Ask most people what a racing trip is about and they'll tell you the racing. They're half right. The racing is the reason you book the flights, but it's everything around it that you're still talking about months later: the long lunch that turned into dinner, the bar that only fits four people, the plate of veal you'll be chasing for the rest of your life.
That's exactly what our weekend in Milan turned out to be. Three nights, a racecourse ten minutes from the front door, a Group 2 with the most famous horse in British jump racing in it, and a city that seems to have been built around eating and drinking well. Here's how we did it, what it cost, and everything we'd tell a mate who fancied doing the same.
Planning a racing trip to Milan
Flights and parking
We flew British Airways from Heathrow Terminal 5 into Milan Linate for £177 each, return. We went out on the Saturday evening and came back on the Tuesday lunchtime, which is the sweet spot for a racing weekend: you don't burn a day's holiday getting there, and you get a full Monday to do something other than racing.
We used the Heathrow long-stay park and ride, which came to £99 for the whole trip. Split across a car-load, that's hard to argue with.
Where we stayed: an Airbnb in San Siro
We booked an Airbnb in the San Siro area, and it was the best decision of the trip. It worked out at £130 each for three nights between four people, about £43 a night per person. For that we got a spacious flat with two bedrooms plus a sofa bed.
The real selling point was location. The racecourse was ten minutes away, and one of the best restaurants we ate at was a two-minute walk from the door. If the racing is the reason you're going, staying in San Siro makes complete sense.
For breakfast, you won't struggle. There are plenty of options around Zone 7, the part of Milan San Siro sits in, including some cracking bakeries.
Getting around Milan
We used Uber for most journeys and found it fair value, generally £10 to £25 a trip. Split between a group, that's often the easiest option after a long day, and far less hassle than working out the trams.
Raceday at San Siro: the Gran Premio del Jockey Club
We timed the trip around Sunday 25 October 2026 and the Gran Premio del Jockey Club at the Ippodromo SNAI San Siro. It's a Group 2 over 2,400 metres on turf, worth around €500,000, and one of the biggest days in the Italian Flat calendar.
This year's renewal had a British angle you couldn't miss: Constitution Hill. Yes, that one. Nicky Henderson's former Champion Hurdler, now reinvented on the Flat, was making his first Flat start on turf, with Rossa Ryan riding him for the first time. He ran a creditable race to finish fifth behind the German-trained Stingray.
Getting there and getting in
We took an Uber from the Airbnb, about ten minutes. The racecourse sits right next to the San Siro football stadium, home of Inter and AC Milan, a few miles north-west of the city centre.
Entry was €10. Compare that with a big Saturday at a British track and it's an absolute steal.
What to wear
Whatever you like. There's no dress code to speak of, so leave the suit at home unless you fancy however we thought as we were in Milan it would be rude not to go suited and booted in the double breasted 2 piece suits from House Of Cavani.
Where we ate in Milan
La Pesa Trattoria dal 1902
If you only book one dinner in Milan, make it this one. La Pesa is a proper, traditional trattoria serving Milanese specialities, the kind of place where the menu hasn't needed to chase trends because it's been getting the basics right for over a century.
It was fully booked inside when we turned up, so we took a table outside with heaters at either end. It was absolutely fine, but if you want to guarantee a seat indoors, book ahead.
We started with the classic saffron risotto alla milanese. Simple, but cooked to perfection and loaded with flavour. For mains, Matty went for pappardelle with wild boar ragù, and I ordered my favourite meal of all time: veal Milanese, still on the bone, served with baked potatoes. Ordering your all-time favourite dish in its home city is a risk. It didn't disappoint.
A strong menu, a great wine list and top-class service, for roughly €60 a head. Two minutes from our front door didn't hurt either.
An evening in Navigli: where we drank in Milan
Navigli is Milan's canal district, and the stretch along the Naviglio Grande is where you want to be for a drink. Both of our favourite bars of the weekend sit at the same address on it, Ripa di Porta Ticinese 43.
Back Door 43: the smallest bar in the world
This was the highlight of the weekend away from the track, and we'd give it a straight 10/10. Back Door 43 bills itself as the smallest bar in the world, and with room for just four people, we're not going to argue. The name comes from the fact it sits round the back of MAG.
You book a time slot online, and booking is strongly advisable. Ours lasted about an hour. Once you're in, there are chairs lined up in front of the bar and it's just you, your group and the bartender. You can order from the menu, or tell the bartender what you like and let them make something for you. Do the second one. I had a mezcal-based sour, then he freestyled a completely different mezcal cocktail for me.
The whiskey collection is serious, running to well over 200 bottles, and the music and ambience are spot on. Drinks start from €15. For the practical-minded: there's a toilet inside, and you can still smoke in there if you want to. It feels personal in a way a normal bar never can.
MAG Café
MAG is Back Door 43's big sister, run by the same team, right next door on the canal. It's one of the bars credited with kicking off Milan's craft cocktail scene, with an old apothecary feel and an antique back bar that came out of an Argentine pharmacy.
We sat outside by the water, and I had a mezcal margarita. If you can't get a slot at Back Door 43, MAG is a very good consolation prize. Their Negroni del Marinaio is the one the locals rate.
A day trip to Lake Como
If you've got a spare day either side of the racing, get yourself to Lake Como. The train cost us €5 each way and took around 45 minutes.
There are two main routes. From Milano Centrale, trains run to Como San Giovanni, about a 15-minute walk downhill to the lake. From Milano Cadorna, Trenord trains run to Como Nord Lago, right on the lakefront, in about an hour. Either way, it might be the best-value fiver you spend all weekend.
Lunch at Wow Pasta
First stop for Jimma was Wow Pasta, and it lived up to the name. Egg tagliatelle in a butter and Parmesan sauce, with guanciale added on top, followed by a really good tiramisu and a glass of red. All of that came to €40.50.
An afternoon at Platea
Then came one of our favourite parts of the trip. Platea sits right on the lake, facing the sun, with proper tablecloths and napkins and waiters in bow ties. You'd expect the prices to match the setting. They don't. It's reasonably priced and nothing like the tourist trap you might expect for the location.
The others worked through spaghetti vongole, a calzone, another pasta dish and some crispy prawns, washed down with plenty of Aperol spritz, limoncello spritz, Hugo spritz and white wine. Six or seven drinks each, at least. Later on we ordered two margherita pizzas, and they were fantastic.
We sat there from around 2pm to 7:30pm and it came to €92.50 each. For an entire afternoon of eating and drinking with a lake view, that's very good value.
Sunday morning on Via Belfiore
Jimma headed to Via Belfiore on the Sunday morning to buy some shoes, and found a lot more than that. It's a long street lined with men's shops, cafés and bakeries, and there's a market selling fresh fruit and veg, cured meats, honey and clothes, with a fishmonger, a butcher and a hot food counter. He came back with a chunk of Parmigiano Reggiano, which is about the most Italian souvenir there is.
