This 2-day food and cultural escape from Madrid combines visits to three historic cities, a winery, and Don Quixote's windmills. Spend the night in a boutique hotel and see Toledo at its most peaceful after the day trip crowds have left.
Overnight Tour from Madrid to Toledo, Segovia & Avila
Summary Description
Highlights
- Discover Avila and Segovia with expert guides.
- Taste estate wines at a prestigious winery.
- Visit Don Quixote’s iconic windmills.
- Spend the night in Toledo in a 4-star hotel.
- Travel with a dedicated local tour leader.
- Relax with all transport and logistics handled.
- Enjoy a small group experience with max 10 people.
Description
Travel deeper into Spain on this curated 2-day journey to Toledo, Segovia, and Ávila. This is small group experience with a maximum of 10 people. With all logistics seamlessly handled and a dedicated local tour leader guiding you throughout, you can focus on what matters—slowing down and truly experiencing central Spain. From estate wine tastings and a legendary Castilian feast to Don Quixote’s windmills and a peaceful evening in Toledo after the crowds are gone, every moment is designed for deeper discovery. You'll round out your trip with a stay at a boutique hotel inside the historic walled city of Toledo.
Leave Madrid behind and head into the open plains of Castilla-La Mancha. Your first stop: the iconic windmills that inspired Don Quixote. Step inside one and see how these giants really worked—it’s a moment where literature suddenly feels very real.
Next, it’s time for lunch, but not just any lunch. At a family-run winery with prestigious Pago status, you’ll taste estate wines and sit down to a full countryside meal of regional dishes. This is slow travel at its best.
By late afternoon, arrive in Toledo, dramatically perched above the Tagus River. Explore its historic streets and cathedral with your guide before checking into your boutique hotel inside the old town. Then comes the highlight: Toledo at night. The crowds are gone, the streets are quiet, and the city feels entirely different. Wander, dine, and soak it in. This is the side most travelers never see.
Day two starts with breakfast at the hotel. Then, head to Ávila, home to some of Europe’s best-preserved medieval walls. After, it’s on to Segovia, where lunch is an experience in itself. Sit down to the city’s famous cochinillo asado, roast suckling pig cooked in wood-fired ovens until perfectly crisp and tender. You'll have time to explore Segovia’s highlights, including its towering Roman aqueduct and alcazar, which is said to have inspired Cinderella's castle.
By late afternoon, you'll return to Madrid with a deeper understanding of central Spain's gastronomy, history and culture. And the best part: all of the logistics are handled for you.
Included / Excluded
- Roundtrip private transport by minibus
- English-speaking tour leader
- 1 night in a 4-star hotel
- Tour and lunch at winery
- Entry to Don Quixote's windmills
- Cathedral of Toledo ticket
- Synagogue of Toledo ticket
- Lunch in Segovia (roast suckling pig)
- Alcazar of Segovia ticket
- Headsets (when needed)
- Max 10 people
- Dinner on first night (every other meal included)
- Hotel Pick-Up/Drop-Off
- Gratuities
Start / End Locations
Start Location: Pl. del Emperador Carlos V, 9, Centro, 28012 Madrid, Spain
Start Location Notes: Please arrive 15 minutes prior to the start of your tour, your guide will be holding TBD. This tour meets outside Rodilla Cafe (Pl. del Emperador Carlos V, 9, Centro, 28012 Madrid) in Plaza Carlos V near Atocha train station.
Start Location Directions: https://maps.app.goo.gl/cqx7oVVHjzfGKMur7
End Location: Pl. del Emperador Carlos V, 9, Centro, 28012 Madrid, Spain
Important Information
Know Before You Book
- Unfortunately due to the nature of this tour it is not suitable for guests with mobility impairments or with wheelchairs, or strollers.
- This is a walking tour. Guests should be able to walk at a moderate pace without difficulty.
- Due to limited luggage space in the transport, each traveler is allowed a maximum of 1 suitcase and 1 carry-on bag. We recommend storing larger bags in Madrid and traveling with a small overnight bag where possible.
- This tour is adaptable for: Vegetarians, Pescatarians, Gluten free (not celiacs), Dairy free, Non-alcoholic options & Pregnant women, however, please note that you may not have a replacement food option at every stop.
- This tour is not recommended for vegans and those with celiac disease.
- Those with dietary restrictions need to contact us before joining the tour so we can arrange your food, or we may not be able to accommodate you.
- Guests with serious food allergies will need to sign an allergy waiver at the start of the tour.
- Please arrive 15 minutes before your tour start time for check-in. Out of courtesy to other guests, we’re unable to wait for latecomers. No refunds can be provided for late arrivals or no-shows.
- This tour is an overnight tour and will not return until the evening after.
- Those with dietary restrictions or food allergies need to email our Guest Experience team at [email protected] after booking the tour so we can arrange your ingredients.
- Guests with serious food allergies will need to sign an allergy waiver at the start of the tour.
- Due to limited luggage space in the transport, each traveler is allowed a maximum of 1 suitcase and 1 carry-on bag. We recommend storing larger bags in Madrid and traveling with a small overnight bag where possible.
- Tips/gratuities (for your guide) are always appreciated.
- Walks and Devour comply with all local government regulations. Please refer to local government guidelines for the most up to date information.
Cancellation
Cancellation Cutoff: 30 days
Cancellation Notes: Up to 30 days before the beginning of the activity: full refund Less than 30 days before the beginning of the activity or no-show: no refund
Terms and Conditions
Before you travel, please read the "Know Before You Go" section for essential information, requirements, and possible disruptions regarding your tour.
Additional Information
Ticket age ranges:
- Adult (15+)
- Child (2-14)
- Infant (0-1)
About operator:
Walks (takewalks.com, walksofitaly.com) began over a decade ago (2008, to be exact) in Rome, Italy. We quickly became the premier walking tour company in 7 countries - Italy, Spain, France, the UK, Greece, and Portugal. Our US cities include San Francisco, NYC, Boston, Chicago, and New Orleans.
In 2021, we joined The Hornblower Group (cityexperiences.com) expanding our reach and working alongside this powerhouse travel brand.
Our tour products vary but predominantly we #takewalks, exploring the world by foot - we believe, the best way to get into the heart of a city and its incredible people. From introductory strolls to food tours, day trips, cooking classes, and below the surface, in-depth tours, we have our hand in everything a traveler could want. Oh, and we also like to give our clients exclusive access to the biggest attractions in the world...
Despite the big changes in our brand over the years, our focus has remained simple - to relentlessly create tours with the client experience at the forefront and anchored upon the dedicated, intelligent, and above all, passionate local guides who want to share their cities with you.
Our tour products vary but predominantly we #takewalks, exploring the world by foot - we believe, the best way to get into the heart of a city and its incredible people. From introductory strolls to food tours, day trips, cooking classes, and below the surface, in-depth tours, we have our hand in everything a traveler could want. Oh, and we also like to give our clients exclusive access to the biggest attractions in the world...
Despite the big changes in our brand over the years, our focus has remained simple - to relentlessly create tours with the client experience at the forefront and anchored upon the dedicated, intelligent, and above all, passionate local guides who want to share their cities with you.
Basic Information
- Duration: 2 days
- Trip difficulty: Moderate
- Max Group Size: 10
- Category: Day Trips & Excursions
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