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Chiang Mai is the fifth largest city in Thailand, but its old town area remains charming and compact enough to make repeat visits enjoyable, in addition to the many natural and tourist attractions just outside the city.
While I love living in Bangkok, I also like an occasional escape to Chiang Mai to enjoy its laid-back vibe and forested mountain areas, especially during the "winter" months. I usually spend time in the old town area, then go to the Nimmanhaemin area just to the west, which offers more hip cafes, restaurants and galleries that are worth exploring. Going further west from the city are the mountain regions bordering the Chiang Mai valley, including the two most famous: Doi Suthep and Doi Inthanon. Motorcycle drivers will especially enjoy the well-maintained roads winding their way through the peaks and valleys.
Anyone visiting Chiang Mai for the first time should read Wikitravel for a brief overview on its history, areas and tourist information. Foursquare and Tripadvisor can also be useful for choosing places and attractions, although you should sift through the reviews carefully depending on whether you want a more local or a more tourist-oriented experience. I'll link relevant pages under my suggestions so you can look at location, reviews and opening hours for each one.
Arriving and Taxis: On arrival, airport taxis have flat rate of 150 baht to anywhere in the old city region, but otherwise are not common in the region. Uber and Grab are more reliable alternatives to tuk-tuks and songthaews(pickup trucks with benches used as buses) for transport, as well as cheaper in general unless you speak Thai and bargain well. Many people choose to rent a motorbike or car for their visits, as driving is generally much more doable here than in Bangkok.
Motorcycle rentals: Many larger shops are on the ring road that circles the old town, which is also where the gas stations are in the old town, although you can purchase gas from many local shops in 1L bottles, especially in rural areas where there are no gas stations at all. Most hotels will have a delivery arrangement with a local rental shop, which offers convenient for a slightly higher daily fee. Take pictures before accepting to avoid the occasional damaged bike repair scam, and be sure to fill it to the same gasoline level before returning. I've used Buddy Motorbike on north ring road a few times and haven't have any problems.
Lanna cuisine is distinct from other regions in Thailand, and tends to be slightly less spicy and sour with more influence from Burmese flavors. Most traditional Lanna restaurants will sell an appetizer or meal set which will include 3-5 of their most popular dishes, making this a great choice for first-time visitors. Most of my suggestions for Lanna restaurants serve authentic local flavors, which may be too spicy/bold for some palates. Not all Lanna dishes are spicy, but for some dishes you should ask for mild versions so you can enjoy the flavors. For more details on popular Lanna dishes, you can read this page and this one.
Huen Muan Jai Restaurant
My long-time favorite for local Lanna cuisine, set in a nice old wooden house quite close to the old city, with English friendly menus and some English-speaking staff. Everything I've had there was good over multiple visits over the years and is a must-visit whenever I'm in Chiang Mai. Order the appetizer set to try their excellent Sai Oua(Lanna sausage), two Nampriks(spicy green chili and milder tomato dips served with veggies and pork rinds), fried fermented pork ribs and Geng Hang Lei(sweet braised pork belly curry). They close Wednesdays though, which is different from most restaurants in the area that close Sundays or Mondays. [Foursquare, TripAdvisor]
Han Thung Chiang Mai (Cafe Nature)
My second favorite Lanna place, a little outside the main Chiang Mai area, but not far from Chiang Mai University. They have a huge menu of smaller portioned and cheap dishes so you can and should order many to try a little of everything. The menu has some English, and someone will usually be able to suggest their most popular dishes if you can't decide. They usually have ant egg dishes if you want to try something different(don't worry, they don't really taste like much, more like bland caviar). The main restaurant is actually the outdoor bamboo-covered area behind the modern glass Cafe Nature coffee shop, but I think they will serve food in there as well if they are full outside or if it's too hot. [Foursquare, TripAdvisor]
Khun Yay’s Khao Soi
