ahoyne9Bologna, San Marino & Milan: Honeymoon on Points 🇮🇹🇸🇲
October 5-8, 2025
Pizza mission complete. Time for Bolognese.
After wrapping up our time in Naples, we boarded the train at Napoli Centrale bound for Bologna, about four hours north. Bologna had been calling me for a while, not just for the food (though that was absolutely the main draw), but because it also put us within striking distance of San Marino, a country I had been wanting to tick off for years. Country number 42.
🚆 Getting There: Napoli to Bologna
Pro tip before anything else: create an account with Italo Trains before you book. They send out promotional emails with discounted fares that are worth waiting for. I booked first class tickets for $70 per person against a standard price of $125. Four hours in first class for that price is a no-brainer.
Bologna’s central station, Bologna Centrale, is one of the busiest rail hubs in Italy and sits right on the main Milan-Florence-Naples high speed line, making it an easy base for day trips across the region.
From the station we took the bus to the hotel. We were staying a bit outside the city center at the IHG Holiday Inn Bologna Fiera, which I booked for 55,000 IHG points for three nights. It was not the most central location, but it was the only property I could cover on points and the bus connections into town were straightforward enough.
🏛️ October 6: Bologna City Centre
After a low-key first evening to recover from the travel day, we headed into the city on October 6th. Bologna is one of Italy’s most underrated cities. It has one of the oldest universities in the world, the University of Bologna, founded in 1088, and the city’s medieval towers and miles of porticoes (covered walkways) are unlike anywhere else in Italy. The porticoes stretch for about 38 kilometres throughout the city and are a UNESCO World Heritage Site.
We started at Piazza Maggiore, the main square and beating heart of Bologna. The square has been the civic centre of the city since the 13th century and is surrounded by some of its most important buildings.
From there we walked into the Basilica di San Petronio, one of the largest churches in the world by volume. Construction began in 1390 and it was never actually finished, which you can see clearly on the facade where the marble cladding just stops partway up. Inside there is a famous sundial on the floor, installed in 1655, which was used to verify the Gregorian calendar reform.
We also passed by the Due Torri, Bologna’s two famous medieval towers that have become the symbol of the city. The taller of the two, Torre degli Asinelli, stands at 97 metres and leans slightly. You can climb the 498 steps for panoramic views over the city, though we gave that a miss. Worth doing if you have the energy.
What we didn’t get to but worth adding to your list:
- The Archiginnasio, the original main building of the University of Bologna, with its stunning Anatomical Theatre where medical dissections were once performed for audiences
- Mercato di Mezzo, a covered food market in the heart of the old city, great for grazing
- Santuario di Madonna di San Luca, a hilltop basilica connected to the city by the world’s longest portico, about 3.8 kilometres of covered walkway
For lunch we stopped at 051 Osteria right on Piazza Maggiore and had traditional Bolognese ragù and lasagna. Bologna is the birthplace of both dishes, though it is worth noting that what the rest of the world calls “spaghetti bolognese” does not actually exist here. The locals serve the ragù with tagliatelle, always. The lasagna was exceptional.
🏔️ October 7: Day Trip to San Marino 🇸🇲
This was the day I had been looking forward to. San Marino is one of the world’s smallest countries and also one of the oldest republics, founded in 301 AD according to tradition. It sits entirely within Italy on top of Mount Titano, covers just 61 square kilometres, and has a population of around 34,000 people. It is also one of only three countries in the world completely surrounded by a single other country, alongside Lesotho (South Africa) and Vatican City.
Getting there from Bologna:
I had pre-booked Trenitalia tickets for $29 to get to Rimini, from where you take a bus up to San Marino. Here is where I made a rookie mistake: I accidentally booked us on the wrong train. It was still Trenitalia but it was not the express, so it stopped at more stations and took longer. The ticket inspector clearly clocked that we had taken the slow train on a fast ticket but honestly just waved it through. I think he took one look at us and figured we were just tourists who had made a mess of it. He was not wrong.
