Iberian Adventure: Spain, Portugal & the Azores - 21 Days

Day 1: Arrive in Madrid (Spain), Tapas Experience

Welcome to Spain! Touch down in the vibrant capital, Madrid, where a driver will be waiting to take you to your hotel in the heart of the city. Settle in and then head out on a food tour with a local guide, where you'll experience Madrid's picoteo culture. The origins of the word picoteo lie in the verb "picar," which means eating small bites from several shared plates. This is also known as tapeo or tapas.

Your culinary journey starts at a traditional bodega serving delicious Spanish tapas, a local favorite that's been around for decades. Over the next three stops, you'll try some meat and fish dishes from Madrid, along with some cold draft beer and local wines. To conclude your picoteo in Madrid, visit a traditional restaurant specializing in northern Spanish cuisine.

Day 2: Madrid History, Culture & Architecture Tour

Get to know Madrid better today on a history, culture, and architecture tour of the city. Accompanied by a local guide, head to the historic Habsburg district, the oldest part of the city, known in Spanish as El Madrid de Los Austrias. You'll visit the striking Baroque Royal Palace, Almudena Cathedral, and Plaza Mayor. Along the way, your guide will stop at hidden gems and tell you stories about Madrid's history.

Afterward, continue to explore the city independently. Spend some time in peaceful Retiro Park and browse famous art exhibitions at the Prado Museum and Reina Sofia, Spain's national museum, which was named for Queen Sofia and is packed with 20th-century art. Art lovers will also enjoy the Sorolla Museum, which celebrates the work of famous artist Joaquín Sorolla, and the Thyssen-Bornemisza Museum, which traces the history of European painting.

For shopping, head to Serrano Street, or if it's a Sunday, explore Madrid's famous flea market, El Rastro. The market takes over the city center, stretching from the Plaza Mayor into the surrounding streets, with stalls piled with everything from paintings to clothing and antiques. Make time to enjoy coffee in one of the main plazas, where you can sit outside and people-watch. The Latina district is one of Madrid's oldest regions, filled with narrow medieval streets, leafy plazas, and cathedrals.

Day 3: Free Day in Madrid

Today is yours to spend as you please in Madrid. Continue sightseeing or take an optional day trip, such as a kayaking tour in the River Duratón Natural Reserve in Segovia. You'll Kayak the calm waters surrounded by limestone walls home to the biggest colony of griffon vultures in Europe. Watch wildlife and paddle under the ruins of the 13-century Franciscan monastery, Monasterio de la Hoz. The trip ends with a tour of Segovia's old town.

Alternatively, hop on a train for the half-hour journey through the countryside to Toledo. This UNESCO World Heritage Site dates to Roman times and was the capital of Spain in the 16th century. Toledo's cluster of clay rooftop buildings, cobbled lanes, and church spires are crowded onto a hilltop overlooking the Río Tajo and encircled by protective walls you can enter through massive iron gates.

Take a guided tour of Toledo, known in the Middle Ages as the "City of the Three Cultures," where Christian, Muslim, and Jewish communities all peacefully coexisted. As such, the city is crammed with religious buildings, including the 12th-century Iglesia de Santo Tomé, the Moorish Sinagoga de Santa María la Blanca, considered the oldest synagogue in Europe, and the grand 13th-century Toledo Cathedral.

Day 4: Train to Granada, Explore

This morning, take the train south to the historic city of Granada. Set in the foothills of the Sierra Nevada Mountains, the city is renowned for its Moorish architecture and history, as well as its modern bars and flamenco venues. Check into your hotel and then explore the city, starting with its oldest square, Plaza Nueva. Wander around the Albaicín, the medieval center, to admire the Moorish architecture.

Other Granada highlights include the Jewish Quarter, Barrio Realejo, and the 16th-century Catedral de Granada, the city's largest and most opulent Roman Catholic church. End the day at a local eatery to enjoy traditional tapas. Bring your appetite—Granada is known for its huge portion sizes.