My favorite local khao soi spot in chiang mai, just next to a wat on north ring road and set in the yard of their family home. Her beef khao soi is my favorite, but she also has chicken and pork versions, and all are very cheap. It's become quite popular among tourists and Thais, so you may have to wait for a table, but it's worth it. Other people rave about Khao Soi Mae Sai which is just next to Huen Muan Jai, but I think Khun Yay's is slightly better. [Foursquare, TripAdvisor]
Warm Up Cafe
Chiang Mai university hotspot for dinner and drinks, Warm Up also has club music in the back room for partying later at night. Great food and drinks, good prices, an English friendly menu and huge dining area good for larger groups, all make this very popular every night, and packed on the weekends. It will be mostly Thai locals, but they usually have a cover band for 2 hours of English songs and another one for 2 hours of Thai songs, with some foreigners finding their way there to drink and eat. The food steers more towards Isaan and central Thai favorites although there are some Lanna dishes as well. [Foursquare, TripAdvisor]
Tong Tem Toh
Fern Forest Cafe
This cafe offers an excellent assortment of dessert dishes, although their regular food menu was just ok. I loved their coconut cream cake which was not too sweet, and their french toast dessert was very tasty as well. The cafe is set in a pretty garden space, with a relaxed vibe that makes it a good choice for a break after walking around old town on a hot day. [Foursquare, TripAdvisor]
Swan Burmese Cafe
Very good coffee, although their original location is quite small. They offer standard coffee choices, as well as a number of cold brew and charcoal-activated hipster choices. They have a new and much larger location at One Nimman mall, near the start of Nimman road. [Foursquare, TripAdvisor]
Rock Me Burger
Solid Mexican/Texmex food for Thailand. I enjoyed their fresh-fried corn tortilla chips, guacamole and carnitas soft tacos. Most meals are served in large portions compared to Thai places, especially if you order one of their burrito lunch combinations. [Foursquare, TripAdvisor]
Khao Soi Islam
Muslim run, so no pork dishes, but their beef khao soi and goat biryani were solid. Larger menu than most Khao Soi places, which tend to just serve that and the other popular Lanna noodle soup (Khanom Jeen Nam Ngiao). [Foursquare, TripAdvisor]
Lanna Folklife Museum
Excellent modern museum focusing on the arts/crafts of the local Lanna culture. Small enough to enjoy in an hour, as well as having great AC to cool off on a hot day. This area is the center of town, and has some nice statues and buildings scattered around. Across the street from the museum is an older museum on Chiang Mai history that can be skipped unless you're interested in the historical background of the region. [Foursquare, TripAdvisor]
The only animal-themed attraction I really liked, they take good care of the animals, and the tigers are not drugged. All visits with tigers are timed and under supervision from handlers, so it's a rare opportunity to experience these magnificent felines up close and personal. If you’re lucky, they’ll have baby tigers you can feed and take pictures with. It's not cheap but definitely worth a visit. [Foursquare, TripAdvisor]
Mon Cham Viewpoint
Worth a stop if you’re visiting the mountain temples, botanical gardens, tiger kingdom, etc with your own transport. This is close to all of those attractions and has a nice drive up past the royal project farms to a view of rice terraces and valleys, with hill tribe and local people selling some goods at the base of the final viewpoint. Food/drink at the actual viewpoint restaurant aren't great, but it's ok for a snack/beer while you enjoy the view after wandering around for pictures. Food at the newer market/parking area just below the main viewpoint has better local menu choices, although English will be very limited. [Foursquare, TripAdvisor]
Doi Suthep Attractions
There are many other attractions around the Doi Suthep area, of which the Chiang Mai Zoo, Queen Sirikit Botanical Gardens, Siam Insect Zoo and Mae Sae Waterfall are all worth at least one visit and I enjoyed these the most out of the many I've gone to in the area. There are also many other tourist-trap style attractions such as the Mae Sa Elephant camp or longneck hilltribe villages that I don't really recommend to everyone because of ethical/authenticity/value concerns. Do your research and visit what's best for you as they are all in the same general area.
Chiang Mai Walking Street
The main walking street market is only on Sunday evenings, starts at Thapae Gate and runs most of the way through the city. Great for local crafts, people watching, and snack food. Can get crowded, but you can leave on a side road if you don't want to traverse the whole thing.
