Deciding on When and Where Your Family Should Go on Vacation

Research and planning are necessary for any family vacation. Many people do not want to think about making a schedule for vacation. After all, our lives are always so busy and vacation is for downtime. I completely agree, but also know research and planning are a key to vacation success. Are you shaking your head? Just hear me out…

Know your family wants (needs) a vacation but aren’t sure where to start? Been there. It can be overwhelming because there are so many options. Over time, we’ve perfected the process. Read on to see how we pick our next DeRo Destination.

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Visiting places in their off season, such as Arizona in the summer, can be a huge money saver

The first step for vacation planning is figuring out when and where you’re going to go. For my family, and most with kids, you’re time is limited, as your vacation must coincide with time off from school. Naturally, these are the busiest times for the main family destinations. This includes all theme parks, family resorts, and basically the entire Orlando area. haha. We’ve come to accept this and know going to a place like this, there will be crowds. However, it may be the opposite for other destinations. This includes places that have their ‘peak’ season during the winter or other times us families are in the trenches of the school year, such as the various ski cities in Colorado and desert areas such in the west. Additionally, because you’re traveling during their slow season, you can snag some amazing deals!

Type of Vacation

You will need to have an idea of what type of vacation your family is looking for. Beach? Theme Park? Outdoor adventures? The internet and social media have made researching this so much easier than in the past. I don’t even know where one would start without these tools. You can get a real feel as to what each place has to offer for your family. I have found social media fantastic for this. Searching hashtags have helped us find lot of information, both good and bad, as we are seeing real posts from guests. Searching hashtags have helped us find lot of information, both good and bad, as we are seeing real posts from guests. And yes, I fell down the Instagram rabbit hole, time and time again, doing this.

Transportation and Accommodations

Transportation and accommodations are something that should be looked into at this time. You’ll need to figure out if your family will be flying or driving there.

San Francisco

If you’re flying, check all of the travel websites, for the potential dates you’re looking for, to get any idea of the cost. Airline prices are constantly changing. While you’re in the stage, you’ll just be looking for a cost estimate and to get an idea what flights are available.

If you’re driving, you have two options. If you’re taking your own car, you’ll be able to calculate approximately how much gas will cost. Another option is renting a car. It may sound like a weird thing to do, but it’s a great option if you want to save the wear and tear on your car. Look online to price out your options. The rates also vary from day to day.

Factor in the estimated costs of this. Check online on the various travel websites, such as Expedia, to price out hotels. They will give you a good idea of where the hotels are located in vicinity to where you are planning on going. If you are flexible with dates. Run numbers for all time frames for both, and decide which is most cost-effective for your family. Keep in mind that both of these rates do fluxuate and you’re only getting and estimate.

One other thing that research is the weather. You can look online to see what their average temperatures and weather are during that time of year. Learn from my mistakes: We went to San Francisco in July. I assumed it’d be warm. WRONG. It was chilly and windy. I had to buy pants and sweatshirts for everyone while we were out there.

After you’re done all of this and, if you have a few places in mind, I’d suggest making a list. It would outline what each place has to offer, transportation, and accommodation estimates. With that information all in one place, it should be easy to discuss with your family and make a decision.


Once you’ve made a decision, time to lock it in!


If you’re flying, continue to check those flights and book when you see a good deal. Many airlines give you a grace period after booking, and will reimburse you if the flight prices drop, so keep watching the days after you book. Some airlines also offer a 24 hour cancellation period. This varies from airline to airline, so be sure to check this before booking.

Road Trippin’?

A huge money saver is driving. If you’re taking your own car, be sure the oil changed and is ready to go before you start your trip. If you’ve decided to rent a car, you can book this online. We suggest looking at all different car sizes and all rental car companies. Sometimes, a bigger car can cost less than a smaller one. Here’s a great thing about doing this, usually you can book and cancel without any penalties. So, you can continue to look to find the best deal. This may not be the case for every car rental company; be sure to read the fine print.


Charleston Place in Charleston, SC Beautiful hotel

Picking out a hotel can be so much fun! Once you see all the resort has to offer, decided it’s for your family, and know you’re dates, it’s time to book it. We suggest the same thing here, check all the travel websites to compare the costs. Usually they’re the same across the board, but sometimes you may luck out and find a deal. Many times, the websites may not include the taxes and resort fees on the initial price per night. Be sure to check all of that to get the price out the door, so there isn’t any sticker shock. If you’re going to have a car, check to see if there’s a parking charge. In large cities, this charge can be up to and over $50 a night! Most hotels take a deposit and can be cancelled up to 48 hours ahead of time. If you find a great deal, you may be locked into that and not be able to cancel, so always check that.

Get Excited!

Once these are booked, you can check it right off your list! It’ll feel great to know your vacation dates, where you’ll be heading, and where you’ll be staying.

The next things to plan will be the smaller details. Don’t stress about this either. After years of planning, we also have a system that has worked for us on how to get these details ironed out, before heading out of town and will be featuring this soon.

Heading to Disney? Contact me directly at to help plan your family’s magical Disney vacation!!

Don’t forget to check out our YouTube channel, Destination DeRo.

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