Day 5: Alhambra & Generalife Gardens Tour, Flamenco Show

Discover Granada's most famous landmark, the Alhambra, on today's guided tour. Set on a hill above Granada, this imposing Muslim fortress dates to the ninth century. It was rebuilt in the 14th century by the Nasrid Dynasty. It was a Moorish palace until the Christian reconquest in 1492 when it became the Royal Court of Ferdinand and Isabella. 

Tour this UNESCO World Heritage Site's grand buildings, which include striking examples of Moorish history. Observe features such as the hand of Fatima on the gateway of the Puerta de la Justicia (Gate of Justice), fingers outstretched to ward off the evil eye, or the extravagant design in the Patio de Comares (Court of the Myrtles). You'll also stroll through the Generalife park and gardens with panoramic views of Granada.

End the day with a flamenco show in a Sacromonte Cave. Flamenco is the ultimate artistic expression of Andalusia, and Granada's Sacromonte neighborhood is one of the best places to explore this art form. The area is the birthplace of the zambra, a flamenco dance party that dates to the 16th century, and the marital rituals of the Moors. Between the 18th and 19th centuries, locals waited at cave entrances, ready to perform their flamenco show for travelers.

Day 6: Las Alpujarras Andalusian Tour

Today's adventure takes you an hour from Granada into the idyllic Alpujarras Mountains. Visit tiny mountain villages that were the last stronghold of the Spanish Muslims, or Moors, who, soon after the Castilians took Granada in 1492, were forced to convert to Christianity or flee. Those who refused to convert opted to take to the hills, settling in this remote, inaccessible area. 

These communities have also spent centuries maintaining the medieval structure of the buildings and streets. Many villages have a reputation for excellent cuisine based on locally grown, high-quality produce. Enjoy a traditional lunch in one of the villages and learn about the area's history and geography from your guide. 

While you travel through the countryside, watch out for the area's abundant birdlife. Bird-watching is a popular pursuit in Las Alpujarras. One of the avian highlights is the distinctive hoopoe, with a haunting cry that often echoes through these mountain valleys. After the tour, you'll return to Granada to spend the evening as you please.

Day 7: Transfer to Seville via Caminito del Rey

Travel west this morning to Seville, the capital of Andalusia. Along the way, you'll stop for some adrenaline-pumping hiking on the Caminito del Rey—a stunning network of walkways built along a deep gorge carved out by the Guadalhorce River. In some sections, the gorge reaches staggering depths of 2,297 feet (700 m).

You'll arrive at the park's northern entrance and put on your safety equipment. Then it's time to head off along the trail. As you hike, you'll be treated to incredible views over the gorge to the river valley below. This one-way trail typically takes about three to four hours to complete. Afterward, you'll continue to Seville, where you'll check into your hotel and spend the rest of the day recharging.

Day 8: Seville by E-Bike

Start the day with an e-bike tour of Seville, which blends Gothic cathedrals, stately mansions, and palaces. Stop at key sights like Plaza de España, Guadalquivir Riverfront, Setas Marketplace, Plaza de San Francisco, and some of the city's most beautiful gardens and parks. During the excursion, your local guide will share anecdotes and explain some of the mysteries and stories behind the city of Seville. The rest of the day is yours to soak up the atmosphere in this beautiful city.

Day 9: Transfer to Lisbon (Portugal), Roots, Food & Culture Walk

Say goodbye to Spain this morning; your driver will pick you up for the four-hour journey to Lisbon. The Portuguese capital is full of winding cobbled streets traversed by yellow trams, with medieval towers, Baroque palaces, and dome-topped monasteries. That's not to mention world-class restaurants, buzzing markets, and a lively bar scene.

Settle into your hotel, then explore two of Lisbon's most ancient neighborhoods, Mouraria and Alfama. Stroll from 12th-century alleys into the modern-day city, soaking up the laid-back vibes of each area and stopping along the way to sample authentic Portuguese dishes and snacks. You'll also learn about Mouraria's roots as the birthplace of fado music and the most multicultural neighborhood in Lisbon.

