For our 20th anniversary, visiting the Maldives had always been a dream of ours. However, after considering the long flights and the distance from our daughters, we decided to bring them along. Since we’d already be in that part of the world, we saw it as the perfect opportunity to enhance the trip with a culturally immersive experience. While our daughters have been lucky to travel extensively, we realized that deeper cultural exploration has been missing from their journeys. This felt like the ideal moment for them to gain a richer understanding of different cultures.
The flight times were very long (surprisingly manageable), but absolutely worth every minute! That said, I highly recommend flying premium economy or business/first class for added comfort on such long journeys.
Here’s a day-by-day look at our itinerary:
January 1, 2025 – Departure from Omaha & San Francisco LayoverWe kicked off our adventure by leaving Omaha, with an 11-hour layover in San Francisco. Making the most of our time, we rented a Jeep and visited iconic spots like Chinatown, the "Full House" house, and the Golden Gate Bridge before heading back to the airport for our long-haul flight to Singapore (17-hour flight).
Pro Tip: Dress in layers and wear comfortable shoes! San Francisco’s hills are no joke, and the weather can change quickly throughout the day.
January 2, 2025 – Flight Detour to Chiang Mai
Our original plan was to fly directly to Chiang Mai, but due to a missed connection, we rerouted through Kuala Lumpur, Malaysia, before finally arriving in Chiang Mai. After a total of 46 hours of travel, we were relieved to reach our destination and settle into our hotel.
January 3, 2025 – Chiang Mai ArrivalWe arrived in Chiang Mai and were warmly greeted by our private guide, Tippy, who would be with us for the duration of our stay and was a true joy. The rest of the day was open for leisure, so we decided to relax at the hotel, enjoying the rooftop bar, pool, and fine dining restaurant. We were surprised at the low prices—what would’ve been over $100 in the US was under $50.
January 4, 2025 – Chiang Mai: Elephant Farm & Night MarketThe day began early with an unforgettable visit to Patara Elephant Farm, where we became “Elephant Owners for a Day,” visitors are taught how to assess elephant health and care for them. This experience was one we will never forget. The evening took us to the vibrant Chiang Mai Night Market, perfect for shopping and soaking in the local culture.
Pro Tip: You must try Khao Soi, a rich and flavorful Northern Thai curry noodle dish.
January 5, 2025 – Chiang Mai to Bangkok: Temples & TransferWe spent the morning visiting the breathtaking Doi Suthep Temple and other key Chiang Mai temples before flying to Bangkok. Once there, we checked into our hotel and enjoyed a quiet evening to relax.
January 6, 2025 – Bangkok: Grand Palace & Canal TourOur private tour included visits to Bangkok’s most iconic sights: the Grand Palace, Wat Pho, and Wat Arun. We also enjoyed a klong (canal) tour, where we experienced traditional Thai life along the waterways. Lunch was included, and the evening was free for personal exploration.
Pro Tip: You can’t visit Bangkok without trying Pad Thai! The head is considered the most sacred part of the body in Thai culture, so avoid touching anyone’s head.
January 7, 2025 – Bangkok: Jim Thompson House Museum & IconSiam MallThe morning was spent exploring the fascinating Jim Thompson House Museum, followed by an afternoon at IconSiam Mall. Our favorite part of the mall was the markets, offering a delightful mix of traditional and modern Thai goods.
Pro Tip: ICONSIAM The food court on the lower level is fantastic for experiencing Thai street food in a mall setting.
January 8, 2025 – Bangkok Departure on to MaldivesWe left early in the morning for our flight from Bangkok to the Maldives and were escorted to the seaplane lounge area, excited for the next chapter of our journey. It was our first time on a seaplane, and it turned out to be much easier and more enjoyable than we expected! We split the next six days between two stunning resorts: two nights at the InterContinental Maldives and three nights at the Conrad Maldives.
One important thing to keep in mind is that when transitioning between resorts in the Maldives, you’ll need to return to the main airport in Malé and take another seaplane. This can be an additional expense, costing around $600 per person for a round trip. On our first seaplane ride, we were a bit nervous about what to expect, but it turned out to be much smoother than we anticipated—not shaky at all. Plus, the views from above were absolutely breathtaking!
Pro Tip: Best time to visit - the Maldives has a tropical climate, with dry season (December to April)
Jan 8 - 10, 2025 - First part of our journey in the Maldives we stayed in a stunning 2-bedroom, 2.5-bath villa at the InterContinental Maldives Maamunagau Resort. One of our favorite features was our expansive private back deck with the infinity pool, offering breathtaking ocean views. Each guest was given a bike to explore the beautiful property, and the main pool area and beach were absolutely serene. The food throughout the resort was exceptional, with every meal exceeding our expectations. The resort offers an exclusive and tranquil escape with activities like snorkeling with manta rays, sunset dolphin cruises, and indulgent spa treatments in overwater villas.
Jan 10 - 13, 2025 - The Conrad Maldives is spread across three islands, each offering its own unique experience. One island is exclusively for adults, featuring a serene infinity pool at its quiet beach zone, perfect for relaxation. The main island offers beautiful beach villas, ideal for families, with a variety of activities and family-friendly amenities. The resort boasts several exquisite dining options, a fantastic mixologist, and the most incredible overwater spa—fun fact, they even have toilets outside of the treatment rooms! Whether you're snorkeling, enjoying a private dinner, or indulging in a spa treatment, there's no shortage of unforgettable experiences. The staff is exceptionally friendly, always eager to make your stay extraordinary.
Without a doubt, the trip felt far too short! The crystal-clear waters were the most stunning we’ve ever seen, and staying in an overwater villa was a dream come true. At both resorts, there was never a need to fight for a beach chair or dining reservation. The staff’s “yes” mentality ensured that anything was possible, making for a truly luxurious and unforgettable experience.
This itinerary blended cultural immersion, relaxation, and bucket-list moments, creating a family adventure we’ll always cherish.
Wondering what to pack? And yes—we all traveled with just carry-ons and a personal bag!
Thailand Packing List (Short & Essential)
Lightweight Clothing – Breathable, moisture-wicking fabrics (shorts, t-shirts, dresses, linen pants)
Modest Outfit – For temples (shoulders/knees covered)
Comfortable Sandals/Sneakers – For walking and exploring
Swimsuit & Cover-Up – For beaches and islands
Bug Spray & Sunscreen – Tropical weather essentials
Rain Jacket/Poncho – If visiting during rainy season
Small Backpack/Crossbody Bag – For day trips
Power Adapter – Thailand uses Type A, B, C, and O plugs
Medications – Basic first aid, motion sickness, stomach relief
Maldives Packing List (Short & Essential)
Light, Flowing Clothing – Beachwear, resort casual (no need for heavy clothing)
Swimsuits & Rash Guard – You’ll be in the water a lot
Reef-Safe Sunscreen – Required to protect marine life
Flip-Flops & Water Shoes – For the beach and coral areas
Sunglasses & Hat – Strong sun protection is a must
Underwater Camera/GoPro – Capture the stunning marine life
Light Sweater/Shawl – For breezy evenings
Snorkel Gear (Optional) – Resorts provide, but you may prefer your own
Dry Bag – To protect electronics while on boats
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