Should I Plan the Next Big Family Trip Myself?

(Revised and Republished January 2024.)

Have you ever…

• Spent 8 hours on hold with airline customer service?
• Conducted business in a foreign language?
• Researched and hired a boat captain?
• Planned a trip for people with diverse interests, so that everyone could have a good time?
• Replanned that trip 3 more times, accounting for the evolution of the guest list?
• Known there are places where you could be fined for taking a photo?

Not Yet? 

That’s okay!  But, it probably means you are not a travel professional.  It also explains how “the life” may not be as glamorous as some would think… Of course, it involves visits to amazing places and being highly knowledgeable about all sorts of things, but a travel planner also handles the potentially stressful aspects of a vacation, allowing you to just kick back and enjoy your trip!  In short, this one might be best to leave as a “not yet.”

Organizing any adventure, even just for yourself, involves research, consideration, and precaution.  Each additional traveler provides new considerations to the task list.  Any International destination demands even more knowledge!  Every country has its own reading list full of regulations, cultural expectations, and logistical time savers.  Why not employ someone who already knows and regularly studies all of this?  Ultimately, it is often safer and much more enjoyable to hire an expert!

But really, why?  What benefits will you see?

 With an upcoming multi-generational trip… Let’s first look at some of the stress points: 

1. Coordinating dates. The more people in the group, the more conflicts there will surely be.  Once we have everyone’s availability, we move on to looking for a good price on a flight with reasonable times for departure, arrival, and acceptable layovers.  (Many will give up on planning right here.) 
2. Where to stay?
   1. The retired generation, the very young, and those with various ailments are likely to have medical concerns requiring various accommodations.  For our upcoming trip, we need to ensure my parents can use their breathing machines while sleeping, and that the lodging provides reasonable ports to plug them into.  Your group may include concerns with allergies, climate factors, and a variety of other issues you may not have expected.  A seasoned professional anticipates and prevents many of the potential nightmares.
   2. Privacy!  I probably don’t need to explain why this is important.  Just imagine a trip with your partner, your child, and your parents, all sharing one room!  No thanks! 
   3. Proximity to places of interest.  See “planning tours and other excursions” below for further explanation, but choosing the important locales can be difficult.  Once you have narrowed it down, the trick becomes finding a and b near c, which can also be more complicated than it sounds, especially within the date range of everything else. This is where being realistic comes into play as well. You will not see trees covered in flower blossoms if you visit in your destination’s winter, and you will not watch the sunset over the water during dinner if you are dining on the wrong side of the island.
3. Planning tours and other excursions.  This challenge level increases any time part of the group wants to see mountains, while the rest wants to go to the beach, museums vs. amusement parks, zoo vs. zipline, etc.  Basically, if there is any demographic diversity at all, you will have this problem, more so with each additional participant. How do you determine what everyone will enjoy? Do they all have the same entertainment budget? Will the experience be acceptable for everyone’s level of physical fitness?

Considering a major trip is a large investment for most people, one they can only budget time for once per year, and that many borrow additional funds to cover…. Most find it worthwhile to consult a pro! Here is the difference at each of the points above: 

1. Coordinating dates.  The professional travel advisor may collect each individual or/ groups availability and compare for overlap, typically when the best rates are available.  If you select a travel advisor who specializes in the trip you want, they likely know when, where, and how to buy for the best rates and opportunities, as well as have special access to unadvertised promotions! 
2. Where to stay?   Ever buy something online that looked way better in the picture than it did when you opened the box?  This may happen with lodging and excursions also. A travel expert should have the experience to know which accommodations will actually meet and exceed your expectations! Don’t go for the overhyped, when you can enjoy the vastly underrated!
3. Planning tours and other excursions.  This one seems fairly obvious, after all we’re talking about a multi-generational trip!  Coordinating a calendar filled with activities for all vs. breaking up the groups for more tailored outings, leaving free time for the “we’ll play it by ear” members…. All of it can yield a migraine pretty fast!  If you hired a professional, you could simply relay your budget and the types of things everyone enjoys, and let your agent handle the rest!  Approve the suggestions you like, and you’re done!  Someone else’s headache! 

For those of you paying attention, this entire article may seem a bit out of place… I completely understand!  After all, this website endorses many travel options that you may book yourself.  Why am I endorsing hiring someone, rather than using the links that help pay for this site?!! Because I fully believe what I published above!  Safety concerns and laws vary around the World.  There is a lot to know, and it’s wise to have help from an expert!

Please, purchase through our links for add-ons not available through your agent, last-minute impulsive decisions during a break in your itinerary, when you have down time, or for excursions in your local area.  Be safe, see everything, and have fun! 

Please note: 

If you have already hired an agency, please ask them if excursions can be added to your group’s package.  Go through your travel professional first, because they may be able to provide the best deal, while considering your overall experience.  They may also be your best advocate if something goes awry. If your agent is somehow unable to add a trip we recommend, you should be able to easily add it yourself, for an unscheduled portion of your vacation, through the sponsored links on our site. Booking through our sponsored links supports our site!