How To Take 1 Vacation Every Month (Hint- It’s Easier Than You Think)

How to Take One Vacation Every Month

No More Stress From Work by Taking 1 Vacation Every Month

Do your days seem to drag by more slowly than ever?

Is the only break you seem to get from your job/daily life a once a year celebration?

Don’t you wish you could enjoy the vacation days you have more?

You’re not alone.

The obsession with the “massive annual vacation” as a concept has long been a focus of the full-time employee. The visions of relaxing on a beach, being massaged, enjoying some of the best food in the world for a month leads many to put off more frequent but equally satisfying experiences in favor of great escapes.

The problem is that studies have suggested that more frequent siestas offer far more satisfaction than those of monumental trips and a higher baseline of happiness. For this reason, we put together a step-by-step guide for readers that are willing to enjoy the finer things in life more often.

The Truth About Taking A Vacation Once A Month

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Everyone wants to know, how is it possible to enjoy a vacation once a month? More often than not, the answer is simpler than you might think. Here are a few of the more common questions we receive:

How Many Days Should a Vacation Be?

The ideal vacation can be as little as three days to as long as five days to eight days. The longer a vacation doesn’t automatically mean that it will be a more enjoyable one. While the traveling cost itself is a priority, the other factors such as jetlag & travel time itself play into the overall choice for the length.

The smaller vacations should be about 2-3 days. The mid-range ones should be about 4-6 days. The bigger ones can be 5-9 days ideally.

What Is the Best Month to Go on Vacation?

There is a complexity to vacation planning based on yearly trends that most people overlook. Many take the end of the year months off as habit to enjoy the end of the year with loved ones or just because it’s what everyone else does. The best months to go on vacation is January, June, & September.

The reason? These are the least used times in their respective seasons. These are the lighter holiday times that offer cheaper costs for travel as well as accommodation as well and are less likely to be requested off. October, November & December each have several family-oriented holidays. Summer is busiest in the middle to late in the season.

January’s inclusion is because it is past the New Year’s Christmas rush which means if you are at work during December before while everyone else is clamoring to wait in long lines elsewhere, you are offered a bit of tranquility.

Why to Opt for Quantity Over “Once in a Lifetime”?

Once In A Lifetime” vacations are rarely what you expect them to be. There is no correlation between the length of a trip and the ability to enjoy it/satisfaction. The best way to use vacation time is to use them as breaks in the monotony of long work weeks without respite.

They’re the opportunity to lower stress levels and prevent burning out. Yes, bigger trips offer the chance for adventure, new experiences, and travels, but going all in on one trip a year or every few years doesn’t work in the long term.

Figuring out Your Trip Plans/Making It Work for You

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It’s better to go on at least one vacation a month broken up based on time, distance, and cost.

Step 1: Isolate What You Want out of Your Holiday on Three Levels

  • Smaller trips act as quick reprieves. These can be as simple as spending one to three days going camping, to a city nearby, or any other quick experience that's in line with your hobbies/interests. Sightseeing, museums or gallery visits and more are all smaller parts that can make up how your time is spent. The biggest key is to minimize travel time and map out what you want to get through as realistically as possible.
  • Medium sized trips should be anywhere from four to six days, these can be slightly farther trips to places within six to eight hours travel time. If you're based on the south-east, for instance, traveling to many top destinations such as Montreal, New York, Miami, A host of Caribbean islands and more can be done for as low as a couple of hundred dollars. Within each boasts their own unique culinary and entertainment opportunities that can be taken advantage of regardless of budget and you can experience a different rich culture than what you are used to.
  • The biggest trips can be anywhere from at absolute minimum five days to nine days. These are trips/vacations that are travel based that include either a final destination that is up to twelve hours away by flight. These trips require more planning and more resources, but they tend to mean taking a bigger leap than the rest out of your comfort zone.
  • ​When picking locations, don’t pick based on what is popular.

​Answer these questions​


  • ​What do you want to do at each level of trip? (Make a list of activities you enjoy that you normally don't have time for)
  • ​What is your priority/main factors for picking a vacation/destination?
  • ​What responsibilities will need to be handled on each level of trip? (This includes pets, kids, and home maintenance but can also include job responsibilities that need to be covered)

Step 2: Research Which Locations Are Easily Accessible and Fit Your Criteria & Which Ones Aren't & Rank Them

  • ​When picking when to go which places and how to go, take into account your location. Major cities have the benefit of having a plethora of flight options and depending on which airline is based or has a hub in your city/nearby the locations that you can easily access cheaper flights from will be specific.
  • ​Within each vacation, make an extensive list of the options that fit the activities/experience you want to have. You wouldn't go to Miami for camping any more than you would go to Tijuana for a family trip. Rank your locations & respective activities based on cost, distance, and how much you value the chance to enjoy the experience.​

Step 3: Plan the More Extravagant Trips First

  • ​If cost-effectiveness if your priority, then looking at location's offseason or slower season is a great chance to make the most of your vacation. As long as the offseason weather in the destination you choose isn't bad, you can still benefit from much of what the area has to offer without dealing with the massive tourist influx and pricing of the high season.
  • ​When it comes to longer trips, accommodation needs to be thought of differently. There are a myriad of specials and discounted deals that are offered by travel and hospitality providers. If you don't intend to rent a car or use a shuttle service beyond Uber and Lyft or whatever local option is available, then looking for more comprehensive housing options beyond hotels gives more control over what you need vs. what you pay. Airbnb's are the most flexible option because of the range of possibilities for amenities and price range as well as location.

