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Top Five Stress-Free Vacation Tips

Imagine this: you’re on a secluded beach sipping the beverage of your choice – doesn’t matter if it’s a pina colada or a plain old South style sweet tea; you’re listening to the waves rolling in, and wondering whether you’ll order the fresh lobster or the more exotic conch for dinner. That decision – what’s on your dinner plate – is your biggest worry. There’s nothing else bothering you, no financial troubles hidden in the depths of your mind, zilch, zip, nada. You’re feeling completely, 100 percent stress free.

You’re probably saying, “Yeah right, Daniel. On what planet do you live?” Fair enough. But the truth is, I live on a planet where vacations can be stress free… as long as you take your time planning and financing them.

Stress Free Vacation Tip #1: Don’t Follow The Crowds

Remember back when you were a teenager, and you wanted a tongue piercing because everyone else was doing it? Your mom said no, using the age-old adage, “If everyone else were jumping off a bridge, would you?” to dissuade you. Well, the same theory holds true when it comes to vacation planning.

There’s a reason why a five-star hotel on a popular Florida beach goes for $400 a night – because the property’s managers know they can command that price tag. They know that their rooms are filled on a regular basis, and can charge a premium for that very reason. Hotels – and, more generally speaking, resort towns – that are off the beaten track are more likely to be the ones offering you room discounts, free meals, and other perks to entice you to bring your business to them. Same goes for traveling in the off-season; if everyone is traveling to the Bahamas in the late winter – the region’s peak season – that shouldn’t be reason enough for you to follow them. Instead, find out when your destination’s slow season falls, and book your vacation accordingly to get the lowest prices.

Stress Free Vacation Tip #2: Set A Budget And Stick To It

This sounds like a no brainer, right? Say you plan to spend $2,500 on your family vacation, setting aside
the following amounts:

  • $800 for travel costs
  • $1,000 for hotel rooms
  • $500 for food
  • $200 for entertainment

But once you arrive at your destination, you’re bombarded by incidentals you didn’t plan on. Maybe it’s a $12 photo of you and your spouse about to board a Royal Caribbean cruise ship; or maybe it’s a $15 boogie board at a surf shop. Whatever it is, if you’re not setting aside a little extra cash for expenses that creep up along the way, you’re not accurately budgeting your trip. My standard rule of thumb is to set aside an additional 10% of your budgeted vacation expenses for incidentals.

But this vacation tip goes both ways; just as you shouldn’t overspend on your vacation, you shouldn’t underspend either. I have a friend who recently scored a great deal on a beach condo – I’m talking a deal of a lifetime here: she saved hundreds of dollars, slashing her estimated hotel budget by more than half. Instead of stashing that money back in her bank account, she plans to use it to indulge herself and her family on their vacation. After all, they’ve worked hard for it, and using those funds to pay for a few extra dinners out will definitely make for a more stress free trip than if she was slaving away in the condo’s kitchen every night.

Stress Free Vacation Tip #3: Save, Save, Save

There’s nothing worse than going on a vacation, only to find yourself wondering halfway through the trip, “How am I going to afford all this?” If you’ve ever traveled with this type of vacationer, who charges everything that comes their way without having the necessary funds already in their checking account, you know how miserable they can be. They’re constantly obsessing over every little expenditure, from the hotel bill to gas prices to tipping a waitress.

Instead of stressing over expenses, set the money aside before you leave – long before you leave. Say you’re planning a family vacation to Universal Studios six months from now. Take your budget (don’t forget that extra 10% for incidentals!), divide it by six, and make it your goal to set that amount aside every month until you leave. If you do, you’ll be able to pay for your entire vacation in cash – or, if you use a credit card simply for rewards, you could go that route – without worrying about whether you’ll have enough.

Stress Free Vacation Tip #4: Use A Travel Rewards Card (If Applicable)

I know this is a risky piece of travel advice to give on a personal finance blog, but I’m going to dole it out anyway. Using a travel rewards card can really pay off for certain destinations. For example, Disney offers a Visa card from Chase that includes a $50 gift card to Disney the very first time you use the card. If you’re planning a family vacation to visit Mickey, Minnie, and the gang, that $50 gift card can help defray the cost of your park tickets or room fees. On top of that, you can also earn 1% in rewards dollars, which can also go toward your Disney vacation. Sure, this option doesn’t work for every destination, but there are plenty of hotel chains and airlines that offer credit card and loyalty programs that can help reduce your costs if you know you’ll be using the company’s services.

Stress Free Vacation Tip #5: Leave Your Home In Good Hands

This isn’t technically personal finance advice, but that’s why it’s so important. So many travelers head out the door for their vacation without a second thought to what’s going on at home, only to come back to discover they’ve been the victims of vandals or, worse, thieves; this happened to a good friend of mine when he and his fiancé went out of town over July 4th. Here are three ways to avoid problems:

  1. Let people know you’ll be out of town. I’m talking about your neighbors, family, and – most importantly – the police. Many municipalities will do an extra drive-by of your home if they know you’ll be out of town.
  2. Don’t let the world know you’re going away. This means Facebook – do not, I repeat, do NOT leave a message on your profile stating that you’re going out of town. Even if you think you have your profile information set to private, there’s still no guarantee.
  3. Make it look like you’re still home. You should stop the mail, set light timers, and ask a neighbor to pick up your newspaper (if you’re one of the 1 in 100 Americans who still gets home delivery) so robbers won’t get the idea that you’re out of town.

Following these simple tips can make sure your vacation goes off without a hitch.

Readers, what are your vacation tips for a stress free trip?



  1. Don’t forget travel insurance if you’re going overseas! My wife and I were sick as dogs in Thailand with no insurance and it was miserable. I vowed never to not be covered again. It just leads to peace of mind to have it just in case.

  2. I’m going to be going to NYC in a month or so and we really want to stay up front and center in the action.. I will be certainly more expensive but we do fear that if we don’t, we’ll be spending a ton of cabs and subways anyway.

  3. I always suggest #5. I even wrote a post on it. Make sure there is someone that can watch your house so that you aren’t worrying about it while you are out on vacation! I also am a huge fan of having it paid for in advance. There is nothing worse than wondering how you’re going to pay for your vacation while you’re supposed to be enjoying it!

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