St. Augustine America’s Oldest City Leads the Way as One of the World’s Most Enchanting Historic Towns: Know More About it

Published on September 19, 2025

St. Augustine, Florida, known as the Oldest City in the United States, is a must-visit destination for history enthusiasts, earning its spot as one of the world’s most charming historic districts. According to a study conducted by Tourlane, an online travel planning specialist, St. Augustine is among the top contenders globally for its remarkable blend of history, affordability, and pedestrian-friendly layout. In the study, 65 cities from five different regions—North America, Europe, Latin America, Asia, and the Middle East and North Africa—were analyzed based on their historic appeal, walkability, and social media popularity.

Founded in 1565 by Spanish explorers, St. Augustine stands out as the oldest continuously inhabited European-founded city in the United States. Its charm lies in the preserved colonial Spanish architecture, cobblestone streets, and the presence of significant landmarks such as the Castillo de San Marcos, the fortification that once protected the city from invaders. This combination of history and accessibility makes St. Augustine a perfect location for travelers seeking an authentic and immersive historic experience.

Tourlane’s extensive analysis considered factors such as the cost of guided tours, the city’s historical age, and its walkability. St. Augustine scored exceptionally well in the walkability department, making it easy for visitors to explore its many cultural and historic sites on foot. The city provides a seamless blend of old-world charm with modern amenities, creating an inviting atmosphere for both history buffs and casual travelers alike.

St. Augustine: A Walk Through History

Founded: 1565
Guided Tour: Approx. $35
Walkability: 100/100

As the oldest city in the U.S., St. Augustine’s Old Town remains remarkably preserved. The historic district is home to buildings dating back to the Spanish colonial period, making it a fascinating place for anyone interested in the early days of American history. The city’s oldest structure, the Castillo de San Marcos, was constructed in 1672 and stands as one of the best-preserved military structures in the U.S. Today, visitors can tour this imposing fortress, learning about its role in protecting the city from pirate attacks and other threats over the centuries.

St. Augustine’s historic district is made for exploration on foot. The city’s small size and pedestrian-friendly streets make it ideal for leisurely strolls. Walking tours, often priced around $35, allow tourists to gain deeper insights into the city’s rich history. From its colonial-era architecture to its charming courtyards and alleys, St. Augustine offers an intimate glimpse into the past. Visitors can enjoy the sea breeze along the waterfront and explore the many museums, boutiques, and cafes that line the historic streets.

According to Roman Karin, Head of Travel Experience at Tourlane, what makes St. Augustine stand out among the world’s historic districts is its accessibility. Unlike many other cities, where tourists are often forced to navigate heavy traffic, St. Augustine offers an easy and relaxed exploration experience on foot. The blend of natural beauty, history, and a welcoming atmosphere makes it a must-see stop on any Florida road trip.

The Top Historic Old Towns Around the World

While St. Augustine is one of the top old towns in the U.S., it competes with many other fascinating historic destinations around the globe. Tourlane’s study also identified the most charming historic centers in Latin America, Europe, Asia, and the Middle East and North Africa, highlighting cities that offer unique historical experiences.

Latin America’s Best: Cartagena, Colombia

First Settlement: Approx. 10th Century
Guided Tour: Approx. $16
Walkability: 99/100

Cartagena’s Old Town, known as “Ciudad Amurallada” or “The Walled City,” is a UNESCO World Heritage Site and one of Latin America’s most striking historic districts. Surrounded by massive stone walls, Cartagena offers a vibrant, picturesque setting with narrow streets, colonial-era buildings painted in vibrant colors, and lively public squares. The city is particularly famous for its beautiful bougainvillea-covered balconies, which add an extra layer of charm to the old town’s architecture.

Cartagena’s Old Town is perfect for walking. Visitors can stroll through narrow alleyways, visit the famous Plaza Santo Domingo, or stop at the impressive San Felipe de Barajas Castle. The city’s affordability also makes it an attractive destination, with guided tours available for about $16.

Europe’s Most Charming Old Town: Krakow, Poland

First Settlement: Approx. 7th Century
Guided Tour: Approx. $14
Walkability: 90/100

Krakow’s Old Town, with roots going back to the 7th century, is one of Europe’s best-preserved historic centers. A UNESCO World Heritage Site, the city is known for its beautiful medieval architecture and well-maintained historical landmarks. Key highlights include the Main Market Square, St. Mary’s Basilica, and Wawel Castle, all of which are easily accessible by foot. Visitors can take a leisurely stroll through the square, admire the gothic architecture, and learn about Krakow’s rich history on a guided tour.

The city’s Old Town is compact and walkable, with guided tours priced around $14, offering great value for history enthusiasts looking to explore centuries of culture. Krakow’s old town is not just a place of historical interest but also a lively cultural hub with restaurants, shops, and street performers, making it one of Europe’s most vibrant destinations.

Asia’s Hidden Gem: Hoi An, Vietnam

First Settlement: Approx. 16th Century
Guided Tour: Approx. $2
Walkability: 100/100

Hoi An, a coastal town in central Vietnam, is one of Asia’s most charming and well-preserved historic towns. Its Old Town is a UNESCO World Heritage Site and features a delightful mix of traditional merchant houses, Chinese temples, and iconic architecture from the 16th century. The town’s narrow streets and lantern-lit alleys are perfect for a peaceful stroll, offering a serene atmosphere that contrasts with the busy pace of modern-day life.

Hoi An has earned its spot as one of Asia’s most charming old towns, with its affordable guided tours (approx. $2) and a walkability score of 100/100. Visitors can explore the historic district at their own pace, savoring the local street food, shopping for handicrafts, or visiting the famous Japanese Bridge.

Middle East and North Africa’s Top Historic District: Sousse, Tunisia

First Settlement: Approx. 800 BC
Guided Tour: Approx. $35
Walkability: 99/100

Sousse, Tunisia, boasts one of the oldest and most impressive medinas in North Africa. With its origins dating back over 3,000 years, the Medina of Sousse is a UNESCO World Heritage Site that continues to preserve its ancient charm. Its narrow, winding streets are lined with spice markets, carpet sellers, and traditional workshops, making it a fascinating place to explore.

Sousse’s Old Town offers a unique blend of history and modern life. The city is famous for its beautiful white walls and its impressive fortress, the Ribat of Sousse. Guided tours cost approximately $35, offering a chance to delve into the city’s rich cultural and historical heritage.

Why Walkable Historic Districts Matter

The concept of walkable old towns is vital to preserving these historical districts for future generations. Not only do pedestrian-friendly cities encourage exploration, but they also help protect the integrity of the historical sites. St. Augustine’s walkability, for example, allows visitors to experience history in a personal, up-close way, while minimizing environmental impact. Additionally, the growth of social media and the desire for shareable travel experiences has highlighted the appeal of these destinations, further promoting their global popularity.

The best historic districts, like those in St. Augustine, Krakow, and Hoi An, are not just visually stunning; they offer immersive cultural experiences that can only be truly appreciated by walking through their streets. These towns are living museums where history comes to life, offering a unique blend of past and present for curious travelers.

From St. Augustine to Hoi An, the world’s most charming historic districts offer an incredible opportunity to step into the past while enjoying modern-day comforts. Whether it’s the colonial streets of St. Augustine, the ancient alleys of Cartagena, or the vibrant squares of Krakow, these destinations allow travelers to experience history in a way that is personal, immersive, and unforgettable. These walkable old towns remain a testament to the enduring power of history and culture, welcoming visitors to explore and appreciate their remarkable stories.