Multi-Generational Thailand Adventure

Beaches, Waterfall Hikes, and Historical Highlights

Thailand may be far-flung, but its diversity of landscapes and experiences makes it a wonderful destination for a heartfelt, culturally enriching trip for the entire family. Whether you’re traveling with young kids in tow or taking that once-in-a-lifetime trip with your parents—or both—our Multi-Generational Thailand Adventure itinerary offers a spellbinding mix of cultural encounters, fascinating history, and nature adventures that can be adapted to every traveler in your group.  

Visit a hidden island in the middle of Bangkok and then embark on a tuk-tuk tour for your tastebuds around the city’s top foodie spots. Visit thundering waterfalls and ride a section of the infamous Burma Railway before learning more about this complicated history. Cycle down idyllic countryside backroads, watch elephants at play, and immerse yourself in a technicolor underwater world on an island snorkeling adventure. 

We’ll tailor accommodation to villas and properties that cater to families without compromising on the authenticity and beauty of the experience. 

Multi-Generational Thailand Adventure: 14 days / 13 nights

Multi-Generational Thailand Adventure Trip Highlights

Begin your journey through Thailand in Bangkok, where your VIP escort will whisk you through priority customs and immigration. Your personal guide and driver will welcome you to the city and bring you to the Avani+ Riverside Bangkok, a contemporary property where dining options and amenities abound, including an infinity pool with panoramic city views. 
Board a rocket boat at Nonthaburi Pier and cruise over to Koh Kret, an island set between two bends of Bangkok’s Chao Phraya River. Explore this peaceful green space in the city on a bicycle, weaving through the bucolic landscape past charming teak cottages and beautiful Buddhist temples. You’ll get the chance to connect with the Mon, one of Myanmar’s Indigenous peoples, learn about their artisan pottery tradition, and even try making a piece of your own. End the excursion with a stroll through the local market to sample sweets unique to the island. 
Embark on a tuk-tuk foodie tour, beginning at a northeastern Thai restaurant to sample the region’s specialties, including spicy raw papaya salad, deep-fried crispy catfish with spicy sauce, spicy pork salad, and spicy pork meatballs. Then hop back in your tuk-tuk and make your way to a favorite local spot for crispy chicken noodles before stopping to enjoy the colors and scents of a flower market. End the day by skipping the line at Bangkok’s best Pad Thai restaurant.  
Immerse yourself in the world of Muay Thai, Thailand’s ancient martial art, with a hands-on training session. Originally created for the Thai military, Muay Thai is an integral part of Thai culture as much as it is a sporting event. As you learn the fundamental skills and combat techniques of this martial art, you’ll also gain a rich perspective on the sport’s heritage and artistry, including its traditional and ceremonial clothing.   
Journey south from Bangkok to Kanchanaburi, a province rich in history and natural beauty. Peruse the Maeklong Train Market, a unique and lively market built along the railway tracks, before boarding a train to ride a section of the infamous Burma Railway. Take in the beautiful River Kwai outside the window while learning about the railway’s difficult history, built during World War II by POWs and forced laborers under Japanese orders. 
From your home base in Kanchanaburi, a serene floating villa at the riverside Float House River Kwai, set out on a private, full-day tour to explore the region’s natural and historical highlights. Visit Erawan Falls, an impressive seven-tiered waterfall regarded as one of Thailand’s most beloved natural wonders. Manageable paths lead to each level of the waterfall, with spectacular views from the top, and the area also has natural swimming pools and spectacular caves to explore.  
After visiting the invigorating falls, the day continues on to Hellfire Pass, a solemn memorial and museum that honors the lives lost during the construction of the Thai-Burma Railway. Visit the museum to reflect on this sobering history through artifacts and stories, and then walk the Bamboo Path, tracing the steps of the POWs who endured unimaginable hardship while working on the railway. You’ll leave with a deep understanding of what gave Hellfire Pass its ominous, haunting name.  
Kick things off in the mountainous northern Chiang Mai region with a visit to an elephant sanctuary. Guided by experienced mahouts, the elephants’ traditional keepers, you’ll walk alongside these magnificent creatures on verdant forest trails. Witness elephants at play and learn how to communicate with these gentle animals from the mahouts. The experience ends with a delicious vegetarian lunch and a stroll along a leafy mountain trail. 
Gear up for a day of adventure in Sri Lanna National Park just outside Chiang Mai, where you’ll arrive at Bua Tong Waterfall. Mineral deposits allow you to climb the waterfall against the current without slipping—a unique and refreshing experience. Take in lush rainforest views from the top of the falls and visit a sacred natural spring before breaking for Thai snacks. Next, hop on a bicycle to meander down peaceful rural backroads, passing orchards and rice fields before arriving at a reservoir and boarding a long-tail boat. The boat travels across calm waters to reach a floating restaurant serving a mouth-watering lunch of Thai specialties.  
Skip the packed ferry and take a private speedboat over to the island of Koh Lanta off the Andaman Coast. While Koh Lanta is a bit harder to reach than other islands in the region, the reward is serenity and seclusion away from the crowds. Settle in for a restful night at your private ocean-view pool villa at Pimalai Resort & Spa. The elegant property feels like a world unto itself, with everything you could possibly need at your fingertips. In the morning, unwind on the beach before setting out for a sunset snorkel and cruise. Lose yourself in the bright underwater world of coral reefs and neon fish around Koh Haa, a small string of islands. As the honeyed sun sets, savor canapes and cold cocktails along with views of the tangerine sky from your private boat.  
Head back to the mainland and enjoy your last leisurely couple of days under the sun on the stunning Railay Peninsula. This region is known for its iconic karst formations, and you can take them in from Phra Nang beach, head to popular Railay, or simply kick back at your luxury family pavilion ensconced in tropical gardens and coconut groves.  

Price

Starting at $9,500 per person based on four persons sharing in 2025

Multi-Generational Thailand Adventure On a Map

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