Follow the Sun in Portugal: Azores, Lisbon & the Algarve - 14 Days

Day 1: Arrive on São Miguel Island, Explore Ponta Delgada

Welcome to São Miguel, the largest island in the Azores archipelago! This cluster of nine volcanic islands sits 870 miles (1,400 km) west of Lisbon and is known for its geothermal landscapes and waters teeming with marine life. Touch down at the airport in Ponta Delgada, pick up your rental car, and then explore the capital of the Azores independently.

Cultural highlights in Ponta Delgada include the São Sebastião Church, the 16th-century Nossa Senhora da Esperança Convent, and the fascinating Carlos Machado Museum. You can also visit the famous Azorean pineapple plantations outside the city center or tour the Gruta do Carvão, a lava tube that's 5,413 feet (1,650 m) in length.

Day 2: Explore São Miguel's Sete Cidades

Take the day to explore the western side of São Miguel. Drive the coastal route, which includes access to São Miguel's region of lagoons. You'll find Sete Cidades, which translates to "seven cities" but refers to a series of natural landmarks. The sites include glistening blue-green lakes like Empadadas, Santiago, and Twin Lakes.

Sete Cidades is a favorite place for hikers, and the Cumeeiras Trail runs along a crater rim, making it one of the most scenic walks on the island. The Sete Cidades can also be experienced by kayak or canoe for a different landscape perspective. Don't miss the Ponta da Ferraria, a warm pool in the middle of volcanic rocks formed from a mix of hot springs and seawater.

Wildlife fans should book an optional whale watching tour, where you'll spot one (or more) of the 20 different species of whales in the Azores, as well as pods of dolphins dancing through the waves.

Day 3: Discover São Miguel's Central Region

Today your guide will introduce you to the central area of São Miguel, located between the two biggest cities on the island: Ponta Delgada and Ribeira Grande. Heading north via a mountain road, your first stop will be at a panoramic viewpoint that overlooks the staggering Lagoa do Fogo. Farther down the road, you'll find the Caldeira Velha, a geothermal phenomenon with balmy pools where you may want to go for a dip.

At Ribeira Grande, visit the Jardim do Paraíso (Paradise Garden) before continuing to Areais de Santa Bárbara, one of the island's most stunning stretches of shoreline. Next, drive through the emerald tea plantations of Gorreana and Porto Formoso. Along the way, admire the scenery from show-stopping viewpoints like Ponta do Cintrão and Santa Iria.

Day 4: Self-Guided Tour of Furnas

Discover the geothermal wonders of São Miguel today at Furnas Valley, home to some of the most dramatic landscapes in the Azores. Highlights include the village of Furnas, famed for its hot springs and fumaroles (volcanic vents), and the Terra Nostra Garden, where you can plunge into steamy pools.

Be sure to visit the Furnas Lagoon, where you can try a cozido das Furnas. This particular stew is slow-cooked by thermal heat in a pan placed underground. Afterward, visit the Lagoa do Congro, an isolated lagoon surrounded by lush vegetation. Return to your hotel afterward for a restful evening.

Day 5: Fly to Lisbon, Explore the Capital

It's time to say goodbye to the Azores and fly to Portugal's vibrant capital, Lisbon! Settle in and then head out to explore the city's calf-busting streets by foot or hop on a yellow tram. Take in views of medieval towers and dome-topped monasteries, peruse buzzing markets and praças, or stop in at one of Lisbon's world-class museums.

The quickest way to acquaint yourself with Lisbon's culture is through its cuisine. Highlights include pastéis de bacalhau (cod fritters), grilled sardines, squid stuffed with sausage and onions, queijo de azeitão (a creamy cheese made from sheep's milk) and pastéis de nata (egg custard tarts).

Day 6: Half-Day Guided Tour of Lisbon

Tour Lisbon this morning with a local guide, who'll take you to some of the city's most iconic districts, each perched on a different hill. Start in Alfama, the oldest quarter of Lisbon, which initially lay inside the walls of Moorish St George's Castle. Enjoy views of the castle and wander the steep labyrinthine streets, where fado (a musical art form that dates back to the 1820s) is performed.

Continue to the bohemian Bairro Alto, famous for its bars, restaurants, and nightlife, and get some recommendations for later in the day. Pause at Pedro de Alcântara Viewpoint, which offers sweeping views of the red-roof topped downtown. Finish in the trendy Graça neighborhood, where street murals grace the buildings, and the Senhora do Monte offers a rival viewpoint of the city.

End the day with an optional dinner accompanied by traditional fado music, where you can dine in an intimate eatery while being serenaded by fadistas (fado singers) and Portuguese guitars.

