Bangkok

Accommodations

• Old Capital Bike Inn: 3-star super boutique hotel. I loved this as my first accommodation experience in Bangkok, as they also do free nighttime city bike tours which gives you a good lay of the land. The staff is incredible, super friendly and willing to share recommendations, help you book tours, flag down taxis and also give you personalized welcome notes with a couple small gifts. This also had the best breakfast, hands down, out of anywhere I stayed in five weeks in Southeast Asia, it was stuffing-ly delicious. The only thing I wished for was a mosquito net over the bed. There was one obnoxious blood sucker flying around my room that I could not successfully swat down. Check out my TripAdvisor review.
• Phranakorn-Nornlen: Another 3-star super boutique hotel, but I ended up checking out early of this one. If you like cute and unique, this is full of it! That said it is not walking distance to any attractions and be prepared that the shower in the bathroom has little separation and no door or curtain. I actually left early to avoid a chirping gecko staying with me. Check out my TripAdvisor review.
• Villa Phra Sumen: 3-star boutique hotel just down the road from the Old Capital Bike Inn. I was only here for a layover so had about 7 hours here total, but loved the room. It was large and comfortable with my room overlooking the canal. I would definitely come back here.
• Inn A Day: 4-star extra boutique hotel. Again, I only stayed here one night on a layover, but I loved the concept. Each room is based on a time of day. My room was 8AM and school room concept interior with a garden and city view. You can also walk up to the top floor for stellar view of the Wat Arun temple across the water. Staff was super helpful and friendly, they even made breakfast for me earlier than their start time because I had to catch a flight. It's not easy walking distance to attractions but I just hopped in an Uber to get around.
• Siam@Siam Design Hotel Bangkok: 4star high-rise hotel located in walking distance of the Jim Thompson House. I only stayed here one night and booked on the fly after leaving Phranakorn-Nornlen. The hotel is updated and pretty standard with what you'd expect for 4 stars. This does have a nice pool area but it's small so you have to get there early. The other plus to this hotel is the rooftop restaurant for great city views.

Sites/Tours

• Jim Thompson House: Home of Jim Thompson, founder of the Jim Thompson Thai Silk Company. Worth a visit, the architecture and decor of the house each has a story and a purpose. Be prepared to take your shoes off!
• Nighttime Bike Tour: I did this with my hotel, Old Capital Bike Inn. It was great to ride around and see things such as the Grand Palace, Giant Swing, night markets and locals playing Sepak takraw. Make sure to yell if you fall behind, we had a bit of a search party scenario on our ride (no, it wasn't me).
• Khao San Road: One of the main party drags in Bangkok. It's worth seeing once and if you want to get crazy, this is the place for you. After a couple hours I felt like I was going deaf on this street. I think it's easier with 20-year-old eardrums.
• Ayutthaya and Summer Palace: Outside of the city but definitely worth getting a driver for the day to go out and visit. Ayutthaya is an ancient capital with vast temple ruins and the Summer Palace was historically used my Thai kings. Stick around Ayutthaya and find a temple near the river to see the sun go down behind the temple.

Food

• Susie Wong's Beers and Buns: On Khao San Road, has delicious bánh mì sandwiches.

Chiang Mai

Accommodations

• Art Mai Gallery Hotel: 4.5-star boutique hotel in the Nimman area (named for Nimmanhemin Road), it's located Northwest of the old town border. Hence the name, the interior of the hotel has art exhibits from local artists and each room also has a play on art decor. This is a newer hotel and the rooms are great, super comfy. Service is also extremely helpful and friendly including the breakfast staff who would remember what kind of tea I drank. It takes about 25 minutes to walk to the old town border but if I didn't feel like the walk to Old Town I could easily grab an Uber, taxi, or use one of the red trucks. I actually really enjoyed being in this area vs old town as this is a hip area with a lot of great restaurants and cafes to check out. Would love to stay here again. 

Sites/Tours

• Elephant Nature Park: If you want to see elephants in Thailand, please please please, do not go for an elephant ride or support/pay for activities where the elephant is painting pictures. This forced labor of elephants is supported by the government because of the tourism dollars it brings in, but the practice is incredibly inhumane. Instead, research "legitimate" elephant sanctuaries. Elephant nature park is a notable sanctuary and rescues elephants. Check them out, they offer a variety of on-site visits depending on how much time you have and how much you want to open your wallet. I did the "Pamper a Pachyderm" full day experience and it was amazing! 
• Old Town: Filled with temples on every street, just spend a day walking around and getting lost.
• Wat Phra That Doi Suthep: Located at the top of a mountain, this temple carries with it many stairs, but wonderful views on a sunny day. You can join a red truck to get up the mountain or hire a taxi. I did the latter as I was on a time constraint and the red trucks only leave once they have a minimum number of passengers. This was my favorite temple in Chiang Mai.

