Travel Past 50 Tour: Classic Castile and León

Castile and León, Spain

Nov 3 - 15, 2024
Group size: 10 - 12
Travel Past 50 Tour: Classic Castile and León
Castile and León, Spain

Nov 3 - 15, 2024
Group size: 10 - 12

About this trip

Join Travel Past 50 Tours visiting the classic region of Spain: Castile and León. We'll start in Madrid and then work our way across the central plains (where the rain mainly stays) to the picturesque cities of Segovia, Ávila, Zamora, León, and Burgos. 

We'll see iconic cathedrals and castles, experience Spain's famous cuisine and wines, and dip into the history of kings and saints. 

Don't miss out on the best of Spanish food and wine with a Spanish cooking class and a tasting tour at a Ribera del Duero winery. Plus, enjoy a special visit to the tiny village of Pedraza (Segovia), where Kris and Tom lived for a month, way back when. 

Itinerary Highlights

This TP50 Tour of Spain's largest autonomous region delivers us to some of the country's most iconic cities and sites, yet not the most visited. The essence of Spain's legends and lore come to life here.


Highlights of this 13-day, 12 night itinerary include:

* Plenty of time to get to know Madrid and its great museums

* A personal tapas tour in Madrid

* A visit to El Escorial and Spain's Royal Monastery

* Four UNESCO World Heritage Sites

* The stunning Roman Aqueduct in Segovia

* Optional hot air balloon and horseback ride over the Castilian countryside

* The medieval city of Ávila

* Great art and architecture – from Romanesque castles to a Gaudi-designed home and contemporary art

* Wine tour in Ribera del Duero, one of the most important wine regions in the world

Why our tours are unique

* Accompanied by Kris and Tom, with benefit of their life-long travel experience

* Small group tours (maximum 12 guests)

* Custom-created itineraries combining cultural experiences with local cuisine and active tour options

* Sufficient unscheduled time

* Additional local expert guides as appropriate

* Local secrets not usually on tourist itineraries

* Comfortable travel, luxury touches, and affordable rates

* Kris and Tom’s helpful travel tips, shared with the group via  personal communications in advance of the trip: getting ready to travel,  what to pack, recommended reading, and how to enjoy to the max

In all, we've spent more than four years of our lives in Spain, and we both speak fluent Spanish. We've led two previous tours to Spain, in Fall 2022 and Spring 2023.

Our goal is to introduce our tour guests to new destinations and new insights, offering everyone the opportunity to enjoy independent travel and free time along with the pleasure of meeting new people in our select small group. Join us!


See what our previous guests say about Travel Past 50 Tours on our TP50 Tour Page.

Accommodation style

We will stay in comfortable and convenient 4-star hotels. All rooms have a private bathroom. There are a maximum of eight single rooms available.

Physical demands: Moderate

Activity level for this tour is light to moderate. We'll be doing a good amount of walking in the cities we'll be visiting, and in some cases there will be two to three hours of slow walking and standing in the attractions. To be comfortable on this tour, you should be able to walk for a mile or more – or at least half an hour – without problem. Also, be aware that often the walking will be up and down hills. Cobblestone streets and stairs are not uncommon. Don't worry though. We'll make frequent stops for refreshments.

The tour itself is not very strenuous, but please note that it can involve the following: somewhat long days, walking tours in the cities  on uneven pavement, being outside in potentially cold temperatures, a couple of long journeys, early morning wake-ups, and other similar scenarios.

Important travel notes

The specifics of the tour itinerary are subject to change. It's unlikely, though, that there will be any substantive changes. 


Important: do not make any travel reservations that cannot be cancelled or changed until we confirm that we have met the minimum number of travelers and that the trip is a “go.”

Most North American flights to Spain depart late afternoon or evening. So plan to depart a day earlier than your arrival in Madrid.


If you'd like to extend your time in Madrid before or after the tour, let us know and we'd be happy to recommend hotels and attractions or day trips from the city.


We use Allianz Travel's annual policy, but you can find their single trip travel insurance plans here. Note, you must have travel insurance that covers medical expenses for this tour. It doesn't have to be Allianz.

Payment and other terms

A $1500 deposit per person due before July 6, 2024 (or June 6, 2024 for Early Bird purchasers). Refundable for 10 days, should your plans change for any reason. After that, the deposit becomes non-refundable.


The balance payment is due 65 days before the tour start date (August 30, 2024.)


Cancellations between 60 and 89 days prior to the tour start date will receive a 50 percent refund of the balance amount; cancellations within 59 days of the tour start date will be non-refundable.

Here's all the fine print. Please note these terms and conditions may vary depending on the specific tour destinations and timing.

For more general information about Travel Past 50 Tours, including up-to-date COVID policies, visit our introductory Tour Page.

What’s included

  • Private tour
    Private tour experience throughout
  • Small group
    Maximum group size of 12
  • All accommodations
    12 nights at 4-star hotels
  • All transport in Spain
    Trains and private vans where needed
  • All activities
    All included activities and entrance fees mentioned
  • Local experts
    English speaking local guides
  • All breakfasts and more
    Breakfast every day and other meals as listed in the itinerary (beverages not included)
  • All airport transfers
    We will pick you up on arrival and deliver you to the airport on departure day
  • Flights
    Flights to and from Spain not included
  • Some individual meals
    Meals and activities not mentioned are not included
  • Travel insurance
    Travel insurance including medical coverage is mandatory
  • Gratuities
    Gratuities for guides, drivers, hotel staff, etc. are not included
  • Passport fees
    Passport or visa fees not included

Available Packages

Early Bird Double Occupancy
Available until June 6, 202412 left
Early Bird Single Occupancy
Available until June 6, 20248 left
Double occupancy
Available until July 6, 202412 left
Deposit: $1,500
Single occupancy
Available until July 6, 20248 left
Deposit: $1,500


Day 1
Madrid (Arrival day)


  • Upon arrival at the Madrid Airport or train station, you'll be  picked up by our private driver and taken to our hotel in the center of  Madrid. Once everyone has arrived, we'll have an evening orientation and  welcome dinner featuring traditional Madrid dishes
  • Included meals: Dinner

Your Organizer

Travel Past 50 LLC
Travel Past 50 offers custom built small group tours, featuring culture and cuisine, for travelers over the age of 50.