Vacation Planning 101 : Where Should We Go?

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Vacation Planning 101: Where Should We Go on Vacation?

Some of the questions we are often asked are: Where should we go?  How do you decide where to go? How do you plan your vacations? This is a general process (Vacation Planning 101) that we follow when we are planning our trips:

1. Think about your travel goals and dreams

One person’s dream is another person’s nightmare, so these desires, goals, and choices are highly subjective.  I may say that my dream trip is an African Safari and you may have pachydermaphobia (aka fear of elephants). Just because I love to frolic lay around on a tropical beach somewhere does not mean that it should be a goal for you.  I hate the snow, so a ski trip (even if it involved the Swiss Alps or someplace else that sounds really dreamy) is not on my travel wish list, but it may be at the top of yours.  So start by thinking of the places or experiences (even if they are vague, like going to the beach) that feel desirable to you and your travel companions.  Heck, even get a pretty little notebook (or use a google doc spreadsheet if you are a geek and/or a man) and write them down. My list was too long for an average American lifespan, so I came up with this travel goal.

2. Think about when you can take your vacations

Depending on your work and life situations, hopefully you have a good sense of some times throughout the year that you are able to take a vacation.  In our case, we knew that summer would be a good time for us.  We are also able to take some days surrounding various school holidays (Thanksgiving, Christmas, Easter) and can also plan some weekend trips as well.  Knowing that we almost always travel during “high” seasons (because kids are out of school and family-friendly destinations are in high demand), we know that we have to plan far in advance for our longer and more specific trips.  In general, we plan our longer summer trips over a year in advance.  We are already in the planning stages for Summer 2015 (I know…I know…).

Sometimes we know WHERE we want to go (like very specific places in Hawaii for 2014), and sometimes we know WHEN we want to go (for example, our 15 year wedding anniversary in the Fall).  With enough advanced planning, those two conditions combine and the WHERE and WHEN come together perfectly.  Other times, we decide on our WHERE based on our WHEN….flexibility with one or both of those aspects is very helpful in this case.

For example, I have not yet planned our 15 year anniversary trip (which is much less than a year away).  We don’t have our exact dates yet, so I will have some destinations in mind and plan the trip around what is available at the time of booking.  I am flexible with my destination, but will probably not be very flexible with the dates.

Another consideration is the weather in specific destinations during the times you are able to plan your trip.  If you want to go to a warm and sunny beach, but can only go on a vacation in November, you will be limited (within the USA) as to where you can travel in order to meet that goal.  Because we have the goal of visiting all 50 states, we will try to match the desired locations, dates, and historic weather conditions to make a trip that is desirable to us.

For me, this is the most exciting part of traveling (besides the actual vacation, that is).  I love looking through travel guides, reading travel magazines, and scouring the internet for ideas.  It helps to have a partially photographic memory, so I can remember most of what I have read even after reading for many hours about various different places. I like to talk to my kids about where they might want to go (New York City is the number one answer) as well.

3. Think about your Vacation Budget

If you are using Miles & Points to fund your travel like we do, then you will want to obsessively check your AwardWallet balances to see which of your programs are going to fund your next adventure.  Sometimes I even choose the vacation destination based on my Miles & Points balances & not the other way around.  For example, I have some credit cards where we get a free hotel night each year (after paying the annual fee, so “free” isn’t totally free).  I recently had a situation where the “free” night was close to expiring, so we chose to plan a weekend getaway based on that hotel night.

If I know that we are going somewhere specific, then I will plan my Miles & Points accumulation strategy in order to gain the Miles & Points that I might need for that specific trip.  For example, I knew that we wanted to take the Amtrak California Zephyr train and needed 25,000 Amtrak points, so I planned my earning strategies accordingly.  This does take prior planning if you have specific goals in mind & lack flexibility.  I booked that Amtrak trip well in advance and planned for the points many months prior to booking.

If you are funding your trip with that other currency, you know, money…then you have to set up a vacation budget and plan your trip within those parameters that are appropriate for your individual situation. Almost all of our travel is funded through Miles & Points, but I do also plan trips that we have to (gasp!) pay for, cruises for instance.  In these cases, it helps to shop around, and in this internet accessible era, this is easy to do.  There are countless websites out there that offer travel bargains.  Here are a few that I like and have used:

Here are a few that I have been planning to use (or have an upcoming trip booked), but don’t yet have first hand experience:

 

TIP:  Do not forgot to check your TopCashBack click on the ‘Travel’ tab on the toolbar and you will see various places where you can earn).

Do you have any Vacation Planning 101 tips that you use to plan and dream about your next vacation?