14-day luxury Thailand itinerary for couples, friends, and families
A tropical journey for romance, adventure, and serious food lovers
Thailand is a dream destination that checks all the boxes for the perfect romantic getaway, adventurous girls’ trip, or unforgettable family vacation. That’s why I’ve curated this luxury Thailand itinerary for travelers who crave culture, nature, indulgent hotels, and a good dose of adventure.
Whether you’re celebrating a honeymoon, birthday, or planning a long-overdue escape with your favorite people, this two-week Thailand vacation takes you from bustling Bangkok to serene Chiang Mai, onto the limestone cliffs of Krabi, and ends in island paradise on Koh Samui. And the food along the way? I still dream about the pad thai and crave the som tam that just can’t be found anywhere else but Thailand.
Days 1–3: Bangkok: Where city buzz meets artistic soul
Wat Arun Ratchawararam
Where to stay in Bangkok:
| Perks with The Travel Club | |
| COMO Metropolitan Bangkok |
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| Four Seasons Hotel Bangkok at Chao Phraya River |
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| SO/ Bangkok |
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The highlights:
Kick off your Thailand luxury itinerary in Bangkok, a city where ancient temples meet sky-high rooftop bars. After checking in, spend your afternoon at the Bangkok Art & Culture Centre (BACC), a peaceful space filled with contemporary Thai art and thought-provoking exhibitions.
Spend your second day exploring the local food and markets. Wake up early for a guided tour of the Chatuchak Weekend Market, one of the largest open-air markets in the world. In the evening, head to Yaowarat (Bangkok’s Chinatown) and indulge in a street food crawl—oyster omelets, coconut ice cream, and crispy duck noodles are must-tries.
Spend your final day visiting the Grand Palace, Wat Pho, and Wat Arun, followed by a traditional Thai massage at The Oriental Spa. At sunset, sip cocktails at Vertigo, Bangkok’s iconic rooftop bar with breathtaking skyline views.
Days 4–6: Chiang Mai: Temples, traditions, and countryside charm
Grand Palace in Chiang Mai, Thailand
Where to stay in Chiang Mai:
| Perks with The Travel Club | |
| Raya Heritage Chiang Mai |
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| Four Seasons Resort Chiang Mai |
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| Anantara Chiang Mai Resort |
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The highlights:
This northern gem is the cultural heart of Thailand. Start the day off by beating the crowds with a sunrise hike with a former monk at Wat Phra That Doi Suthep, a golden mountaintop temple with panoramic views of Chiang Mai. In the afternoon, return to your hotel for a nice lunch and rest, then enjoy an evening bike ride through Chiang Mai’s old city to learn about its history before ending at a night market for some delicious dinner options.
Embark on a full day outdoor adventure, complete with white water rafting, ATV ride through the countryside, and take a refreshing dip a local waterfall. Cap off the day with dinner at Kiti Panit, an updated take on traditional Lanna cuisine.
On Day 6, discover the culture and cuisine of the Akha, a local minority, through a hands-on cooking class. Kick off the morning with a visit the local market to buy ingredients before learning how to prepare a meal’s worth of Thai and Akha dishes for lunch. Spend some time in the afternoon indulging in a spa appointment before trying some traditional northern cuisine at Huen Muan Jai. After dinner, watch a muay thai boxing match before heading back to your hotel for the night.
Days 7–9: Krabi: Turquoise waters and jungle-draped cliffs
Ko Phi Phi Don
Where to stay in Krabi:
| Perks with The Travel Club | |
| Rayavadee |
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| Banyan Tree Krabi |
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| Phulay Bay, A Ritz-Carlton Reserve |
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The highlights:
Krabi is where adventure meets paradise. On your first full day, set out on a long-tail boat to explore the Hong Islands, famous for white-sand beaches and snorkeling in emerald waters made popular by the James Bond movies.
On day 8, head to Phra Nang Cave Beach, where you can swim in warm lagoons, walk beneath limestone formations, and snap some surreal photos. That night, dine inside a real cave at The Grotto, a rare dinner experience that’s perfect for a special night out.
If you’re feeling active, try beginner-friendly rock climbing at Railay Beach, followed by sunset kayaking through Krabi’s mangroves. These immersive experiences make Krabi a standout on any Thailand girls’ trip or romantic escape. End your day with grilled seafood at Lae Lay Grill.
Days 10–14: Koh Samui: Island hopping, barefoot luxury, and spa days
Indulge in an epic spa day.
Where to stay in the Koh Samui:
| Perks with The Travel Club | |
| Six Senses Koh Samui |
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| Four Seasons Resort Koh Samui |
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| Anantara Lawana Koh Samui Resort |
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The highlights:
Koh Samui is the perfect place to slow things down. After arriving at your hotel, start your stay with a visit to Tamarind Springs, a forest spa offering herbal steam caves and coconut oil massages.
On the next day, hop aboard a private catamaran cruise to Ang Thong Marine Park, a spectacular archipelago of 42 islands. Snorkel in hidden lagoons, kayak past sea caves, and enjoy a beachside picnic lunch. It’s a highlight of this two-week Thailand vacation. For dinner, Khaw Glong delivers bold, authentic flavors in a charming space.
On Day 12, visit a local coconut farm and then head to Smiley Cook for a casual and fun cooking class. Unlike the class you took in Chiang Mai, this class will focus on classics from the south. In the evening, relax and enjoy your resort’s amenities.
Your final full day is for soaking it all in—whether that’s lounging on Chaweng Beach, chasing waterfalls, or shopping in Fisherman’s Village. As the sun sets, grab a drink at Coco Tam’s, a buzzy beachfront spot perfect for a toast to your Thai adventure.
Customizing your Thai getaway
This 14-day journey in Thailand is a must for luxury-seeking honeymooners, family vacationers, and those who just want to go on an incredible adventure. This itinerary is just a jump-off point; we’d be thrilled to design a custom journey for you to cater to your special milestone. Below, we’ve answered a few commonly asked questions to help you start dreaming.
Is this a good 14-day Thailand itinerary for couples?
Yes! Every stop on this itinerary is designed with couples in mind—whether you’re on a honeymoon, babymoon, or just want some alone time in paradise.
Is Thailand a safe destination for a girls’ trip?
Absolutely. Thailand is one of the most welcoming places for female and female-identifying travelers, whether solo or in a group. Locals are kind, many speak English, and there’s a strong community of fellow travelers you’ll meet along the way.
Can I customize this itinerary with The Travel Club?
100%. We’ll work together to make sure it’s the perfect fit for your travel style, dates, and budget. From VIP perks to local guides, we’ll handle the details so you can relax and enjoy the ride.
Should I get travel insurance?
Buying travel insurance is a personal choice depending on your trip and circumstances. We can help you decide if you need to purchase travel insurance for this (or any other trip).
Can I extend this trip or add day trips?
Yes! We’re happy to work with you on creating an adventure you’re excited about. There are many amazing places to explore from every city point, whether it’s an additional day trip or adding a few extra days in another city. Reach out to us at concierge@the-travel-club.co to customize your trip!
