Define your travel goal

One thing that I usually start with is to define what I’m looking for in this trip. Do I have a specific place in mind that I want to go and why? Did I just have a stressful work week and needed somewhere to unwind? How am I on budget?


Depending on the answers, my destination varies from flying to a neighboring city like Seattle, Portland or Los Angeles, driving to the closest national park or splurging on two-nights at Post Ranch Inn in Big Sur (this never happened because it’s crazy expensive but it could be one of your options if you can afford it :p).

Now, here are the 5 steps that I usually take..

1. Always get the hotel reservation first 

The hardest part of traveling is making it happen. We’re always thinking about it but it’s so hard to take that first step, isn’t it? One trick that I always do is making a hotel reservation first. Even though the dates are probably not set yet.. or I haven’t even asked for that vacation yet.. it tricks my mind into thinking that the trip is happening because hey, I already got a room.


The reason why making a hotel reservation is the ideal first step is because sites like booking.com and hotels.com offer options to pay when you stay AND free cancellation. That means you have zero commitment until the rest of your trip is settled and finalized. Just remember to set reminder on your calendar to cancel if you can’t make it!


Don’t spend too much time worrying about which hotel room to get. Just find a decent one that fits right in your budget and offers free cancellation. The fun in finding the right hotel can wait until you get to the later step.

Also, I’ve heard friends saying that making restaurant reservation does the same trick to them as well.

2. Look for flights

Now once you finally get that vacation approved or a date settled.. it’s time to book your flight. You can skip this part if your weekend travel doesn’t require flying.

I have been a huge fan of frequent flyer programs and many of my flights were paid by miles.  I’d introduce you to the world of churning but I don’t think I have enough expertise or confident to write a blog post about it, so if you’re curious, google it. And thank me later.

I wrote a post about how I got my first class ticket on Singapore Airlines for only $48 on a previous post. In the post, I briefly explained how the whole credit card point -> miles works so check it out if you haven’t. It is also important to pick an airline that you love and be loyal with it. I have been a loyal flyer of two airlines - Alaska Airlines and Delta. I have credit cards for both company so that gives me free checked bag on every flight. Both also offers affordable tickets for as low as 5,000 and 9,000 miles per flight.






Alaska Airlines also often have deals for as low as $49 to certain cities. I just saw this a couple of days ago.

3. Find the perfect accommodation for your trip

Once the flight is booked, you know for sure the trip is happening. This is where the real fun begin.. looking for the right accommodation. If the hotel that you booked on the first step checks all the box, that’s great, skip this part. If you love looking for just the right hotel as much as I do.. feel free to spend a bit of time doing your research. And if you find a much better accommodation than the one that you’ve already reserved, always remember that it costs nothing to cancel :)



First thing that I do is to only choose hotels that have a rating of higher than 8.8 on booking.com / hotels.com. I find their rating system to be pretty accurate when it comes to the hotel’s service, cleanliness, comfort, location and amenities. Then, I’ll head to Trip Advisor and look for the recent comments. I find people are way nicer on Trip Advisor than Yelp so I would cross reference with Yelp just to make sure there are no red flags. I also like to read the one-star comments just to get a sense of why people aren’t liking it. If it’s about the service, I won’t care as much. What concerns me most is the hotel’s hygiene and safety.

Oh and one more thing.. whether or not the hotel is haunted. Yes I’d look for keyword like ‘haunted’ or ‘ghost’ on Trip Advisor just to make sure I don’t end up staying in a ‘nice but creepy’ hotel.



I also tend to look past all the professionally taken photos of the room and look for real photos taken by hotel guests because sometimes they can look way WAY different.

4. Start planning your itinerary

Depending on the kind of trip you are taking, this step is completely optional. If you’re super chill, go-with-the-flow types of travelers, you can swing the whole scene and not worry too much about itinerary. I personally can go to both extreme ends;  some trips I’d take it chill and some I would be super prepared. My favorite tool to help me get started with is Google Map. It helps me visualize where all the sites/activities are located and how far they are from my hotel. This also reduces the element of surprise. You won’t be discovering that a particular site or activity is much farther than you anticipated.

An example of my super thorough itinerary would look something like this:


Always remember that your itinerary only serves as a guidance and not something that you should get too attached to or you’ll be disappointed.

When it comes to finding list of things to visit or do, my go-to resources have always been people’s blogs. I find them more personal and less ’touristy’ than the typical ’Top 10 things to do’ article on U.S News Travel. An easy way to get to those blogs is to search through Pinterest. I don’t spend too much time on it though because we all know how much of a rabbit hole Pinterest can be.



Travel vlogs on Youtube are also great resources and entertaining! Strongly recommended to those who don’t like doing research through reading multiple blogs.

5. Go and have fun!

You’ve now done all the hard work, it’s time to pack your bags and go! I always believe that if you spend extra time doing your research before the trip, you’ll minimize the amount of time spend in your hotel frantically trying to figure out what to do and where to go for the day. Also, since it’s a vacation, you’d probably want to spend less time looking at your phone browsing the internet!

I hope this post will help you find some clarity and get excited to plan your next trip.

Also, if you’re looking for some ideas for your next destination…

I hate to make the title sound like a clickbait marketing but I really did fly Singapore Airlines First Class and only paid $48 last year. Here’s how I did it..