Vacation Planning 101: Factors to Keep in Mind for a Stress-Free Travel Experience

By: Katie Wegener

Planning a vacation can be an exhilarating experience, filled with anticipation and excitement, but it’s also time consuming. In addition, knowing where to start the planning process and where to find the best options can be overwhelming and exhausting. To help get the best out of your vacation, I recommend you consider using a travel agent, like Wegener Travel and Cruise 😉 to ensure you have a smooth and enjoyable experience. I’ve included some things for you and your travel agent to think about when you start to plan your next trip.  They are also factors that we ourselves think about when we plan our own vacations. We’ve done lots of traveling and hours of research, so you don’t have to, and we’ve made some mistakes along the way and learned some valuable lessons. As travel agents, we can use our firsthand experiences to provide you with a more relaxing vacation.

Time Frame

When planning, we prefer to start with a timeframe. There are a few factors that should go into consideration:

  • Are you able to take a vacation with short notice, or do you need to plan far in advance?
  • Can you only take trips at certain times of the month or year, or are you more flexible?
  • Do you have time for a short weekend jaunt or a two-week getaway?

Often flexibility provides more opportunity for savings since it allows for travel in the off season, non-holiday times, and you can take advantage of last-minute deals. There are also some destinations that are only available to visit for a part of the year. As a travel agent we’ll also have a good idea about the seasonal crowds that frequent a particular destination (examples include the number of children present, a late-night party crowd, etc.). The amount of time you have available to you can also affect the destinations up for consideration. If you only have a weekend, traveling somewhere with a long flight or a hefty drive time might not be ideal. You may be best suited for a long weekend trip -we have some great shorter itineraries that can still take you all over the world! Making sure you plan the right amount of time for your activities is most important. It is probably not realistic, in fact it sounds incredibly stressful, to cram all of the Disney parks at Walt Disney World into one day. On the other hand, you don’t want to allocate a whole week at Peppa Pig World when it can typically be done in one day.

Vacation Goals

It’s important when you start planning your vacation to think about the kind of vacation you’d like. We’re here to help make sure your goals are in line with the type of vacation you’re interested in. From a relaxing beach day, something more adventurous at a water park, a foodie experience, or a heavy museum itinerary, there are loads of options available to you, and we can help narrow down the activities that will best suit your needs. Whether your vacation goals are straightforward or everyone in your family wants to do something different, this is what Wegener Travel and Cruise is here for. In fact, this incongruity is our family! Darren is more adventurous, and I prefer to relax and maybe visit a museum. We’ve found options that allow us to compromise and let everyone in the family have a wonderful time. As travel agents, we can help find a solution to accommodate everyone by offering suggestions on locations, activities, and types of travel that will meet everyone’s needs. Our own family experiences have given us real-world examples to be able to offer you a variety of options that are sure to leave your whole group with the vacation experience that they had in mind. We often choose cruising to help meet everyone’s expectations of a vacation, but we have also balanced itineraries on vacations to London and Paris.

Consider the Weather

Weather patterns can play a huge role when planning a vacation. Temperatures can vary wildly depending on the season; do you prefer the hot or cold? You can find some great cruising deals during hurricane season but be prepared to be flexible if your itinerary changes due to a storm. Summer in Alaska is the driest and sunniest time to travel there but if you’re alright with cooler temperatures and a higher chance of rain, spring or fall are also options and it comes with less crowding. One thing we’ve learned firsthand is that the Mexican Riviera in January can be cold and rainy. Consider traveling there in another season if you’re hoping for a sunnier, beach focused trip. On the flip side, this is the best season for whale watching and we’ve personally gone on some great winter whale watching tours and gotten amazing views of these notoriously elusive creatures, so it really does depend on what you want to accomplish with your vacation. Alternately, we once spent an extremely hot, humid September day in San Juan, Puerto Rico. Walking up to El Morro, a colonial fort situated on a very steep hill, was beautiful but I can tell you we enjoyed it much more when we went back and did the same trek a few years later, but in February. Another consideration for travel in the off season: many seasonal attractions may be closed, which can make travel during those times a non-negotiable no if you have specific activities you want to do. If you let us know what you really want to accomplish, we can help find the most ideal time for you and your party to travel.

