From City to Jungle to Island Hopping: Best 2-Week Thailand Itinerary

Advisor - Rachel Havens
Curated By

Rachel Havens

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  • Nature Escapes

  • Beaches

  • Arts & Culture

  • Thailand

  • History

  • Relaxation

  • Sightseeing

Thailand taxi tuk tuk next to a temple in Bangkok.
Curator’s statement

Welcome to Thailand, the land of smiles! Where vibrant culture and warm smiles invite you on a journey like no other. From breathtaking beaches and bustling cities to tantalizing street food and friendly locals, Thailand offers a unique and diverse experience for every traveler. Immerse yourself in the beauty of Koh Samui's sun-kissed shores, uncover the depths of Chiang Mai's ancient traditions and savor the world famous flavors of Thai cuisine. Whether you seek adventure in elephant sanctuaries and snorkeling or tranquility in temple visits and pristine nature, Thailand captivates the soul with its rich heritage and genuine hospitality. Embrace the magic of Thailand, where each moment is an invitation to create unforgettable memories.

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Where to stay

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Conrad Bangkok

A luxe haven in the vibrant heart of Thailand's capital, where guests can enjoy Bangkok's bustling energy and cultural treasures.

Fora Perks
  • $100 hotel / resort credit.

  • Breakfast daily.

  • Upgrade whenever possible.

Rosewood Bangkok

Contemporary luxury hotel boasting refined rooms and suites with floor-to-ceiling windows, two restaurants and a saltwater pool in the heart of Bangkok.

Fora Perks
  • $100 hotel / resort credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out, whenever possible.

137 Pillars House Chiang Mai

In a restored 19th-century teak building, this special stay is a destination unto itself, known for its glamorous suites, spa and plugged-in tours.

Fora Perks
  • $50-$100 hotel or spa credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

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Advisor - Rachel Havens

Unlock perks by contacting Rachel to book your trip.

Day 1: Welcome to Bangkok

People roaming in the local market of Bangkok.

On your first day in Thailand, you will arrive in the vibrant city of Bangkok. After a long journey, take some time to check into your hotel, drop off your belongings and freshen up. Once you're ready to start exploring, venture out into the surrounding area and soak in the lively atmosphere. If your hotel has a pool, consider taking a refreshing dip and unwinding before your evening activities. As night falls, indulge in the culinary delights of Bangkok by experiencing the bustling energy of the Chatuchak Night Market, which is considered one of the most famous markets in the world. Get lost in its labyrinthine lanes, where you'll find a vast array of vendors selling everything from unique handicrafts to delectable street food (some of the best food you’ll eat in Thailand is street food.) Take your time to browse, haggle (be sure to bargain in Thailand!) and immerse yourself in the vibrant atmosphere of this bustling night market. It's the perfect way to kick-start your Thai adventure and immerse yourself in the local culture right from the start.

Day 2: Diverse Experiences in Bangkok

A view of temples with red and yellow roofing and intricate stonework in Bangkok surrounded by green trees.

On Day 2, begin your day early by visiting the majestic Royal Palace in Bangkok. To beat the crowds, aim to arrive when it opens at 7 AM. Explore the intricate architecture and beautifully manicured gardens that surround the palace. Marvel at the ornate details of the various buildings, including the stunning Wat Phra Kaew (Temple of the Emerald Buddha).

Afterward, make your way to ICONSIAM, a colossal shopping complex that offers a truly immersive experience. Lose yourself in the vast array of shops, from high-end luxury brands to local boutiques. Take your time to browse, shop and don't miss the opportunity to visit the market area, where you can savor the flavors of Thai cuisine and indulge in a traditional Thai massage to relax and rejuvenate.

Next, head to Wat Arun, also known as the Temple of Dawn, situated along the Chao Phraya River. Marvel at the stunning architecture of this iconic temple, adorned with intricate ceramic tiles and impressive spires. Climb to the top for a breathtaking view of the river and the surrounding cityscape.

