They say that the world is your oyster, but sometimes the knowledge that you can go anywhere becomes overwhelming. With hundreds of countries and thousands of destinations to choose from, the question “where should we travel next?” is not always an easy one to answer.

Friends, family, and our lovely readers often reach out to us for recommendations on great holiday destinations. But instead of rattling off a list of our favourite places around the world, we start by asking a few questions.

What Is the Purpose of Your Trip?

There are lots of reasons to strap on a backpack or pack a suitcase and head to the airport, so what is yours?

Myanmar Bagan O&M-8607

  • Have you been working 10 hour days, 6 days a week, and you just need a break from it all?
  • Are you hoping to get away for a special occasion? Maybe to celebrate a birthday? Or an anniversary?
  • Do you want to escape the from your day-to-day routine and shock your system by experiencing a different culture?
  • Do you want to challenge yourself and add a sprinkle of adventure to your lifestyle?
  • Carefully consider your deepest desires to get to the root cause of what’s driving your desire to travel.
  • What needs are you hoping to fill? What feelings are you hoping to evoke?

The more you think about the why, the easier it will be to figure out if a certain trip will help you reach your objectives and fulfill your physical, mental, and emotional needs.

Who Are You Traveling With?

Whether you admit it or not, your travel partner (along with his or her likes, dislikes, and wants) will play a huge role in the selection of your next travel destination.

Our Croatia sailing crew at Odysseus Cave in Mljet, Croatia

Our Croatia sailing crew at Odysseus Cave in Mljet, Croatia


If you are planning a trip with friends, get together and talk about each one of your “whys”. Get on the same page about what you want to take out of the trip, and what you want to do, see, and experience. Trust us — just talking about the adventures will get your creative juices flowing!

Planning to travel as a couple? Don’t assume that just because you have been dating for one year or have been married for five, you know each other’s preferences, needs, and expectations. Even after years of traveling as a couple, we are still learning to compromise when it comes to our travel plans. Having a chat early on in the planning process is a great way to get on the same page about your upcoming trip.

Max & Oksana overlooking San Juan del Sur. Nicaragua

Overlooking San Juan del Sur. Nicaragua

Traveling with family is a whole other ball game. You’ve got to take into account differences in lodging expectations, activity preferences, physical abilities, travel experience, and much more.

Make sure to have a conversation with your potential travel partners to discuss your wants, needs, and expectations and hear theirs. Try to come to a compromise, but don’t settle for something you know you won’t be happy with. After all, if you can’t find anyone to accompany you on your dream trip, traveling solocan be just as exciting (and often more rewarding) as it is to travel with others.

What Type of Destination Do You Want to Visit?

Once you have an idea of why you want to get away, who you’ll be traveling with, and what your travel buddies hope to get out of your trip, you’ll be in a better position to start talking about specific destinations.

Consider the following questions to help narrow down potential destinations:

  • Warm or cold?
  • City or nature?
  • Beaches or mountains?
  • Adventure or relaxation?
  • Easy to navigate or tough to get around?
  • Historical sites or nightlife and entertainment?
  • Shopping or culinary?
  • Sightseeing or cultural immersion?

How Much Time Do You Have?

Whether you are planning a weekend escape or a six-month backpacking trip, knowing how much time you will have to enjoy in each country and, subsequently, in each city will help further guide your selection process.

If you live in North America and have only one week of vacation to spare, traveling across the world to Australia, may not be the best choice. Consider the time it takes to get to and from your destination and the time you spend moving around within each country.

When we worked full-time and had just two to three weeks of vacation a year, we had a tendency to cram too much into one trip — too many destinations, too many activities, too much moving around. We would come back from our trips exhausted, needing a vacation from our vacation.

Don’t make the same mistake! Instead, plan to take the time to enjoy every destination. If you only have one week, go to one or two spots and allow yourself to really take in the area. Travel is not a race (despite the popular bucket list concept); it’s all about the experience.

Know that the faster you travel, the more expensive your trip will be and that you will most likely need to book activities and reservations in advance to make sure you don’t miss out on adventures due to lack of availability.

What Is Your Budget?

We have managed to travel to dozens of countries around the world on just $50 per person, per day, so we refuse to accept the excuse that you don’t have enough money to travel. You do! The question is, how much can you save before your next trip?

*PS. Here are some of our best tips to help you save for travel!

If your budget is tight, consider traveling to a budget-friendly destination — perhaps somewhere in Central America, Eastern Europe, or South East Asia.

Looking for ways to save without sacrificing your travel style? Look for cheap flights, search for hotel deals, and consider other ways to minimize your travel expenses.

If Travel Planning Isn’t Your Thing…

We think planning for an upcoming trip can be just as much fun as going on it, but we know that a lot of you hate the idea of travel planning. If the idea of doing loads of research and arranging every single detail of your trip makes you dread the idea of travel altogether, consider going the easy route. Book a cruise, jump on a pre-arranged tour, or book a pre-packaged vacation and take the hassle of planning out of travel. You’ll probably pay a bit more than what it would cost you to travel independently, but the hassle free experience might be worth it!

Disclaimer: This is a sponsored post brought to you by Good Search

Have an idea about where you’d like to go next but need a little bit of inspiration? Head over to our Destinations Section and check out all the amazing places we’ve seen on our travels. You never know what might grab your attention!