5 Questions to Ask Before You Book a Trip with Your Bestie

So you want to go somewhere with your bestie for the first time.  You’ve never escaped your busy lives to take some time out to adventure the world and you decide, why not spend it with this person I’ve known for years. How exciting!  Or is it?  How would you feel if you’ve anticipated this wonderful trip for so long to be left with a terrible experience as your only memory?  You thought since you both loved the same food and you both knew all the words to every Beyoncé song you’d have the trip of a lifetime. Sometimes the key to a successful trip is less about how long you’ve known each other and more about how well you know each other’s travel habits.  Here are five questions to ask each other to guarantee a smooth drama free getaway.

  1. Where do you want to go?  Seems like an obvious question, but some people try to be more open than they truly are. If you have your heart set on a European getaway where your inner foodie can experience some of the best cuisine you’ve ever tasted in your life, don’t agree to go backpacking in the Rockies. Once you straddle that 8 pound bag full of today and possibly tomorrow’s necessities you will be mad that you ever agreed to such a thing.  Venturing through the unexpected can definitely open your eyes to things you thought you’d never do, but if you know without a doubt where you want to go doesn’t match the vibe your travel companion is looking for at the time, don’t go. If you are a little more flexible and don’t know exactly where you want to go, having a general idea will eliminate frustrations in the long run.
  2. Are you a budget buster or fairly frugal? There is nothing worse than planning a trip you cannot afford.  You don’t want to end up arguing over prices at a restaurant or missing out on an excursion of your dreams because your travel partner didn’t bring enough money. Be honest and let each other know your spending plans. Not only should you discuss your budget for accommodations and airfare, estimate what you can set aside for food, activities, nightlife, airport transfers, luggage fees, taxis, rental cars, souvenirs, and most importantly…the unexpected. It may seem tedious, but trust me it will be worth it.
  3. Are you a planner or do you go with the flow?  Some travelers have to map everything out and there is nothing wrong with that. Especially if you don’t travel often, maximizing your time may be a key priority.  But for others, having a wake up call and planned down time is just not their cup of tea.  Vacations are supposed to be enjoyed and cherished, what good is it to be subject to a miserable itinerary day in and day out or have to endure the person who just goes with the wind because they can’t make up their mind about anything if that’s not your idea of a good time?
  4. Do you prefer Resorts and Villas or will a Hostel do? Never let someone pick where you stay if you haven’t given them an idea of your expectations. The budget you discussed should definitely send off signals, but it doesn’t tell all.  If you both decide where you lay your head is the least of your concerns that’s great! More funds can go towards exploring or a spa treatment, but if you hope to at least have a private bathroom or a bed for each of you, let it be known.
  5. Is the primary purpose of your trip to relax or to explore? Imagine trying to convince your travel mate who just finished the most fulfilling meditation session to go out for drinks and dancing at a local club. Chances are it’s not happening. But what are you to do? Wait for them or just go on your own? The whole purpose of the trip is to spend time together, but you may miss out in the process. Coming to an understanding will facilitate to what extent you do or don’t do certain activities.

One thing you don’t want out of your trip is to create distance and resentment in a relationship. Letting your intentions and expectations be known beforehand will lead to one unforgettable getaway! Now…where to?

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