Cover photo by A Stockphoto

Happy New Year, overthinkers! We are now in 2024 and a new year means new trips to plan.

If you work in a corporate office, it might be time to put in your vacation time. Or you’re someone just trying to figure out what days to choose for a trip.

We’re going to take a look at how to choose time for four trips: Two long trips and two short trips. Of course, not everyone may want to take four vacations in a year but this can be used for a little as just one vacation. For me, the easiest way to plan is to have each trip in a quarter of the year.

My birthday is in the first quarter so I’ll almost always have a longer trip during that time. Sometimes the second quarter also has a long trip but for balance I aim to have another long trip in the third quarter. The second and fourth quarter would have the shorter trips.

Of course you don’t have follow this pattern, especially if you have birthdays or special occasions in other parts of the year for longer trips. Block those times out first. I have a few other things to consider looking at when planning your trips.

Federal Holidays

After any birthdays or important special occasions, look at federal holidays. For 2024 in the United States the federal holidays are:

• Monday, January 01 – New Year’s Day
• Monday, January 15 – Birthday of Martin Luther King, Jr. (MLK Day)
• Monday, February 19 – Washington’s Birthday/Presidents Day
• Monday, May 27 – Memorial Day
• Wednesday, June 19 – Juneteenth National Independence Day
• Thursday, July 04 – Independence Day
• Monday, September 02 – Labor Day
• Monday, October 14 – Indigenous Peoples Day/Columbus Day
• Monday, November 11 – Veterans Day
• Thursday, November 28 – Thanksgiving Day
• Wednesday, December 25 – Christmas Day

That’s 11 different days off! A lot of them are on Mondays which means they are perfect for a three-day weekend trip or longer. I’d suggest planning these for your short trips. You’ll use less vacation time and PTO that way (but it could mean more people in your travels so be wary if you don’t like crowds).

Prices and Flights

Other factors that effect when you go could be prices. For instance, if you go to Disney World in September it’s much cheaper than going in June. Or flights around Christmas or Thanksgiving are going to be more expensive than flights on President’s Day.

If you don’t have a specific destination, Google Travel’s “Explore” option is a great tool to use to figure out where you’re going for your trips for the best flight price. This would be good for someone who doesn’t have limited vacation or PTO hours.

Put in the city of where you’ll be leaving from and just select explore. A map will come up with different prices. Usually the default is for a 1-week trip within the next 6 months. You can choose specific months however, the only downside is that it can only give you up to 6 months and not the whole year.

Cruises

If you’re like me and you like cruising, it’s a great way to spend time for a trip! Cruises can also determine your vacation time if there’s a specific destination or ship you wanted to go on. Cruise dates and lengths will vary so this may also be good for someone that doesn’t have limited vacation time or PTO. Keep in mind the costs to fly or drive to your port of call.

There are so many cruise lines out there. You can use a travel agent, club memberships like Costco or Sam’s, or search engines like CruiseCritic.com or Delta Cruises.

We’ll try blocking out time for the year using these tools. I’ll also be basing this off of 10 days of Vacation time (two work weeks) so you can use your PTO for other things like doctor’s appointments, family emergencies, or more vacation.

If your job lets you carry days over to the next year, you don’t have to use all the days and maybe take an even longer trip.

Federal Holiday Option

First Quarter Trip: Long – 1 Week

I’ve highlighted the federal holidays in blue. Because MLK Day is on January 15^th, this would be a good week to use so you’ll have an extra vacation day to use elsewhere. My birthday is usually around MLK Day so that’s why I’d choose this week: January 14^th-20^th.

Vacation days used: 4 days

Vacation days left: 6 days

Second Quarter Trip: Short – 3-day Weekend

There are two Federal holidays in this quarter just like the first. Memorial Day is always on a Monday so it would be great to plan a trip for a 3-day weekend so you don’t have to use any vacation days! You could fly out Friday night after work or Saturday morning and fly back in on Monday.

This holiday in particular would probably have a lot people traveling because kids would be getting out of school and it signifies the start of summer travel.

A trip could be taken around Juneteenth as well if you wanted to use two vacation days to give yourself a 5-day weekend.

