When to Plan a Trip: Tips to Save Time, Money, and Stress

Trip planning is often a stressful process requiring too many open tabs in your browser, hours of frustrating searching, and ultimately, time and money wasted. The timeline for booking a trip is largely dependent upon when and where you are traveling, what you are doing, and how you are getting there. As a good rule of thumb, planning as far in advance as possible will save you money and ensure that hotels, flights, excursions, rental cars, etc., are available for your specific travel dates.

However, planning a quick weekend trip or stay-cation 12 months in advance is nearly impossible and defeats the purpose of a spontaneous trip altogether. This blog will help narrow down your trip planning timeline and make the preparation process for an unforgettable trip less stressful-- saving you time and money in the process.

image of a map with travel accessories


(About a month ahead)

Money Saving Tips:

According to a study done by TripAdvisor, the best time to book a hotel is about a month before your arrival date to save the most money. On the contrary, Conde Nast reports that the cheapest time to book a hotel is within 7 days of your arrival. However, that’s risky if you are traveling during the destination’s most popular season. 

High Season Travel:

If you plan on traveling during a major holiday vacation (winter break, spring break, Easter, Thanksgiving, etc.) planning far in advance is often necessary to get better deals and find availability. Begin planning about 6 months in advance for high season trips. You might not get the best deals, but it will ensure you have a room. However, if you are forced to plan a last minute trip during the destination’s high season, make sure you first call up your favorite hotels, even if they don’t show availability online. You might get lucky with a last minute cancellation, which happens more often than you would expect. If you didn’t luck out with the most popular hotels, hostels and some less popular hotels usually reserve rooms for walk-in guests; meaning, you can go to reception on the day you arrive and hope they have room availability.

Low Season Travel:

If you are traveling during low season, most hotels won’t be fully booked, so planning far in advance isn’t as necessary or expensive. Hotels offer discounts during low and shoulder seasons, so if saving money is your number one priority, book trips to places that aren’t in their peak tourism period. Compromising a little rain or slightly colder weather for a less expensive or less crowded trip might be worth it.

Check out the graphic below made by Lastminute.com showing the high/low seasons by month.

Image from lastminute.com showing color changes depicting when destinations are in high or low season

Lastminute.com is also a great resource for planning flights, hotels, day trips, and more only a few days before you want to go. It seamlessly searches for the best deals on flights and hotels for trips a few days away. Lonely Planet also has a function on their website that allows you to see the best times to go to certain locations. Simply search a destination and click on “When to go.”


(Depends on popularity)

Activities to Plan a Few Days Ahead:

For the most part, there is no need to book excursions too far in advance. A few days before, or even the day of, is all the time you need. Activities with virtually unlimited space, for example: snorkeling in Belize or parasailing in the Bahamas, tend not to require planning ahead of time. There are, however, exceptions to this rule for extremely popular or special activities.

Activities to Plan Well Ahead:

If you are planning a trip to Peru and want to trek to Machu Picchu, planning in advance is generally necessary if you want a guide. If you want to catch a popular show on Broadway in New York City, these tickets sell out well in advance as well (you can buy them on resale sites but they are usually marked up), so planning ahead would be best. If you are going to Iceland, many things sell out well in advance. Make sure you are booking popular attractions like the Blue Lagoon and popular cave tours well ahead of your arrival date. 


(5 months for international flights, 50-60 days for domestic flights)

The best time to book a flight is the big mystery. Flight pricing algorithms are dynamic and constantly taking in heaps of information in order to maximize profits. If any website or person tells you they have the key, take it with a grain of salt. There are sites that might make it easier, but by no means do they have the solution.

Tools to Simplify the Process:

Google has made it dramatically easier to find which airlines are flying to your destination. Simply search something along the lines of, “Flights from Denver to Mexico City,” and you will find a list of flights—but more importantly—the airline or airlines that fly that specific route.

