This 10-day trip through the historic, cultural, and culinary highlights of Madrid, Toledo, Segovia, and Avila begins and ends in Madrid.
Popular itinerary for senior travelers in Spain:
Day 1: Madrid
Steeped in history yet bursting with modern energy, Madrid, Spain’s capital, offers an unforgettable blend of tradition and contemporary flair. Every traveler will find something to love in this vibrant city, from majestic palaces and historic churches to rich art museums, lush parks, and a culinary scene that comes alive at night.
After checking into your hotel, take a stroll towards Puerta del Sol and Plaza Mayor, the heart of Madrid. Plaza Mayor, the city’s main square since the 17th century, has hosted markets, bullfights, and coronations. Today, it serves as the venue for various events throughout the year, including concerts, art exhibitions, and holiday markets. The rectangular square is known for its symmetrical layout and uniform buildings, with the most prominent feature being the Casa de la Panadería (Bakery House), adorned with beautiful frescoes depicting scenes from Madrid’s history. The square is surrounded by narrow cobblestone streets, charming shops, and cozy cafés, making it a perfect starting point for exploring the city’s cultural treasures.
For lunch, visit the Mercado de San Miguel, a former covered market turned food court with many stalls offering a variety of dishes. Sample small tapas portions of seafood, chicken, jamón, and enjoy a refreshing glass of sangria.
Next, walk to Puerta del Sol. “Gate of the Sun,” as the name translates, was derived from the eastern city gate that once stood here in the 15th century. Over time, Puerta del Sol became a central point for important events. Spaniards gather here to ring in the new year and watch the clock tower’s famous countdown. In the middle of the square, take a picture with the bronze statue of El Oso y el Madroño (The Bear and the Strawberry Tree), representing the city’s coat of arms.
Enjoy dinner at one of the many restaurants around these two squares before exploring the vibrant nightlife or catching a flamenco performance.
Spend the night in Madrid.
Day 2: Madrid, continued
Today is dedicated to exploring the world-renowned Prado Museum, built as a royal museum in the late 18th century. Marvel at masterpieces by Spanish giants like Goya, El Greco, and Morales, alongside works from Flemish and Italian masters. Take a leisurely break at the museum’s coffee shop before exploring the nearby Retiro Park, a serene oasis with beautifully landscaped gardens and a peaceful lake where there are row boats for rent. For art enthusiasts, the Velázquez Palace and Glass Palace, both Reina Sofia Museum exhibition spaces, offer additional cultural exploration.
Spend the night in Madrid.
Day 3: Madrid, continued
Delve into the grandeur of Madrid’s Royal Palace, a testament to the Bourbon dynasty’s power. Built in the 19th century on the site of a former fortress, the palace boasts a breathtaking Baroque façade adorned with intricate sculptures, columns, and balconies. Inside, opulent rooms and halls await, showcasing lavish furnishings, priceless artwork, and rich frescoes. Explore a selection of the over 3,000 rooms, including the Throne Room, Hall of Mirrors, and Royal Chapel, each offering a glimpse into Spanish royal life. The palace houses impressive collections of art, furniture, tapestries, and porcelain, providing a window into Spain’s rich heritage. While no longer the royal family’s primary residence, the palace remains a venue for state ceremonies and events.
Continue your historical exploration at the Almudena Cathedral, a relatively new cathedral constructed in the 19th and 20th centuries. This architectural marvel blends Neo-Gothic, Neo-Romanesque, and Neo-Classical styles. For a touch of tranquility, stroll through the picturesque Campo del Moro gardens behind the Royal Palace.
Cap off your day with a delicious dinner in the Barrio de La Latina. This vibrant neighborhood, once the city’s Jewish quarter in the Middle Ages, retains its historic charm and boasts bustling tapas bars and local restaurants. Savor the atmosphere and delectable Spanish cuisine before retiring for the night in Madrid.
Day 4: Toledo
After breakfast, collect your rental car and embark on a journey south towards Toledo. Once a Roman fortified settlement, Toledo rose to prominence as the religious and administrative center of Hispania (Spain) under Visigothic rule. This fascinating city then witnessed nearly 300 years of Islamic influence, followed by a period where the Jewish population flourished, earning it the nickname “The Jerusalem of Spain.”
Toledo’s beauty unfolds as you approach. Nestled amidst rolling hills, the town is encircled on three sides by the Tagus River and adorned with impressive fortification walls. Before entering the historic center, take a moment to appreciate the panoramic views from several key points – the Mirador Alcántara, the Mirador del Valle, and the Mirador del Puente de San Martin II.
