In under a week, this adventurous itinerary takes you from the bustling streets of Lisbon to the remote Atlantic island of São Miguel. After visiting the highlights and hidden corners of Portugal's colorful capital, catch a flight to the Azores for three nights in a secluded paradise of lush greenery, volcanic lakes, and unspoiled beaches.


  • Hop on an iconic tram to discover Lisbon like a local
  • Lace-up your hiking boots to explore Sintra's forests & castles on foot
  • Take your pick of São Miguel's breathtaking beaches
  • Embark on an off-road adventure to the crater lakes of Sete Cidades

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon & Explore Lisbon with a Local Lisbon
Day 2 Sintra Heritage Hike Lisbon
Day 3 Fly to São Miguel Island, Explore the Beaches São Miguel Island
Day 4 Free Day in Ponta Delgada, Azorean Culinary & Wine Experience  São Miguel Island
Day 5 Sete Ciudades Jeep Adventure São Miguel Island
Day 6 Depart São Miguel Island  
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Detailed Itinerary

Day 1: Arrive in Lisbon & Explore with a Local

Colorful houses in Libson center
Colorful houses in Lisbon's historic center

Welcome 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. Grand plazas and pastel-colored buildings dot hilly waterfront neighborhoods, many dating back hundreds of years. Old cable cars lurch up winding cobbled roads, and medieval castles sit perched atop the highest points in the city. 

In the afternoon, you'll get your bearings on a privately guided tour of the city's most happening neighborhoods as you hop on board an iconic tram and head into the Bairro Alto. Continue to Chiado and discover a cultural enclave where the great writers and philosophers of the 20th century used to gather to hone their ideas. Next up is the picture-perfect neighborhood of Alfama. Here, you'll get a feel for traditional Lisbon with its narrow cobblestoned streets and the stunning 12th-century Sé de Lisboa Cathedral.

Day 2: Sintra Heritage Hike

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

Located just outside the capital, Sintra's lush hills dotted with fairy-tale palaces and extravagant villas have enchanted visitors for centuries. Today you'll hike through these remarkable landscapes of dense forest and exotic flora as you discover this mystical region's best trails and viewpoints. Reach the incredible eighth-century Moorish Castle, then continue to the mountaintop Pena Palace. Towering above the clouds, this Romantic-era national monument is full of historical treasures and is considered one of the Seven Wonders of Portugal.

At the end of the hike, your driver will be waiting to transfer you back to Lisbon for the evening, where you can put your feet up or head back into the Bairro Alto for a night of mouthwatering Portuguese fare and the melancholy sounds of traditional fado music.

Day 3: Fly to São Miguel Island, Explore the Beaches

Soft sand and crashing Atlantic surf at Praia de Santa Bárbara 

Bid the mainland farewell today as you transfer to the airport and catch 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 a driver will be waiting to transfer you to your hotel.

Spend the rest of the day exploring the plentiful praias (beaches) of São Miguel at your own pace. Head to Praia de Santa Bárbara for over half a mile of soft sand and a great lunch spot at the nearby Tuka Tulá Bar. You'll find vast stretches of volcanic sand, clear water, and dramatic cliffs at Praia de Água D'Alto, while the sheltered Vila Franca do Campo Islet is a swimmer's paradise and a great snorkeling spot. If the Atlantic is a little chilly for your taste, take a dip in the waters around Praia do Fogo, where the ocean remains naturally warm due to nearby hot springs. 

Day 4: Free Day in Ponta Delgada, Azorean Culinary & Wine Experience 

Ponta Delgada's Portas da Cidade (City Gates)

Today, you'll have a free day to enjoy Ponta Delgada and São Miguel Island however you'd like! Despite being the most populous metropolis in the Azores archipelago, this is hardly a typical European city; Ponta Delgada retains a quiet, small-town charm with quaint cobbled streets, historic churches, pedestrian squares, and serene parks. You'll also find a lengthy seaside promenade and 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.

This evening you'll discover some of the best food and wine in the Azores with a guided walk through Ponta Delgada's trendiest eateries and neighborhood bars. Wind through the downtown of this vibrant city as you sample a progressive menu of fruit, honey, bread, pastries, seafood, artisanal meats, and homemade desserts—all washed down with locally-produced wines. Along this flavorful culinary experience, you'll visit some of the main city sights, discover off-the-beaten-path highlights, and pick up some great local recommendations for your time in the Azores.

Day 5: Sete Ciudades Jeep Adventure

Go off-road to explore the wonders of Sete Cidades

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 Island, 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 Jeep trip, you'll stop at several viewpoints, such as Carvão and Vista da Princesa, where you can contemplate this breathtaking landscape accessible only by foot or 4WD vehicle.

Weather permitting, 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 local church and enjoy a cup of tea or coffee in the village 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.

Day 6: Depart São Miguel Island

Sunrise over São Miguel's Ponta do Arnel Lighthouse

It's time to bid your island paradise farewell. After a final morning on São Miguel, your driver will transfer you to the airport for the flight back to Lisbon and your onward journey. Safe travels and boa viagem!

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Map of Adventure to Lisbon & the Azores - 6 Days
Map of Adventure to Lisbon & the Azores - 6 Days