It is Taiwan's oldest city and its former capital during the Qing Dynasty.
Tainan, a city of 1.9 million and about 260km from Taipei, is often overlooked by tourists, but its laidback charm and gentle pace are very appealing.
Wander down its old streets to discover thriving hipster enclaves, eat your way around its night markets or grab a late-night tipple at an award-winning bar - the place abounds in old-world elegance and contemporary experiences.
As we set foot on Xinmei Street, my travel companion exclaims: "Looks and feels like Haji Lane, but less commercial."
The bohemian vibe here is reminiscent of the Singaporean hipster enclave. The rows of shophouses with peeling paint on century-old exposed brick walls are Instagram-worthy, as are the narrow alleyways.
Cafes, art galleries, gift stores, ice cream parlours and homestay inns (minsu) stand alongside an old clinic with its original signboard intact and Jiu Lai Fa Bakery, which makes traditional Tainan confections such as peanut candy.
A shop called Han Long has been selling incense, joss sticks and other religious offerings since 1850.
Xinmei Street, formerly known as Rice Street and a major thoroughfare for wholesalers of things from rice to toys in the 1800s, is undergoing a chic makeover.
But unlike its more popular cousin on the other side - Shennong Street - Xinmei has retained its soul and old buildings even as younger tenants move in. As we wander down the street, many shop owners are happy to chat and show us around.
Where: Xinmei Street, West Central District
From the outside, the place looks like an abandoned garden. But I am intrigued by bags of seeds hanging over my head as I walk through a wooden gate.There are also bottles of all sizes filled with, yes, seeds.
In the Thousand Fields Seed Museum - about a 15-minute walk from Tainan train station - there are about 500 species of seeds. They include seeds of the Cannonball Tree and the eye-catching Abrus precatorius, also called the Love Pea. However, when ingested, these bright red seeds can cause nausea, liver failure and even death.
Believed to be Taiwan's only seed museum, it showcases the private collection of seed enthusiast Chiang Kun-chiang, built up over 30 years.
Taiwan is a "global seed bank", he believes. "You just need to take some soil, water it and something will grow," says Mr Chiang, 67.
Where: Thousand Fields Seed Museum, 29-1, Lane 451, Dongfeng Road
Admission: NT$100 (S$4.60) a person
Info: Call +886-6236-0035 to book its thrice-daily, 45-minute guided tours on weekends. Go to www.facebook.com/QianQiZhongZiGuan
In its heyday, the Hayashi Department Store was the place to see and be seen. Set up in 1932, it is Tainan's oldest department store and housed Taiwan's first mechanical lift.
Today, the five-storey building, classified as a Municipal Heritage Site, is still the pride and joy of Tainan and offers items such as ceramics, cards and handicraft from local designers.
Head to the rooftop to see what is believed to be the only Shinto shrine atop a shopping centre.
You will also find bullet holes from machine guns from World War II.
Where: Hayashi Department Store, No. 63 Section 2, Zhongyi Road, West Central District
If you need a break from the calorie-laden grub from Taiwan's night markets, you will like the honest-to-goodness cooking in Grainful Diner.
As they say, mum knows best and restaurateur Allen Wu understands that.
There is no menu. You just eat what his mum, popularly known as Mummy Wu, feels like cooking.
Tonight, she whets our appetite with a crisp Dragon Beard Vegetable salad, drizzled with her homemade sesame sauce. She does not disappoint with dishes such as chye poh omelette, milkfish simmered in ginger vinaigrette and braised pork belly with preserved cabbage. I also slurp up the bowl of clear radish soup.
Mummy Wu tells me: "It is simple cooking that will remind you of Taiwanese cooking in the 1950s and 1960s, without the fancy Western cooking or modern fusion styles."
The only modern intrusion is the doo-wop renditions of pop songs by Scott Bradlee's Postmodern Jukebox. We quench our thirst with housemade tea, made with kumquat, chrysanthemum, rock sugar, pineapple and winter melon ale.
Where: Grainful Diner, No. 47 Section 3, Guohua Street, West Central District
Info: Call +8869-1173-0519 for reservations
"Be prepared to be rejected at the door," warns our taxi driver as we head for TCRC, the Tainan waterhole which was named one of Asia's top 50 bars last year.
People start queueing an hour before the bar opens at 9pm. "Leave your name and we will call you," our hostess tells us. We snag seats 21/2 hours later.
Located in a repurposed garage, the dimly lit grungy space littered with wooden stools exudes a casual bohemian vibe. The bar, set up in 2015, stocks about 500 labels of whiskies on wooden shelves.
It lives up to the hype, delivering the classics with precision, and also impresses with its original creations. My favourite is the Penicillin, a heady cocktail of Scotch, coriander-infused gin and Russian-made cumin and fennel-infused vodka.
My go-to classic, the Vesper, also packs a punch.
Where: TCRC, No. 117 Xinmei Street, West Central District
Despite the late night, I drag myself out in the morning for a walking trail to learn how Tainan has evolved since its days as a bustling trading base during Dutch rule.
