.7-mile (4.3 km) loop trail to the Miradouro Pico do Ferro. Follow your guide through the dense forest, gradually ascending the summit of Pico do Derro. When you reach the top, enjoy sweeping views of the Furnas Valley and its surrounding volcanic craters. Then, after the 1.5-hour trek, continue the drive to Parque Terra Nostra, the oldest botanical garden in the Azores. 

Day 15: Free Morning on São Miguel, Whale Watching Tour

Start your final full day in Portugal's São Miguel Island with a free morning to spend as you wish. Revisit a nearby beach to soak up some sun or drive 50 minutes east to Nordeste, a picturesque town with well-preserved colonial architecture and vibrant gardens. Venture down the cobbled streets lined with charming churches and traditional houses. Look out for colorful azulejos adorning the buildings, and stop in the inviting squares for a snack. Lastly, check out some of the town's viewpoints, like Miradouro da Ponta do Sossego, for far-reaching views of the lush mountains and glittering ocean.

In the afternoon, set off on a boat cruise to spot the vibrant marine life of the Azores archipelago—one of the best whale watching destinations in the world. Keep your eyes peeled for the sperm whales who frequent the area, along with over 20 other species, like blue whales and humpback whales, depending on the season. Learn about their behavior from your knowledgeable biologist guide, and see playful dolphins and curious turtles as you cruise down the coast. Finally, stop at the Islet of Vila Franca do Campo to view the tranquil lagoon nestled in a sunken volcanic crater before returning to Ponta Delgada.

Day 16: Depart São Miguel

After discovering the highlights of mainland Portugal and the Azores, your 16-day adventure ends today. If you have some time before your flight, revisit the beach for one more swim in the Atlantic or head to a local market, like Mercado da Graça, to shop for artisanal goods and traditional crafts to take home. Pick up a traditional Azorean pastry before you leave, like a queijada da vila franca do campo, a muffin-like pastry made with fresh cheese, sugar, eggs, and citrus. When it's time, return to the hotel to meet your driver for a transfer to the airport for your flight home. Safe travels!

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