We all know how dreadful layovers can be sometimes. However, it doesn't need to be that way for most of your trips. So, we asked around, and our founder, who travels frequently, shared with us one of his recent experiences for escaping the grind during a 38-hour layover.
Day 1 — Arrival in the City of Style
0700 — Touchdown at Milan Malpensa
We landed in Milan Malpensa during the autumn season. We were welcomed by the chill in the air the moment we stepped off the plane. However, the morning light is a sight to behold.
1130 — Lunch at Pescetto: A Hidden Gem for Seafood Lovers
Tucked away in the bustling heart of Milan is Pescetto, a seafood haven adored by locals. Travel tips: In Italy, if there aren't any English menus, it often means you’ve struck culinary gold.
Thankfully, the Meta Ray-Ban smart glasses came to the rescue — live-translating the menu and providing a means to communicate with the locals. While waiting in line (it opens at noon), the restaurant offered complimentary prosecco. This definitely livened up the overall experience.
Fresh seafood is laid out over ice — you pick your favorites and choose how you want them prepared: fried or grilled. We went for both—Crispy calamari, baby anchovies, grilled squid, and Mediterranean prawns, which tasted amazingly awesome.
Pescetto
Alessandro Volta, 9, 20121 Milano MI, Italy
https://maps.app.goo.gl/DCuGw1gEo7K5xQQH7
1400 — Wandering the Streets of Milan
Post-lunch stroll in Milan is the best way to experience the city. The bustling side streets are lined with pop-up art stalls, abstract paintings, portraits, and street art that caught my attention.
Surrounded by well-preserved rustic buildings, Milan is truly a place that hums with timeless charm.
1630 — Duomo Dreams and Street Snacks
The late afternoon walk around the Milan Cathedral (Duomo di Milano) is quite an experience. The marble glowed like something out of a vintage cinebloom photo, and you can hear the tourists clicking through their cameras, capturing this amazing architecture.
I, too, was able to do a nice wrist check with the Cathedral in the background.
Before calling it a day, I stopped by Luini Panzerotti — a Milanese institution famous for its fried pizza puffs—Crispy outside, molten cheese and tomato inside — perfect fuel for a quick dinner on the go.
Panzerotti Luini
Santa Radegonda, 16, 20121 Milano MI, Italy
https://maps.app.goo.gl/wsi9uYWF3MrVUjtc7
1830 — Early Night, Crew Style
Jetlag management 101 for short layovers: stick to your home time zone. By 6:30 p.m. (12:30 a.m. Singapore time), I was tucked in, ready to recharge for the next day.
Day 2 — Espresso-Fueled Exploration
0330 — Midnight Gym Session
Woke up at 3:30 a.m. and started my day with a workout session. It was pretty enjoyable working out in this hour, as I had the gym all to myself. After a solid 90-minute workout, I made tea in my room, ate some food rations I had brought with me, and waited for the daybreak.
0800 — Coffee, the Italian Way
By morning, it was time to join the locals for a caffeine fix. I found a small Bar Atlantic in the quiet San Siro area. Italians don’t “grab coffee”; they savor it — standing shoulder to shoulder at the bar, chatting with the barista.
Bar Atlantic
Novara, 86, 20153 Milano MI, Italy
A double espresso and a pistachio croissant were spot on. And the best part is that coffee prices are pretty consistent across Italy — around €1.20, regardless of whether you’re in a suburb or a café that's located in the heart of the city. It would be impossible to find such pricing consistency in Singapore.
1100 — Into the Heart of Milan
Catching the hotel shuttle, I started the day at Piazza Cordusio, a historic square that bridges the Duomo and Sforzesco Castle. The mix of Neoclassical façades and modern hustle gives it a unique charm.
First stop: Venchi, the legendary chocolate and gelato shop that dates back to 1878. My go-to combo, pistachio and vanilla, is highly recommended. Creamy, nutty, and just the right amount of indulgence to kick off another round of city exploration..
Venchi Cioccolato e Gelato, Milano Via Dante
Dante, 5, 20123 Milano MI, Italy
(Multiple locations in Italy)
1300 — The Sandwich Worth the Hype
Next on the list is All’Antico Vinaio, the sandwich shop that took over the internet and for good reason. Started in Florence and now an Italian street-food icon, it’s been crowned by Saveur magazine as “home of the world’s best sandwiches.”
Rows of freshly baked schiacciata bread, endless cured meats — mortadella with pistachio, porchetta, prosciutto — and cheese that melts just enough to make you weak. Coming from a country where “ham” is just ham, this was a revelation.
All'Antico Vinaio
Orefici, 5, 20123 Milano MI, Italy
(Multiple locations in Italy and Milan)
1430 — A Walk Through History
Milan’s Galleria Vittorio Emanuele II is a masterpiece — Italy’s oldest active shopping arcade and one of its most elegant. Built in the 1800s, it’s an open-air cathedral of fashion, where glass ceilings meet marble floors and history meets haute couture.
Window-shopping here feels like walking through a living art gallery.
1700 — The Final Stroll
Before heading back to the hotel, I made one last espresso stop near the Duomo — this time with a bombolone, Italy’s version of the filled doughnut, a simple yet sweet perfection.
As the sun dipped and the streets filled with evening chatter, I felt that familiar bittersweet tinge of a layover ending too soon.
Reflections: 38 Hours in Milan
Layovers like this remind me why I love my job. In just 38 hours, Milan gave me a short yet fulfilling experience, from the espresso-fueled mornings to grabbing local delicacies around the city. Whether you are there over the weekend or just for a few hours, Milan rewards those who wander and those who savor.
Massive shoutout to Travis for sharing his 38-hour layover experience with all of us. We certainly look forward to hearing more of his stories in the near future.
*All photos are taken by Travis on an iPhone and his Meta Ray-Bans.
