The Calzada de los Frailes is one of the most iconic spots in Valladolid, Yucatán, an ideal destination for lovers of colonial tourism and history. Built in the 16th century by Franciscan friars, this cobbled street originally connected the Spanish town of Valladolid to the indigenous neighborhood of Sisal.

Today, the walkway stretches along 41A Street, between 46 and 54, forming a historic path that leads from the city center to the remarkable Convent of San Bernardino de Siena, whose construction began in 1552. Originally a devotional route for monks, it’s now one of the most photogenic strolls in southeastern Mexico.

Thanks to architectural restoration, the area now boasts vibrant facades, colonial-style lanterns, and charming sidewalks, creating an authentic experience for those seeking cultural tourism in Yucatán. The pastel-colored houses, carved wooden doors, and blooming bougainvillea capture the spirit of a bygone era.

Las Cinco Calles and the Story of a Legendary Mansion

At the end of the Calzada lies the famous intersection called “Las Cinco Calles” (The Five Streets), where five roads converge in a star-like shape. Standing here is a historic mansion that once belonged to Don Marcial Vida, a prominent merchant and revolutionary figure tied to the uprising known as “La Primera Chispa” ("The First Spark"), which preceded Mexico’s national revolution in 1910.

Over the years, this house served as the original location of the Valladolid Preparatory School and later as a handicraft shop. Its patio still features original garden columns and part of the old courtyard, once known by locals as the Plazoleta de las Cinco Calles, a public garden that became part of the city's architectural heritage.

What to See and Do on Calzada de los Frailes

Walking down the Calzada de los Frailes is like stepping into a peaceful, historic world. Along the way, you’ll find art galleries, local cafés, handcrafted design shops, and charming boutique hotels. It’s a must-see for anyone wanting to experience colonial Valladolid in a more intimate setting.

Whether at sunrise, with golden light hitting the facades, or at dusk under warm lanterns, this walk is perfect for photos, relaxation, or beginning a tour toward the majestic Convent of San Bernardino de Siena. Visiting this street isn’t just a tourist activity—it’s an immersion into the cultural heritage of Yucatán.

If you’re planning a trip to southern Mexico, make sure to include Calzada de los Frailes in Valladolid on your itinerary. Its beauty, history, and unique atmosphere make it a true gem of southeastern Mexico tourism.

• Visit their cafes and craft stores
• In the evening enjoy local cuisine in its restaurants
• Stay in some of the hotels that are on the road
• You can enjoy it walking or cycling
• Don't miss the Friars Walk
• Enjoy VideoMapping at the San Bernardino Convent
• Get your camera and/or phone ready as it is one of the most instagrammable places

Photos - Calzada de los Frailes