We spent a weekend in San Marino in May 2026, meeting up with our friend Meghan before attending our friends Laura and Tom’s wedding in Lucca, Tuscany. While it was a tad out of the way, visiting San Marino was beautiful, interesting, and generally a fun time. This post details what we did over a weekend in San Marino.

SAN MARINO QUICK FACTS

Where it is: A landlocked country of its own inside Italy, wedged between Emilia Romagna and the Marche, a 30 minute drive inland from Rimini and the Adriatic coast.

How to get there: Train to Rimini, then a taxi or a shuttle bus up the mountain. Our Frecciarossa from Milano Centrale to Rimini took just over two hours, and the taxi took another 30 minutes.

How long to stay: Two nights was plenty. One night covers the towers and the views, and after our wine tasting Dan spent a good part of the second afternoon asleep.

Currency: The euro, used under a monetary agreement with the EU even though San Marino is not an EU member.

Passport: Bring it and expect nobody to ask. There is no routine border check in either direction.

Language: Italian, with a Romagnol dialect spoken alongside it.

Where to stay: Città, the highest of the nine districts, where the towers, the restaurants and the balconies are.

When we went: Late May 2026, which happened to land on the same weekend as the Borgo diVino in Tour wine festival.

SAN MARINO

Before getting into our itinerary, for those unfamiliar, San Marino is its own country landlocked inside of Italy. Situated between the Marche and Emilia Romagna, San Marino feels a lot like Italy, but also a lot not like Italy. While it’s a separate country that, fun fact, is not part of the European Union, there is no routine passport check and one can generally move freely between Italy and San Marino. San Marino is not in the Schengen Area either, so random police checks are possible, but nobody looked at our passports in either direction.

For those planning to visit, San Marino uses the euro under a monetary agreement with the EU, has Italian as its official language (you will hear a Romagnol dialect too), and observes many of the same rules and customs as Italy, at least from a general tourist perspective. It does, however, have many of its own things, including delicious wine, shopping without VAT, and stunning views of both mountains and the Adriatic Sea. San Marino has been in a customs union with the EU since 1991 but sits outside the EU VAT system, charging a single stage import tax called the monofase instead. That is why the leather shops in Città advertise “tax free” prices. From personal experience, San Marino does have good leather prices.

HOW TO GET TO SAN MARINO

San Marino has no airport and no train station, so every route runs through Rimini. We took the Frecciarossa direct from Milano Centrale to Rimini in just over two hours, then hired a taxi for the last 30 minutes up the mountain. A shuttle bus runs the same stretch from Rimini railway station in about 50 minutes (on the bus, not waiting for it, etc.) for 7.00 euro one way. We paid for the taxi to save time, though the bus would have cost a small fraction of what we spent.

Rimini also makes San Marino easy to pair with the rest of the Adriatic coast, including Senigallia down the coast in the Marche, or with a fast 24 hours in Milan at the start of the trip.

OUR WEEKEND ITINERARY IN SAN MARINO

For those stealing our trip, here’s exactly what we did in San Marino, day by day.

Day 1: Taking the train from Milan, and the BEST dinner in San Marino.

San Marino was our first stop on this trip. As such, we took the Frecciarossa train directly from Milano Centrale to Rimini, which took just over two hours. Once in Rimini, we hired a local taxi, San Marino Taxi, to pick us up and drive us to San Marino, which took another 30 minutes. There is also a popular public bus, but we opted for the more expensive taxi to save time. The views driving up to San Marino were truly stunning.

We were dropped right in front of our hotel, Hotel Cesare, located in the Città district of San Marino. Of nine districts, Città is the highest point in the country, and also the most touristy. We were able to check in right away, and we stayed in the hotel’s sole Deluxe room, which truly did offer stunning views of San Marino and the surrounding hills.

After checking in and getting settled, it was just about sunset. As such, our first order of business was for an Aperitivo on one of Hotel Cesare’s many balconies. We met our friend Meghan here! I ordered an Aperol Spritz, and watched the sun set over San Marino. The views in San Marino are truly unbeatable. If you are only here for a few hours, find yourself a balcony and have a drink or coffee (there are many places to do this in Città).

After aperitivo, we walked about one block to Ghetto da Ottavio for dinner. I found this restaurant on Facebook after doing a very deep dive on decent San Marino restaurants, many of which are apparently not great. It turned out to be delicious, by far one of the best meals of this entire trip in San Marino and Italy (and that’s saying a lot!). I have a full guide to where to eat in Città di San Marino, but if you are in San Marino, you must eat at Ghetto da Ottavio.

We called it a night after dinner, as we were exhausted from traveling all day. That being said, there did not seem to be much going on in San Marino after the dinner hours.

Day 2: San Marino Wine Tasting, A San Marino Wine Festival, and a bad dinner with great views

We began our first official morning in San Marino with breakfast at Hotel Cesare. The breakfast was included, served buffet style, and it was giving old school Italian hotel. While not the best hotel breakfast I have had in Italy, it was serviceable.

A taxi from San Marino Taxi picked us up promptly at 10:15 AM to drive to Cantina di San Marino for what I thought was a visit to an actual winery in San Marino.  Nope!  Instead, it is a wine tasting at Cantina di San Marino, which is a consortium of grape growers in San Marino.  The Cantina makes San Marino wine out of the grapes it receives from various San Marino growers. Very interesting! We sampled four local wines here, as well as paired the wine with local bread, meat, and cheese. We taxied back to Città after our tasting, arriving around midday. This was actually quite interesting, and a bit off the beaten path in San Marino! We were the only tourists there, and we saw several locals come and fill large containers of wine for home consumption.

