How to Max Out Your Vacation Days

Kay Rodriguez
advo
Published in
5 min readOct 5, 2017

For an adventure-loving young professional, adulthood is all about playing the game. For me, this game was simple: 15 vacation days per year to cram in as much travel as possible.

Challenge accepted.

With 104 weekend days, approximately 11 public holidays, and 15 days of vacation, I have ~130 potential travel days each year to work with. I sought to maximize these days off and take on as many new adventures as possible. In my quest to travel as much as I could, I ended up being able to visit 12 countries and take over 20 trips, all in one year.

After some trial and error, I quickly learned that traveling frequently and working full-time aren’t mutually exclusive. If you play your cards right, you can do both!

A cheap flight and an impulsive decision brought me to Copenhagen for a weekend in August

Be a Weekend Warrior

If you want to travel more while working full-time, you have to learn how to best utilize your weekends. You get 52 of these a year, which gives you plenty of opportunities to get up and explore. “Exploring” can mean jumping in your car to the nearest state park, or checking out a part of your city that you’ve never seen before.

However, weekend trips don’t have to be nearby. In the past year or so, my weekend adventures have taken me to places as close by as Baltimore and as far away as Japan. It can be fun and exciting to think creatively about what kinds of weekend trips you can take — near or far — that make sense for your budget and travel style.

Hiking Mount Fuji was one of the most exhilarating and exhausting weekend trips I’ve ever taken

Prioritize

Almost every single one of my weekend trips involves two things: 1) a great flight deal and 2) an objective. Cheap flight deals are easy to find if you know where to look — some great places to start include The Points Guy and The Flight Deal. The objective, however, can often be a little bit more difficult to pinpoint.

Think, for example, about a weekend trip to Tokyo. Realistically, if you go on a 3-day weekend and leave Friday night, you have approximately 36-48 hours to see everything you want. However, if you go to Tokyo with the objective of stuffing yourself full of sushi and learning about the food culture, your trip will be a lot more manageable. Coming up with just one objective per trip can be hard, but it can also help you focus your limited time on what’s most important to you.

Thanksgiving is always my favorite time to travel — last year I spent it trekking in Patagonia

Extend Long Holiday Weekends

Now that you’re ready for a good handful of weekend trips, plan your longer vacations around holiday weekends. You can easily turn a 3-day weekend into a 5-day weekend by adding in a few extra vacation days.

What’s the jackpot of holiday weekends? American Thanksgiving. With most US employers, 3 vacation days during Thanksgiving gets you an entire week off. Not only is this the best bang for your vacation buck, but it’s also a shoulder season for many destinations, which means you’ll likely see lower flight prices and reduced tourist numbers. Last year, I trekked in Patagonia for Thanksgiving. This year, I’m planning on chasing the Northern Lights in Norway.

Enjoying the sunset in Big Bend National Park during a long weekend trip

Ask for Flexibility

In today’s working world, working remotely is becoming more and more common. Depending on your role, if you feel that you can work remotely, ask your supervisor if you can take a few out of office days throughout the year. This can help you extend your potential travel time even further. If you can work remotely on a Friday before a long weekend, that gives you four whole days to explore a new place. If you have a good relationship with your boss, it doesn’t hurt to ask, and the potential reward is 100% worth it.

At $116 for a round trip flight, I couldn’t say no to the opportunity to visit Cuba!

Be Opportunistic

When I found a $116 round trip flight to Havana, Cuba, I bought it immediately. After stumbling upon a WOW Air flight sale to Copenhagen for $400, I couldn’t resist. Upon entering and winning a contest to go to Iceland for free, how could I say no?

You might think that this kind of aggressive travel is an exception to the rule. Perhaps it is. However, by being strategic and taking a leap of faith on interesting travel opportunities, you, too, can see the world, no matter how many vacation days you have.

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And while you’re on your flight, waiting to arrive in your next destination…

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Kay Rodriguez
advo
Writer for

The only thing I want to do with my life is see, feel, and understand the world.