Vacation Packages vs. Plan it Yourself?

Vacation Packages vs. Plan it Yourself?

A common question I often get asked is if I use packaged vacations to travel or if I plan out the trip myself?

In truth, I do both!

Depending on the location of the trip and the reason behind it helps determine which style I go for. Below is how I usually decide between the two.

Initial Questions:

You’ve decided you’re to take a vacation!! Let’s start with the same common questions I go through each time to determine which option is best for you.

  1. Why are you traveling? – Are you going to visit family or for a friend’s wedding? If you are traveling for any reason besides pure leisure, then fully packaged trips may not work for your schedule. Smaller combination packages that simply include your flight and hotels may work better though.
  2. Who is going on this trip? – In the initial thoughts about traveling somewhere, do you imagine going with someone else or traveling solo? Having done both, knowing this ahead of time can really speed up your planning process if you don’t have to review all the decisions with another person or group.
  3. Where do you want to go? – While answering this may seem easy for some, it can often be the hardest question I have to answer. If you’re stuck on answering this question then go through the following sub-questions to help you out:
    • Do you want to travel locally, nationally, or internationally?
    • Is there a particular event or festival that you want to tie into your trip?
    • Do you have all the required travel documents you’ll need should you decide to travel out of the country?
  4. What is your budget? – Each trip you take will be at a different point in your life and therefore can affect how much money you have to allocate to your travel budget. Review your finances and have an honest conversation with others who will also be joining you so you are all on the same page with what you’re willing to spend. There is nothing worse than under-budgeting initially and being financially stressed while on your trip. Stay within your means!
  5. When do you want to go? – Depending on the time of year you have available to travel will really narrow down where you will want to visit. Do you want to go to upstate New York during the winter or the Maldives during the monsoon season? Knowing the month you want to travel in will help narrow down where in the world you go.
  6. Are you a planner? – I’ve learned that some people are and others just aren’t. Personally I am! I get super excited to travel and love putting together all of the little details. For others, though I can understand that this sounds overwhelming or like torture. Figure out if you want to decide on every specific detail around your trip or if you’d rather have a majority of the bigger decisions made for you.
  7. How comfortable are you with winging it? – Could you fly to another country and decide on where you’re staying the night of? For people who consider themselves planners, this thought can be terrifying, though it can also be exhilarating! I typically have my hotels booked ahead of time, but on trips where I am traveling to multiple cities throughout my time there, I’ve waited until the day of to book.

Now that you’ve answered through these initial questions you should be able to narrow down which option will work for you. Below I will give some pros and cons for each option if you’re still on the fence.

Individually Planned:

These trips are planned & booked exclusively by you.

  • Pros
    • Your own pace – By booking the trip on your own, you set the pace. You can choose to add as much or as little to your trip as you see fit.
    • Lodging Flexibility – Without having a set hotel package you’re free to choose a new hotel every night if that’s what you want. You can customize your room selections and even spring for an upgraded experience for a night or two.
    • Flight Time Flexibility – Booking your own flights allows you to choose if you get a direct flight, what time of day you want to leave, and if you want to upgrade your seating in any way. I’m super picky of the time of day I book my flights for, so I enjoy controlling the time I have to be there.
    • Saving Money – Sometimes booking these items separately will end up saving you money, rather than trying to upgrade or modify a specific package. You do have to do the research though and compare to see if it works for your trip.
    • Unique Experiences – When self-planning you’re really able to customize the trip as much as you want.
  • Cons:
    • Planning can be hard – Deciding every detail, looking up all hotel options, and researching how to get from city to city can be tiring and overwhelming.
    • Additional Expenses – While you may save more on the upfront cost, you could have unforeseen events that could also cost more in the end. Not having pre-arranged transportation to the airport and missing a flight is one way this has happened to me before.
    • Challenging moments – There is going to be a point in your trip when something is wrong, whether it be a wrong turn or flight, and you’ll have to decide how to overcome it. Breathe, do some quick research, and ask questions! It may seem like the end of the world, but more often than not your not the person who’s ever done it. Don’t forget to google it and don’t be scared to ask locals for help.

Fully Packaged:

These packages are the ones you’ll see through Groupon and other tour companies.

  • Pros
    • Pricing – Depending on where you’re going you may be getting a better deal by having your airfare, hotels, and ground transportation all in one.
    • Convenience – These trips are booked from beginning to end with a schedule that’s manageable for the traveler. Tour companies arrange for your flights, hotels, rental cars or transport and sometimes even excursion packages at the destination.
    • Ease of Mind – It’s often very relaxing to know that your trip is pre-arranged and all you have to do is show up for it!
  • Cons
    • Lack of Flexibility – These packages are often out of specific cities and at particular times in order to cut costs for the tour company. Expect early flights and economy class on for the airline portion.
    • Hidden Fees – Read the fine print before booking these packages! Often there are hidden fees or additional expenses for luggage, departure cities, and cancellations/adjustments.
    • Pricing – Sometimes the packaged price is higher than doing it on your own. Remember, you are paying for the convenience of having the trip planned for you, so keep that in mind when looking at the price.


When thinking of this category think of an Expedia bundle. Basically this option you would use for booking your flight and hotel together.

  • Pros:
    • Discounts – You can save some major money when booking your flights and hotels together. Hotels are known for offering larger discounts when bundling and using your points can help offset the costs even more.
    • Loyalty Points – Most of the sites that offer these bundles, Expedia,, Priceline…etc., all offer loyalty points for using them. If you travel often, then building these points are great, as they can be applied toward future stays!
  • Cons:
    • Accommodation Restrictions – The way sites like this work is the longer or more “bundled” your package is, the greater the discount. When booking airfare and hotel together you are unable to bunder multiple hotels under the same package, so usually you’re stuck with the same hotel for the duration of your trip.
    • Booking Restrictions – Working in hotels I know that not all hotels allow for bundled deals through third-party sites. If the hotel you want is unavailable online, then always make sure to check their site directly, to see if they are truly unavailable or not.

Hopefully this breakdown will help with your trip selection! Overall I use self planning when feeling adventurous and trying to see a lot in a short amount of time. I use fully packaged options when I want to vacation without the headache of trying to figure it all out myself and I use the semi-packaged when going somewhere for a quick trip away for a few days!


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