Toledo’s ancient, medieval character is evident in its narrow, mostly pedestrian-friendly streets. Park your car outside the town walls and enter through the Puerta del Cambrón gateway. Your exploration begins with the Monasterio de San Juan de Los Reyes, a stunning Gothic monastery built by the Catholic Kings to commemorate a victory. Admire the Mudéjar elements (Islamic architectural influences) and the symbolic chains adorning the main facade.
Next, immerse yourself in the heart of the old Jewish quarter, the Juderia. Look for the ceramic tiles with Hebrew inscriptions marking this historic area. Witness the fascinating blending of religions through repurposed buildings, like the Sinagoga de Santa María La Blanca, a former Jewish synagogue later converted into a church. Continue your journey through Jewish history at the Synagogue of El Tránsito. This exquisitely decorated synagogue, boasting inscriptions in Hebrew and Arabic, now houses the Museum of Sephardic Life in Spain.
Art enthusiasts will be captivated by the Museo del Greco, dedicated to the renowned Greek painter who made Toledo his home. Explore works by El Greco alongside Spanish furniture and ceramics.
Standing tall at the heart of the old town is the majestic Santa Iglesia Catedral Primada De Toledo. Built in the late 13th century, this Gothic cathedral boasts exquisite art pieces and a breathtaking Mudéjar-style cloister.
As you approach Toledo’s main square, the Plaza de Zocodover, encounter the El Alcazar De Toledo. This imposing fortress served as a strategic point since Roman times, all the way to the Spanish Civil War. The Plaza de Zocodover, once an entry point and bustling market, now offers a vibrant atmosphere with souvenir shops and cafes.
End your exploration with a delectable local dinner. Savor specialties like carcamusas (tender pork with flavorful tomato sauce and peas) or cuchifrito (deep-fried pork pieces with garlic). Don’t miss the chance to try the famous Toledo marzipan for dessert.
Spend the night in Toledo.
Day 5: Consuegra
Not far from Toledo lies a landscape reminiscent of Don Quixote’s adventures: Consuegra, home to the iconic Molinos de Viento windmills. These majestic white giants, once used for grinding flour, stand proudly as testaments to Spanish ingenuity. Immerse yourself in the world of Cervantes’ masterpiece as you explore these well-preserved windmills.
Your next stop is Ciudad Real, a town steeped in royal history. Founded by a royal charter in the 14th century, the city boasts a rich tapestry waiting to be unraveled. Visit the Puerta de Toledo, the last remaining gate of the Alcázar, a powerful fortress that once guarded Ciudad Real. Next, step inside the Iglesia de San Pedro, the final resting place of Fernando Alonso de Coca, confessor and chaplain to the Catholic Monarchs. At Museo del Quixote delve deeper into the world of Don Quixote with the museum’s fascinating interactive exhibits dedicated to Cervantes’ literary masterpiece.
Savor a delicious lunch break featuring local specialties before returning to Toledo to spend the night.
Day 6: Ávila
Bid farewell to Toledo and embark on a journey to Ávila, a captivating city nestled within the Castilla y León region. A UNESCO World Heritage Site, Ávila is renowned for its awe-inspiring medieval walls. Dating back to the 11th century, these remarkably well-preserved fortifications are some of the finest in Europe.
Scale the accessible sections of the walls and enjoy the breathtaking panoramas of the city and its surrounding landscapes. Explore the various gates and turrets, with the imposing Puerta del Alcázar and Puerta de San Vicente serving as noteworthy entry points.
Immerse yourself in Ávila’s religious heritage at the magnificent Ávila Cathedral. This grand Gothic masterpiece, seamlessly integrated into the city walls, is a must-see. Construction began in the 12th century, making it one of the earliest Gothic cathedrals in Spain. Step inside and marvel at the exquisite stained-glass windows, the striking altarpiece, and the impressive collection of religious art.
Next, head to the Convent of Saint Teresa, an important pilgrimage site. Standing proudly on the birthplace of Saint Teresa of Ávila, a prominent mystic and writer of the Counter-Reformation, this convent offers a glimpse into her life and works through its captivating museum.
Wander through Ávila’s ancient streets, soaking in the city’s unique atmosphere. Conclude the day with a delectable dinner featuring local specialties at one of the charming restaurants.