[Foursquare, Tripadvisor] Saturday nights there is a smaller walking street on Wua Lai Road, starting near the South gate, that's similar to the Sunday market. [TripAdvisor]
Chiang Mai Night Bazaar
If you want some souvenirs and you can't make the weekend night markets, the Chiang Mai Night Bazaar is open every night. Make sure to go inside the large main buildings and not just along the stalls on the street. Be sure to haggle here if you're going to shop, although I prefer the boutique shops scattered throughout the city for nicer quality souvenirs that are less generic. [Foursquare, TripAdvisor]
Ploen Rudee Night Market is a newer night market across the street, although it's primarily food and drinks. It is worth stopping by for a beer as they usually have a good band around 7-9pm, but the food is mostly foreign and not very good so I'd generally avoid eating here. [Foursquare, TripAdvisor]
There are hundreds of temples in the Chiang Mai area and seeing them all would keep you busy for weeks. The following four temples are the ones I enjoy most among the dozens in the old-town area and are easily visited by walking around for an hour or two.
Wat Phra Singh Waramahavihan
Wat Chedi Luang Varavihara
Wat Loke Molee
Wat Inthakin (City Pillar Temple)
Wat Phrathat Doi Suthep
This temple is on Doi Suthep mountain outside the city,and is one of the most famous in the region. It's well worth at least one visit, although it's usually a bit crowded as a result of its fame. The view of the city valley is worth the trip up the mountain on a nice day, although the road is a bit steep and narrow in some places. If you're riding a motorcycle and have a passenger, drive carefully and make sure you have enough CCs for the climb as well as reliable brakes for the descent. [Foursquare, TripAdvisor]
The main foreigner/backpacker bar/club party area is centered around Zoe In Yellow [Foursquare, TripAdvisor]. This block also includes venues for live reggae/ska music at Root Rocks Reggae Bar and live metal/rock bands at Pentatonic Rock Bar, while Zoe is geared towards DJ/dance music in the middle. After this area closes at 12, most go to Spicy [Foursquare] nightclub on the ring road a few blocks away, which is EDM primarily. Spicy is worth going to if you want to keep partying, as there aren't really any other choices anymore after the recent military crackdowns. Spicy recently moved to a newer venue, so it's more organized and like a modern club instead of its previous sketchy, after-hours venue.
For indoor live cover bands with food and drink, head over to Warm Up Cafe with a younger Thai crowd. For a mellower night at an outdoor riverside venue, Riverside Bar & Restaurant and The Good View are both geared more towards an older tourist crowd. All of these have reasonable food and drink prices, with plenty of tables. Another popular bar for Jazz enthusiasts is North Gate Jazz Co-Op, which is more barebones and much smaller, but has excellent jazz jam bands most nights.
Trips near Chiang Mai
If you have an extra day in Chiang Mai, a day trip to Chiang Rai is well worth the time to see it's two most famous attractions, the White Temple [Foursquare, TripAdvisor] and the Black House [Foursquare, TripAdvisor]. Both were created by famous Thai artists and are open year round to the public. Most tours from Chiang Mai will include both in their itinerary as well as a stop for lunch to enjoy the Lanna cuisine in Chiang Rai. If you hire a private tour or driver, from hotel or a website such as https://www.klook.com/, then you can go to one of the many restaurants along the Krok river to have a laid-back meal with a view. I enjoyed my lunch at Lulum Rimkok [Foursquare, TripAdvisor], and they had an English menu as well as an English-speaking manager when I went.
Pai is a small town in the mountains a few hours west of Chiang Mai. This was hugely popular among backpackers for many years and as such has become mostly a tourist town, without many of the charms it must have once possessed. Even worse, the popularity of a recent Chinese movie featuring Pai and Chiang Mai has resulted in growing hordes of Chinese tours over the past few years, making it even less enjoyable as a holiday destination. While it has some pretty areas, and a variety of trekking and rafting options, overall I don't think it's worth the travel time from Chiang Mai unless you want a stopover on the way to Mae Hong Son.