Segovia, Avila & Toledo with Winery visit in 2 days

Madrid Multi-day Tours

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Overview

Live a two-day journey through the cultural heart of central Spain. From the ancient Roman aqueducts of Segovia to the storied medieval walls of Ávila, and the timeless beauty of Toledo, this premium experience blends guided discovery, local flavors, and the rich heritage of three iconic cities. Spend the evening discovering Toledo at your own pace, an enchanting city that truly comes alive by night. Travel in comfort, enjoy curated experiences with expert guides, and end your journey with an exclusive wine tasting in a picturesque vineyard near Toledo.

Itinerary

Day 1. Madrid – Segovia – Ávila – Toledo

· Segovia – Roman aqueduct, Alcázar, historic city streets

· Ávila – Guided tour of the walled medieval city (UNESCO site)

· Toledo – Arrival and visit to the Toledo Cathedral (Spanish Gothic treasure)

· Overnight in Toledo – Free evening to explore

Day 2. Toledo – Winery Experience – Madrid

· Morning free in Toledo – Optional e-bike ride, Mirador del Valle, cafés, plazas

· Lunch and wine experience in Castilla-La Mancha

· Return to Madrid in the late afternoon

Day 1 – Madrid – Segovia – Ávila – Toledo

Your experience begins early in the morning in Madrid. After meeting at Plaza de San Miguel, you’ll head to Segovia, one of Spain’s architectural gems. Marvel at the iconic Roman aqueduct, explore the fairytale Alcázar, and wander through its winding streets filled with history.

Next, continue to Ávila—known for its impressively preserved medieval walls. Enjoy a guided visit through this UNESCO World Heritage city.

In the afternoon, head to Toledo—the final stop of the day and a city where cultures intertwine. Upon arrival, delve into the historic center and step inside its greatest treasure: the Toledo Cathedral, a masterpiece of Spanish Gothic architecture.

As the sun begins to set, the atmosphere of Toledo transforms. Cobblestone streets glow under warm lights, and centuries-old buildings take on a new magic. The evening is yours to enjoy at your own pace. Wander through quiet alleys, discover intimate plazas, and feel the stillness of a city rich in soul and silence. Then, let your senses awaken over dinner — explore charming local restaurants and savor traditional Spanish dishes that tell the story of Toledo with every bite.

You’ll spend the night in a handpicked boutique hotel in the heart of the city—chosen not only for its comfort and charm, but also for its unique setting, allowing you to live Toledo not just as a visitor, but as part of its living history.

Day 2 – Toledo – Winery Experience – Madrid

Wake up in the heart of Toledo, where the early light casts a golden glow on ancient stone streets. After breakfast at your boutique hotel, the day begins at your own pace so you can experience the city in your own way. Whether you’re looking for culture, calm, or a bit of adventure, Toledo has something for everyone. Enjoy panoramic views from the Mirador del Valle, relax in a quiet café, or rent an e-bike to explore the hills around the old town. This is your time to slow down, connect with the city’s soul, and make the morning your own.

In the early afternoon, you’ll meet your guide once again and leave the city behind as you journey into the quiet landscapes of Castilla-La Mancha. Rolling hills and rows of vines lead you to a charming boutique winery, where tradition and terroir come together.

Here, you’ll enjoy a guided walk through the vineyard and cellar, learning about the region’s unique winemaking heritage. The experience concludes with a tasting of three local wines—an invitation to slow down, savor the moment, and toast to two unforgettable days. Afterward, return to Madrid feeling relaxed and inspired, with the vineyards in your memory and the city just on the horizon.

Available: Daily
Duration: 2 Days
Departure: 8:00 am (CHECK IN TIME: 7.45 am)
Languages: English & Spanish
Child Policy: Minimum age 2 years old: Free charge / 4-8 years old: special discount / 9+ years old: adult price
Meeting Point: Calle Bailen 25, Madrid

Highlights

Discover three of Spain’s cultural jewels: Segovia, Ávila and Toledo, with expert guides
Overnight stay in a handpicked boutique hotel in the heart of Toledo
Free time to discover Toledo at your own pace, with both an evening and a morning to explore the city in your own way
Premium vineyard visit with guided tasting of 3 wines
Travel in comfort with round-trip transportation for maximum comfort

Included

Transportation in premium vehicle (with pickup options)
Guided visits in Segovia, Ávila and Toledo (incl. Cathedral entry)
Traditional lunch in Ávila (Day 1)
1-night accommodation in Toledo (boutique or 4-star hotel with breakfast)
Vineyard and winery visit with tasting of 3 wines (Day 2)
Local expert guides throughout
Travel insurance and customer assistance

Not Included

Meals and drinks not specified
City taxes, personal expenses, optional monument entries
Dinner in Toledo (free night to explore at leisure)

Conditions

Please, be at the check in point 15’ minutes before departure time.
This product is subject to cancellation or rescheduling based on inclement weather.
There is a minimum of people required to operate the tour. In the event that this minimum is not met, customers will be offered an alternative date, another tour of equal or superior value, or a full refund.
There is a minimum number of people required to operate on languages that are not English Spanish. if this minimum is not reached, the tour will be offered in English.
Tour may be affected due to special circumstances.
If the cancellation is made by The CLIENT more than 7 days of the Event: 15% (Confirmation Payment) is non-refundable. Additionally, any costs incurred for ticket and entrance management will not be refundable. If there are Space Reservations and External Providers, their cancellation terms will apply.
If the cancellation is made by The CLIENT within 7 Days of the Event: 50% is non-refundable. If there are Space Reservations and External Providers, their cancellation terms will apply.