In the evening, join a market tour that takes you through the bustling streets of Chinatown. Experience the lively atmosphere and sample delicious street food. Visit a local temple to gain insight into the spiritual side of Bangkok's culture, and wander through the vibrant flower market, a feast for the senses. As part of the market tour, hop aboard a tuk-tuk, an iconic mode of transportation in Thailand, for a thrilling ride through the city streets. This evening market tour will provide you with a unique and immersive experience of Bangkok's local life, bustling markets, and vibrant street scenes.

Day 2 of your itinerary in Thailand promises a combination of cultural exploration, retail therapy, culinary delights and a glimpse into the local way of life. It's a day filled with diverse experiences that will leave you with unforgettable memories.

Day 3: Floating Markets

People on boats in a floating market.

On Day 3, immerse yourself in the unique charm of Thailand's floating markets and rail market tour. Start your day by joining a floating market tour, where you can experience the vibrant and bustling atmosphere of these traditional markets set on the water. Witness local vendors selling an array of fresh fruits, vegetables, handicrafts and delicious street food from their boats. Take a leisurely boat ride along the canals, soak in the lively ambiance and indulge in the flavors of local delicacies.

Afterward, make your way to the famous Maeklong Railway Market, also known as the "Rail Market." This market is situated right on the railway tracks, and as the train approaches, the vendors swiftly retract their stalls to make way for the passing train, creating a fascinating spectacle. Witness this unique interaction between commerce and transportation and browse the various stalls offering an assortment of goods.

In the evening back in the city, elevate your experience by visiting a rooftop bar or lounge in Bangkok. Here are a few highly-rated options to consider:

  • Sky Bar at Lebua State Tower: Located on the 63rd floor of Lebua State Tower, Sky Bar offers breathtaking panoramic views of the city skyline. Enjoy a sophisticated ambiance, signature cocktails, and a memorable experience.

  • Octave Rooftop Lounge & Bar: Situated atop the Marriott Hotel Sukhumvit, Octave Rooftop Lounge & Bar offers a three-level rooftop experience. Sip on crafted cocktails, marvel at the 360-degree views of Bangkok, and enjoy the lively atmosphere.

  • Vertigo and Moon Bar at Banyan Tree: Perched on the 61st floor of the Banyan Tree Hotel, Vertigo and Moon Bar offer stunning views of the cityscape. Savor delicious drinks and gourmet cuisine while taking in the breathtaking scenery.

These rooftop venues provide a perfect opportunity to unwind, soak in the panoramic views of Bangkok and enjoy a memorable evening against the backdrop of the city lights.

Day 4: Chiang Mai

A golden statue in front of a gray colored hut.

On Day 4, fly to the enchanting city of Chiang Mai in the morning and check into your hotel to begin your adventure in this cultural hub of northern Thailand. After settling in, head to Fern Forest Cafe for a delightful lunch. This charming eatery offers a serene atmosphere amidst nature, allowing you to savor delicious food while surrounded by lush greenery.

After lunch, set out to explore the town. Make your way to Wat Chiang Man, one of the oldest temples in Chiang Mai, located within the old city walls. Discover the rich history and intricate architectural details of this revered temple, which houses ancient artifacts and beautiful Buddha images. Take your time to wander through the temple grounds and soak in the peaceful ambiance.

In the evening, immerse yourself in the vibrant atmosphere of a local evening market. Indulge in a variety of street food delicacies, including the famous Chiang Mai dish called "Khao Soi," a unique and flavorful noodle soup. This culinary gem features a fragrant curry broth with tender meat, fresh herbs, pickled cabbage and crispy noodles on top. Khao Soi is a must-try dish that encapsulates the distinct flavors of Chiang Mai's cuisine. As you explore the bustling evening market, make sure to savor this local delicacy and experience the explosion of flavors it offers.

Hotel recommendations: Consider staying at 137 Pillars House or Anantara Resort in Chiang Mai for a luxurious and comfortable accommodation experience.

Day 5: Elephant Sanctuary

Elephant in the Safari.