While we can try and use seasons to our advantage, there is no predicting the weather, and it’s best to always be flexible in your plans and expectations. As many of you know, in the South and the Bahamas it’s common during the summer months to have an afternoon thunderstorm roll through. We have been disappointed more than once by a rainy vacation forecast only to remember that this is par for the course in this part of the world and that most likely it will be perfect all day with an hour of rain. We just use it as built in time to go grab another drink! Unpredictability can also make vacations fun and memorable. We’ve raced for shelter in many downpours and taken a cruise to nowhere when itineraries got canceled. Blips in plans can make for great stories and we encourage you to go with the flow and make your own.


We all have a budget, and it is obviously a big factor in deciding what to do and where to go. Flexibility and thinking outside the box will give you more opportunities in planning a vacation. Darren and I had a chance to get out of town for a kid-free three-day weekend last summer and it turned out it was cheaper to fly to California and take a short cruise to Mexico than to drive to the Oregon coast and stay in a hotel for that timeframe. Traveling off season also allows for more budget friendly options, but as I discussed above that can potentially come with some weather-related pitfalls. On the other hand, if this is your once-a-year trip or the vacation of a lifetime you have been saving for, we can make sure that you are still getting a ton of value in your vacation. Exotic locations with exclusive access, once in a lifetime experiences, and incredible service are just some of the perks that are available to you, along with larger rooms, priority boarding/early entry, and in some cases, you can even get your own personal butler for the duration of your vacation! Small or big budget, we can work with what is the biggest value to you and your family. From experience, we can tell you priority boarding when you have small children is everything, and we’re willing to pay extra for that if needed. This might not be valuable to you though, so we’ll make sure to listen and offer suggestions based on what is important to you and your family.

Your Travel Party

Consider who will be joining you on your vacation. Adults-only getaways, trips with your kids, or whole family events all have different boxes to check to keep everyone happy.

As a couple:

When we travel by ourselves, we often try and do more adventurous excursions where children aren’t allowed, and if we’re cruising I might consider taking advantage of a higher level drink package. We might consider later dinner times, fancier dining options, and (like most parents) we plan to sleep in as late as possible. The activities we plan might have less cushion time and involve more walking. When we consider activities for our trip, we will probably schedule later events and choose less kid-friendly things like a longer variety show or adult comedy. When flying, arrival/departure times and connections won’t be as high of a priority since we don’t have to consider nap times or if it’s dinnertime at our destination.

With Kids:

For family trips, we often try and consider things like room access around naptime, close activities for the non-napping parent and older child during this time, daytime schedule flexibility for those toddler meltdowns, and food/snack availability when we travel, which are all less important if we’re vacationing by ourselves. Additional factors we consider when we travel with our children include transportation availability and a travel cushion day. Since both our kids require car seats, travel arrangements can be more complicated. We prefer having a travel cushion day to relax at the beginning of our family trips to account for any grumpiness due to time changes and alleviate any stress from delayed or canceled flights. It also gives our kids a day to adjust to the changes in their routines, so everyone has a better time. We learned this one the hard way so let our mistake help you! For theme and water parks, also consider any height or weight requirements for entry to a ride or slide. We run into this problem occasionally since our son is on the smaller side for his age. Most importantly, make sure that you are mixing in activities that they want to do.  Trying to keep toddlers in a good mood when you are walking through quiet museums all day can be next to impossible but if you take them to the Children’s museum (or other child approved activity) and let them run around and play for a few hours, there is a better than average chance they will nap in their strollers after lunch and let you partake in less toddler-approved activities.

With a large group

If you’re planning a large family gathering, it’s important to be cognizant of everyone’s physical capabilities. Older members of your party might not want to ride the water slide or be able to go on a hike to a waterfall (or they might!). In addition to physical abilities, everyone in your party is going to have a different palate, so it’s important to find food options that fit everyone’s tastes. If you’re going to a resort, some have limited options for children, or they’re not allowed at all. It’s important to do your research and make sure to have age-appropriate, ability-appropriate, and enjoyable activities and options for everyone who you’re traveling with. We have experience with large group vacations and as your travel agents we can help make sure there is something for everyone.

Planning a vacation requires careful consideration and thoughtful decision making. There are many factors that go into the planning process, and these are some of the more important ones to us. As travel agents, we can utilize our knowledge and experience to collaborate and help you create a well-rounded itinerary that caters to your desires and needs and ensures an unforgettable travel experience, no matter the type of vacation.  If this sounds like a lot to think about, that’s because it is! But that’s why we are here. Let us think about and remember all these little questions and nuisances that go into planning a vacation. Give Wegener Travel and Cruise a call and we’ll start the planning!


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