Dappered Classics: How to take a vacation & actually enjoy it.

Originally Published 12/20/2010

1. Know the difference between a vacation and an obligation filled trip.

When someone asks you what you’re going to do with upcoming time off, you should be borderline if not totally thrilled with your plans.  If the words “We have to…” start your answer, then that’s not a vacation.  Running yourself all over the country attempting to spend time with every distant relative is futile.  And it’s not just relatives either.  If you feel obligated to see someone and the purpose of the trip is to rid yourself from the guilt of not seeing them, then it’s not a vacation.  No one ever felt relaxed after a whirlwind tour of desperately trying to prevent hurt feelings.  If these people are getting offended because you’re not killing yourself to see them, who are they more concerned with anyway?  Planning a vacation is like planning a wedding.  It’s not about the people on the guest list.

2. Stay disciplined on your time off.

Just because you don’t have to work the next morning doesn’t mean there aren’t consequences for being fat, drunk and stupid.  Even if you’re heading to Las Vegas, reconsider any plans to reenact The Hangover during your time away.  Get some sleep, don’t get drunk (every night), and if you’re into exercise?  Exercise.  Bring a pair of running shoes and make use of the hotel’s fitness room.  Or better yet… find a few running trails and get outside.

3. Go somewhere with a group of friends

Hardly anyone ever thinks to travel with the group of people they choose to spend the most time with.  The cliche is “you can’t choose your family.”  Right.  And that’s why you should think about taking off with your friends on a vacation.  Doesn’t need to be some month long tour of Europe.  Maybe it’s just booking all the rooms in a cool looking Bed and Breakfast.  Or renting a cabin in ski country.  You don’t need a set plan and you don’t need to all be attached at the hip.  Plus, a lot of places will offer group discounts.  Keep the planning uncomplicated.

4. Come back a day early.

It makes a massive difference.  Having that extra day at home to get back into your routine can be remarkably enjoyable.  You’re not rushed, you’re not stressed, and you won’t be exhausted the next day at work.  Plus, if for whatever reason your travel plans get disrupted, you won’t have to take an extra day of unpaid time off.  Always leave some wiggle room, and having a whole day to get back in the swing of your day to day life pays serious dividends.

5. Don’t even leave in the first place.

You can take a vacation without actually going anywhere.  Chances are you’ve worked really hard to make where you live a place you love to be.  Always leaving it behind when you have the time to enjoy it seems counterproductive.  Make a short list of the things you love to do, then do them.  Maybe splurge on dinner at an amazing restaurant, then stay at the best hotel in town for a night.  That’ll be cheaper than airfare.  Watch a movie.  Hold a poker party.  Go to a game or a show.  Make a drink, sit in your favorite chair, and doze off guilt free.  Could be the most cost effective yet completely relaxing vacation you’ll ever take.

Got any other tips for how to make the most of your vacation?  Leave them in the comments section below…