Grand Two-Month Adventure Itinerary - Road Trip Supreme

Thailand Travel Itinerary: The Grand Two-Month Adventure (With a Dash of Chaos and Mild Sunburn)

Start: Bangkok (5 Days)  

Your gateway into Thailand! Start strong with temples, tuk-tuks (or Grabs), and an excessive amount of street food. Brave the floating markets, attempt to navigate Chatuchak Market without getting lost (impossible), and sweat profusely while pretending it's all part of the charm.  

Moving on: Ayutthaya (2 Days) → Lopburi (2 Days) → Sukhothai (2 Days)  

Train to Ayutthaya, where history oozes from every ancient ruin (along with humidity). Move on to Lopburi by train, home of the legendary monkeys who WILL steal your food (and possibly your dignity). Then, take a bus to Sukhothai for more stunning ruins, imagine Angkor Wat’s smaller, underrated sibling.  

The north: Phrae (2 Days) → Lampang (2 Days) → Chiang Mai (7 Days)  

Roll into Phrae by bus, a town so peaceful that even your travel stress takes a break. Then, on to Lampang by bus, where horse-drawn carriages make you feel like Thai royalty (or like you're trapped in a historical drama). Hop on the train to Chiang Mai and enjoy its temples, amazing food, and, of course, a 3-day trek; don’t worry, it only feels like you’ll die halfway through.  

Mountain Magic: Pai (3 Days) → Mae Hong Son (3 Days) → Chiang Mai (1 Day)  

Bus to Pai, Thailand’s hippie haven, where the banana pancakes are plentiful and self-discovery is mandatory. Then, bus to Mae Hong Son, where remote beauty and fresh air cure all regrets about overloading on street food. A pit stop back in Chiang Mai before taking a flight to Krabi because sometimes, your legs deserve a break (and it's simply way too far).  

Beach Time: Ao Nang/Railay (5 Days) → Koh Phi Phi (Day Trip) → Koh Lanta (5 Days)  

Hit the beach, swap trekking boots for flip-flops, and embrace the island life. Railay is famous for climbing, while Phi Phi is famous for The Beach but you'll actually get caught in a tourist whirlwind. Bus plus ferry to Koh Lanta which offers tranquil beaches and fewer selfie sticks, so an actual paradise.  

The Penultimate Chapter: Hat Yai (2 Days) → Bangkok (2 Days) → Kanchanaburi (4 Days)  

Hop over to Hat Yai and wonder why more tourists don’t come here. Then, fly back to Bangkok because no Thailand trip can escape the gravitational pull of the capital (unless you're a die-hard road tripper by now and decide to bus all the way up there). After some R&R in Bangers, head to Kanchanaburi by train or bus for history and nature, and consider not reenacting dramatic train scenes on the Death Railway (but who am I to stop you?).  

The Finale: Bangkok (3 Days)  

Time for one last round of indulgence before heading home. Thai massages, last-minute souvenir shopping, and one final epic street food binge because that’s what memories (and mild regret) are made of.  

This two-month itinerary guarantees adventure, the occasional questionable decision, and enough stories to fill a lifetime. Try not to get your snacks stolen by monkeys, and remember: hydration is key. 

Explainer: Spare Days (What Spare Days?)

Two months equals 60 days, but eagle-eyed readers may have noticed that the itinerary only covers 50 days. What gives? Well, it's a good idea to allow a travel day between destinations that are a bit further apart, so that you can enjoy your journey to the fullest instead of always being in a hurry. Use those travel days well or, alternatively, save them up to add more destinations to your trip. Up to you.

Also, what if you're really feeling a place? Stay longer! Use your spare days or nibble away elsewhere in the itinerary. If you fall in love with a particular island or city, don't hesitate to extend your stay.

Need a break? Take a chill day! Traveling for two months can be tiring. Use your spare days to relax by the pool, get a massage, or simply do nothing.

Discover something unexpected? Go for it! Sometimes the best travel experiences are the unplanned ones. If you hear about a cool festival or a hidden gem, use your spare days to check it out.

Final Important Notes (aka Things Your Mom Would Tell You):

Don't book all your transportation and accommodation in advance, unless it's peak season. There's always a room available somewhere and a spare seat on a bus. This will give you more flexibility.

Don't think or expect everything to be bookable online. And know that online bookings of tours and transport can be much more expensive than booking on the ground. Be adventurous!

Pack light! You'll be moving around a lot, and lugging a giant suitcase up three flights of stairs in a guesthouse is no fun. Also, they do have shops in Thailand, you know.

Bring enough cash and at least two cards (debit and/or credit). Cards can malfunction or be swallowed and cash is still king in Thailand.

Stay hydrated! Thailand is hot. Drink lots of water (and maybe a Chang beer or two in the evenings).

Learn a few basic Thai phrases. It will go a long way with the locals and might even get you a better price at the market.

Be respectful of local customs and traditions. Dress modestly when visiting temples and be mindful of your behavior in public.

Smile! The Thai people are incredibly friendly, and a smile can go a long way.

Embrace the chaos! Thailand can be a bit overwhelming at times, but that's part of its charm. Just go with the flow and enjoy the adventure!

Have an absolutely amazing (and slightly hilarious) two months in the Land of Smiles! May your pad Thai be plentiful and your tuk-tuk rides few but exhilarating (be sure to bargain). Safe travels!