On Day 5, prepare for a day filled with incredible experiences in and around Chiang Mai. Begin your day by embarking on an Elephant Sanctuary tour, where you'll have the opportunity to interact with these majestic creatures in a responsible and ethical manner. Learn about their conservation, feed them, and even bathe them in the refreshing river. This experience will leave you with a deep appreciation for the gentle giants and their well-being.

After the Elephant Sanctuary tour, make your way to Doi Suthep National Park, a stunning natural area located just outside of Chiang Mai. Ascend the mountain to visit the iconic Wat Phra That Doi Suthep, a sacred temple with breathtaking views of the city below. Explore the temple's intricate architecture and admire the golden pagoda that dominates the skyline. Take a moment to soak in the tranquility and spirituality of this revered site.

In the evening, treat yourself to a well-deserved Thai massage. Chiang Mai is renowned for its traditional massage techniques, which can help relax your muscles and rejuvenate your body after an eventful day of exploration. Choose from one of the many reputable massage establishments in the city and indulge in a blissful session of relaxation and pampering.

To end your day with a touch of excitement, consider watching a Muay Thai fight. Chiang Mai offers opportunities to witness this traditional Thai martial art firsthand. Experience the electrifying atmosphere as skilled fighters showcase their skills and techniques in the ring. It's an exhilarating spectacle that reflects the rich cultural heritage of Thailand.

Day 6: Chiang Rai

A golden colored temple in Bangkok

On Day 6, embark on an exciting day trip from Chiang Mai to the captivating city of Chiang Rai, known for its stunning temples and unique cultural heritage. Prepare for a day filled with awe-inspiring architecture and enriching experiences. Start your day early to make the most of your time in Chiang Rai. After a scenic journey, your first stop will be the White Temple, officially known as Wat Rong Khun. Marvel at the intricate details of this breathtaking temple, adorned with delicate carvings and shimmering white surfaces. Explore the surrounding grounds, which feature unique art installations and sculptures, adding to the ethereal atmosphere.

Next, venture to the Blue Temple, also known as Wat Rong Suea Ten. Admire the mesmerizing blue hues that dominate the temple's interior and exterior, creating a serene and enchanting ambiance. Marvel at the intricate artwork and intricate design elements that make this temple a true gem. Continue your temple tour by visiting the Golden Triangle, where the borders of Thailand, Laos and Myanmar converge. Take in panoramic views of the Mekong River and explore the opulent Wat Phra That Chedi Luang, which houses a revered Buddhist relic. As you explore Chiang Rai, take time to immerse yourself in the local culture and cuisine. Sample local delicacies at the bustling markets or try traditional dishes at one of the charming local restaurants. In the evening, return to Chiang Mai and reflect on the enchanting day you've had. Take a moment to relax and soak in the memories of the stunning temples and cultural wonders you encountered during your visit to Chiang Rai.

Day 7: Cooking Class

A covered market with colorful stalls in Thailand.

On Day 7, spend the morning relaxing and exploring the charming city of Chiang Mai at your own pace. Take a leisurely stroll through the bustling streets, visit local markets to pick up unique souvenirs or try delectable street food or simply unwind in one of the city's picturesque parks or cafés. Immerse yourself in the local atmosphere and embrace the unique vibe of Chiang Mai.

In the evening, prepare for a culinary adventure as you join a cooking class at Zabb E Lee Thai Cooking School. This exceptional school offers an immersive and hands-on experience that starts with a visit to a local market. Accompanied by expert instructors, you'll explore the vibrant market stalls, selecting fresh ingredients that will be used to prepare the dishes during the class. Learn about the essential herbs, spices, and produce that contribute to the authentic flavors of Thai cuisine.

After the market visit, head to the cooking school where you'll delve into the art of Thai cooking. Under the guidance of skilled instructors, you'll learn the secrets behind traditional recipes and techniques. From aromatic curries to savory stir-fries and refreshing salads, you'll have the opportunity to prepare and cook a variety of authentic Thai dishes. Discover the balance of flavors and the harmony of ingredients that make Thai cuisine so distinctive.