The silver lining was that the extra travel time actually gave us a comfortable buffer in Rimini to grab a coffee before catching the bus, so it worked out fine.
The bus to San Marino:
The bus is operated by Bonelli Bus and picks up outside a hotel in Rimini city centre. The ride takes about an hour up the mountain and the views are genuinely stunning. We did not buy tickets in advance online and managed to get on fine, but I would not recommend leaving it to chance. Seating on the bus is first come first serve, so if the bus fills up before you board you are waiting for the next one. Buy your ticket inside the shop as recommended and get there with time to spare.
At the top:
San Marino’s historic centre sits at the peak of Mount Titano and is a UNESCO World Heritage Site. The three towers along the ridge, Guaita, Cesta, and Montale, are the iconic image of the country and you can walk between them on a scenic footpath. We wandered around, took photos with the views over the Italian countryside, and had lunch with a view that was hard to beat.
A few things worth knowing about San Marino:
- There are no border controls entering San Marino since Italy and San Marino share a customs union, but you can get your passport stamped at the tourist office for a small fee, absolutely worth doing
- San Marino has its own euro coins which are highly collectible and much rarer than standard Italian issue
- The country has no airport and no railway, so the bus from Rimini is the main way in
After coming back down to Rimini we had some time to kill before the train but nothing was open for dinner at that hour, a very Italian problem. We grabbed coffee in the city centre and then took the correct train back to Bologna.
Rimini itself is worth a quick mention. It is a major Adriatic beach resort but it also has a genuinely impressive historic centre, including the Tempio Malatestiano, a 15th century Renaissance church, and the Arch of Augustus, the oldest surviving Roman triumphal arch in Italy, built in 27 BC. If you have time between the bus and the train it is worth a short walk around.
✈️ October 8: Bologna to Milan, Then Off to Barcelona
The next morning we headed to Milan, staying near the airport since the following day we were flying to Barcelona for one night before heading home.
The point of the Barcelona stop was to fly American Airlines Business Class back to Chicago, booked with Alaska Airlines miles for 55,000 miles per person plus $42 in taxes and fees. A great redemption. With Global Entry we flew through customs and made it to the Delta check-in counter with 10 minutes to spare. We managed to grab standby seats on a flight four hours earlier than our original booking, got home ahead of schedule and paid nothing extra for it. The perfect way to close out a honeymoon.
We also squeezed in a Singapore Airlines Business Class flight from Milan to Barcelona, booked with Air Canada Aeroplan miles transferred from a partner for just 15,000 points plus around $55 in taxes and fees. Not the most efficient miles redemption in terms of pure value, but I wanted to fly Singapore Business Class again and for that distance and that price it was worth every point.
In Barcelona we stayed for free using a World of Hyatt award night, which was a perfect way to close out the trip.
🍝 Final Thoughts & Total Trip Cost
Bologna delivered exactly what it promised. The food was genuinely outstanding and the city itself has a warmth and authenticity that Naples, for all its history, could not quite match for us. San Marino was a genuine highlight, a micro-country with a big personality and views that stay with you.
Total points used for the entire 10-day honeymoon (both of us, all flights and hotels): ~340,000 points
Total out of pocket for fees, transport, food and activities: just under $2,000
Not bad for ten days across four countries.
📌 Bologna & San Marino Cost Breakdown
- 🚆 Naples to Bologna (Italo, first class): $70/person
- 🏨 Holiday Inn Bologna Fiera (3 nights): 55,000 IHG points
- 🚆 Bologna to Rimini (Trenitalia): $29
- 🚌 Bonelli Bus Rimini to San Marino (return): buy at the bus stop, ~€15 return
- ✈️ Milan to Barcelona (Singapore Airlines Business): 15,000 Aeroplan points + ~$55 taxes
- ✈️ Barcelona to Chicago (American Airlines Business): 55,000 Alaska miles + $42 taxes
- 🏨 Barcelona (Hyatt): 1 award night
Cheers!