Step 4: Plan for Combined Holiday & Weekend Vacations

  • ​Combined holiday and weekend vacations fall into the medium tier.
  • ​These work by making the most out of the natural weekend extension that happens from holidays. These usually offer the best chance for the longest trips without taking too much of your paid leave.

Step 5: Ensure the More Mundane Tasks Are Accounted for & Plan for Your Returning Transition

  • ​When wrapping up your planned schedule for the year regarding when and how you will take your vacations, don't forget to take into account your transition from working/daily life and what you have to do to get back to it.
  • ​Have babysitters/pet sitters/homesitters accounted for long in advance with backups in place.

Example Vacation Schedule

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Let’s say Sarah has 21 days of paid vacation a year, and nine days of sick leave. Altogether, roughly about a month’s worth of time. This can be broken up into a handful of sick/mental health days and the rest used for vacation.

So, imagine three days spent with the flu during the flu season and one for a court date, with 26 days left over that are usable.

If Sarah is a federal employee for the VA hospital, she gets a federal holiday schedule.

The main holidays for federal employees in the US are:

  • New Year’s Day (January 1).
  • Birthday of Martin Luther King, Jr. (Third Monday in January).
  • Washington’s Birthday (Third Monday in February).
  • Memorial Day (Last Monday in May).
  • Independence Day (July 4).
  • Labor Day (First Monday in September).
  • Columbus Day (Second Monday in October).
  • Veterans Day (November 11).
  • Thanksgiving Day (Fourth Thursday in November).
  • Christmas Day (December 25).
Escape Monthly Holidays 2019

The Federal Holidays in USA for 2019, and example of vacation ​length in bracket. Click here​​​​ to download full-sized image for print out.

A majority of the off days are in the first and fourth quarter. That means in between; there is even more opportunity to use time off during those times to elongate holidays into combined weekends suitable for trips.

  1. If MLK’s birthday is used, that means a three day weekend can be turned into a four or five day weekend, or used as is.
  2. Memorial Day and Labor day also fits.
  3. The other days with a similar calendar setup can be used, but the main point is to use the natural opportunities for the middle to bigger trips. That means it’s possible to spread time apart over those three holidays for medium to longer holidays and then use the remainder days to elongate regular weekends into small to medium holidays without needing to miss out on any family time or run afoul of vacation days.

Bolivia Exploration

Assuming she’s located in Atlanta, Georgia that turns into:

January:

  • The third weekend extended could be a middle to grand trip to Mexico for the weather.

February:

  • The third weekend could be a small to medium trip to Tampa.

March:

  • No Natural Holiday, so a weekend can be extended to a small to medium trip to Miami.

April:

  • Same as March, Charlotte as a closer option.

May:

  • Last Monday that could be elongated and turned into a massive trip since it could bleed into June by taking the week off. Perfect opportunity for a summer starting trip that requires going a distance such as London.

June:

  • Earlier to the middle of the month is better to take a small vacation, since the closer to the end of the month the higher the chance of running into 4th of July and school’s letting out, so consider an in-state escape.

July:

  • Middle to end of the month is better for small to medium trips since to avoid the 4th of July season, or, take a longer weekend to celebrate the 4th of July.
  • Suggestion: Charleston, South Carolina

August

  • Same as March.
  • Suggestion: Asheville, North Carolina

September

  • Labor day is a chance to take an elongated trip and turn it into a medium to large sized trip.
  • Suggestion: Dominican Republic, Bolivia

October

  • Earlier in the month is better due to Halloween. Columbus day is a perfect holiday for an extended trip to Portland.

November

  • Two opportunities, one for family and one to get away on a medium/smaller trip to New York or Boston.

December

  • Best chance to take a smaller trip early to Augusta and still get back in time for family. If the idea of freezing cold weather and family arguments are simply too much to handle, then a Christmas getaway to the warm tropics might be just the ticket.
  • Suggestion: Cities from the Southeast Asia region like Singapore, Philipines and Bangkok are some of the perfect places to spend a relaxed holiday away.
Escape Monthly Destinations 2019

Example of the destinations you can travel to in a year. Click here to download the full-sized calendar template for print out.

To Wrap Things Up

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With a schedule like this, as you can see it’s easily doable to fit a variety of different travels or vacations inexpensively into a year without needing to compress it all into one month.

You can have something to look forward to every single month opposed to living for just one month a year. Its worked great for us, and we are sure that it will work just as well for you.

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​Starting planning your first few trips today, you won’t regret it!

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