As the class progresses, savor the enticing aromas that fill the kitchen and witness the transformation of ingredients into a delectable meal. Finally, sit down to enjoy the fruits of your labor—a flavorful feast that you've prepared with your own hands. Indulge in the satisfaction of mastering Thai culinary techniques and delight in the rich flavors that define this remarkable cuisine.

Day 8: Fly to Koh Samui

A swing on an island with blue water.

On Day 8, fly to the tropical paradise of Koh Samui. After arriving at the island, take the day to unwind and indulge in relaxation. Whether you choose to bask in the sun on the beautiful beaches or lounge by the pool at your hotel, this is a day dedicated to pure leisure and rejuvenation. Koh Samui is renowned for its pristine beaches and crystal-clear waters, offering the perfect setting for a day of blissful relaxation. Feel the soft sand between your toes as you take a leisurely stroll along the shoreline or find a cozy spot to lay down and soak up the sun. If you're in the mood for some water activities, you can also consider snorkeling, kayaking or even taking a boat tour to explore the nearby islands. Alternatively, hang at the splendid hotel pool area, spend the day lounging by the poolside, sipping refreshing drinks and immersing yourself in the tranquil ambiance. Take this opportunity to disconnect from the outside world, unwind and recharge your energy levels.

Day 9: Day Trip to Pig Island

Beautiful island with a Thai boat in the water.

On Day 9, embark on a thrilling day trip to Pig Island, also known as Koh Madsum. This secluded island is famous for its pristine beaches and adorable inhabitants—the swimming pigs! Spend the day basking in the sun, swimming in the turquoise waters and interacting with these friendly and playful creatures. It's a unique and memorable experience that will surely bring a smile to your face.

After enjoying the beauty of Pig Island, head back to Koh Samui and treat yourself to a delightful dinner at The Jungle Club. Nestled amidst lush greenery and offering panoramic views of the island, The Jungle Club provides a magical setting for a memorable dining experience. Indulge in a delectable meal featuring a fusion of Thai and international flavors while immersing yourself in the enchanting atmosphere of the jungle surroundings. The combination of delicious food, breathtaking views and a serene ambiance makes for a truly unforgettable evening.

Day 10: Angthong Marine Park

A boat on a deserted Thai island.

On Day 10, embark on an exhilarating day trip to Angthong Marine Park, a breathtaking archipelago consisting of 42 islands. Explore this natural wonderland, known for its towering limestone cliffs, turquoise waters and vibrant coral reefs. Set sail from Koh Samui and immerse yourself in the beauty of Angthong Marine Park. Marvel at the stunning scenery as you cruise through the clear waters, passing by picturesque islands along the way. Upon reaching the park, engage in a variety of activities such as snorkeling, kayaking or simply relaxing on the pristine beaches. Dive into the vibrant underwater world, encountering colorful tropical fish and coral formations that make this marine park a diver's paradise.

As you explore the park, don't miss the opportunity to hike up to the viewpoint on one of the islands. From the top, you'll be rewarded with panoramic views of the surrounding islands and the glistening ocean. Capture the beauty of this natural oasis with your camera or simply take a moment to appreciate the serene and untouched landscape. After a day of adventure and exploration, return to Koh Samui with memories of the awe-inspiring Angthong Marine Park. Relax and reflect on the incredible sights and experiences you encountered throughout the day.

Day 11: Krabi

Aerial view of Thai island Krabi.

On Day 11, bid farewell to Koh Samui and make your way to the beautiful coastal province of Krabi. After arriving and checking into your hotel, take some time to relax and unwind by the pool, soaking in the serene atmosphere and enjoying the tranquility of your surroundings. In the evening, venture out to Krabi City market for a delightful dinner experience. This bustling market is a vibrant hub of local culture and flavors, offering a wide array of street food stalls and local eateries. Take the opportunity to indulge in the diverse culinary delights of Krabi, sampling traditional Thai dishes and regional specialties. Immerse yourself in the lively atmosphere of the market, enjoying the sights, sounds and aromas as you wander through the colorful stalls. Krabi City market not only offers a fantastic culinary experience but also serves as a great place to shop for souvenirs and local crafts. Explore the market's vibrant displays of handmade products, textiles and unique trinkets, and take home a piece of Krabi's local culture.

