Explore the diverse coastal landscapes of the Algarve, the rich history and culture of Lisbon, and the natural wonders of the Azores with this 10-day adventure through Portugal. This active itinerary includes a kayaking expedition to the mesmerizing Benagil Cave, a challenging ascent to São Miguel's highest peak, and plenty of outdoor adventure. Get ready for a journey that will leave you with lifelong memories of Portugal's breathtaking landscapes and vibrant urban charm.


  • Hike, relax, and kayak the beautiful Algarve coastline
  • Explore the best of Lisbon on foot and in a tuk-tuk
  • Go whale watching, hiking, and on a Jeep tour in the Azores
  • Feel the volcanic core of the Azores in Furnas on São Miguel Island

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon, Drive to the Algarve, Explore Lagos Algarve
Day 2 Algarve Kayaking Trip to Benagil Caves, Beach Time Algarve
Day 3 Hike Seven Hanging Valleys Trail, Sunset Experience Algarve
Day 4 Transfer to Lisbon, Guided Tuk-Tuk Tour, Lisbon Roots, Food & Cultural Walk Lisbon
Day 5 Portugal Scenic Trails: Sintra Coastal Hike Lisbon
Day 6 Fly to São Miguel Island, Whale Watching Cruise São Miguel Island
Day 7 Full-Day Sete Cidades Jeep & Hike Adventure São Miguel Island
Day 8 Hiking Excursion to Pico da Vara São Miguel Island
Day 9 Full-Day Volcanic Experience in Furnas São Miguel Island
Day 10 Depart São Miguel Island  

Detailed Itinerary

Day 1: Arrive in Lisbon, Drive to the Algarve, Explore Lagos

Much of the western Algarve coast features rocky cliffs, secret beaches, and crystal-clear blue waters

Bem-vindo (welcome) to sunny Portugal! On arrival at Lisbon airport, collect a rental car and prepare for the three-hour drive to the Algarve. It's an easy journey with a fast and direct highway, so enjoy the ride on the way to Portugal's southern coastal region. Down here you'll explore the Algarve coastline, adorned with golden-sand beaches, hidden coves, and breathtaking rock formations.

This afternoon is yours to explore Lagos, a vibrant yet laid-back coastal town with a captivating character. Here you'll find a charming inner-walled Old Town and a pretty harbor with dramatic sandstone cliffs and beautiful beaches nearby. Explore the narrow cobblestone streets and colorful center, then visit the town's golden beaches, such as Meia Praia and Praia Dona Ana. Later, take your pick of the town's authentic restaurants and enjoy a buzzing nightlife scene.

Day 2: Algarve Kayaking Trip to Benagil Caves, Beach Time

Kayaking towards the caves
Kayaking along the Algarve coastline gives you a whole new perspective 

Today you'll get to visit one of Europe's most spectacular sea caves, Benagil Caves, by kayak. You'll paddle past an extraordinary section of the coast west of the Praia de Albandeira, full of fantastic geological features such as natural rock arches and rock stacks. Your skilled and knowledgeable guide will lead you to the most hidden caves, beaches, and rock formations on your 90-minute kayak adventure toward Benagil Cave. Finally, you'll paddle inside and land on the sandy beach within the world-famous cathedral cave, which has a hole in the roof that lets in a warm sunbeam of light.

Spend the rest of today discovering some of the Algarve's spectacular beaches at your own pace. Praia Dona Ana is the Algarve's most photographed beach, a 534-foot (160 m) sandy stretch flanked by rugged rock formations, while Ponta da Piedade, or "Mercy Point," is hidden behind tall cliffs, brimming with crystal-clear water. Head to Praia do Pinhão for a tranquil, wilder beach hidden behind tall ocher cliffs, or opt for one of the most iconic Algarve beaches at Praia do Camilo, where a dramatic staircase winds down to a small patch of sand where you can explore grottoes and rocks.

Day 3: Hike Seven Hanging Valleys Trail, Sunset Experience

Alfanzina lighthouse
Enjoy views of the Alfanzina Lighthouse on the Seven Hanging Valleys Trail

Today, you'll hike the Seven Hanging Valleys Trail, a clifftop walk on the Algarve's central coast. This 3.5-mile (5.7 km) trail rewards you with mesmerizing views over turquoise seas as you breathe in the salty air and admire geological wonders. Pack your swimsuit and start on the boardwalk near the beach of Vale de Centeanes. As you explore, enjoy views of the Alfanzina Lighthouse and the twin arches over the water near Praia da Mesquita. The walk passes right above the Benagil Cave, and you can enjoy a swim at Praia do Carvalho or at your final destination, Praia da Marinha.

This evening witness a beautiful sunset from the most southwesterly point in continental Europe. As twilight approaches, you'll spectate from the St. Vincent Cape of Sagres, where you can watch the sun sink into the Atlantic Ocean as you enjoy a glass of Portuguese wine with bread and chorizo.

Day 4: Drive to Lisbon, Guided Tuk-Tuk Tour, Lisbon Roots, Food & Cultural Walk

Lisbon from above
São Jorge Castle sits high on the hill overlooking the city of Lisbon and the Tagus River
Plan your trip to Portugal
Chat with a local specialist who can help organize your trip.

