full itinerary
B = Breakfast, L = Lunch, D = Dinner, R = Reception
Day
1:
En Route from U.S.
Saturday, August 8, 2026
Day
2:
Arrive in Madrid, Spain | Chinchón
Sunday, August 9, 2026 (R)
Upon arrival at Adolfo Suárez Madrid–Barajas Airport an Orbridge representative will be waiting to assist with your transfer to a hospitality room before continuing to the property in Chinchón.
Take time to unpack and settle in before meeting fellow travel companions for beverages and tapas during a welcome reception.
Day
3:
Chinchón
Monday, August 10, 2026 (B,D)
Following breakfast at hotel set off on a guided city tour of Chinchón, a town rich in history featuring several notable landmarks including the 15th-century Church of Nuestra Señora de la Asunción, which houses a painting by Goya, and the 11th-century Castillo de los Condes, a fortress with a turbulent past.
Enjoy lunch on own with free time to explore Chinchón's narrow, winding streets full of old-world charm.
This evening gather for dinner in a wine cave restaurant, or cueva del vino.
Day
4:
Segovia
Tuesday, August 11, 2026 (B,L)
After breakfast depart for an exciting full day of touring in Segovia, first seeing the city and gardens. The most iconic landmark in Segovia is the Roman Aqueduct, a UNESCO World Heritage Site and one of the best-preserved Roman structures in the world. Built around the 1st century AD, this engineering marvel stretches for more than nine miles and is composed of 167 arches, standing without the use of mortar.
Following a group lunch continue to the Alcázar de Segovia for an inside visit.
Day
5:
Eclipse Day
Wednesday, August 12, 2026 (B,L,D)
This morning after a leisurely breakfast visit an olive oil farm for a tour and tasting followed by lunch at a local restaurant.
The afternoon is reserved for special eclipse activities. Depart for a local park for unobstructed viewing opportunities. Witness this celestial phenomenon where the moon slowly encroaches on the sun. At the moment of totality you can safely remove your solar viewing glasses for a brief period. The sky darkens dramatically, resembling twilight, and the sun’s outer atmosphere becomes visible creating a breathtaking halo of light around the darkened sun. This is the most magical moment of the eclipse, often lasting only a few minutes. Enjoy a tapas dinner before the main event.
Day
6:
Toledo
Thursday, August 13, 2026 (B,L)
Today explore Toledo, a diverse city whose historic center was designated a UNESCO World Heritage site in 1986.
Visit Toledo Cathedral, one of Spain’s most important Gothic structures and a stunning masterpiece of medieval architecture. Completed in the 13th century, it boasts an intricate façade, an ornate interior filled with beautiful chapels and a collection of religious artwork including paintings by El Greco.
After lunch at a local restaurant continue to the Synagogue of Santa María la Blanca. Originally built as a synagogue in the 12th century under Christian rule, this building is an architectural marvel with its mix of Moorish and Jewish design elements.
Enjoy leisure time for independent exploration before returning to Chinchón.
Day
7:
Aranjuez | Alcalá de Henares
Friday, August 14, 2026 (B,L)
Following breakfast set out for Consuegra to see the 12 legendary windmills prominently featured in Don Quixote, written by Miguel de Cervantes—one of the greatest writers in Spanish history.
Continue to Cervantes' birthplace, Alcalá de Henares, for lunch. Afterward visit the Cervantes Birthplace Museum, a beautifully restored 16th-century house displaying exhibits related to the life of Cervantes, the era in which he lived and the influence of his literature on the world.
Day
8:
Cuenca
Saturday, August 15, 2026 (B,R,D)
This morning depart for Cuenca, a UNESCO World Heritage Site.
Cuenca’s most iconic landmark, the Casas Colgadas—or Hanging Houses—appear to defy gravity as they perch dramatically on the edge of a steep cliff overlooking the Huécar Gorge. These medieval houses were originally built in the 14th century, although many have been reconstructed and re-purposed over time.
Take advantage of free time in Old Town's square—a great place to explore the city’s medieval streets and sample wonderful cuisine and a variety of cafés and restaurants.
This evening gather with fellow travel companions for a special farewell reception plus dinner featuring a delicious assortment of tapas.
Day
9:
Chinchón | Madrid | Depart for U.S.
Sunday, August 16, 2026 (B)
After breakfast guests departing during the suggested times take the complimentary transfer to Adolfo Suárez Madrid–Barajas Airport for flights home.
(Itinerary subject to change.)
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