14-Night Thailand Itinerary

Thailand Itinerary

2 Nights in Bangkok, 3 Nights in Chiang Mai, 3 Nights in Koh Samui, 3 Nights in Railay Beach, 1 Night in Bangkok

  • Day 1: Travel Day
  • Day 2: Travel Day
  • Day 3: Bangkok
  • Day 4: Bangkok
  • Day 5: Chiang Mai
  • Day 6: Chiang Mai
  • Day 7: Chiang Mai
  • Day 8: Koh Samui
  • Day 9: Koh Samui
  • Day 10: Koh Samui
  • Day 11:  Railay Beach
  • Day 12:  Railay Beach
  • Day 13: Railay Beach
  • Day 14: Bangkok

Trip Description: This once-in-a-lifetime trip starts in Bangkok, where you'll first experience Thai culture via ornate temples, palaces, countless plates of fried rice and $5 massages (only the safe kind). Once your body is fully adjusted, a short 1-hour flight will take you to the culture capital of Chiang Mai -- the gateway to adventure. Whether you're marveling at city views from impressive hilltop temples, learning how to cook spring rolls and pad thai or playing with baby elephants, Chiang Mai will captivate you with its cultural and historical charm.

After all of these activities, you've earned some lazy beach days on Koh Samui. But fear not, adventure seekers can also venture to Ang Thong National Marine Park, where 42 islands are connected by towering limestone cliffs, white-sand beaches and waterfalls. Hey, ever wanted to eat dinner in a treehouse? You can do that here, too.

Saving the best for last, you'll transfer from Koh Samui to the picturesque island of Railay Beach. This is the Thailand you've been dreaming of -- imagine emerald waters, cascading cliffs and golden beaches lined with colorful longtail boats. The vibe on Railay Beach is super relaxed, but there are plenty of boozy beach bars to kick back on.

The trip ends in Bangkok, to make sure you're back in town for the flight home (unless you want to conveniently miss it, and stay in Thailand forever). We'd be lying if we said we hadn't considered this ourselves.

*ESTIMATED LAND ONLY PRICING (no international air)

Ballin' On a Budget

  • 4-star hotels throughout the trip
  • Daily breakfast
  • All ferries and intra-country flights
  • All taxes and fees

The Damage (what your wallet can expect):

  • April-October: $1499 per person
  • November-March: $1899 per person

The Splurge:

  • 5-star hotels throughout the trip
  • Daily breakfast
  • All ferries and intra-country flights
  • Car service to/from all airports, ports and hotels
  • All taxes and fees

The Damage (what your wallet can expect):

  • April-October: $2999 per person
  • November-March: $3499 per person

*Note: Prices listed on this page are based on season, and may rise or fall based on the exact dates you select.

Click here to start planning your Thailand trip!