Feeling relaxed after your coastal escape, today you'll make the return drive to Portugal's colorful capital, Lisbon. Start by getting to know the "City of Seven Hills" with an electric tuk-tuk tour. Led by a knowledgeable guide, you'll zip through the charming capital's modern and historic districts, from the neoclassical avenues of Baixa to the cobblestone alleys of bohemian Bairro Alto. Discover the city's fascinating history and hidden corners, and stop at stunning panoramic viewpoints such as São Pedro de Alcântara, Parque Eduardo VII, Senhora do Monte, and Santa Luzia.

Later, explore on two feet with a food and culture walking tour. Explore two of Lisbon's most ancient neighborhoods and step through time as you stroll from old 12th-century alleys into the bustling modern-day city. Along the way, sample authentic Portuguese dishes and learn about why the neighborhood of Mouraria is such a unique place, historically and today.

Day 5: Portugal Scenic Trails: Sintra Coastal Hike

Portugal Scenic Trails: Sintra Coastal Hike
The rocky coastline of Sintra-Cascais Natural Park
Lace up your sneakers for another active day, this time exploring the gorgeous coastline of Sintra-Cascais Natural Park. Today's 12-mile (20 km) hike will immerse you in nature for the whole day while trekking along the fantastic blue coast. Along the way, you'll visit the westernmost point of Continental Europe, Cape Roca. Here a beautiful historic lighthouse has illuminated the coast since 1772. Continue inland, passing by the small towns of Ulgueira and Azoia, where people still live a relaxed life close to the city. When the adventure is over, you'll return to Lisbon.

Day 6: Fly to São Miguel Island, Whale Watching Cruise

São Miguel - Azores
The lush green landscape of São Miguel Island in the Azores

This morning a private driver will transfer you to the airport in time for your flight to São Miguel, the biggest of the nine volcanic Azores Islands. Known as "The Green Island" due to its lush landscapes, volcanic craters, and vibrant vegetation, São Miguel offers a diverse range of things to do and see. A driver will collect you from the airport at Ponta Delgada and transfer you to your hotel.

The Azores is considered to be among the best whale watching destinations in the world. Here you can spot more than 20 different species found in the archipelago's waters. Later today, you'll board a boat to spot these fantastic and majestic marine creatures with the help of a local biologist 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.

Day 7: Full-Day Sete Cidades Jeep & Hike Adventure

Sete Cidades Jeep & Hike Adventure Full Day
A spectacular view of São Miguel's Sete Cidades from above

Explore the wild side of the Azores' most famous attraction—Sete Cidades—with an off-road excursion. 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. 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 with a 4WD vehicle.

If the weather is playing nice, you'll 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 charming local church and enjoy a cup of tea or coffee in the village located 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 8: Hiking Excursion to Pico da Vara

Hiking Excursion to Pico da Vara
Ribeira dos Caldeirões Natural Park is a protected area in the Azores

Today you'll hike to the highest point of the island, Pico da Vara, at 3,625 feet high (1105 m). From here, you'll enjoy a privileged view over the whole island of São Miguel. Taking around eight hours to complete, start the hike by crossing the Pico da Vara Nature Reserve. Follow a dirt track through the cryptomeria forest and experience an area rich with biodiversity, including the important laurissilva forest and the priolo, one of the few species of fauna endemic to the Azores.

After the trail, visit the Ribeira dos Caldeirões Natural Park. Here you'll find one of the most spectacular natural waterfalls in the Azores, along with verdant ferns and lush greenery. Enjoy the picturesque and tranquil atmosphere as you explore the old water mills and charming stone bridges, which connect you to the island's rural heritage.

Day 9: Full-Day Volcanic Experience in Furnas

Volcanic Experience in Furnas Full Day
Feel the raw volcanic energy in Furnas

From mystical secret gardens and natural thermal pools to steam vents and fumaroles to a magnificent gastronomic experience cooked with the power of the volcanoes, experience nature's power in Furnas. One of the most emblematic villages of the Azores, the Furnas Valley, is where the volcanic nature of the islands is most readily apparent. Join a day trip to the area, first stopping at Pico do Ferro circuit trail to take in one of the best sights of Furnas Lake

Your next stop will be Terra Nostra Botanical Garden, the first and oldest botanical garden of the Azores. Dip in the iron-rich orange thermal pools and natural Jacuzzis surrounded by vibrant green scenery. For lunch, you can choose to try a traditional dish called cozido, a stew that's cooked underground using volcanic power. After, explore the area's volcanic steam vents, fumaroles, and mineral waters fountains with various temperatures and flavors. On the way back to Ponta Delgada, pause at Gorreana Tea Factory to enjoy the local tea and wander the plantation.

Day 10: Depart São Miguel Island

Ponta Delgada
The historic Portas da Cidade is the city symbol of Ponta Delgada

It's the final morning of your 10-day vacation through Portugal and the Azores. If you have time before your flight, you could join another outdoor adventure, explore another corner of the island, or go horse riding or canyoning. When the time is right, take a transfer from your hotel to the Ponta Delgada airport for your departing flight. Safe travels!

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Map of Adventure in Mainland Portugal & the Azores - 10 Days
Map of Adventure in Mainland Portugal & the Azores - 10 Days