Spend the night in Ávila.
Day 7: Ávila, continued
Start the day with a visit to The Basilica of San Vicente. This 12th-century Romanesque masterpiece is renowned for its captivating architecture and intricate carvings. Immerse yourself in history as you explore the church built on the site where Saints Vincent, Sabina, and Cristeta were martyred.
Next, head to the Plaza del Mercado Grande, or the Big Market Square. This central square boasts a fascinating juxtaposition of architectural treasures. On one side, admire the Romanesque Church of San Pedro, one of Ávila’s oldest churches dating back to the early 12th century. On the opposite side, soak in panoramic views of the city walls, with the imposing Puerta del Alcázar standing tall in the center.
Wander through the Plaza’s charming arcades, remnants of the bustling artisan shops that once lined the square. Today, these refurbished arcades house a variety of inviting shops and boutiques.
A short stroll away, discover Plaza Mercado Chico, the heart of the town. Here, you’ll find the Town Hall, built during the reign of the Catholic Monarchs. This structure replaced the traditional meeting place at the doors of the San Juan Church, also integrated into the square. The current building dates back to the mid-19th century.
Spend the night in Avila.
Day 8: Salamanca
Your next stop is the captivating city of Salamanca. Nestled near the Portuguese border, Salamanca exudes a rich academic and historical ambiance as the birthplace of Spain’s oldest university, founded in 1218.
The heart of the old town is the stunning Plaza Mayor, an 18th-century Baroque masterpiece. This vibrant square invites you to leisurely stroll, people-watch, and savor the local atmosphere while enjoying a coffee or meal at one of the charming cafes.
Embark on a journey through history as you explore the city’s architectural treasures. The Casa de las Conchas, a 16th-century mansion adorned with intricate shell motifs, now houses a library and exhibition space. Marvel at its stunning interior architecture. Nearby, the Clerecía Church, a former Jesuit college, offers panoramic city views from its bell towers.
Salamanca boasts a unique distinction: two cathedrals. The grand New Cathedral, a 15th-century Gothic masterpiece, stands as one of Spain’s last Gothic structures. Its smaller predecessor, the Old Cathedral, offers a glimpse into the city’s earlier architectural styles.
Immerse yourself in the local culture by indulging in a delicious dinner featuring regional specialties and a glass of renowned Ribera del Duero wine.
Spend the night in Salamanca.
Day 9: Salamanca and Segovia
Begin your day by exploring the renowned University of Salamanca. Discover the university’s rich history as you wander through the old building, keeping an eye out for the famous “frog” sculpture hidden within the façade. Continue your exploration at the Escuelas Menores patio, admiring the captivating “Cielo de Salamanca” painting by Fernando Gallego.
Step outside the old town walls and stroll across the Roman bridge over the Tormes River, a remarkable relic from the Roman era.
In the afternoon, head to Segovia, a city brimming with history and charm, and enjoy dinner in one of the city’s restaurants.
Spend the night in Segovia.
Day 10: Segovia
Segovia, a city brimming with historic treasures, is perhaps most famous for its iconic Roman aqueduct. This awe-inspiring feat of engineering, dating back to the 1st century AD, still stands remarkably well-preserved, its most impressive section dominating the Plaza del Azoguejo. Imagine over 20,400 granite blocks meticulously assembled without mortar – a true testament to Roman ingenuity!
Wander through the narrow streets of the Judería, the Jewish Quarter, where historic buildings whisper tales of the city’s vibrant Jewish history from the medieval period. Explore the Jewish Cemetery and the former synagogue, now a museum dedicated to preserving this rich heritage.
Next, prepare to be captivated by the cathedral, aptly nicknamed the “Lady of Cathedrals” for its exquisite Gothic architecture. Its beauty and intricate details are a sight to behold.
Segovia’s crowning jewel might just be the Alcázar, a majestic castle perched on a rocky cliff. Originally built as a fortress, it has transformed throughout history, serving as a royal palace, state prison, and even a military academy. This fairytale-like structure boasts a unique ship-like silhouette and boasts richly decorated rooms, including the Throne Room, Hall of the Kings, and the Torre de Juan II, offering breathtaking panoramic views. After a day of exploration, unwind and savor a delicious local dinner.
Spend the night in Segovia.
Day 11: Return to Madrid
Conclude your Spanish adventure back in the vibrant capital city of Madrid. Indulge in shopping, explore world-class museums, and savor the city’s renowned culinary scene.