Food

• Manifreshto: Super duper small smoothie/bakery place on Nimmanhemin Road. No seating inside but a handful of tables outside. I had a smoothie and brownie, healthy meets sinful.
• TongTemToh: Traditional Northern Thai food on Nimmanhemin Road. I read a ton of good things about this place and passed by but didn't have time to sit down. On the list for next time.
• Italics Restaurant: Need a respite from Thai food? Here's a tasty Italian restaurant also in the Nimman area.
• Chiang Mai Night Market: Head back towards Old Town and hit up the food stalls in the night market for some good local food.

Kanchanaburi

Accommodations

• U Inchantree Kanchanaburi: 4-star hotel on the banks of the River Kwai and only five minutes walking from the bridge over River Kwai. I loved the location of this hotel, it has excellent seating and views directly on the river banks. The rooms are very large, modern and spotless. The hotel pool with river views is also a great way to cool off in between activities. 

Sites/Tours

• Bridge over River Kwai: This bridge has so much history, yet it's still shocking to see how many people flock to this bridge. Mid-day on a Saturday and you'll be shoulder to shoulder with people standing on the bridge, that has an active railway line it - it's crazy. Get here at sunrise and you'll actually be able to walk the whole length by yourself or maybe a handful of early risers.
• Erawan Falls and Hellfire Pass Day Tour: I booked this small group day tour through my hotel, which was a great way to get out and see these sights too far to access without a car hire. You start at the seven-tier waterfall in Erawan National Park and can climb as many tiers as you desire but the higher tiers are a harder hike. You can take a break by splashing at the bottom of any of the falls. You have an early lunch at the park and then head to Hellfire Pass where you can view the museum indoors and walk a portion of the pass outside (bring water). On the way back you'll walk over the Death Railway Wooden Bridge and can check out the Krasae Cave.
• Long tail speed boat ride: You can hire these long tail boats at the bridge over River Kwai and then take the stairs down to the dock to hop on. After you agree on a price (you can haggle a bit but don't undercut them) and for a few hours the boat can be your transportation down the River Kwai to check out the JEATH museum, Chungkai Cemetery, and Khao Poon Underground Cave Temple. Personally I could have done without the cave temple, I was the only person inside at one point besides the bats flying around...yeah, creepy.

Kata Beach/Phuket/Southwestern Islands

Accommodations:

• Nook-Dee Boutique Resort: Listed as a 5-star boutique hotel, I would give this 4 stars as service isn't very friendly. The property and rooms itself are great through! Rooms have balconies, interiors are large and you'll find a giant stuffed elephant sitting on the bed to welcome you. The outdoor pool is an infinity edge pool with views of the ocean. I didn't love the location of the hotel though as it sits high on a hill. Great for views but crappy for walking, especially in the heat and non existent side walks. There's a shuttle but it only runs on the hour so if you miss it, you're stuck with the walk or getting a taxi.

Sites/Tours:

• Simba Sea Trips: Absolutely loved this company and did two different sea trips with them below. The cost is a bit more than other boat tours but well worth it. You can read a lot of sad reviews of other companies where they are shoved uncomfortably like sardines onto crappy boats with 75 people. Simba trips max out at 16 guests and pick you up early to beat the rush of all the other boats. They also keep you fed with delicious snacks all day and a full lunch. 
  • "Phi-Phi Sunrise": We were lucky to catch the sunrise on the boat while heading out to Phi-Phi and then made our way to Maya Bay well ahead of most boats so we could make the sand and water our playground. Some of the other highlights on the tour are Pileh Lagoon, and snorkeling.
  • "Phang Nga Bay & Koh Panyee": Another excellent trip and a chance to see an entire floating community. Highlights of this tour were; Koh Phanak for cave exploring, Koh Hong canoeing, Koh Panyee floating village and lagoon swimming.
• SUP (Stand Up Paddle): I love SUP so I try to do it any city I visit that offers it. I arranged a lesson with SSS Phuket, but unfortunately they had to cancel due to an ill instructor. So I can't vouch for the experience but on my list for when I go back. They also offer diving and snorkeling outings.
• Phuket Big Buddha: This was the perfect pit stop on my way to the airport. I left a couple hours early so I could go and see this and per it's namesake, it IS big! It's also perched at the top of a mountain so the views are incredible. 

Food

• Mom Tri's Kitchen: Local Thai cuisine and seafood with panoramic sea views. I had read a lot of good things about this place and the view is pretty good but I had an issue with the food. I had the salmon curry which was very tasty going down but unfortunately gave me food poisoning. I have to think this was a one-off incident and if you travel enough it's bound to happen anyways.