On this immersive 6-day itinerary, you'll get a local's eye view of Madrid as you explore its culture and cuisine with a series of guided walks and excursions. After visiting the capital's landmarks and sampling its best tapas, set out on a selection of easy day trips into the surrounding countryside of Castilla y León. Visit the historic towns of Segovia and Pedraza as you tour and taste your way through cheese farms, olive groves, and wineries, returning to the bustle of Madrid each evening.


  • Discover Madrid's buzzing culinary scene
  • Explore the capital's famous museums, plazas & palaces
  • Take day trips into the Castilla y León countryside
  • Visit the historic city of Segovia
  • Tour & taste your way through wineries, olive groves & cheese farms

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Madrid - Evening Tapas Tour Madrid
Day 2 Historical & Cultural Tour of Madrid Madrid
Day 3 Day Trip to Segovia & Pedraza Madrid
Day 4 Gourmet Walking Tour of Madrid Madrid
Day 5 Countryside Food & Wine Tour Madrid
Day 6 Depart Madrid  

Detailed Itinerary

Day 1: Arrive in Madrid - Evening Tapas Tour

The fountain of Cibeles is a beloved Madrid landmark
The fountain of Cibeles is a beloved Madrid landmark

Welcome to Madrid! Upon arrival at either the airport or train station, you'll be greeted by a private driver who will transfer you to your hotel in the city center. Take some time to settle in and get your bearings before heading out to explore. 

Spain's capital is made for walking—with wide, elegant boulevards showcasing a range of architectural styles and expansive, manicured parks such as the Buen Retiro. It's also renowned for some of the best art museums on the continent, including the Prado Museum with works by Goya, Velázquez, and other Spanish masters.

This evening, you'll meet your guide for a walking tapas tour to get a genuine feel for the city and sample the best local cuisine in a compact time frame. See Madrid through a local's eyes as you get a feel for its many districts and neighborhoods. The tour begins with a two-hour city walk taking in the main sights, followed by delicious tapas in local and authentic bars in "Las Letras"—the historic heart of the city.

Day 2: Historical & Cultural Tour of Madrid

Madrid's central Plaza Mayor
Madrid's central Plaza Mayor

Today, you'll discover the city of Madrid and explore its cultural highlights with the help of an expert guide. On this enlightening walking tour, the guide will recount the history of the city and its development from a medieval seat of Spanish power to a modern metropolis of international renown. You'll also learn about current social and cultural events to ensure you're up to date on what's happening in 21st century Madrid.   

After you've experienced a bit of the city, the guide with leave you at a great local restaurant for lunch. You'll then have the rest of the day to explore on your own. Make sure to visit the expansive plazas in the heart of the city, such as the Plaza Mayor and the Puerta del Sol, which date back to the 15th and 14th centuries, respectively, and embody classic icons of Old Madrid. 

Madrid is also home to can't-miss museums like the Prado Museum, which boasts one of the finest collections of European art spanning the 12th through the 20th century and featuring the works of masters like Goya, Bosch, El Greco, Titian, and Diego Velázquez. There's also the Museo Nacional Centro de Arte Reina Sofía, Spain's national museum of 20th-century art, which highlights works by masters such as Picasso and Salvador Dalí. 

After a bit of culture, you might consider visiting El Retiro Park. This 308-acre space is the city's green lung, abounding with sculptures, fountains, a man-made lake, and a 400-year-old Mexican conifer, which is regarded as the oldest tree in Madrid. There are also must-visit gardens here, including the Jardín de Vivaces ("Garden of Vivacious Plants"), Jardines de Cecilio Rodríguez (inspired by the Andalusia region), and a garden home to over 4,000 roses (which bloom from May through June). 

When evening arrives, why not head up to one of the city's many rooftop bars for a sundowner? There are many solid options with great views of city lights, including:

  • A chic bar and restaurant sits at the top of the Círculo de Bellas Arte cultural center, which dates to 1880 and boasts incredible views of Calle Alcalá and Madrid's cityscape. Pay the four euro entrance fee and enjoy a cocktail and photo-op. 

  • The Hat rooftop bar is in the heart of the city behind the Plaza Mayor and features prime views of the city's old buildings. It's part of a well-known hostel, so it draws a bit of a hipster crowd.

  • The Hotel Emperador's terrace sits ten floors up at this elegant four-star hotel—except it's much more than a terrace. With the largest rooftop pool in Madrid, this is like a beach party right in the center of the city. In the summer, it's packed with fashionable revelers enjoying smart cocktails. The terrace is free for guests; non-guests can enter for a fee.