Simple google travel search of flights from Denver to Mexico city

Kayak, Expedia , Rome2Rio, and Skyscanner

operate in a similar fashion as the simple Google Travel search seen above. They are good tools to get an idea of your options, whether that be different airlines, different layovers, or even different methods of travel. However, it’s often best to cross reference those prices with the prices offered on the specific airline or hotel’s website. Expedia also has bundle deals, where you can book your flights, hotel, and rental cars all in one place, making planning the major aspects of your trip straightforward and easy.

Money Saving Tips:

It is also best to avoid flying on weekends. Friday-Sunday are often the most expensive days of the week to fly, so instead try Monday-Thursday to find deals. Having flexibility in your travel days is a great way to save money.

There is no secret code to getting the cheapest flights. Although there are small tips and tricks that experienced travelers and agencies use to get deals, ultimately, planning far in advance, usually around five months is best for international travel. For domestic travel aim for 50-60 days in advance. You can also check out CheapAir, a website that allows you to search for the cheapest flights and best deals to and from almost anywhere in the world. It’s by no means perfect, but it’s a decent tool that is less overwhelming than Expedia or Kayak. It also allows you to receive alerts when fares change through their fare tracker system.

Helpful Tip:

Most airlines allow you to pay a small amount (or use miles) to hold a fare for up to a week. Spending a few dollars then could save you more money in the long run if you think you found a cheap ticket, but aren’t positive you want to book right then.


It’s a common misconception that website cookies affect flight prices. If you’re afraid of visiting an airline’s site multiple times in a day or on consecutive days because they will increase the price, don’t worry. Skyscanner and Time have done studies disproving this theory. Many factors play into changing flight prices, so you shouldn’t be suspicious of airlines using cookies.

Don’t fall for the classic trap of “10 others have viewed this hotel (or flight, cruise, rental car, etc.) today! Hurry and book now!” It’s a simple psychological marketing tactic to get you to make an impulse purchase. Shop around before making a decision on an important aspect of your trip, and most importantly, be flexible. That spontaneous trip you want to take next weekend may not be the most budget friendly. If you push it out a few weeks, you might be able to find a few deals on flights, hotels, or rental cars.


(A few weeks)

Booking a rental car is also a bit of a tricky process. Much like airlines, rental car companies have algorithms that try to maximize revenues. Interestingly, booking just a few weeks before arrival tends to be cheaper. Check out this article onTravel Supermarket, for a more in-depth break down on why this might be. On the bright side, rental car price changes tend to be less dramatic than airlines. Consider joining free royalty programs for your favorite car-hire companies, which have a bunch of benefits if you are a frequent traveler. Booking on short notice will likely be less of a rip-off if you are part of a membership program as well.

Image of a Hertz Rental Car search a few weeks away showing prices for an economy car

Booking a few weeks in advance.

Image of a Hertz Rental Car search a few months away showing prices for an economy car

Booking a few months in advance.

That’s a difference of nearly $10 per day.


Purchasing trip insurance is a good idea if you are planning anything long before your departure date. You should shop around. Some insurance companies will even refund those “non-refundable” deposits you paid for the flight, hotel, or rental car you planned 12 months ago. Check out InsureMyTrip to compare plans easily. This is a good tool for all trips you plan well ahead of time.

In conclusion, unfortunately, there is no single website, list of tips, or simple secret to planning or booking a cost effective trip easily. However, here is an overview of when we think you should book each aspect of your trip:

  • Hotels: about a month ahead of time

  • Activities: depends on the popularity, but in general, the day of or a few days before is adequate

  • Flights: About 5 months ahead of time for international travel and 50-60 days for domestic travel

  • Rental cars: a few weeks is more than enough time

Beautifully clear, blue, mountain-side lake littered with boats

Too big of a hassle?

Use an Agent

This Daily Mail article claims that people spend an average of 30+ hours planning a trip, and use an average of 38 different resources over five weeks, before a trip is completely planned and booked. That’s a lot!

Agents like Jubel can save you time, money, and stress by planning your ideal trip. No need to scour the internet trying to find the best destinations, bargains, and dealing with fluctuating prices; let an experienced team of travel experts, with a knack for personalizing trips to your style and budget, handle it for you. Stress and hassle free.

Looking to take a new trip soon? Jubel crafts you a personalized experience matching

Your Style. Your Budget. Anywhere