Day 10: Lisbon Tuk-Tuk Tour

Explore the "City of Seven Hills" in style today by electric tuk-tuk. Led by a knowledgeable guide, you'll zip through Lisbon's modern and historic districts, from the neoclassical avenues of Baixa to the cobblestone alleys of the bohemian Bairro Alto. Discover the city's fascinating history and hidden corners and stop at stunning panoramic viewpoints like São Pedro de Alcântara, Parque Eduardo VII, Senhora do Monte, and Santa Luzia.

Spend the rest of the day exploring Lisbon at your own pace. For shopping, head to the Feira da Ladra flea market on Tuesdays and Saturdays, where you can find everything from vintage clothing to quirky antiques. Then there's the daily Mercado da Ribeira and all kinds of food under one roof at the Time Out Market next door. 

Famous sites include the Elevador de Santa Justa, a thin iron elevator built in 1902, which you can ride to the top of a 150-foot-tall (45 m) tower showcasing views of the city and the sea beyond. Pass through the grand archway, Arco Monumental da Rua Augusta, which leads into Commerical Square, and discover the colorful Chiado district and Bairro Alto's hilltop views over the city.

Day 11: Sintra Coastal Hike

Day 12: Sailing the Arrábida Marine Reserve

Enjoy a peaceful sailing trip along the breathtaking coastline of the Arrábida Marine Reserve. This protected area is full of biodiverse marine life, making it a top snorkeling spot. As you sail, admire the reserve's soaring limestone cliffs and explore secluded beaches guided by your private skipper. You'll anchor in various locations to enjoy the sun, dip in the sea, and swim to the shore to relax on sandy beaches.

Day 13: Train to Porto & E-bike Tour

After breakfast, head to a Lisbon train station for the journey to Porto. The country's second-largest city is beloved for its colorful Ribeira (riverside), lined with port cellars and cafés, and the colossal steel skeleton of Dom Luis I Bridge which spans the Douro River. Upon arrival, your driver will drop you at your hotel, where there's time to relax before your afternoon food tour of the city.

Today you'll tackle Porto's steep streets effortlessly on an e-bike tour. Your guide will lead you along cobbled streets lined with tiled churches and pastel-colored historic buildings. Pass some of the city's most iconic landmarks, from the Clerigos Clock Tower to Porto Cathedral and the Livraria Lello, a bookshop with a distinctive spiral staircase said to be one of the real-life inspirations for Harry Potter's Hogwarts. En route, your guide will give you an overview of Porto's history, culture, and architectural heritage. Negotiate the streets on your e-bike, stopping for photos. After the tour, the rest of the day is yours to soak up the city sights, dine, and relax at your hotel.

Day 14: Visit Matosinhos

Discover one of Porto's lesser-visited gems today: Matosinhos. Located just a few miles from the city center, Matosinhos is where Porto's residents come to kick back and dine. As it once made a living from the ocean, Matosinhos has an affinity for seafood, and the best place to experience this tradition is at the Municipal Market on Rua França Júnior. 

The market lies in a curving white pavilion that dates to 1944 but has been revamped in the last couple of years. As part of this renovation, offices and studios have been set up for young designers in the galleries above the market floor. It's one for the early birds, as the best time to visit is first thing in the morning.

Matosinhos also has one of the best beaches in the Porto area, with surf-friendly waves all year round. 17th-century forts defend the oceanfront, and there's history in the shape of Baroque and medieval churches, as well as the stellar Sea Life Aquarium. Don't miss the Piscina das Marés, remarkable saltwater swimming pools cut into the rock face.

Day 15: Free Day in Porto

Take an optional day trip to the mountains and valleys of the famous Douro Valley wine region, where you'll visit traditional vineyards accompanied by your expert guide. After wine tasting, you'll enjoy a traditional lunch at one of the valley's famous quintas (estates) and hop aboard a riverboat for an hourlong cruise down the tranquil Douro River.

If you're feeling active, tackle one of Europe's most beautiful riverside hikes, the Paiva Walkways. Follow a 5-mile (8 km) wooden boardwalk along the Paiva River among lush forests, finished with a traditional lunch. The Peneda-Gerês National Park offers more stunning hikes. Located outside of Porto, the park has trails leading to waterfalls, lagoons, and ancient villages—you might even spot wild horses.

