Planning Your Dream Trip…On Your Own!

So, you want to go on that dream trip, and you want to plan it on your own but don’t know where to begin? You’ve come to the right place! This Travel Planning Guide will hopefully serve as a blueprint for your perfect trip and help you make it memorable and avoid unpleasant surprises or disappointment.

Generally speaking. We like planning our own travel for a variety of reasons. We’ve come to enjoy the challenge of putting together the itinerary. We’ve had mixed experiences with travel groups and tours (with guides, itineraries, and fellow travelers). Our interests may vary from the mainstream in that we might prefer more nature walks, scuba diving, or some foodie highlights.

In a nutshell, once you’re over the scary part of ‘where to begin’, it’s wonderful to have the flexibility at the destination to have the perfect vacation for YOU even if it does not match the ones tailored to the masses. On top of that, we can generally save a fair amount of money by bypassing the tour companies.

Of course, for those that don’t have the time or are already getting stressed out at the prospect of all that planning, well, maybe for you an organized tour is perfect. Even then, we hope you’ll get some insight from our guide that may help you better prepare, better choose a tour, or even come to realize that YOU CAN DO IT and give it a try…

The basics: Where? What? When? How long?

Choose WHERE you want to go

So where to start and how to begin. Of course, the first step is where to go! Yes, perhaps you are past this point, and have a destination or a general area selected. Maybe you’re just thinking of going to a beach resort to relax or you want to take a cultural trip to Europe. Well, search around for some trip ideas and have a look at some of our travel destinations in our travel ideas section. For example, I hear people tell me that they want to visit Canada. It’s hard not to laugh considering how large and diverse Canada is as a country!

Figure out WHAT you want to see

Once you have an area selected, be that a country, a region or a city, you can start doing more research: What do you want to see and do there? How far apart are the attractions? How much time are you thinking of staying in each place? This helps you start planning the itinerary and group together attractions and destinations.

Decide WHEN you want to go

Consider the best time of year to visit. If flexible, we’ve often found the shoulder seasons (just before or just after the busy season) to be the best times to visit. Less crowds, discount accommodations, and more availability on flights!

Of course, sometime outside influences  will dictate when we can take our vacation. For example, the decision might be taken out of your hands if you have pre-determined vacations dates set by your employer or if you find a  flight deal that you can’t pass-up.

Have a rough idea of HOW LONG you want to (or can) stay

Sometimes, we don’t have the luxury of unlimited time or budget to spend as much time as we would like on our travels. But that being said, regardless of whether you have 3 days, a week, two weeks or a month, splitting up the itinerary to make the most of your visit is best. Start by including attractions that are ‘must-sees’ and work your way down the list to the ‘nice to haves’ and see what you can fit in.

Further, make sure you don’t spend all your time on the road between stops, you want to enjoy the attractions (not just tick them off a list as done!). For more details on this topic see our post: Make the Most of Your Vacation… Power travel!

Now that we have the basics, let’s get into some details.

Research the place

Today with so much travel information available online it would be difficult NOT to find a myriad of information on all but the most extreme exotic destination there is.

Some ideas are:
  • Look at what some of the major tour companies do in that region. National Geographic, Globus, Trafalgar, look at their itineraries, and check out how long they stay in each area. Note down your must-see places.
  • Look at flight options and compare pricing and routing to get to your destination. Note that sometimes flights go on only certain days of the week.  See our other travel tips about flights.
  • Two One-Way Tickets Can Save You Money
  • Check hotel availability. Ask family and friends for recommendations and use sites like TripAdvisor for reviews of hotels too. But remember that there are always some bad reviews for most hotels. Look at the most recent reviews and take some of the complaints with a grain of salt!

Where to stay

Choose your accommodations based on location primarily, and of course comfort level and amenities. It’s great to have a pool, but if it closes at 6pm and you’re sightseeing all day, why pay the premium?

Make sure you are close to the attractions, so you don’t waste your time commuting when you are at your destination. Also, make sure that there’s a choice of eateries near your hotel and look on sites like TripAdvisor for reviews of local restaurants. (See our reviews)

How to get around

If you’re staying in multiple cities, research the transportation options between your stops. You have lots of options:

  • Hire a driver.
  • Take the train (this is often ideal for European destinations).
  • Fly on a cheap local flight.
  • Rent a car.
  • Take the intercity bus.

Useful posts about transportation:

Depending on where you are visiting these choices may vary a lot based on the safety of the location, your own comfort level and cost vs. convenience.

You also have to consider local travel options at each destination. You should also group sites together into general areas to minimize local travel time.

  • Use public transportation
  • Consider the tourist bus (Hop-on Hop-off) if offered.
  • Take taxis or ride-sharing services (Uber, Lyft).
  • Walking

Before you book

  • Check the timing of your plans and look also for any local festivals going on. You don’t want to be running with the bulls to get to the airport—unless you were planning to!
  • Before booking any of the flights or hotels, we like to have a basic plan in place or at least a general idea. This may be as simple as knowing we want to spend 2 weeks in a place and booking the international flights.  In most cases, hotels can be booked with free cancellation so that if your plans change or you can’t get the flights you wanted you can easily adjust your plan.

Before you go

  • Verify if you need a tourist visa.
  • Check on vaccines and health warnings.
  • Make sure you have a supply of meds ordered ahead of time.
  • Double check your reservations to ensure all is in order
  • Get some local currency.
  • Read up on the culture to avoid faux pas (blunders).
  • Ideally learn a few words in the local language or note some down (or get an app).
  • Email the hotels and highlight any special occasions and ask for their nicest rooms in your category.
  • See if the hotel offers a free shuttle to/from the train station or airport, perhaps they offer tours.
  • Check our packing list and take into consideration the destination’s weather.

Now we are starting to get something that is shaping up like a plan.

As things start to come together, keep them in a folder or binder and keep them up to date as the trip approaches. If you are up to the challenge, it’s extremely rewarding planning your own itinerary and making the trip of your dreams come to life.

Good luck and safe travels!