Family Vacation Planning Checklist


The family vacation planning checklist is the first thing you should work out ahead of time before going anywhere. Family trips can be stressful enough. If you plan ahead of time, this can be a fun trip after all. This list can even be used for empty nesters and single people on trips with others! 

Ways to Keep Your Sanity While Planning a Family Trip

Before going, figure out and plan for the following:  

  1. Who’s paying for this?  
  2. Where are you living for 3-7 days? 
  3. When are you going?
  4. How are you getting there? 
  5. How are you getting around?
  6. Will you have a break for some “me” time?

Family vacation planning checklist


Let’s face it, the budget is the most important thing in regards to family vacation planning. Whether you are traveling with your own family, or traveling with another family or friend – the budget informs you of what you can or can’t do while away, including:

  • Travel costs
  • Hotel costs
  • Food Costs
  • Excursions
  • Souvenirs

You know how much money is in your savings, or what you’ll need to save in order to go.  However, if you have major priorities that you need to use the money on, don’t go on the trip. Be responsible first and save for next year. As a personal rule, I save $200 per pay check to go towards travel. That way I have may own virtual cookie jar for saving towards something I like to do.

Depending on where you are going, you’ll want to take into consideration costs for airlines, vehicle rental, local transportation (monorails, street cars, buses, taxis). Google Flights is a great place to start. You can set travel alerts to learn if the costs of flight have decreased or increased, as well as see what the general costs are during the year.  Before purchasing the trip, go directly to the airline’s website and act as if you are going to book the flight. This gives you a even better idea of how much it’ll cost depending on if you are flying economy, economy plus, etc.

If you are planning a trip overseas, be sure to have your passport. The steps to getting a new or renewed passport can take some time, and there are some costs associated.  

My husband and I own two timeshares through RCI, allowing us to travel via points or by weeks – within the U.S. or internationally.  By owning, we’ve saved so much on hotel costs; and we typically always have a suite with a kitchen, multiple bedrooms, and top notch amenities. However, there are times where we don’t use our timeshare, and using a local hotel has better advantages. Either way, if you are using a timeshare, you’ll want to plan a head of time. Sometimes the best locations can be booked up to a year in advance. There are some locations that have last minute deals too. 

Family vacation planning checklist

When and Where Are We Going?

When the family vacation is planned can dictate where you are going. Fortunately, I’m an empty nester, so I can take trips any time of the year. I’m not a fan of summer trips – mostly because that’s when everyone is vacationing. I don’t like crowds, whiny children, or heat; so vacationing post-spring break and when kids are back in school is the best time for me. 

If I’m traveling with others, I may not have my favorite choice of when and where I’m going. While planning, everyone should look at a time frame that is best for them – including if it’s a full week or 3-5 day trip. If possible, pick out a range of dates during different times of the year. 

Once you have the dates together, everyone should list out three places they’d like to go.  A lot of times, people don’t know where they want to go without knowing what they want to do.  If you like to hang out at the beach or skiing, pick a timeframe and destination that caters to beach-friendly or ski-friendly trips. 

Before going anywhere, I do an extensive search on Google and Pinterest to learn the best things to do at a destination.  This can include things to do with children, places to go on a date (single/married), daytime and nightlife activities, and where to eat, including kid friendly dining. 

If you are overweight, like me, you can also do a Google search on plus-size friendly destinations. There are some cool plus-size influencers on YouTube and TikTok that can give some suggestions on airline, hotels / resorts, and what outfits to wear. 

Because I’m a person of color, I also search online the ethnic demographics of a location. For instance, when I had a roadtrip to Louisville, Kentucky, I checked ahead of time to learn what the demographics were in Louisville.  This keeps me from being shocked if I see a lot of others that don’t necessarily look like me.

Family vacation planning checklist


The last important thing to do is have some memorabilia.  Take lots of photos and videos! Capture the moments of being with loved ones.  Remember to use horizontal framing. You can always crop to vertical for Instagram Reels or TikTok, but you can’t easily go from vertical to horizontal for YouTube. Know your channel and audience.

Also purchase a few souvenirs. My favorite are magnets because I get to stick them on my refrigerator.  I’m always in the kitchen, so I get to see the locations I’ve been all the time. 

Last thing to remember is to have fun, but honor the locals.  Most times, those involved in the hospitality industry at your destination are not making a lot of money, and they are doing this job because they need it.  When you can, tip the hotel staff, taxi drivers, and wait staff. Learn about the local cultures, but honor and respect those who live there. 


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