How to Plan Your Dream Vacation

How to plan your dream vacation

Planning a vacation is never easy, but if it is your dream vacation that makes it even more of a challenge. It can be downright overwhelming as you try to get the absolute most out of your dream vacation. Where do you even begin? Well that’s where this guide comes in. It will help you go through the entire planning phase of your dream vacation so you can get everything out of it that your heart desires.


It All Begins With Big Dreams

Planning your dream vacation
Don’t be afraid to dream big for your dream vacation.

Once you’ve settled on a destination, or destinations plural it is time to start dreaming. All good dreams start with a list. Or is that just me? Make a list of everything you know about your dream destination that you are even slightly inclined to see or do. Right now nothing is too small, too difficult, or too outlandish. Put it all on the list.

Once you’ve exhausted your knowledge of your destination then it’s time to take the research online. I like to use a combination of Pinterest and TripAdvisor for this part. Which destination you have in mind should inform what search terms you start with. Is Ireland your destination? It’s a small enough country you can easily drive across it in a few hours. So, it is conceivable that a trip to Dublin could include a day trip to Galway or Cork on other ends of the country. But, if your destination is Los Angeles, you aren’t going to be taking a day trip to New York. So start with the largest region that makes sense; Ireland, Southern California, and New South Wales are just a few examples.

See what Pinterest has about travel in those locations and add anything that catches your eye to the list. I recommend looking at 10 different websites to get a variety of ideas. There is going to end up being a lot of overlap between them because these are quite simply the biggest draws for that are but also, would you listen to a list of things to do in Paris that didn’t include at least stopping to look at the Eiffel Tower? Unless the article is specifically named “Things to do in Paris that aren’t the Eiffel Tower” then no.

After you’ve looked at the wider picture it’s time to narrow your search. You will end up getting different must-see sights. So for instance if you’re traveling to Ireland, you’re most likely going to end up in Dublin. So search specifically for Dublin and again, write down everything that catches your eye, no matter how small it is.

Do this again for other cities or regions you might go to. In the Ireland example, this might include Galway, the Wild Atlantic Way, or even Northern Ireland. To use an American example, perhaps you had previously looked up Southern California, now you’re searching Hollywood, Orange County, and San Diego just to name a few options.

Head over to Trip Advisor and go through the “Things to Do” category for each city or region you might go to. Personally, I like to look at the top 100 things to do for each area and again, write down everything I might want to do.

In the end you will have a pretty massive list but try not to get overwhelmed by it. You’re going to be working on making it a bit more manageable soon enough.


Prioritize Your Dreams

Yosemite Valley
Going to Yosemite might be high on your list if you’re going to California, it would be on mine!

So you’ve got your list put together of things you’d like to see and do on your dream vacation, what comes next? Well, next you need to give each one a priority rating. Rate each item on the list either a 1,2,3, or 4.

1 – Must-See, non-negotiable. Examples: Eiffel Tower, the Colosseum in Rome, or the Great Pyramids

2 – It would be nice to see/do. Examples: An LA Lakers game, Climbing Half Dome in Yosemite

3 – Sort of Interesting. Examples: The Marsh Library in Dublin, the California Academy of Sciences in San Francisco

4 – Least Important. Examples: Street Art, The Little Museum of Dublin

The examples I gave are just some of my personal examples, you might find that different things rate higher or lower for you. This is the time to be completely honest with yourself. Remember that just because other people consider something a must-see for a particular destination doesn’t mean you HAVE to go there. If you don’t drink then there is no reason to go to the Guinness Storehouse in Dublin. Dublin doesn’t have a great skyline so you’re really only there for the drinking.

Any of the ones that you’ve given a 4 go ahead and put a line through them. Strike them out just list this. This way you aren’t deleting them but you are quite clearly showing that for now at least, you are not going to go do those things. This might change though, you might finish your planning and discover that you have extra time leftover or you might find that the Street Art is only around the corner from the Eiffel tower and squeeze it in any way.

At this point, I recommend taking a day or two to consider the list you’ve made. Are you happy with the rankings you’ve given everything? Don’t be afraid to second guess yourself. This is your dream vacation. Make it everything you want it to be.

Figure Out the Timing

Sydney New Years Eve
If you travel for an event like Sydney’s NYE you might find a minimum booking of 7 days for many hotels.

Now it’s time to set aside your lists for a few minutes and consider time. Do you know what time of year you’re going to go on this trip? Visiting Switzerland for example is a wildly different experience in summer than it is in the winter. For some destinations, though like Los Angeles it doesn’t really make much of a difference if you’re visiting in Spring or Fall, the environment doesn’t change all that much from season to season. Once you’ve worked out what time of year you will be there head back to Pinterest and see if your destination has anything special that comes up for that time of year. It might be fireworks in Sydney for New Years, KFC for Christmas dinner in Japan, or a Full Moon Party in Thailand. This might result in you adding a few new things to your list, don’t forget to give them a ranking too.

This stage isn’t just about figuring out when you’re going to go, it’s also about how long you’ll be there. How much time off can you get from work for this trip? This will help you prioritize things even more and it might see you going back to the list to make some more adjustments as you see that there simply isn’t enough time to see it all, there never is.


Work Out Your Budget

Five star hotel with a view
We would all love to stay in five-star hotels, but that doesn’t mean we should…or can.

Now that you’ve got your dream lists compiled it’s time to start getting a little bit more down to Earth. Don’t do anything with the lists just yet. Now is the time for you to work out what your budget is for this trip. Be realistic, be honest, and don’t bankrupt yourself. Give yourself a budget that will grant you comfort on your trip as well as after it.

Also, be sure to take into consideration how much time you have until your trip. Could you possibly get a part-time job between now and when you go on your trip? Or maybe there are things around your house that you could sell to make some extra cash. Give yourself a cut-off date for earning money before your trip so you know what to expect and still have plenty of time to make adjustments to your plans.


A Dose of Reality

Big Castle
Chances are you aren’t going to be staying in any of the big tourist destination castles of Europe…but there are castles you can stay in.

This is the point where budget meets dreams and you get an awful dose of reality. As much as you might want to, chances are you aren’t going to be staying in the Ritz-Carlton for your New Year’s Eve trip to New York City. Or maybe it’s so important to you that you’re willing to cut out other things to make it happen.

This is the stage where you balance your checkbook so to speak. If there is anything you want to go to or do that has an admission cost factor that in. Decide what your budget will be for meals each day you’re there. I like to plan for one really fancy meal each week of my trip so I might double the cost of one of the dinners.

Don’t forget to factor in gifts, souvenirs, and whatever other shopping you might want to do there. If you’re planning on getting a lot you might also want to add a bit more on top for shipping. You never know when you’re going to go to Japan and buy a kotatsu table then have to work out how to ship it back home. Seriously, it’s on my list for my trip to Japan.

Have a Schedule

Finally, unless your dream vacation is one of those where you just spend all day laying on a beach I recommend making yourself a loose schedule. You don’t have to follow the schedule religiously but having a schedule will help serve as a reminder of all the things you want to do on your trip. You don’t want to do what I did in Malta and decide to go see the Azure Window next time only for it to collapse before you made it back!

Azure Window RIP
Not my photo…for obvious reasons.