The Vacation Booking Timeline

Step One

Where Should I Go?

6+ Months Out

The most important question you need to ask yourself; this is where it all begins. Having an idea of where you want to go way in advance is very important. Knowing where you want to go enables you to you accurately estimate your vacation costs and allows you to set budget goals.

This can be anywhere in the world, no place is too expensive as long as you have time and patience. If you need ideas, check out some of my trips!

Where to Go
Vacation Booking Timeline

This is the part where you really start looking into prices and start planning around your budget. This is a pretty in-depth step, but I’ll outline some of the key points and link to some great resources for more detailed instructions.

Step 1. Google the on/off seasons for your destination.

Off-season prices will always be lower!

Step 2. Use Google Flights to find the cheapest days to fly.

Find Instructions Here!

By simply combining those two tips, you can save yourself hundreds, if not thousands of dollars on your next vacation. Even if you want to travel during the on-season, looking up specific days in Google Flights will still get you on the right track to saving money!

Step Two

WHEN Should I Go?

6+ Months Out

Vacation Timeline

Step Three

Book Your Flights

2-4 Months Out

Now for the exciting part; this is when things get REAL. You have done your research, you have some dates in mind, it is now time to go ahead and book the flights.

Let’s say, for example, after your reasearch you have determined that the cheapest and best time to fly to your destination in August. This means you should be looking to book your flights in the May/June timeframe. Statistically this is when prices will be at their lowest.

Enter the dates you found on Google Flights into our Flight Booker by clicking below; powered by JetRadar. This scans ALL the companies that offer those flights across the Internet and delivers to you the best deal possible.

Vacation Booking Timeline

Now that your flights are booked and your dates are set in stone, it’s time to book your lodging. You have a few choices:




Hotels are the easiest; Airbnbs are the best deal; and hostels are the cheapest. There are pro’s and con’s to each. You can read more about Airbnbs and Hostels, here and here; respectively.

Unless you’re looking into an exclusive resort, booking your lodging two months out will give you plenty of time to find the perfect spot. When it comes to booking hotels, book with us by clicking the button below. For Airbnb, go with And for hostels go with

Step Four

Book Your Hotel

2 Months Out

Vacation Timeline

Step Five

Book Your Activities

1 Month Out

The heavy lifting is now out of the way! You have means of transportation and a place to stay; the two most important pieces. Now time for the most exciting piece: the adventures!

Your best bet is to use to book all of your activities. One month ahead of time offers various benefits which I cover in-depth here. A cliff notes of the article is that it saves you money and saves you time. Who doesn’t love saving money and time?

A quick way to get to the TripAdvisor page for wherever you’re going is to simply go to Google and search “Things to do in ‘City’.” Replacing “City” with wherever you’re going, of course. TripAdvisor will be one of the first results.

Floaterly Home Page
Vacation Booking Timeline

Now that you’re about two weeks away from the big day, it’s time to do some last minute arrangements. This could be booking a rental car, reconfirming with work that you are clear to take off, or even ensuring you have a ride to and from the airport. 

This is pretty much final review of everything to ensure that your trip runs smoothly and everything is taken care of to make you as stress free as possible. My advice would be to sit down and brainstorm/write down a checklist just so you could be extra sure!

Step Six

Last Minute Arrangements

15 Days Out

Vacation Timeline

Step Seven

Enjoy Your Trip

The Day Of

You have made it to the end, congratulations! You have earned your vacation. Make sure you have your passport if needed, your medicines, and any other crucial stuff. 

I hope you have a great time. Feel free to email me about your trip and share your story! I can be reached at

Smooth Travels!

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