For this example, we’ll use Memorial Day weekend: May 25^th-27^th

Vacation days used: 0 days

Vacation days left: 6 days

Third Quarter Trip: Long – 1 Week

For the third quarter, I’d try to plan a trip around Labor Day because it would most likely be cheaper that traveling during the 4^th of July (at least in the U.S.). September 1^st-7^th

Vacation days used: 4 days

Vacations days left: 2 days

Fourth Quarter Trip: Short – 4 to 5-day Weekend

Fourth Quarter has the most federal holidays. You could probably squeeze in a longer trip if you wanted. Thanksgiving never changes so you could use your 2 days for Wednesday and Friday around Thanksgiving if your job doesn’t already give you those days off. Same for Christmas however, Thanksgiving and Christmas will be super busy.

You could use the 2 days for Indigenous People’s Day and/or Veterans Day to give you a 4 or 5-day weekend.

For the example we’ll use Christmas: December 25^th-28^th

Vacation days used: 2 days

Vacation days left: 0 days

Google Travel Explore Option

First Quarter Trip: Long – 1 Week

Using a 1- week trip in January, most options are giving the weeks surrounding MLK Day but not the actually week of MLK Day.

I chose New Orleans for the example based on the price (and because I’d love to go back).

Once you click on the destination, it shows the dates which are January 18^th-24^th. It’ll also show things to do, flight options, and hotel prices.

Vacation days used: 5 days

Vacation days left: 5 days

Second Quarter Trip: Short – 3-day Weekend

Using a weekend trip in May, again most options are giving the weekends outside of Memorial Day weekend. A lot places show the weekend of May 4^th-6^th. New York and Miami had good prices but I’d probably try Chicago (my favorite city) or Arizona (on my travel wish list).

Vacation days used: 1 day

Vacation days left: 4 days

Third & Fourth Quarter Trips

Because Google Travel only goes out to 6 months, we can’t see the third and fourth quarter trips yet. This is where I’d suggest using the federal holidays or special occasions to plan it out but it can be adjusted once the time opens up.

I also want to note, you can use the explore option for international trips as well, just move around on the map to find more flight prices for the different cities.

Cruise Option

First Quarter Trip: Long – 1 Week

Since we’ve been looking at January dates for a week long, I’ve put that in for the search. However, you can leave it at any length or choose the months for the quarter.

There’s a 7-Night Royal Caribbean cruise that leaves out of Galveston, Texas from January 14^th-21^st to Mexico. I’d still suggest flying in a day before but this should only use up 4 vacation days because of the federal holiday.

You could look for cruises in other places overseas but the long and potentially overnight flights could force you to use more vacation days.

Vacation days used: 4 days

Vacation days left: 6 days

Second Quarter Trip: Short – 3-day Weekend

When searching, all the 3-night weekend cruises leaving from the U.S. were on Fridays. Depending on where you live, you could fly in or drive in the day of but it’s usually best practice to fly in the day before. I did find one the weekend of Memorial Day; Celebrity Cruises leaving from Fort Lauderdale, Florida to the Bahamas on May 24^th for 3-nights. We’ll use these dates as if you fly in the night before (after work): May 24^th– 27^th.

Vacation days used: 1 days

Vacation days left: 5 days

Third Quarter Trip: Long – 1 Week

The third quarter of the year is summer time so there plenty of cruises during this time. I found a 4-night Royal Caribbean Cruise that leaves out of Port Canaveral in Florida on July 1^st-5^th. Fourth of July is in those dates so technically you can use one less vacation day.

Vacation days used: 4 days

Vacation days left: 1 day

Fourth Quarter Trip: Short – 3-day Weekend

The same Celebrity cruise from the second quarter (3-night cruise to the Bahamas) showed for the fourth quarter but for the dates October 11^th-14^th. Luckily, the 14^th is a federal holiday this year.

Vacation days used: 1 day

Vacation days left: 0 days

Yay! All the vacation days planned and accounted for. I hope this different examples can help you plan out your vacation dates whether it’s to plan around work or just to make sure you take some time for yourself.

Next week, I’ll talk about setting a budget for four trips in a year. See you then, overthinkers!