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Step-by-Step Planning for Vacations

I'm quite serious when it comes to planning for an upcoming vacation. With limited paid time off and a set amount of funds, I like to make sure that my holiday away is the absolute best it can be. I take no risks- a lot of blood, sweat, and tears go into my itineraries.

Now, at this moment, I probably have some of you thinking, "this person is nuts," or "the fun of vacationing is the unknown," and I completely respect this. My style of planning is not for everyone, and that's ok. Some folks enjoy not knowing which accommodations they will be staying at each night. Some folks like to fly by the seat of their pants when figuring out what attractions they will see that day, or what hikes they will venture out on. I am not that person. So for all of you out there that enjoy structured and detailed preparation of an upcoming adventure, this blog post is definitely for you. Heck, even if you don't like it, I still encourage you to read this because you just may get a kick out of how anal I really am.

I also think it is important to point out that, yes, I develop very, very, VERY detailed agendas, but I don't plan out every single second of the day. I am flexible (thank goodness). Although I enjoy looking up must-see spots in the areas I am visiting, it doesn't mean that I need to stop at each one. I still like having the option to pick and choose things to do once I am on vacation, especially since there are so many wonderful adventures to go on once there.

But now down to the nitty gritty details. My planning process always follows the same trajectory and relies heavily on research. It takes time. I don't think it is possible to go quickly through any of the steps listed below, so I preface this blog post by saying be patient and expect to make many edits along the way. Since this article is packed full of dense information, I have included a key that can help you navigate the vocabulary I frequently use.

  • Place: The city, state, country, or countries you are traveling to. Basically where you are going on your vacation.

  • Region: The part of the place you plan to visit. For example, you may be vacationing in the country of Ireland (place), but you may only be visiting the western region.

  • Areas: Different parts within a region. While visiting western Ireland, you may be planning to visit the villages of Dingle, Doolin, and Connemara; this would be an example of three areas within a set region.

  • Favorite Spots: The BIG LIST of things you've chosen to do/see/experience. This comes from your first round of research.

  • List: Anytime I talk about this list in my blog post, I am referring to the document where you have listed your favorite spots.

  • Final Spots: This refers to the top or final picks from your list of favorite spots.

  • Itinerary: The itinerary is the final agenda you create based off of your research and maps.


Research the basics

Once you've figured out the place you're visiting, you will need to start researching some of the basics. These basics help determine where you can go within a place based on any constraints you may have. As mentioned before, my biggest constraints are paid time off and money, so these are usually what influence my trips.

  • Travel style: Are you a person that likes to stay somewhere new each night or immerse yourself into one area for a few days? This is a really important question to ask and it will determine how far you travel, how much you see, and the amount you learn about the area you're visiting. My wife and I have found that we like to pack in as much as we can without feeling exhausted, but we also like to experience local culture. For us, 2-3 nights in one area offers a good balance with each of these things.

  • Transportation: Do you like public transportation? Are you comfortable renting a car in a new place? Again, very important things to think about. Some countries have wonderful public transit, while others require a vehicle to take you from one village to another. Public transportation is quite reliable (most of the time) but it leaves little flexibility in your schedule. Driving may be more expensive and require things like paying tolls or purchasing an international license, but offers the freedom to go wherever you want whenever you want. We have found that our choice of transportation relies heavily on the place we are visiting, so I can't stress it enough: do your research!

  • Accommodation: From hostels and room sharing to entire homes and B&Bs, there are numerous options (with varying prices) out there. I've found that the types of rentals vary depending on where you are staying- sometimes a place only offers hotels, while other places may have huge AirBnb markets. As a same sex couple, Ash and I try to find accommodations where we can have our own suite- especially if we are visiting a new area where we aren't familiar with the culture and their acceptance of queer couples. I recommend doing a little research on laws and policies before booking, and if you are comfortable, be upfront with who will be staying in the room. I usually share with the host that we are a same sex couple looking to book a single room, and I've never been questioned or met with negativity in doing this.

  • Finances: You are probably already aware, but some places are WAY more expensive than others. For example, you are going to pay a lot more for a restaurant meal in Iceland than you will in Portugal. Before you go anywhere, research the average amount of money travelers tend to spend daily in that place, and figure out whether or not this budget can be adjusted by what you do, see, and eat.

Keep in mind that these four points are not separate. They have a huge influence on one another. For example, if you aren't willing to drive a car you may not have the option to stay in a new area every night. If you are going to a place where eating out will break the bank, you may want to find accommodation with a kitchen that gives you the option to do your own cooking.

Break the region up

So you have done the research and know your constraints... what's next? Figuring out your realistic region. Basically, what I am getting at, is that you need to think logically about the amount of land you can cover in the amount of time you have. Once you have established this, you can start breaking up that region into areas.

