The Ultimate Guide To Booking The Perfect Vacation

This is my guide on how to book the perfect vacation! I’ve taken many vacations all over the world and continually strive to make things easier and more comfortable for myself. This is what I’ve learned.

How To Book The Perfect Vacation

I’m an incredibly lazy person. But the clever lazy that makes me work incredibly hard to make things easy and more comfortable for myself.

I used to plan my trips meticulously, blocking out a few days to explore a city before moving on to the next. Now, I never do any major pre-planning. Vacations are easier when you can actually relax and take your time to explore a place. Sometimes you run into bad weather and lose a few days. In rare occasions you might get sick while traveling and miss out completely on a destination if you have a multi-city trip planned.

Book One-Way Flights!

On a typical vacation, I only book one-way flights. It makes more sense if you want to see more places while saving time and money.  Let’s say you live in Los Angeles want to go to London and Paris. Booking a round trip ticket to London would be a waste of time if you’re also going to Paris. Typically the costs are almost the same if you try booking a multi-city ticket. You could book a flight from Los Angeles to London and then fly back from Paris to Los Angeles.

Block Out Time And Have A Flexible Schedule

The perfect vacation is made with a flexible schedule and loose plans. You have to account for bad weather, getting sick, canceled flights and anything else that could cause your plans to change. That’s much easier when you have loose plans.

So if you’re planning a trip to Berlin and Rome and can be on vacation for 16 days, then just start with the airline ticket and book everything else when necessary. Even booking things on the same day is fine. Sometimes I’ve arrived in a city without a hotel, walked into a hotel, got on their wi-fi and booked the cheapest rate I could find for that hotel. In very RARE cases, the booking rate in person is cheaper. A majority of the time it’s MUCH more.

Loose Plans Allow You To Stay Longer Or Leave Earlier

If you’re exploring a new place or a place you’ve been before, it’s hard to determine how long you want to stay in a city.  Conditions like weather and political strife also play a role. Sometimes you might not like a place and want to leave. Other times you might love a place and want to stay longer. Loose plans allow you to have the vacation you want.

FYI, I always give a city at least 3-nights. It lets me get a good feel of the city and I can give a solid opinion if I like it or not.

Loose plans also allow you to make last minute changes with no problems. I plan my vacations around sunny weather because I go out much less when it’s raining.

Book Hotels in Advanced But With Free Cancellation

You’re not always getting the best deal when you book a hotel, so I book hotels with free cancellation. I also create Google Calendar notices when the free cancellation is about to expire. Because sometimes when you book a hotel in advance, the price drops! When you have a non-refundable booking you’re absolutely out of luck (unless of freak weather). So it makes sense to book in advance and have that free cancellation ready in case the price drops.

Free cancellation is also great because you have the option to adjust your vacation plans WHILE still on vacation.

On previous vacations, I’ve had week-long stays booked for Melbourne, Dublin and Chiang Mai. During my vacation in Melbourne and Dublin, I did not enjoy the city and wanted to get out of town. Luckily I booked 3-nights, and then individual days after that with free cancellation. In Chiang Mai, I had a week booked and ended up staying there for 10-nights.

Traveling While Sick

Have you traveled while being sick before? It’s awful. Traveling while hungover can be just as bad. You’re body just wants to rest and recover instead of traveling to/from airports with luggage and waiting around in chairs. That’s not a great way to spend a vacation and not a great way to recover from being sick.

I always travel with some cold medicine or ibuprofen if I get sick. I’ve been in situations where I was traveling alone and had to make it to a pharmacy while being delirious and trying to explain that I need medicine. This happened to me in China, Iceland and Mexico. Now, I carry medicine.angel statue

Book Tours

In most big cities there are free walking tours. You can just go to Google and search “(city name) free walking tour” and you’ll find a few.  Free tours are a nice intro to the city with no obligation of having to pay them unless you think they deserve it. In every free walking tour I’ve been on, they’ve deserved a tip, which is how they get paid.

Other than free walking tours, you can book paid tours. When I first started traveling I didn’t believe in taking tours. I thought it was a waste of money. In some cases, it is. But if you go on a good tour it helps you learn much more about a place and you’ll have a deeper understanding of the city and the people.

For paid tours, avoid BIG tours. Big tours mean you’ll move much slower and you won’t learn as much from the guide because they have to cater to a big audience. Small tours tend to cost more but it’s a more casual experience where you can learn a lot from the guide and from the other people on the tour. On some of the small tours I’ve been on, I’ve made really good friends that I’ve been in contact with over the years. the dark hedges


To have the perfect vacation; book one-way flights, block out time for the vacation, keep your plans loose, book hotels with free cancellation, bring medicine and book tour. That’s it. Now go out and have an adventure!

Comments are closed.