Ease into Taipei with dinner at Din Tai Fung (Xinyi A11) in the Xinyi District — it’s the kind of first meal that never lets you down after a flight. If you’re arriving around peak hours, expect a wait unless you have a reservation, but turnover is usually efficient; plan on about NT$500–900 per person and 1–1.5 hours. Order the soup dumplings, a greens dish, and maybe noodles if you’re hungry, then walk it off through the polished Xinyi malls and plaza areas, where the pace is easy and the city feels very modern without being overwhelming.
If you still have energy, head up to Taipei 101 Observatory for the classic first-night skyline. It’s usually open into the evening, and a ticket is typically around NT$600, with the best views coming after sunset when the city lights are fully on. Getting there from Xinyi A11 is simple on foot or by a short MRT ride within the Xinyi area, and the whole visit usually takes about an hour. If you want a more active version of the same skyline view, swap the high-rise deck for a walk to Elephant Mountain Trail instead — it’s about 45–60 minutes round-trip for the main lookout, but the stairs are steep, so bring water and comfortable shoes. The payoff is the most famous Taipei photo angle: Taipei 101 glowing above the city, with the hills behind it.
After the views, keep the night going at Raohe Street Night Market in Songshan District, where the energy changes completely — more local, more chaotic, and better for grazing than for a sit-down meal. It’s easiest to get there by MRT to Songshan Station, then follow the crowd toward the market entrance near Ciyou Temple; budget roughly NT$100–300 for snacks unless you go all in. This is the place for pepper buns, grilled squid, peppery soups, and whatever smells best as you walk past. Finish with Fuzhou Shizu Peanut Cake, a small but very Taipei-style sweet snack near Raohe that’s worth the short stop — crisp, nutty, and warm, usually ready in just a few minutes. If you’re still awake after that, you’ve done Taipei correctly on night one.