Trip Planning 101

Have you ever seen an Instagram picture or a scene in a movie that inspired you and left an imprint in your mind as a place you would love to visit? If the image was that powerful the next thing you might have done was look at a map to see exactly where it was or searched it online to get some information about the place. Inspiration comes from many sources and here are 2 situations that inspired my last 2 vacations.

In the first, I was inspired by an Instagram lifestyle influencer. The picture was of a hotel built into the mountainous landscape surrounded by very diverse vegetation. There were palm trees, cactus trees, and tall cypress trees all in a lush forest covered by the deep blue sky. It was a beautiful scene and it completely inspired me as a place I would like to see. I read further into the post and discovered that she was in the town of Deia, in Mallorca. I had never heard of Mallorca, which is a small island in the Mediterranean Sea belonging to Spain. Spain was on our bucket list, but we never had any specific destination within Spain. Visiting the island of Mallorca became the center point of the trip and everything else worked around needing to get in and out of Mallorca. This led us to explore the beautiful Andalusia region of mainland Spain and we became engulfed in it’s rich history, in addition to discovering the vast amount of sites Mallorca has to offer. It was a wonderful trip that I would highly recommend, and it all started by seeing an Instagram picture.

Deia, Mallorca, Spain

Deia, Mallorca, Spain

During the early days of COVID when everyone was staying home, like many people we watched plenty of television and streaming services. We stumbled upon an Italian movie called Malena that was filmed in Sicily. The scenes were stunning, and the story line was captivating. There was a beautiful piazza that was one of the main backdrops of the movie where many scenes were filmed. The piazza had an enormous cathedral surrounded by cafes, all drenched in a warm, honey-hued, baroque architecture. When the movie ended, we had an appreciation for Sicily. It was inspiring and a bit mysterious since we didn’t know anyone that has gone to Sicily. We went from not knowing anything about Sicily to Sicily being our first trip after the COVID travel restrictions were lifted in spring 2022. Sicily was not on our bucket list, however this initial inspiration led to more reading and research about Sicily and we were continuously attracted to the island.

Ortigia, Sicily, Italy

This is how inspiration starts. We embarked on both trips and had a fantastic time and now have wonderful pictures and memories. But why do many people not go on to make their travel dreams into reality? Why only the initial thoughts?

Available money is an obvious reason, but assuming you have money for travel, why do people not move ahead and make their travel dreams a reality? Probably because the next step requires effort and people do not know where to begin. Planning a trip sounds daunting especially if you have never been to that place before. After talking to friends, family, and co-workers there was a common theme of feedback on our trips. ‘Your pictures were amazing’, ‘it looked like you had a great time’, ‘how did you figure out where to go and stay’, ‘I could never plan my own trip, I wouldn’t know where to begin’. It really surprised me to hear that so many of our friends, family and colleagues don’t know where to begin and I thought that maybe there is a way to help and offer some guidance.

Below are 7 easy steps to start planning a vacation and the questions to ask yourself. These steps are mostly for self-planned travel, but many can be applied for pre-packaged travel as well.

1. Where do you want to go?
Are you looking for a beach vacation, a culture and historical sites vacation, adventure seeking or relaxing vacation? Probably every option sounds great, but which really excites you? What have you been inspired by? If you mentally place yourself there, maybe one of your options will stand out.

2. What is there to do?
A huge mistake people often make is not researching what is there to do. Sometimes we are just inspired by a popular place, but don’t know if there is anything to do there that we would like. Plan your days so that you don’t wake up every morning and say to your travel partner, ‘what should we do today?’ Depending on your destination, you may also want to have a rough plan of what you could do in the evenings as well. Places like Italy, you don’t need to plan evenings unless there is a specific event you want to see, since doing the typical after dinner strolls is enough to satisfy the soul and the sweet tooth by the abundance of bakeries and gelatarias. In North American cities we eat earlier than European cities and towns, and therefore you may want to think about what you could do after dinner. The easiest way to figure out what to do is just search online for ‘things to do in’ your destination, and many articles will appear. Once you start reading you will see that most of the articles have a commonality on the things to do and places to visit. Similarly, if you search on YouTube you will find very informative videos on what to do. If you are still inspired by your destination, keep moving on in the research.

3. When is a good time to go?
You need to know both when can you get away and when is the best time to go to your destination. There are many things to consider and look up before you determine when to go. What will the weather be like? Will it be too hot, too rainy or too cold. Are their festivals, sporting events or concerts that you want to see, and when do they occur? Is there a busy season with many tourists that you want to avoid? How many days should you stay? These questions will help you determine when is the best time for you to go.

4. How do you get there?
Do you drive or do you fly? If you drive what does the route look like? What towns would you go through, what sites are there along the way? Can you take a train or a bus to get there? If you fly, what flight options do you have? Are there many flights, are they direct, how long is the travel time and how many days are spent traveling there and coming home? Your travel time will cut into the amount of time you can spend at your destination. It’s very important to consider travel time and time zone changes when planning your vacation as your time is limited and very precious.

5. Where do you stay?
This is probably the hardest and most important question because having a nice place to stay in an ideal location can make or break a vacation. But if you have never been to your destination before how do you find the optimal place? Where to stay has a lot to do with the things you want to do, and hopefully you created your list from question 2. How do you narrow down to a neighborhood that you’ll be happy with? Read travel books and online articles about the various neighborhoods or towns in your destination to get an understanding of the area. Use one of the popular travel websites like Expedia, Booking.com or AirBnB. Set your dates and search for accommodation, and a long list of accommodation will appear. Go to the map feature, and zoom in. When you pick one of the hotels, look at the distance to the sites you want to visit or the things you want to do. Will it be in walking distance? Once you narrowed down the neighborhood, the next thing is to find the perfect place for you. Consider the price, does the price include breakfast, parking, internet, taxes and fees, which could all add up if not included. What’s the cancellation policy? Look up the hotel in google maps and do a street view, what’s your impression of the neighborhood?

6. How will you get around?
If you decided to fly to your destination, how do you get to your hotel or other accommodation after you land? There are usually several options, such as an airport train, bus, renting a car, ride share or taxi. Research them. What about getting around while you are there? Do you need a car to get to the sites at your destination? Look at a map and see how far away the attractions are. Also, what is it like to drive there? Are the roads heavily congested, are they narrow roads and twisting through the mountain, and does driving make you nervous in this type of landscape? Is there a robust train network? Can you take a train part of the way and rent a car where train travel schedules are scarce or not doable? Maybe you don’t need a car for part of the trip since having a car would be more of a hinderance than help when you consider parking and traffic.

7. What will it cost?
Once you complete the initial research, it’s time to check in with yourself, and ask yourself if this is the trip you want. If it is, then start pricing it out by visualizing every movement. Again, use the popular travel websites. List prices for flights, hotels, taxis, cars, parking, ferries, trains, meals, attractions and entertainment. Do this for every day of your trip. By visualizing every movement you’ll end up with a comprehensive list of costs and an itinerary will start to form. Remember to keep it to your budget and if initially you have a price sticker shock of the full costs, there is likely changes you can make to keep within your budget without making major sacrifices.

At the end of this process, you’ll either be excited to move forward and plan your trip in great detail and hopefully you found things you were never even looking for, or maybe you are not interested anymore. Either way it won’t be wasted time because at the very least you would have learned something about your destination or travel planning that you can use in the future.

Happy travels!