Day 7: Explore Belém

Spend today exploring the historic Belém neighborhood of Lisbon, famed for its UNESCO-listed landmarks that date back to the Age of Discovery in the 15th and 16th centuries. Climb the seafront Torre de Belém and visit the Mosteiro dos Jerónimos, an imposing monastery built in 1501 in a blend of Gothic and Renaissance styles. Stop for a coffee and pastéis de Belém, the neighborhood's cinnamon-sprinkled custard tart.

The afternoon is yours to enjoy Lisbon. For a different perspective of the city and its famous buildings, take a leisurely sunset cruise along the Tagus River, watching the sun light up Lisbon's landmarks in shades of gold.

Day 8: Guided Tour of Sintra & Cabo da Roca

Escape the city today and travel half an hour west to the UNESCO World Heritage Site of Sintra. Set among cool, forested hills, the city once acted as a summer retreat for Portuguese royalty and, as such, is dotted with turreted palaces, extravagant villas, and fairy-tale castles. These striking landscapes served as inspiration for Lord Byron's poems.

Hike to the Moorish Castle, which dates back to the eighth century, and admire the Pena National Palace, a bright yellow and pink building perched on a hilltop with ornate turrets and sculptures. Other Sintra hotspots include the Quinta da Regaleira and the Sintra National Palace. Finish with a stop at the westernmost point of continental Europe, the nearby Cabo da Roca, and the clifftop village of Azenhas do Mar.

Day 9: Day Trip to Évora

Enjoy a day trip to the ancient Roman city of Évora, which lies just east of Lisbon in the rural Alentejo region. As one of Portugal's oldest cities, Évora showcases historic architecture that escaped ruin during the 1755 earthquake, earning the town UNESCO heritage status. Traverse the cobbled streets to discover mansions, Moorish temples, a 2,000-year-old Roman temple, and Portugal's most significant medieval cathedral. End your visit with a meal in the bustling Praça do Giraldo.

For more history, take an optional visit to the nearby Cromeleque dos Almendres (Almendres Cromlech), a prehistoric site that goes back to the 6th Millennium BCE. Here, you can see one of Europe's most significant megalithic structures and the most important on the Iberian Peninsula. Afterward, return to Lisbon for a final night in the city.

Day 10: Transfer to Tavira, Explore

Head three hours south today to Portugal's sun-soaked Algarve, beloved for its honey-hued beaches bordered by rugged, red-tinged cliffs. Spend today exploring the quieter east coast, starting with Tavira, often considered the most charming town in the Algarve.

Tavira straddles the Gilão River and was once a key trading port. Ramble across the Roman bridge, past streets lined with Gothic and Renaissance architecture to a crumbling hilltop castle. Afterward, explore the surrounding area, from the nearby beaches to the postcard-ready village of Cacela Velha, which overlooks the Ria Formosa Natural Park.

Day 11: Explore the Central Algarve

Discover the central Algarve today, stopping to visit sandy coves like Carvoeiro. The maritime region is also home to ancient ports with whitewashed old towns and tiled churches—there's even a hilltop castle to visit in Silves. Stop for lunch in the sprawling resort town of Albufeira and take a boat trip to see the mystical Benagil Caves.

Continue along the sun-speckled coast for more Algarve highlights, including the Blue Flag beaches of Vale do Lobo, Rocha, and Quinta Do Lago. Eventually, you'll hit the region's capital, Faro, where you can visit churches, take a bird-watching boat trip in the Ria Formosa Natural Park, or have dinner in a street-side seafood restaurant.

Day 12: Discover Lagos's City & Coastline

Today you'll reach Lagos, at the western end of the Algarve. The city is known for its walled old town and harbor, which dates to the 17th century and acts as a base for boat trips along the spectacular cave-strewn coast. Thanks to its trading routes, cafés, pretty squares, and beaches, Lagos is filled with Moorish architecture.

Near the city center are several dreamlike beaches where you can enjoy optional boat trips and standup paddleboarding or kayaking. Praia do Pinhão is a peaceful cove known for its secluded setting, while Ponta da Piedade offers sheer sandstone cliffs and bright turquoise water. Meanwhile, Praia do Camilo is a gorgeous spot accessed via 200 steps that lead to a sheltered sandy cove.

Day 13: Explore Southwest Alentejo & Vicentina Coast Natural Park

Complete your journey through the Algarve with a trip to Sagres, which lies at the westernmost tip. Visit the remains of a 15th-century fort, where you can watch monster waves crash against the shore and discover Portugal's nautical past. Sagres sits on the Southwest Alentejo and Vicentina Coast Natural Park, known for its beautiful beaches, cliffs, and pristine coastal landscapes.

Take a trip to the nearby Cabo de São Vicente, the southwesternmost point of continental Europe; locals once believed it was the end of the world. Afterward, return to your hotel for a final night in Portugal. Have dinner at a seafront eatery and take one last sunset stroll along the soft sand.

Day 14: Transfer to Lisbon, Depart