How to Plan the Perfect Itinerary for Southeast Asia (or Any Big Adventure!)

• Packing cubes for organization (bought in 2024, best decision for traveling)

• Smart Tag (thought we lost our backpack in Miami, but finally arrived after everyone had left already)

• Notebook with pre-departure checklist

• Ekrin Bantam (massage gun that weighs 1.1 lbs, bought specifically for travel as we love our Hypervolt, it's great after hikes!)

How to Plan the Perfect Itinerary for a Big Adventure

Planning a trip is an exhilarating process, but it can also be overwhelming, especially when you're stepping out of your comfort zone. Some trips come together easily, while others demand more research, flexibility, and decision-making. Our upcoming two-month journey through Southeast Asia is a perfect example of how much thought and effort goes into crafting a well-rounded itinerary.

Our Planning Journey

When it comes to trip planning, I usually give myself about a month to pull everything together. For Italy—one of my favorite destinations—I’m in my element. I’ve visited the country multiple times, so I can confidently research and refine itineraries, always finding new ways to experience it. However, Southeast Asia (SEA) was a whole new challenge. It required diving into endless Reddit threads, Google searches, and even consulting ChatGPT to make sense of flights, logistics, and cultural nuances.

Our first attempt at a SEA itinerary was overly ambitious, with stops in Laos, Cambodia, and even Australia. But after realizing that rushing between places would sap the joy out of our trip, we scrapped that plan. We opted for a more streamlined clockwise route, but then flight schedules threw a wrench in those plans too. Eventually, we settled on an itinerary that balanced must-visit spots, relaxation, and logistical ease.

The Emotional Rollercoaster of Itinerary Changes

After spending countless hours perfecting a draft itinerary, I showed it to my husband, only for him to suggest changes. I’ll admit—I freaked out. But in hindsight, his input helped us create a more practical and enjoyable plan. Together, we prioritized longer stays (3-4 nights minimum per destination), which has become our golden rule for travel. This approach not only reduces stress but allows us to immerse ourselves in the vibe of each place.

We also came to terms with the fact that it’s impossible to see everything in one trip. Instead, we’re focusing on savoring the experiences we do have, leaving room to return in the future.

The Art of Balancing Exploration and Comfort

A big part of our planning involves booking accommodations ahead of time. Knowing where we’ll sleep each night means we can spend our days exploring and relaxing without scrambling for last-minute options. My husband and I also build in "buffer time" between destinations, whether it’s lounging on a beach or exploring local markets (one of his favorite activities).

Speaking of markets, grocery stores have become a quirky highlight of our travels. Whether it’s hunting for gluten-free products in Puerto Rico or losing track of time in an Italian supermarket, these everyday errands often turn into memorable cultural experiences.

Learning Along the Way

Planning this trip has also inspired me to learn new languages and cultural nuances. I’ve been using Duolingo to learn Japanese and have even dabbled with the Thai alphabet—discovering a knack for it along the way. These small efforts not only enrich the travel experience but also help me connect with the places we’re visiting.

Our Final Itinerary

Here’s what our two-month SEA adventure looks like:

• Japan: Six nights split between Kyoto and Tokyo.

• Thailand: Stops in Bangkok (3), Koh Tao (5), Koh Samui (5), and Chiang Mai (5), blending city exploration, scuba diving, and cultural experiences.

• Vietnam: Exploring Hanoi (2 & 2 Ha Long Bay cruise), Da Nang (3), and Phu Quoc (5) for a mix of historical sites and beautiful beaches.

• Malaysia: A few nights in Kuala Lumpur (3).

• Indonesia: Bali and Nusa Penida Island, plus catching up with friends (10).

• Singapore: Three nights to wrap up the city adventures.

• Thailand (again): Ending with a relaxing stay on the western islands (12).

  
  

In total, we’ll take at least ten internal flights. While the travel pace may feel intense, it allows us to experience a variety of cultures, landscapes, and cuisines—giving us a clearer idea of where we’d like to return someday.

Lessons from Previous Trips

Reflecting on our last big trip to Italy in late 2024, we learned the importance of pacing ourselves. That trip reinforced our preference for staying at least three nights per destination and focusing on quality over quantity. These lessons have shaped our SEA itinerary and will continue to guide our future adventures.

• Clothesline, easy to set up and holds my bikinis while it's windy

• Tide to go, we seem to use it every time

• Wrinkle releaser spray is excellent

• 100 ml bottles for travel

• Laundry detergent sheets (super light and useful)

Closing Thoughts

Planning a trip is a deeply personal process. Whether you love spreadsheets, travel blogs, or the thrill of booking things last-minute, what matters most is creating a plan that works for you. For us, it’s about balancing structure with spontaneity, comfort with adventure, and exploration with relaxation.

As we embark on this SEA journey, we know it won’t be perfect—but that’s the beauty of travel. It’s about embracing the unexpected, learning as you go, and cherishing the moments that make it all worthwhile.

Happy travels, and here’s to planning your perfect itinerary!