Madrid & the Imperial Cities

July 1, 2027
to July 10, 2027

Explore Madrid and the historic imperial cities that shaped Spain’s art, monarchy, religion, and cultural identity.

Madrid cityscape at Calle de Alcalá and Gran Vía

Royal heritage, timeless cities, and the cultural heart of Spain.

Madrid is one the newest Historical Capitals of a country in Europe. Although it was founded as “Capital” of the Nation in the middle of the 16th Century, the nomination as “the Court of the Kingdom” was declared by Phillip II at that time.
In this program you will find History before History and facts that will take you over the present times after two Dynasties of Monarchs.

Follow me!

Tour Booking

This tour is fully booked

Places for this departure are sold out. Leave us your details for the waiting list and we will contact you first if a place becomes available or when new dates are open.

Booking deposit: 1.000€ per person
Balance due 90 days before

Itinerary

by Traveling with Jorge®

Madrid
Day 1: Welcome to Madrid

Welcome to Spain!

After checking into our centrally located hotel, we’ll meet in the lobby at 5:00 PM for our first get-together. This is where strangers begin becoming travel companions.

 

We’ll take a relaxed orientation walk through the neighborhood, giving you the chance to get your bearings and discover the cafés, plazas, and hidden corners that will become familiar over the coming days.

Our first evening finishes exactly as it should: with good food, good conversation, and a traditional Welcome Dinner, included at one of my favorite local restaurants.

 

By the end of the night, you’ll already begin to understand why Madrid is one of Europe’s most welcoming capitals.

Walking: Easy, approximately 3/4 miles on mostly level terrain.

Driving: None.

Meals Included: Welcome Dinner.

Madrid
Day 2: Madrid, The Prado & Spanish Wines

This morning we’ll begin discovering Madrid aboard our private minivan before arriving at one of the world’s greatest museums: the magnificent Prado.

Our private art expert will guide us through Spain’s artistic treasures, introducing the masterpieces of Velázquez, Goya, El Greco, Rubens and many others while revealing the fascinating stories hidden behind each canvas.

The afternoon is yours to enjoy at your own pace.

As evening approaches, we’ll meet again for one of my favorite experiences: an exclusive tasting of carefully selected Spanish wines in one of my favs local wine bar. Many of these wines are produced in very small quantities and are rarely found outside Spain.

Walking: Moderate, approximately 4 miles with museum walking.

Driving: About 2 hour total throughout the day.

Meals Included: Breakfast. Wine tasting with tapas.

Toledo
Day 3: Toledo, City of Three Cultures

Today we leave Madrid behind and travel south to one of Spain’s most fascinating cities.

For centuries, Christians, Muslims, and Jews lived together inside Toledo’s medieval walls, creating an extraordinary cultural legacy unlike anywhere else in Europe.

 

With our private local guide, we’ll visit El Greco’s immortal masterpiece The Burial of the Lord of Orgaz, explore the historic Synagogue of El Tránsito, today home to the Sephardic Museum, and admire Toledo’s breathtaking Gothic Cathedral, considered one of Spain’s greatest architectural treasures.

After our included lunch, you’ll have free time to wander the narrow medieval streets, browse artisan workshops, or simply enjoy the atmosphere before we return to Madrid in the afternoon.

Walking: Moderate to strenuous, approximately 4-6 miles over cobblestones and hills.

Driving: Approximately 2 & 1/2 hours round trip.

Meals Included: Breakfast, Lunch.

Segovia
Day 4: Segovia & A Feast Fit for Kings

Crossing the Guadarrama Mountains, we’ll head north toward one of Spain’s most picturesque historic cities.

Segovia welcomes us with its astonishing Roman Aqueduct, one of the finest engineering achievements still standing anywhere in the world after nearly two thousand years.

Our guided walking tour continues through the charming old town before ending at the magnificent Alcázar, the fairy tale fortress that inspired countless legends and, according to many, even Disney’s famous castle.

Today’s highlight continues around the table, where we’ll enjoy one of Castile’s most celebrated culinary traditions: perfectly roasted suckling pig, served at a carefully selected local restaurant and included in your tour.

Once we a re done with lunch, walk back to the bus and back home.

Dinner if you are hungry, on your own.

Walking: Moderate, approximately 3–5 miles with some uphill sections.

Driving: About 3 hours round trip.

Meals Included: Breakfast and traditional Segoviano lunch.

Madrid
Day 5: Madrid of Kings & Emperors

Today we remain in Spain’s vibrant capital to discover how Madrid evolved from a modest town into the heart of one of history’s greatest empires.

Walking through elegant boulevards, lively plazas, and magnificent architecture, you’ll see how the Bourbon dynasty reshaped the city while learning the stories behind many of Madrid’s most iconic landmarks.

We go into the Retiro park, once Royal grounds with a Palace, (not anymore) and we’ll see the great work created in the final extension of the city that made not so long ago, to be declared all that area as part of the UNESCO World Heritage.

The afternoon is yours to enjoy however you wish. Visit another museum, browse the boutiques along Gran Vía, or simply find a terrace and enjoy watching Madrid go about its day.

Sometimes doing very little is one of the best ways to experience Spain.

Walking: Moderate, approximately 5-6 miles.

Driving: None.

Meals Included: Breakfast.

Madrid?
Day 6: Your Day, Your Spain

One of the advantages of our Staycation concept is having the freedom to slow down and enjoy Spain at your own pace.

Today is yours to spend however you like. Sleep in, revisit a favorite neighborhood, enjoy a leisurely lunch, browse Madrid’s shops, or simply find a quiet terrace and watch local life unfold.

