1. Research

Courtney Maestri 5 Steps to Plan Your First International Travel

Probably not too much of a shock that this is the first step :). I did a TON of research when planning my first International trip. Mainly because I really wanted to ensure I was going to enjoy myself after putting so much time, energy and money towards it.

Below are a list of questions I asked myself (& the internet):

  • Is the area safe?
  • Are there any typical tourist scams that are specific to that area that you should be aware of?
  • What’s the best time of year to visit?
  • Are there any cultural differences you need to prepare for in advance to ensure you’re being respectful of another country’s traditions while visiting?

2. Book Your Flight(s)

Courtney Maestri 5 Steps to Plan Your First International Trip

Just do it! When I decided to go to Greece, which was my first International solo trip, I put off buying the flight for quite some time. Not only does securing your flight mean there’s really no turning back, but it’s usually the most expensive piece of the trip. Once you make the leap, though, the rest seems to fall into place – I promise!

Some helpful bullet points below:

  • Best Site to Purchase Flight:
    • Sometimes I get real crazy and I search for flights in incognito mode via Chrome. This prevents cookies from firing, which is helpful when you’re repeatedly visiting the same sites to check pricing before ultimately purchasing.
  • Best Time to Purchase Flight: Earlier in the week is what I think is the best time to purchase (Mon/Tue and sometimes Wed). I look to purchase my flight at least 2 months out for better prices!

3. Reserve Your Hotel Room(s)

Courtney Maestri 5 Steps to Plan Your First International Trip Santorini Greece Hotel

This is the hardest part! Depending on where you’re going, you’re typically trying to make the best choice out of a zillion and one options. If you’re trying to be a little spontaneous, I’d at least book the first night of your stay, since it’s reassuring after a looooong day of travel to have a bed just waiting for you! Here are a few thought starters on questions I asked myself before booking:

  • Is it centrally located to where I want to be? (ie: bars/restaurants, near the ocean, etc.)
  • Is it safe?
  • Does it not only have positive reviews on TripAdvisor, but a significant amount?
    • When I’ve narrowed down the option and I’m getting close to choosing a hotel, I scroll through the reviews, even the negative ones, to see if there is a commonality between them that I should be considering.

Some Helpful bullet points:

  • Best Site to Purchase Hotel: (rewards)
  • Best Time to Purchase Hotel: This can vary on location but I recommend at least 2 months out, 3 or 4 if you’re not a commitment-phoebe!

4. Plan Your Activities

Courtney Maestri 5 Steps to Plan Your First International Trip

This is the best part!

  • The first place that I started in planning this step is by just simply Googling to see what popped up. For Greece, I used a very detailed blog that is just dedicated to Santorini to plan all my activities. If there aren’t any really good bloggers that nail the items you’re looking for, I recommend searching to see if the country or city has a tourism board. They usually list recommended activities in the area and it’s a place to start!
  • Another good way to find cool things to do is to ask around. I have a good group of friends that do a lot of traveling and just asking what they’ve heard, their opinion of what to do or their specific experience helps shape somewhat of an idea or direction to go in. Worst case, you can always ask your hotel front desk for recommendation, especially if you’re staying in somewhat of a touristy area.
  • I typically plan most of the trip, making restaurant and activity reservations in advance, while leaving a few spots open for flexibility. That way I can decide once I’m there and I’m not stuck to a strict schedule. Asking locals for advice on where to go, what to do or see is a great way to see the area from a different perspective. It takes the ‘commercial’ aspect out of the trip and makes it feel just a little more authentic, giving you a chance to really soak in the culture and people. THIS, to me, is the real appeal of traveling :).
  • Something else to consider when traveling alone: if you’re not staying in a hostel where it’s easy to meet other people, try to book an activity or activities where you’ll likely be with other like-minded individuals. For Greece, I chose a Catamaran boat tour that included alcoholic beverages for the duration of the trip. I knew with this, I’d likely meet other people around the same age and same interests, which I did! We ended up all meeting up later that night for drinks out in downtown Fira.
  • This point kind of goes hand-in-hand with the ‘research’ portion but make sure you know how to get around. Is it walking, taking a cab, a boat or car service? Once you have an idea, be sure to book some of this in advance to make it easier on yourself once you get there (car to your hotel the first night)!

5. Make an Itinerary

This is mainly to appease the organizational freak that lives inside of me, but it’s super helpful if you’re just starting out on the travel game.

  • It ensures that all of your flight info, hotel reservation/confirmation numbers and everything else are in one easy place to reference. I usually put this in an inside pocket in my carry-on bag so that I can easily grab it. I also take a photo of the itinerary so that I have a digital copy handy (versus scrolling through my email attachments).
  • I sent it to my immediate family members so that they feel a little less uneasy about my traveling alone, but also so they can reach me in case anything goes wrong. It made me feel a little better knowing that my family knows where I am at almost all times, especially when traveling alone. I create my itinerary in Excel and it has a few tabs within it. I’m sure this is super old-school but it made me feel better to have a hard, paper copy of all my information. I also don’t need to rely on wi-fi this way!
  • I usually research the emergency numbers in each country and include this in the last tab of my itinerary. I’m a little bit of a freak but in the same breath – you can never be too safe when traveling alone!

Something else that I didn’t include on the list is purchasing some type of International calling plan. I probably didn’t need it but since it was my first trip, it made me feel a lot better knowing I could use it at any time. It also REALLY helped to have a map handy. I referenced it everyday in venturing around Santorini and I would highly recommend doing this if you’re able to afford it!

& That’s it! I promise it isn’t as daunting as it may seem. Just take one step at a time and keep moving forward. Before you know it, you’ll have all your ‘to-do’s’ checked off while enjoying yourself on the vacation you planned!


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