It doesn't matter if you are breaking up a region by town, county, or state; areas can be different sizes depending on the place you are visiting and your constraints. Once you have determined your areas, you will need to put together a list of 10-20 favorite spots in each one. These spots can include anything: Hikes, restaurants, museums... it doesn't matter. Just make sure you dig deep to find the most up-to-date things that each area has to offer.

To give you a real-world example, prior to our trip to Ireland my wife and I determined that we were going to spend 2.5 weeks driving around the island. We knew with that amount of time, and the transportation ease of the car, we could really visit anywhere we wanted. But because we weren't sure exactly what this meant or what we wanted to do, I broke the country into its 32 counties and researched the top things to do in each one (including photos and links that gave us more information if needed). Ireland was our place, the entire island was our region, and the 32 counties were our areas.

Crazy or smart? We will let you be the judge, but personally we tend to agree with the latter. In this case taking the time to figure out exactly what we could do in each county helped us tremendously in the following steps of planning our dream Ireland vacation.

Highlight your favorite spots... don't hold back

The next step is an easy one, and honestly the most fun. It is what really starts to shape the vacation itinerary. Go through and highlight each thing that looks cool to you from the list you made- these will be considered your favorite spots. It doesn't matter how many you highlight or which area it falls within... don't hold back. Include everything you feel you would want to experience in this place.

Plot your favorite spots on the map

Once you've gone through your list and highlighted your favorite spots, it is time to plot them on a map. I tend to find maps online that I can save as a JPEG and open within Microsoft Word. This way that I can easily paste little circles representing each of my favorite spots (this makes editing in future steps easier as well). If you don't want to use an electronic version, that's fine. A physical map and marker will work too.

Once every single one of your favorite spots is marked, start to identifying the clusters. Which areas have you marked up the most? These marked areas will be where you want to book your accommodations. Then begin looking at the favorite spots that fall between the marked up areas. These are things that you can do or see on your way from one area to the next.

Begin eliminating your list

This is the hardest part of the the planning process only because it is where you need to start being realistic about all the things you are able to see and do. Using the information from your favorite spots list and map, begin eliminating spots that don't fall into or between the heavily marked areas.

If you are finding this part of the process to be difficult, start researching distance and travel times from one area or favorite spot to another. This can help determine what you can realistically fit into your allotted vacation time. During this part of the process, I usually have plans A, B, and C- each with distances and times from one destination to the next. I continue to mix and match potential routes I can take until I choose the one that I feel will fit me and my wife's needs the best.

After you have contemplated various routes, and have chosen you favorite spots to eliminate, you will be left with your final spots.

Re-plot your map

Now, plot your final spots on a new map. You may be thinking, "again?" and the answer is yes. Again. This is your final draft, and after you have plotted everything you will be able to see your trip route clearly.

Build your itinerary

Using your map of final spots, start building out your itinerary. A good way to do this is to list each date you will be on vacation. From there, begin dropping in your final spots under each date.

Continue adjusting your itinerary to meet the travel times and any constraints you may have. For example, if you have two final spots listed under one date, and each spot will take at least 4 hours to experience, PLUS you have to drive 8 hours from one to the other... it may be best to separate these final spots into different dates. This in turn may push back something else you wanted to see or do. Continue to re-work your itinerary until you are able to hit all (or almost all) your final spots. Be patient, It is all one giant puzzle.

Once you have figured out your ideal, and realistic itinerary, then you can begin booking accommodations, making reservations, and purchasing entry fees to attractions in order to ensure you hit all your MUST-SEE final spots. I like to add in confirmation numbers, times, and anything else that I may need to reference into my itinerary.

I do recommend leaving some of your itinerary dates free... even if it is just a half day. As I mentioned before, I may be a Type A planner, but I do know that every time I go to a new place I learn about something new I want to see. In order to have this experience, you will want to make sure that you give yourself some down time.

When all else fails...

If you've made it through this long, EXTREMELY detailed blog post, I salute you. I hope my borderline 'obsessive' attention to detail has inspired you to start planning your next vacation. I guarantee you will enjoy learning about everything you are able to see and do in a new place and I welcome you to share your experience below in the comments if you do end up trying my method!

I thoroughly enjoy the trip planning process, but I can understand that some people, especially after reading this, may think that this is just way too much to do in order to go on a trip. No problem, I get it. When all else fails you can always visit my Travel Consultation website at Let me do what I love, and out of it you will get a lovely, personalized itinerary.

Cheers friends, and get out there!

I do ask that this stays a positive and safe space for readers, so please, no hurtful language or remarks about other's experiences. Thank you.

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