Toledo, Segovia & Ávila: An Overnight Journey from Madrid

New tour

48 h
10 max

Overview

What's Included

  • Savor estate wines and homemade regional dishes at a family-owned bodega — one of just 13 wineries in Spain to hold a prestigious Pago designation. Enough for a full countryside lunch.

  • Feast on Segovia's legendary cochinillo asado (roast suckling pig), prepared in wood-fired ovens and served in the traditional Castilian style — crispy, tender, and unforgettable.

  • Sleep inside Toledo's ancient walls at a boutique 4-star hotel and experience the city after the day-trip crowds vanish. (This is the part most visitors never get to see.)

  • Step inside a 16th-century La Mancha windmill, the kind that made Don Quixote charge on horseback, and learn the surprisingly real story behind Spain's most famous novel.

  • Explore three UNESCO-worthy cities — Toledo, Ávila, and Segovia — with expert guides, private transport, and zero logistics to worry about.

  • Walk through Toledo Cathedral, Segovia's Roman aqueduct, and Ávila's medieval fortress walls.

Toledo, Segovia & Ávila Overnight Tour from Madrid Itinerary

Dietary Accommodations

from $1207
Free Cancellation
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Know before you book

What is a Devour Overnight?
It's our answer to the rushed day trip. Overnights take some of our favorite journeys and extend them — adding an overnight stay, an evening to explore on your own, and the time to actually experience a place instead of just seeing it. Think of it as the depth and magic that only happens when you slow down.
Is this a day trip from Madrid?
Nope — and that's the whole point. This is a 2-day, 1-night small-group journey. Staying overnight in Toledo means you get to experience the city after the day-trip crowds disappear. (Trust us, it's a completely different place at night.)
How many people are on this tour?
A maximum of 10 guests. We keep it small so the pace stays relaxed, your guide can actually get to know you, and it feels more like traveling with friends than following a flag.
How much food and drink is included?
Plenty! You’ll enjoy 10+ traditional tapas and 5 drinks (including vermouth, cava, and regional wines) across three family-run stops. It’s a full dinner, Barcelona-style. Come hungry.
What makes the winery visit special?
Bodegas Martúe holds a Pago designation, a title reserved for just 13 wineries in Spain that produce estate wines of exceptional quality from their own land. You'll start with your first tasting paired with a tapa in the barrel room, then move out to the garden for a leisurely lunch of homemade dishes paired with more of the estate's wines. It's the kind of long afternoon that feels like a very good life choice.
What kind of hotel will I stay in?
A carefully selected boutique 4-star hotel inside Toledo's historic center. It's comfortable, charming, and ideally located for evening wandering. We wouldn't put you somewhere we wouldn't want to stay ourselves.
Is this tour suitable for luxury travelers?
Absolutely. Small group, private transport, boutique hotel, expert guides, and a pace that never feels rushed. This is for travelers who value quality, depth, and meaningful access over checking boxes.
Will I have free time?
Yes, especially in Toledo, where the evening is entirely yours. Guided visits throughout the trip are balanced with independent time to explore, shop, eat, or just sit on a terrace and soak it in.
Are dietary needs accommodated?
We’ll do our best. There are usually vegetarian options, but vegan, gluten-free, or allergy-specific substitutions may be limited due to the traditional nature of the tapas. Let us know in advance and we’ll do what we can.
How physically demanding is this tour?
You'll be walking on cobblestone streets with some hills, especially in Toledo and Segovia, but the pace is relaxed and there's plenty of downtime between stops. Comfortable shoes are strongly recommended. (Leave the cute-but-painful ones at the hotel.)
What's included in the price?
A private 2.5-hour tour with an expert family guide, all food and drink tastings (churros, hot chocolate, tapas, coffee, and drinks for parents), entry to the Metropol Parasol, and all activities.
Is entry to Toledo Cathedral included?
Yes. Your guided tour includes entry to Toledo Cathedral, one of the most important Gothic churches in Spain, and one of those places where you'll stand still for a moment and just look up.
Is this tour kid-friendly?
This tour is not recommended for children under 15 years of age due to busy, crowded bars. We love hosting families and we recommend you look at our other daytime offerings for more family-friendly experiences.

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