Itinerary - Madrid, Segovia and Toledo Express: Discover Spain’s Heritage

Arrival in Madrid, Spain’s electric capital, where vibrant culture, grand architecture, and buzzing nightlife await. After checking in at the hotel, we’ll meet our Travel Coordinator and fellow travelers for a brief welcome session.

We'll start the trip toasting with the Welcome Drink, followed by an optional tapas crawl, a the perfect way to ease into Spanish life, one bite and glass of wine at a time. Afterward, we might head into the lively streets of Malasaña, one of Madrid’s most iconic neighborhoods known for its alternative bars and retro energy. a holdover from the city’s countercultural movement in the ‘70s and ‘80s.

This morning we head to Toledo, a UNESCO World Heritage Site where Christian, Muslim, and Jewish cultures have left a lasting mark. Surrounded by ancient walls, this hilltop city is a maze of cobbled streets and stunning viewpoints. We explore iconic landmarks, from the Gothic cathedral to El Greco’s masterpieces, and uncover stories from centuries past. A guided tour will help us dive deeper into Toledo’s layered history.

In the late afternoon, we return to Madrid for some well-earned rest… but not for too long! The evening brings us to Plaza Mayor for more amazing food, followed by a walk through Lavapiés and La Latina, two of the city’s most lively neighborhoods. Tapas, music, and good company close out a memorable day.

We start our morning by diving into the art and soul of Madrid with a visit to the Reina Sofía Museum, home to masterpieces like Picasso’s Guernica, a haunting symbol of modern art. For those eager for more, the Prado Museum awaits just nearby, a sanctuary of classic European art.

Not an art buff? No problem, explore the quirky stalls of El Rastro, one of the largest and most colorful street markets in Europe (open on Sundays), or browse the boutiques around Chueca and Gran Vía.

Later in the day, we regroup to admire Madrid’s regal side. the Royal Palace, Almudena Cathedral, and a guided walk through Plaza Mayor. We’ll take our time, stopping for photos, churros, or even a cheeky vermouth. The day wraps up with free time to relax or join an optional flamenco show or dinner with the group.

Today we take one last day trip, and trust us, it's worth it. We're off to Segovia, a city that looks like it was plucked straight out of a fairy tale. Known for its dramatic Alcázar castle, Gothic cathedral, and one of the best-preserved Roman aqueducts in the world, Segovia will have you staring up in awe more than once.

After arriving, we'll start with the Aqueduct of Segovia, an architectural marvel built without mortar that still stands strong after 2,000 years. Then, we'll wind our way through the historic center, stopping at quaint squares and charming corners until we reach the Segovia Cathedral, perched elegantly above the city.

In the afternoon, back to Madrid for the last night!

As our unforgettable journey comes to a close, we gather for one final breakfast together. It’s time to reflect on the incredible moments we’ve shared, from cultural discoveries to spontaneous fun. With hearts full of memories, we say our goodbyes to Spain.