The Ultimate Vacation Checklist


Summer is just around the corner. Bathing suits and flip-flops hang on store racks, and you can feel the days get longer. While you may still be weeks away from summer vacation, planning ahead on a travel organization app is a great way to extend the life of your vacation mood and help your travel plans get off on the right foot!

Here is our checklist for creating the ultimate vacation, regardless of the season.

Pick A Destination

Photo by Lopez Robin on Unsplash

Maybe there is that one spot you must go to every year; your soul just yearns to be there. On the other hand, you may be an adventurer and prefer to avoid traveling to the same place twice. One of the first things to do is decide on a destination.

There is no shortage of travel inspiration on the internet! Whether you are looking for a classic cozy cabin in snowy woods, or warm sun and sand, the options are endless. Social Media is a great place to start, as countless travel blogs describe destinations filled with gorgeous and enticing scenery. 

Research information on a given location for each season: knowing the weather and environment is essential, as well as any events in the area that you and your party may wish to enjoy.

With a list of potential choices, narrow them down by considering the pros and cons of your top options. You can also list everything you want to do in those locations. If you are traveling with family or companions, include them in this process! This is a great way to get everyone excited about the trip and ensure there is something for everyone.

Schedule a Time

Whether it’s a weekend getaway or an annual family resort trip, consult your calendar to help decide the best time for your trip, considering the season and climate. If you are staying at a resort or vacation rental, check their policies on minimum night stays or durations in advance.

Consider the best way to maximize your available time off. You can gain extra time on your trip by leaving on a Friday instead of a Sunday; however, traveling on weekdays is often less expensive and hectic than on weekends.
Also, don’t be afraid to consider travel dates outside the norm and away from holiday weekends. Making slight adjustments to your schedule can profoundly impact what activities you can add to your list. It will also ensure you get to do everything you hope to do.

Choose Transportation

Poppy modern farmhouse living area
Used with permission of Patterson Custom Homes, Brandon Architects and photographer Darlene Halaby

After you have the “where” and “when,” next up is “how.” This part may seem like a technicality, but eliminating the stress of travel can make your vacation run smoother and fill in the gaps of downtime.

Regardless of your transportation choice, line up some entertainment for your travel days. A great book or road trip game can make time go faster. No rule says you can’t create memories while going to better places!

When your destination is within driving distance, you may find an old-fashioned road trip in order. Take advantage of your travel route; if you can pass through an area with attractions you like, work these into your itinerary. Stopping at an aquarium or a space center will not only stretch your legs but can also add some bonus fun to your vacation plans and break up the monotony.

Feel free to look at smaller local events, too – you may pass through during a town’s annual fruit festival, for example. You can never tell what may end up being a fun family memory for years to come.

Select Lodging

Another item on our checklist that impacts your vacation is where you will stay. From campsites to luxury hotels, there are plenty of factors to consider.

You want to choose a location that feels like it’s part of the reason you chose this vacation. Whether it’s the full resort with an on-site water park, an area with delicious restaurants, or easy access to your favorite theme park, choose a place that works for your plans and contributes to your enjoyment.

Remember to consider AirBnB as well as VRBO as you search for accommodations. While a house on the beach may not have the full-service amenities of a resort, they offer a laid-back, homestyle atmosphere. Plus, the option to stock a kitchen and cook meals will alleviate some of the costs and free up some time for fun!

As you decide on lodging, look through all amenities and services available at each location. There may also be different fees and contract agreements in some cases, so reading through the options will ensure you know what to expect and prevent a headache later on!

Plan Activities

Designed home office with desk, plant and chair
Used with permission of Breeze Giannasio

In many cases, the activities available in a particular destination are the reason for traveling there! Ski resorts, water parks, and theme parks draw millions of visitors annually.

Even if you know you are going to a specific park, look at other activities in the area. You may find seasonal celebrations or hidden gems in the area many overlook. Check local calendars or social media for more information on what else to do.

Think outside the box! You may be in a coastal location that highlights the beach, but there are often fun water sports activities if you look slightly inland or a little further down the road. It is also a great way to have some backup activities in mind if the weather impacts your plans.

Have a Meal Itinerary

After you have mapped out some ideas for where to stay and what fun things to do, it’s time to plan for meals. 

If you have a tight itinerary of events, look for quick service options. But if you have time to explore while you’re in town, evaluate the menus for different restaurants in the area.

Consider eateries popular with locals, whose menu has something for everyone in your party. Many places have websites and photo reviews, so sort through them; you may find options that add extra magic to your trip! 

Alternatively, consider stocking the kitchen and prepping picnics or quick meals where you are staying. This will save time and money and add a new level of relaxation to vacation.

Make Arrangements for Home

Living room with big firework
Used with permission of Alice Lane

A necessary evil of travel planning is to make arrangements for everything back home. Coming up with a plan for pets or plants early in your vacation planning will allow you to focus on the highlights without worrying about home. 

Installing a couple of extra portable cameras around your home before leaving can give you additional peace of mind if you want to check on things while away. You could also find a trustworthy person near your home who can check on it or be an emergency contact. Ensure they have the information and access they need beforehand, and write out any instructions for clarity.

The Bottom Line

The most crucial factor in creating the ultimate vacation is to make plans that will have something for everyone! Whether the purpose is to relax or experience new thrills, taking the time to explore options, fill in the gaps, and eliminate stress beforehand will allow you to make the most of your time. Checking off as many boxes on everyone’s wish list as possible will leave you all fulfilled while recharging your batteries.

Thanks to all the companies linked above.


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