Surrounded by Italy on all sides, this microstate — the third smallest in Europe — has stubbornly clung to its independence over the centuries, even as revolutions and world wars swirled around it. And no, we’re not talking about Vatican City, but another microstate within Italy — the Republic of San Marino, the world’s fifth smallest country, also considered the oldest country in Europe.

With its 61 square kilometers (just over 23 square miles) wedged between the Emilia Romagna and Marche regions of northeastern Italy, San Marino has existed as an organized settlement since at least the beginning of the fourth century and was likely inhabited much earlier. It’s currently home to about 35,000 residents. “San Marino’s picturesque hilltop capital city and surrounding towns have defied all odds to remain independent while being surrounded by Italy (and other foreigners throughout the centuries),” says Gary Portuesi, managing partner of Authentic Explorations and a Travel + Leisure A-List travel advisor. When you cross the border today, a sign proudly proclaims: “Welcome to the ancient land of freedom,” a nod to San Marino’s role in sheltering at least 100,000 refugees, including Jewish people and Italian resistance fighters, during World War II.

Today, travelers come to San Marino not seeking liberty, but for the novelty of visiting a country within a country — a place that feels like Italy, but is somehow different. And while the heavily urbanized approach to San Marino may be marked with uninspiring postwar architecture, things get more interesting once you start to climb Monte Titano, the imposing mountain that dominates the landscape. That’s when historic San Marino comes into view, with its turreted castles, stone-paved streets, Games of Thrones ambiance, and sweeping views of the Adriatic Sea and beaches of Rimini (about 40 minutes away), and on the other side, the rugged wilds of the Apennine Mountains.

Best Hotels & Resorts

Hotel Ristorante Cesare

Set right at the entrance to the picturesque historic district, this family-run hotel strikes a pleasing balance between old and new — rooms have modern fittings, but exposed stone walls are a reminder that you’re in a medieval village. Many rooms have astounding views — even from the bathrooms.

Hotel Titano

Nestled among souvenir shops and restaurants, this hotel offers few surprises — just clean, comfy rooms with just enough personality (and many with great views). Apartments here are a good value for families. Glass-walled La Terrazza Restaurant seems to float above the mountains on the horizon, and there’s also a cozy osteria.

The Regent San Marino

Set in the Borgo Maggiore area below the historic center, this modern hotel offers a rarity in San Marino — a swimming pool and wellness area. It’s a good choice for those seeking modern, unfussy comforts, plus easy access to the cable car, as well as the main roadway back into Italy.

Best Things to Do

Take in the views. 

San Marino’s oldest section, aptly named San Marino, climbs up Monte Titano in dramatic fashion, and several viewpoints offer soaring views of the Apennines to the west and the Adriatic Coast to the east. The Guaita Tower, also called the First Tower, is one of the best places to get the sprawling lay of the land.

Hitch a ride on the cable car.

Forget searching for a legal parking space or unwittingly entering a dreaded ZTL (limited traffic zone). Instead, park below town and take the two-minute cable car ride to the historic center. Soak up those aforementioned views, and exit right into the charming warren of narrow medieval streets.

Climb to the Castle of the Cesta.

The most dramatic of San Marino’s three towers, or castles, sits on one of the highest accessible points on Monte Titano, and looks like it could have inspired Game of Thrones author George R.R. Martin. Your thigh muscles may not thank you, but wandering this jumble of 11th-century structures is worth the climb.

Swing to San Marino Adventures.

If your family needs a break from castles and ramparts, head to this large, well-equipped adventure park in the Aquaviva quarter below the old town. Ropes courses, a zip line, airsoft gun challenges, and a dinosaur maze provide diversions for all ages, and the wooded park offers lots of shade.

Best Shopping

Euromuseumcoins di Stefano Vulcano

Coins and stamps from San Marino are collectors items, and its commemorative euro coins are especially coveted by serious collectors and hobbyists alike. This tiny store is jam-packed with a dizzying array of coins, stamps, medals, and other memorabilia, so it’s a great place to find an authentic souvenir.

Outlet del Profumo

Find designer perfumes at discounted prices here, thanks to San Marino’s low tax rate. They also sell sample sizes, gift sets, San Marino souvenirs and, oddly, tobacco, which is also deeply discounted here.

La Serenissima

Portuesi says San Marino’s “iconic” Torta Tre Monti is worth visiting for: “It’s a traditional Sammarinese cake of multiple layers of wafers that are cemented with hazelnut cream and/or chocolate. The edges of this cake are coated in chocolate fondant.” You’ll find it served all over, but for one to take home, visit this historic bakery in the Domagnano district.

Best Restaurants

L’Angela Veste Piada

The cuisine of neighboring Emilia Romagna wields a heavy influence in San Marino. Witness the piada, the stuffed flatbread that’s somewhat thinner than its cousin, the piadina. This simple joint in Borgo Maggiore is one of the best places in the country to sample a piada, which are typically filled with prosciutto, ham, or salami.

La Terrazza

By just about any standard, settings don’t get much more romantic than that of La Terrazza, the fine dining restaurant of Hotel Titano. Snag a coveted outdoor table on the ramparts or on the outside perimeter of the indoor dining room, and drink in the views, accompanied by deftly prepared Sammarinese and Romagnola cuisine.

Ristorante il Piccolo

If the not-so-distant Adriatic is calling your appetite, this homey seafood restaurant on the approach to San Marino City is a worthy stopover. Sit on the casual patio or in the semi-underground grotto dug into the rock face, and feast on fish-based appetizers, pastas, and mains. Non-fish dishes are available as well.

Best Time to Visit

If it’s high season in Italy, it’s high season in San Marino, too — and that means summers are busy, especially with daytrippers who pour in for a few hours. So for lighter crowds and amenable weather, spring or fall are the best times to visit. But don’t overlook winter, as San Marino’s much emptier streets are even more romantic, especially if you’re treated to a light dusting of snow. From mid-December until Jan. 6 (Epiphany), a Christmas market adds to the atmosphere, and New Year’s Eve sees concerts and a dramatic fireworks show.

If summer is your season of choice, try to plan your visit for the last weekend of July, when a four-day medieval festival takes over the microstate with historical reenactments, crossbow and flag-throwing competitions, and plenty of food, drink, music, and of course, stuff to buy.

How to Get There

Most visitors to San Marino get there by car, as a side or day trip from Rimini, Ravenna, Bologna, or elsewhere in the Emilia Romagna region. There are parking areas within and adjacent to the historic center, including a large lot at Borgo Maggiore, next to the cable car. There’s also regular bus service from Rimini; tickets are €6 one-way for the 50-minute ride to the center.

The closest large airports are Bologna’s Guglielmo Marconi Airport (BLQ) and Florence’s Amerigo Vespucci Airport (FLR).

San Marino is divided into nine castles (castelli), or districts. Visitors will spend the majority of their time in Città di San Marino, the historic center, or nearby Borgo Maggiore.

If you choose to stay in San Marino, you can easily visit Rimini and its beaches in about 20 minutes; Ravenna, famed for its Byzantine mosaics, in about 90 minutes; and the historic Marche city of Urbino in just over an hour.

How to Get Around

Getting to San Marino usually involves a car, but getting around San Marino involves walking, and often, climbing up many series of steps and inclines. The cable car connects Borog Maggiore to the historic center but from there, visitors must go on foot to reach the towers and fortresses.