Day 3: Day Trip to Segovia & Pedraza

Blue skies over Segovia Cathedral
Blue skies over Segovia Cathedral
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This morning an expert guide will pick you up at the hotel for an hour's drive north of Madrid to Segovia. There is no shortage of historic cities in Spain, but Segovia stands out for its famous Roman Aqueduct and medieval Old Town, which are both UNESCO World Heritage Sites. 

Upon visiting these sights on a walking tour, you'll quickly see what all the fuss is about. Segovia's famous Roman Aqueduct is the pride of the city. It runs eight miles (14 km) in length, stands an impressive 93-feet (28 meters) high, and features two tiers comprised of 160 arches. Considering its nearly 2,000-year-old age, it remains in remarkably good condition. 

Then there's Old Town, which is situated on a bluff overlooking the Eresma and Clamores rivers. For a long time, Moors, Christians, and Jews coexisted in harmony here, and this is seen in the unique buildings with architectural influences that run the gamut from Mudéjar to Gothic. You'll see many such landmarks around Old Town, such as the 11th century Alcázar (palace), the 14th-century Old Main Synagogue, and the 16th-century Segovia Cathedral, which dominates the skyline. 

After the walking tour, you'll enjoy lunch in a local restaurant—be sure to try the roasted suckling pig, which is Segovia's specialty. Then you'll leave Segovia and head northeast about half an hour to Pedraza. This medieval walled village is a National Historical Heritage Site of Spain, and walking its central plaza is like stepping back in time. 

After the short tour of Pedraza, you'll hop back in the car and return to Madrid, where you'll have the evening free.

Day 4: Gourmet Walking Tour of Madrid

Enjoy Spain's classic dishes on a gourmet walking tour
Enjoy Spain's classic dishes on a gourmet walking tour

Today's excursion is perfectly suited to any culinary traveler. On this four-hour Madrid walking tour (either morning or afternoon), you'll visit three exceptional gourmet shops accompanied by an expert local guide.

First, you'll visit a purveyor of artisanal cured meats and sample one of Spain's most popular specialties: Iberian ham. It's a delicious and educational tour as you'll not only taste this delectable product but learn about it too. What makes Iberian ham so special? How do you identify it? How is it cured and cut? You'll learn the answers to these questions before continuing to the next delicious location. 

Olive oil is the theme of your next stop. There are over 240 types of olives grown in Spain, each with its own specific flavor profile. At an olive-oil shop, you'll taste oils from different regions of the country and enjoy various olives while learning about the precise definition of extra virgin olive oil, its pressing process, and the ideal foods with which to pair it.

You'll finish the gourmet tour on a sweet note as you visit a chocolatier specializing in handmade chocolate creations in both liquid and solid form. It will be an indulgent delight as the tasting involves using your senses of sight, smell, and taste to decipher and enjoy the different flavor notes and ingredients infused into the chocolate.

After this whirlwind foodie experience, your guide will leave you, but not before recommending a great nearby restaurant in which to enjoy a traditional madrileño lunch or dinner.

Day 5: Countryside Food & Wine Tour

Take a food and wine tour in the countryside around Madrid
Take a food and wine tour in the countryside around Madrid

A private guide will pick you up in the morning for a day trip outside of Madrid to visit some purveyors of Spain's deservedly famous foods. This is a pleasant full-day tour of the countryside with the added bonus of sampling local cheeses, olive oils, and wine. 

Your first stop will be at a small artisanal cheese farm. Here you'll learn about not only the different cheeses they offer but the care and attention that goes into the production process. Then you'll sample a wide variety of cheeses and get a delicious education in their various flavor profiles.

Next up is a local olive farm. Spain is the largest producer of olive oil in the world, and on this tour, you'll see why this golden liquid is so popular. At the farm, you'll meet the people who, day after day, dedicate themselves to producing olive oil of the highest quality. You'll not only learn about the modern production methods but visit an antique mill and see how the oil was produced hundreds of years ago. Then it will be time to sit down to a traditional Spanish lunch.

Afterward, you'll drive amid more spectacular scenery en route to a local winery. Spain boasts the largest area of grape cultivation in the world and is the second-largest producer of wine in terms of volume. In this country, you're never far from a D.O.Q. (Qualified Designation of Origin) viticulture area. You'll see the process that goes into wine production and enjoy a tasting of different varietals with the help of a sommelier.

You'll then return to Madrid, where you'll have the evening to spend at leisure.

Day 6: Depart Madrid

Adiós Madrid
Adiós Madrid

¡Buen viaje! Today you'll transfer to Madrid Barajas Airport to connect with your onward journey.


Map of Off the Beaten Path in Madrid - 6 Days
Map of Off the Beaten Path in Madrid - 6 Days