Feeling adventurous? Spain boasts Europe’s most extensive high-speed rail network, with Madrid at its very heart. If you’d like, I can help you arrange an independent day trip to cities such as Seville, Granada, Málaga, Valencia, or even Barcelona. Whether you’re looking for another adventure or a relaxing day in Madrid, I’ll be happy to point you in the right direction.

After all, this is your vacation.

Walking: Your choice.
Driving: None. Optional train excursions available.
Meals Included: Breakfast.

Madrid
Day 7: Royal Madrid & The Habsburg Legacy

Today we’ll discover the Royal heart of Spain.

Our morning begins at the magnificent Royal Palace of Madrid, officially the largest Royal Palace in Europe. Although its nearly 3,000 rooms are impossible to see in a single visit, our private guide will introduce us to its most spectacular halls while sharing the stories of the kings and queens who once lived here.

From there we’ll continue on foot through the historic Habsburg Quarter, where Philip II transformed Madrid into the capital of a Global Empire. Along the way we’ll stroll through elegant squares, charming streets, and centuries of fascinating history before heading to our restaurant for lunch.

The remainder of the afternoon and evening is yours to enjoy.

Walking: Moderate, approximately 3–5 miles on city streets with occasional uneven surfaces.
Driving: None.
Meals Included: Breakfast, Lunch.

Salamanca and Ávila
Day 8: Salamanca & Ávila: Two UNESCO Treasures

Today’s full-day excursion introduces you to two of Spain’s most remarkable historic cities.

Our first stop is Salamanca, home to one of Europe’s oldest universities, founded in 1218. Its golden sandstone buildings, lively atmosphere, and magnificent Plaza Mayor have earned it a reputation as one of Spain’s most beautiful cities.

We’ll stroll through its historic center before we enjoy our early lunch.

In the afternoon we continue to Ávila, birthplace of Saint Teresa and famous for its remarkably preserved medieval walls. Walking through its ancient streets feels like stepping back in time. We’ll admire its impressive cathedral from the outside, unique for combining the appearance of both a church and a fortress, Santa Teresa Birthplace depending on availability, before returning comfortably to Madrid.

Walking: Moderate, 6 miles with some uneven streets and gentle hills.
Driving: Approximately 5½–6 hours throughout the day.
Meals Included: Breakfast. Lunch.
Overnight: Madrid.

Madrid
Day 9: Spain Through the Eyes of Its Artists

Today’s full-day excursion introduces you to two of Spain’s most remarkable historic cities.

Our first stop is Salamanca, home to one of Europe’s oldest universities, founded in 1218. Its golden sandstone buildings, lively atmosphere, and magnificent Plaza Mayor have earned it a reputation as one of Spain’s most beautiful cities.

We’ll stroll through its historic center before we enjoy our early lunch.

In the afternoon we continue to Ávila, birthplace of Saint Teresa and famous for its remarkably preserved medieval walls. Walking through its ancient streets feels like stepping back in time. We’ll admire its impressive cathedral from the outside, unique for combining the appearance of both a church and a fortress, Santa Teresa Birthplace depending on availability, before returning comfortably to Madrid.

Walking: Moderate, 6 miles with some uneven streets and gentle hills.
Driving: Approximately 5½–6 hours throughout the day.
Meals Included: Breakfast. Lunch.
Overnight: Madrid.

Madrid
Day 10: Until We Meet Again

After breakfast, our journey together comes to an end.

As you prepare for your onward travels, I hope you’re taking home much more than photographs. My wish is that you’ll leave with unforgettable memories, a deeper understanding of Spain, new friendships, and perhaps a desire to return one day.

Thank you for allowing me to share my country with you. It has truly been my pleasure.

Safe travels…

¡Hasta la vista, amigos!

Walking: None, unless you’re exploring before your departure.
Meals Included: Breakfast.
Tour Ends: Madrid.

Meal included: All Brakfast and 7 meals. Specified in itinerary.

Included

Included & Conditions

What’s Included
  • A small group experience of 8-15 people

  • 9 nights accommodation, including breakfasts

  • Seven group meals, drinks included (reasonable limits)

  • All group sightseeing activity entrances and local guides

  • Transport by private bus between cities

  • All tips for guides, hotels, restaurants, and drivers.

  • Pre-tour travel consultation with Jorge

  • Flexible reservation and cancellation policy

Not Included
  • Airfare & airport transportation

  • Activities not included with the tour

  • Hotel extras and room service

  • Extra wine at group meals

  • Travel insurance

Conditions
  • Tour itinerary and What’s Included details subject to change. Future substitutions will be approximately equal or better in value.

  • This tour requires a minimum of 8 travelers booked by September 1, 2026 to be viable.

FAQs

Everything You Need to Know

We specialize in small group cultural journeys across Spain and other carefully selected destinations. Our trips are designed to combine authentic local experiences, cultural discovery, gastronomy, and meaningful connections with people and places.

Yes. Many of our travelers join individually and appreciate the friendly and welcoming group atmosphere. Our small group format makes it easy to connect with others while still enjoying personal space and flexibility during the trip.

We focus on small group travel to ensure a more personal, relaxed, and authentic experience. Smaller groups allow for better attention, smoother logistics, and a more enjoyable connection between travelers and local culture.

Absolutely. We support our travelers before, during, and after the journey. From travel recommendations and preparation advice to answering questions and helping with logistics, we aim to make the entire experience smooth and stress-free.

Our approach focuses on authenticity, cultural immersion, and meaningful travel experiences rather than rushed sightseeing. We combine iconic locations with hidden gems, local traditions, and a slower pace that allows travelers to truly experience each destination.

With more than 27 years of travel and guiding experience, we offer carefully curated journeys built around personal attention, cultural understanding, and genuine human connection. Our goal is not only to show destinations, but to create memorable experiences that travelers will remember long after the trip ends.

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