Due to the wine tasting, Dan was in need of a nap. Meghan and I explored the town a bit while he rested, including doing some tax free leather shopping (very good prices, such as a purse for 60 euro and a belt for 30 euro right in town) and taking the cableway down to San Marino’s Borgo Maggiore area and back up. The cableway was a fun little activity that only took about 15 minutes roundtrip.

We returned to Hotel Cesare to pick up Dan before continuing with the day, which included exploring San Marino’s Towers, eating a traditional San Marino piadina, and having aperitivo overlooking the surrounding area.

This evening, as luck would have it, there was a wine festival in San Marino at the exact time we were in town. The wine festival is a traveling one called Borgo diVino in Tour, which apparently goes all around Italy. We had already planned to visit, but our guides at Cantina di San Marino told us to be sure to book the complimentary tasting in Cava dei Balestrieri, which we did earlier in the afternoon when exploring town. We had no idea what this was or what we were in store for. But hey, it was free!

As such, around 6:00 PM, we checked in and were seated at the most stunning tasting table in the center of Cava dei Balestrieri. There were only 24 seats. We sampled four San Marino wines, and learned a lot about them (in Italian) from the wine makers. This experience was fabulous and truly, entirely free. We could not believe we lucked into this. It was a magical evening in San Marino.

We sampled various wines at the Borgo diVino wine festival after our formal wine tasting. There were wines from all over Italy, including the Marche (where we were visiting next), Tuscany, Piedmont and Umbria (our favorite Italian wines!), among other regions.

Post-wine tasting, it was time for dinner, on which I was sadly a bit iffy. I had made a reservation at La Terrazza Ristorante based on the great reviews it received online. However, I was getting the feeling that the reviews were all done by tourists and highlight the views and not the food and I, unfortunately, was not wrong. I go into the whole meal in where to eat, and where NOT to eat, in Città, but the views were indeed great and the food was, as my not super picky husband described it, inedible. The prices were also higher than almost everywhere else in San Marino. We fished up shortly after sunset.

The one highlight of dinner, or rather directly after, was walking out through Piazza della Libertà, which is particularly beautiful at night when it is (largely) devoid of tourists. La Terrazza Ristorante is located just next to Piazza della Libertà.

Day 3: Breakfast, more views, and departure for Lucca!

We set our alarms early on our final morning, as we wanted to enjoy every last minute of Hotel Cesare’s amazing views. While it was a bit chilly, we had breakfast outdoors solely for the views.

San Marino Taxi picked us up exactly as scheduled and drove us to the Rimini train station, where we boarded a local train to Bologna, before transferring to Florence and eventually Lucca.

HOW LONG TO STAY IN SAN MARINO

Two nights and one full day gave us a full day in Città, a morning at Cantina di San Marino, and enough time to sit on a balcony and do nothing, which is most of the point. One full day is enough to walk the towers, ride the cableway, eat a piadina and have an aperitivo before sunset. If you come up from Rimini only for the afternoon you will see the country, but you will miss the part we liked best, which is Città in the evening once the cableway has stopped running and the piazza has emptied out. I don’t think I would stay more than a 3 nights in San Marino unless you have a specific reason for staying longer.

IS SAN MARINO WORTH VISITING?

For us yes, though not for the reasons we expected. We came solely just to “see it”, as we have traveled a lot around Italy and never been to San Marino. What we did not expect was the food, at least at Ghetto da Ottavio, and the wine. Ghetto da Ottavio was by far one of the best meals of our entire trip through Italy, and the complimentary tasting in Cava dei Balestrieri during Borgo diVino was far better than many tastings we have paid for. The towers are fine, the views are unbeatable, and the restaurant with the best online reviews served us the worst food we ate in Italy. Come with moderate expectations, and you will have a great time. 

STEAL OUR WEEKEND IN SAN MARINO

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Hotel Cesare: Salita Alla Rocca, 7, 47890 Città di San Marino, San Marino.

Ghetto da Ottavio: Contrada Santa Croce, 29, 47890 Città di San Marino, San Marino. Open Wednesday through Monday 12:00 PM to 11:00 PM. Reservations recommended. I made a reservation via Facebook Messenger.

Cantina di San Marino: Strada Serrabolino, 89, 47893 Valdragone, San Marino. Open Monday to Friday 8:30 AM to 12:30 PM and 2:30 PM to 6:30 PM and Saturday 8:30 AM to 12:30 PM. Closed Sunday. Email for a tasting.

San Marino Cableway: The cableway runs every 15 minutes from 7:45 AM, with the closing time varying by season. The cost is 4.00 euro one way, 7.00 euro round trip, and 10.00 euro for a day pass. It also closes for maintenance twice a year, which in 2026 meant February 23 to March 20 and October 21 to 23.

La Terrazza Ristorante: Contrada del Collegio, 31, 47890 Città di San Marino, San Marino. Open daily 12:00 PM to 2:30 PM and 7:00 PM to 10:00 PM. Reservations recommended.

San Marino Taxi: This is the taxi company that I personally used, referred to me by Hotel Cesare. I contacted San Marino Taxi via email. The owner was responsive via email and WhatsApp. Email: https://www.sanmarinosite.com/en/how-to-reach/ropeway/. WhatsApp: +39 331 628 2025.

Borgo diVino in Tour: The traveling wine festival was in San Marino from May 22 to 24, 2026. The dates and the host towns change every year, so check the schedule before planning a trip around it.