Day 12: Phi Phi Islands

Phi Phi islands at sunset.

On Day 12, get ready for an incredible island hopping tour in the Phi Phi Islands, one of the most breathtaking destinations in Thailand. Join a guided tour that takes you on an unforgettable journey through this stunning archipelago. Embark on an iconic longtail boat and set sail to explore the picturesque Phi Phi Islands. Admire the dramatic limestone cliffs towering above the emerald waters as you cruise from one island to another. Visit iconic spots such as Maya Bay, made famous by the movie "The Beach," and experience the beauty of its pristine white sand beach and crystal-clear waters. Snorkel in vibrant coral reefs teeming with marine life, discovering a kaleidoscope of tropical fish and other fascinating sea creatures. Swim in the inviting turquoise waters or relax on secluded beaches surrounded by lush greenery. Each island has its own unique charm, offering you a variety of experiences and photo-worthy moments. Throughout the tour, knowledgeable guides will share interesting facts and stories about the islands, ensuring you have a deeper understanding of their natural wonders and cultural significance. As the day comes to an end, bask in the warm glow of the setting sun as you sail back to Krabi, reflecting on the beauty and serenity of the Phi Phi Islands.

Day 13: Railay Beach

A beautiful island with boats on the water in Thailand.

On Day 13, embark on an unforgettable journey to Railay Beach, a hidden gem renowned for its pristine beauty and serene atmosphere. Hop on a longtail boat from Krabi and be whisked away to this tropical paradise. As you step onto the powdery sands of Railay Beach, immerse yourself in the tranquil surroundings and breathe in the fresh sea breeze. Take a moment to appreciate the awe-inspiring limestone cliffs that encircle the beach, creating a stunning backdrop for your day of relaxation. Indulge in the ancient healing art of Thai massage, a quintessential experience in Thailand.

Find a local massage parlor or beachfront spa and let skilled therapists work their magic, relieving any tension and rejuvenating your body and mind. Feel the gentle stretches, acupressure, and rhythmic movements of the massage, leaving you invigorated and blissfully relaxed. After your rejuvenating massage, continue your exploration of Railay Beach. Take a leisurely stroll along the shore, admire the turquoise waters and perhaps find a quiet spot to lounge under the shade of a swaying palm tree. Railay Beach offers numerous activities such as rock climbing, kayaking and paddleboarding. If you're feeling adventurous, you can venture into the nearby caves or hike up to the viewpoint for breathtaking panoramic views of the beach and the surrounding limestone cliffs.

As the sun begins to set, take the long tail boat back and head to the vibrant Ao Nang Night Market, where an array of tantalizing aromas and flavors await. Feast on delectable street food, savoring local delicacies and traditional Thai dishes. From mouthwatering Pad Thai to fragrant curries and exotic tropical fruits, the night market is a food lover's paradise. Immerse yourself in the bustling atmosphere, marvel at the colorful stalls and enjoy your final night in Krabi with a feast for the senses.

Day 14: Depart the Land of Smiles

Depart from Bangkok at the airport.

On Day 14, it's time to bid farewell to the enchanting beauty of Thailand as you prepare to fly back home. If you require a connecting flight, you'll be pleased to know that Krabi has its own airport offering flights to Bangkok (BKK), providing a convenient and seamless journey. Take a moment to reflect on the incredible experiences, vibrant culture, and natural wonders you have encountered during your two-week adventure in Thailand. Cherish the memories of the stunning beaches, vibrant markets, awe-inspiring temples and the warm hospitality of the Thai people. As you board your flight, carry with you the spirit of Thailand, the Land of Smiles. Take this opportunity to plan your next adventure, dreaming of the countless possibilities that await you in your future travels.

Need to Know

For more travel tips, check out my guide, Perfect Weekend Getaway on Lake Michigan.

Advisor - Rachel Havens

Travel Advisor

Rachel Havens

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This guide is part of our ongoing series on travel to Thailand.