Planning a Trip: Where do I start?

So, you’re ready for your next vacation. You have established two things, the destination and the time frame (or maybe you haven’t). But, where do you go from there? How do you even begin planning an ideal trip? There’s so much information and it’s easy to get overwhelmed.

Well, some people completely wing it. That’s perfectly fine, but I’ll admit that I’m not one of those people. I like to have a plan, an itinerary, an idea of how I’m going to spend my time away from home.

Here are a few steps I take to ensure I’m completely ready for my trip:

  1. Pick your destination and dates: Here is where I may differ from others. I don’t really choose a destination, I let the destination choose me. I always base my trips off of deals that pop up. Flight prices to South Korea are only $500.00 roundtrip? Um, yes please! I see a deal and find dates that work best for my work schedule. After I am set on those, I book immediately. Another way to use this aspect, but not necessarily waiting around for a deal to appear is searching on Skyscanner. This website (or app) allows you to choose a destination and see when will be the cheapest month to visit. Or vice versa. Choose a month and see prices for various destinations. (See my post on Skyscanner for more details )
  2. Ask yourself what type of vacation you’re looking for: Will this be a relaxing, spa themed trip? Will it revolve around food and trying new cuisines? Maybe a trip full of outdoor adventures? Or perhaps all of the above. Once you figure out what you want to get out of your trip, you’ll have a general idea of what sort of activities to look for.
  3. Make a list of different cities (if any) you want to visit: If you’re visiting a country like Italy then this step is crucial. It’s important to figure out what cities are an absolute must to see. Decide if you’re going to make a day trip or stay overnight. Research each city to see what day is best to visit (less traffic, museum openings, etc.).
  4. Accommodations: Research different neighborhoods of that destination. For example, I’m visiting Stockholm in September and discovered six different neighborhoods I could stay in. Each is unique and offers me a different experience. I decided I wanted to stay near the artistic, hipster town of Sodermalm and booked nearby. You can also discover neighboring areas where it is less expensive to stay than right in the city. When traveling abroad, I use Airbnb the most. When traveling domestically, I like to use Priceline’s “Name Your Own Price” option.
  5. Requirements: Make sure you have all the proper documents for your trip, such as visas and a passport. A quick Google search will let you know if the country you’re visiting requires a visa. It will also tell you how many months your passport must be valid at time of arrival. Many counties require that your passport be valid for 3 -6 months even if your trip is only a week long.
  6. Transportation: Do you plan on renting a car? If so, look up parking situations. If my accommodation does not offer free or convenient parking, I usually avoid renting a car. If traveling abroad, be aware of limited zone traffic areas. Also, be sure to get an international license (easy to obtain). If a car is not necessary then look up public transportation. I always research subway/bus routes. I like to have an idea beforehand of which stops are nearby. Write down everything! I write down which routes I will be taking, the website to refer back to, and prices to track. Also, don’t forget to book airport transfers, which can easily be found through the airport’s website.
  7. Plan Specific Activities: Use Google, Yelp, and Tripadvisor to look up restaurants, museums, attractions, etc. Consider the time and cost of each activity to see if they’re reasonable to include in your plans. Depending on your answer to step #2, you can focus on certain things to do. If food is your main concern then research the destination’s delicacy and where to get it. I also map out each location in order to plan the day in the most efficient way. I like to make an itinerary to bring along, but writing down a quick list with addresses/routes would be just as helpful.
  8. Make a Checklist for Packing: I always make a checklist so I don’t forget to pack anything important. I also wait super last minute to pack (ultimate procrastinator), so this definitely helps. Once you’ve got everything you need, you’re good to go!

Enjoy your trip and don’t stress out. There are times where you’ll have setbacks and not everything will go according to plan, but that’s perfectly ok. It’s all part of the beauty of traveling. You learn new things along the way including the art of adapting to changes. These steps will allow you to have peace of mind before your trip. It will also help you be so familiar with your destination that if something does delay you, you’ll be prepared to adjust. Now, go plan for your next trip and I want to hear all about it!




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