The city boasts more Buddhist and Taoist temples than any other city in Taiwan. I am drawn to the Tiangong Temple, Taiwan's oldest and best restored temple. It was built in 1845 and is dedicated to the Jade Emperor, Tiangong.
Other must-go tourist spots and historical monuments include the Confucius Temple.
Where: Tiangong Temple, No. 16, Lane 84 Section 2, Zhongyi Road, West Central District
Explore Tainan's ubiquitous vintage alleyways and you will find cute little cul-de-sacs.
I duck into the Shuansen Cafe to refuel with a cuppa and hearty brunch. It is like entering a Japanese home. I look around and find myself (in good company) with a young and chic crowd.
The cafe is one of many that have sprung up in the last two years. Cafe owner Tong Yi says the overheads are lower compared withTaipei and he prefers Tainan's tranquillity to the capital's frenetic energy.
"I don't feel a need to rush anywhere or do something. No one is going to care either."
Where: Shuansen Cafe, No. 17, Lane 147 Section 2, Zhongyi Road, West Central District
Besides being known as Taiwan's cultural capital, Tainan is also known as the "city of snacks". We find perennial favourites such as oyster omelette and Danzai noodles at Yongle market (No. 183 Section 3, Guohua Street, West Central District).
Fu Sheng Hao's (No. 8, Lane 333 Section 2, Ximen Road, West Central District) mua kueh, a rice cake filled with crunchy pickled vegetables and pork, is a Tainan classic and a calorie-worthy snack.
Also droolicious is the beef soup from Pan Clan Beef Soup (No. 125, Section 3, Guohua Street, West Central District). The hearty stock is topped with vermilion beef slices. People apparently get up as early as 5.30am to queue for a bowl of piping hot beef soup.
Stepping through the doors of the Anping Tree House, I feel as though I have stumbled onto the set of the 2014 Disney movie, Into The Woods.
Only there are not as many trees, but just one big Banyan one that has "swallowed" a disused warehouse of a salt company.
Many superstitious locals used to avoid the area, believing it is haunted. A "skywalk" above the treehouse gives visitors a bird's eye view of the tree.
Where: Anping Tree House, No. 194 Anbei Road, Anping District
Admission: NT$50 an adult, NT$25 a child aged below 12
Info: Call +886-6391-3901 for more details on the tours
I am awestruck by the opulence of the Chimei Museum, which bears an uncanny semblance to the Roman Pantheon and even sports a replica of the Fountain of Apollo in the Palace of Versailles. The 40ha three-storey chalk-white building is what I call a "bao ka liao" (Hokkien for all-encompassing) museum.
The nearly 7,000 art pieces here make up about half the private collection of Taiwan business tycoon Shi Wen-long. The exhibits include Western paintings and sculptures from the 18th and 19th centuries, animal fossils, ancient weapons and what is believed to be one of the largest violin collections in the world.
Noteworthy pieces include the 1860 bronze sculpture Theseus Slaying The Centaur Bianor by French sculptor Antoine-Louis Barye; and a 1907 bronze version of The Kiss by French sculptor Auguste Rodin.
Visitors are required to reserve tickets online at least one day in advance. You can also queue up on a first-come, first-served basis.
Where: Chimei Museum, No. 66 Section 2, Wenhua Road, Rende District
Admission: NT$200 for visitors from outside Taiwan
Hop on the Taiwan High-Speed Rail (HSR) from Taipei Main Station. A one-way ticket costs NT$1,350 (S$62), but the ride - which takes about one hour and 40 minutes - is the most comfortable and seamless journey.
The cheaper option is by Kuo Kuang (King) Bus (NT$450 on weekends; NT$310 on weekdays) or the railway train (NT$530 to NT$738), but the commute will be more than four hours long.
Where to stay
• 3 Door Hotel (www.3doorhotel.com.tw) is a modern boutique hotel with a sun terrace and free bicycles for those who want to explore the surroundings. Room rates start at NT$3,900 a night.
• Hotel Ozzie (www.hotelier.com/en/store/index/xm), a modern boutique hotel, has a lovely lounge with snacks and happy hour drinks. Rates start at NT$4,600 a night.
• Feel free to chat with or ask for help from the locals - they are friendly and helpful. •Take time to explore the charming old streets, stopping at hipster cafes for breaks.
• Take along your appetite for the wide array of food.
• Taipei has adopted the hanyu pinyin romanisation system for its road signs, but Tainan is still using traditional spelling. Google Maps has converted most of the road names to the more familiar hanyu pinyin spelling.
• This is the fourth of a 10-part series. Next week, Hong Kong Correspondent Joyce Lim hikes and shops in the city as well as drinks in a hidden bar.
A version of this article appeared in the print edition of The Sunday Times on May 07, 2017, with the headline Perfect Weekend: Explore lesser-travelled Tainan, Taiwan's oldest city. Subscribe