Day 16: Fly to São Miguel Island (the Azores), Ponta Delgada Food & Wine Experience

This morning starts with a flight to São Miguel, the largest island in the Azores archipelago. Fringed with lava-stained beaches, the volcanic islands are known for their crater lakes, mud pots, and thermal pools. The rich waters surrounding the archipelago are filled with marine life, including whales.

Upon arrival, pick up your rental car and check into your hotel ahead of this evening's food and wine tour. Take a guided walk through Ponta Delgada with a local, stopping at the trendiest eateries and neighborhood bars. You'll sample a progressive menu of fruit, honey, bread, pastries, seafood, artisanal meats, and homemade desserts—all washed down with a series of locally-produced wines.

Day 17: Whale Watching & Sete Cidades Hike

The Azores are among the best whale watching destinations in the world, with over 20 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 and dolphins, 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.

Spend the rest of the day exploring the Sete Cidades, which translates to "seven cities" but refers to a series of natural wonders. The sites include shimmering lakes like Empadadas, Santiago, and the famous blue and green waters of Twin Lakes. There are several viewpoints along the way, such as Carvão, and Vista da Princesa, where you can contemplate the landscape accessible only by foot.

On sunny days the volcano rim, the Cumeeiras Trail, offers one of the most scenic walks on the island, with stunning views from both sides. Visit the local church and enjoy a cup of tea or coffee in the village right inside the crater. On the way back, take a trail along the lake's edge surrounded by native flora.

Day 18: Free Day on São Miguel

Enjoy a free day to relax and explore São Miguel, known as the Ilha Verde (green island), with its enviable landscape of forest-wrapped volcanic peaks, azure lakes, and calderas. Laze on black-sand beaches shadowed by towering cliffs, soak in thermal pools, or visit Ponta Delgada's fortress and 17th-century churches.

A top activity is hiking in Gruta do Carvão, the largest lava tunnel on the island, which plows underground for more than a mile (1.6 km). Marvel at the cave's collection of stalactites and stalagmites in various colors. To get your blood pumping, head on an epic canyoning adventure where you'll rappel down waterfalls, cliff jump, and enjoy natural waterslides.

Day 19: Discover Furnas's Geothermal Wonders 

Discover the geothermal wonders of São Miguel today, from thermal pools to steam vents and fumaroles. Your first stop is the Pico do Ferro walking trail, which offers showstopping views of Furnas Lake. Continue to the Terra Nostra Botanical Garden, the oldest botanical garden in the Azores, where you can enjoy a dip in the thermal pools and natural Jacuzzis surrounded by forest. Here you can sample the traditional dish cozido, a rich stew slow-cooked underground using volcanic heat.

After lunch, continue exploring the volcanic landscape, visiting steam vents, fumaroles, and mineral fountains of various temperatures that gush from lava walls. You'll soon understand why this is one of Europe's richest hydrological regions. On the way back to Ponta Delgada, you'll have time to try some locally-grown tea at the Gorreana Tea Factory. If you still have some energy, there's time for an optional sea kayaking tour along the island's rugged coastline.

Day 20: Lagoa do Fogo Hike

Spend a final day in São Miguel hiking at Lagoa do Fogo (Fogo Lake), one of the island's biggest lakes. Start in Água d'Alto on the south coast, then follow an uphill path, climbing nearly 2,000 feet (600 m) in elevation. This brings you to a levada site, where drinking water for the island is sourced; you can enjoy a flat walk here among lush native vegetation.

As the hike continues, you'll pass an area of aquifers, where rocks filter water into wells and springs, before arriving at stunning Fogo Lake. Relax on the banks with a picnic lunch; you'll have a chance to swim in the crystal waters and lounge in the sun. Afterward, you'll return to your hotel to enjoy dinner and the last evening of your trip.

Day 21: Depart Ponta Delgada

Today your Iberian adventure comes to an end. Drop your rental car off in time to catch your homebound flight. Safe travels!

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