This is one of the most requested posts but it’s one I keep putting off because I couldn’t figure out how to structure it. I like to share things that have a system that can be replicated because I feel that’s most helpful, so I’ll do my best. Fellow travel lovers, how do you plan your travel?

Step 0: Know Thyself

What kind of travel do you enjoy? What kind of travel do you want to do more of? Let your style and desires be a guiding factor for all your vacation planning. For example, what we know about our travel style is:

• We don’t like to repeat destinations often with the limited travel time we have available to us currently. There are so many places we want to see!
• We prefer active vacations, having things to do and see over resting and relaxing.
• We prefer to mix of being able to eat food in our condo/room and going out to recommended restaurants.
• We prefer more remote destinations to crowds and busy cities.

At the beginning of each year, David and I do our State of the Family presentation, which includes an in-depth review of our finances as well as a walk through planning session of the coming year. What does each month bring? What’s already on the calendar?

Step 1: Who is going?

We are fortunate to travel as the four of us and also travel with our extended family. Both mine and David’s sides of the family like to get a trip, or at the very least a family gathering, on the calendar each year. These are trips that obviously involve more people, lending itself to be better for certain destinations and lodging, while a weekend away with just David lends itself to other options, like hotel rooms. How many people? Ages? Any limitations for activities or date rangers that need to be considered?

Another thing I’ve given attention to in planning is ages of the kids for certain experiences. I’m really glad we did the Polar Express Experience and Disney World (and Disney cruise) when the kids were young enough to get wrapped up the magic of it all. Would those still be fun at 12 and 9? For sure! But I really appreciated getting to see those things through their toddler and little kid eyes.

Step 2: What’s the timeframe?

Extended family travel usually has a more narrow date range, as there are more schedules to work around. Usually these trips get planned and booked first and we work our family travel with the four of us around that. Time of year helps us narrow in on the type of destination we’d like to visit. We like to avoid crowds (not always possible), but because of that we try to book off season if schedule allows. For example, we are planning to go to the beach in October this year, which is my favorite time to visit for less crowds and more ideal temperatures for outdoor activities.

We also like to book at least 6 months in advance, usually more is possible. Some places, like Lone Mountain Ranch, require more like a year in advance due to availability. We like planning ahead because more options are available, it’s less stressful to plan, and it gives us time to look forward to it and get excited.

Step 3: Reference our inspiration list.

This is not a formal document, but perhaps it should be. Still, we all have some ideas that float around of places we’d like to try. Under Canvas glamping was on mine for a long time before we planned it for this past September. Blackberry Farm, Primland Resort, the Redwood Forest, and Glacier National Park are some US destinations I haven’t been to yet but are on my wish list. Banff ranks high up, too, and we haven’t even touched Europe as a family yet.

I find inspiration from hearing about friends’ travels and on social media. Searching destinations on IG or Tiktik can give you a detailed and unfiltered look at what the destination will look like. I google destinations and attach “blog” or “review” at the end of it to find firsthand accounts of experiences. And when we are at unique destinations, I chat with fellow travelers about their favorite destinations and add the best to my list.

Step 4: Is there something for everyone/a good fit for the group?

With multigenerational travel I like to consider each person. Are there comfortable beds and a place for downtime? Are there activities for all ages? Is there a place to keep snacks or have some meals that don’t require restaurants (depending on ages)? Can the youngest keep up with the activity plan? You get the idea. I also consider: what is the vibe? Super fancy obviously isn’t the best fit for kids.

Also, what is the lodging like for the destinations we are considering. For bigger group travel, is there a place we can all relax, talk, and play games together? Is there a kitchen so we can make some of our meals? Rentals tend to be a better fit for us for larger family travel and condos are a great fit for our family of four travel. We can do hotel rooms when we travel as a family of four, but if it’s longer than a night or two, I know it will begin to negatively affect everyone’s sleep, which isn’t good for anyone involved. Just David and me? I love looking at hotel options!

Step 5: Research costs and specifics.

How do we get there? Where do we stay? What to we eat? What will we do? I research these topics and get ballpark prices for it all. I search destinations on social media to see first hand experiences and recommendations. I google and read blog posts. I ask you on IG. I take notes of restaurants, activities, special things to do or see in the area, etc.

Step 6: Present, book, and start a google doc.

Oh the fun phase! Gather the decision makers and talk through it all. Does it feel like a good fit for everyone? In the budget? Something we’re excited about? If so, we don’t waste time and move forward with booking it.

We look into any discounts of packages, check our credit card point options (I still feel like such a credit card point newbie, but I understand the basics), and then get in on the calendar. We email all involved parties the itinerary then begin a google document of restaurants, activities, and other tips and pointers for the trip to add to as it approaches.

And that wraps it up! I asked David to read this and see if I was missing anything and the tidbit he added was to think outside the box. It’s easy to get pulled into the ease and convenience of all inclusive super resorts. While those can provide ease and security and can certainly have their own perks for the relaxation-seeking traveler, if you’re seeking something a little different, take your desire (for example, the beach) and see if you can spice it up a bit- maybe you want to try camping or RVing at the beach, or go in the off season when it lends itself to more moderate temperatures and outdoor activities, or maybe find a beach close to a historic town or site and mix up the activities a bit. These are all things we consider as we plan our travel and seek new experiences to share as a family. Happy traveling!