Travel Prep 101: How to plan a vacation (with your family, on a budget)

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If you love to go on vacation but hate spending all the cash in your travel account AND you’re an obsessive planner (or just wish you were) then you’ve come to the right place to figure out how to make your next big vacation happen. I’ve always loved to travel but since we had a kid it’s required more prep work and budget planning. Here are all my top tips on how to plan a vacation to ensure you don’t have to give up on travel just because you have a child (and less disposable income!)

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The list below may seem a little bit out of order, but bear with me – there’s a method to my madness.

Decide if you’re going sans kiddos or bringing children along

This is important to do first as it will impact the rest of the decision-making process. If you want to go on a family vacation or even if you’re planning to bring a kid on a more “adult-focused” trip, the next few decisions will change.

Key things to consider:

1. Do you have a grandparent that can watch the kiddos?
2. If they stay home, would you need to pay for a sitter? (Does your sitter drive, is this a viable option? — This brings up a whole host of other questions I’m not going to address here, but think about it.)
3. How long can you really ask someone else to watch your kid(s)? Even if grandma says she’s on board, I’m guessing a month long trip around the world is still out. While a weekend or 3-4 days may be acceptable, even the most patient grandparents get tired after a week with a toddler.

Alright – now you know if you’re going alone or with a kid, on to the next step.

Determine the general time of year you’d like to go

This is important to figure out next since it will impact the budgeting phase. If you have no cash restrictions and/or are independently wealthy, skip this step. You’re probably also on the wrong blog, but I digress.

If you know you ONLY get one week a year off, and you need it to coincide with summer vacation, this will impact your ability to snag the best deal. However, don’t let this deter you. Decide when works best for you and keep moving.

 

How to plan a vacation location: Choose from your bucket list!

You’ll choose a location from your bucket list that takes into consideration answers to the first two questions. If you’re bringing kids, the adults-only Nassau resort is off the table. Once you’ve determined the kiddos are coming, you’ll probably want to look into destinations that are baby/toddler/kid friendly.

You’ll also likely want to find activities or excursions that are specifically for your kids. It may not be a trip to Disney (or it might be :)) but I’m sure you can find some kid-friendly fun near or in your destination of choice. More on this in a bit.

Same criteria go for hoping to book a ski vacation in the summer. It’s probably not going to happen, and if you figure it out – it’s going to cost you. You’ll need to marry your destination and desired vacation time with seasonal availability.

For instance, if you really want to hike Torres del Paine in Patagonia, but can only go in July, you may want to plan that trip for another year. Although the park is open, a lot of the amenities are closed. This happens a lot with high and low seasons. While I’ll advise you to look in the low season for some high ticket trips, many times you get the great rates because a lot of the cool attractions are shut down.

Create a budget for each phase of your trip

One of the most important things you should take away on how to plan a vacation is that you’ll need a budget. And it should be detailed, not an “eh, let’s wing it” kind of thing.

Now that you know where you’re going and who’s coming with you, it’s important to lock down the budget. If you’re doing a family vacation for four in Hawaii it’s going to be a bit more expensive than a flight for two from New York to Chicago.

Once you have the details, get an estimate of how much it will cost by googling plane tickets, average hotel stays, etc. so you can begin to build your budget for the trip. I love this part so much because it allows me to understand what we can afford to do (see next step) that I created a budget template.

Get immediate access by entering your email below so you can access it from our resource library!

Here are a few of my favorite sites to browse for reference information:

Hotels:

Hotels.com
Booking.com  
Priceline.com

Flights:

Momondo.com
Kayak.com
Priceline.com
WowAir.com

The best thing about Momondo is that it shows you all the low-cost airlines, and you can go directly to their sites if you’re trying to work out baggage fees, etc.

Key budget categories

Here are the major categories we typically plan when looking at the details behind a big trip. These may change depending on what you value, but we spend money on each of them.

Yes, I put food on the list. I know I’ll eat no matter what, but we try to be more conservative when we’re at home. When I’m on vacation I like to go out to eat. I don’t want to break the bank, but I also don’t feel the need to cook every night. Since it’s an incremental expense, it goes on the list.

Airfare
Hotel
Food
Transportation (Rental Car, Parking, Train, Metro Card, etc.)
Activities/Excursions
Childcare
Gifts/Shopping

Build in excursions or fun extras that fit within your budget

After you know how much the basics of getting to and fro are going to cost, you know what flexibility is left in your budget. We use these for things like wine tours, day trips, zoo or attraction admittance, etc.

Our honeymoon was an all-inclusive in St. Lucia, but as everyone knows all-inclusive resorts have “upgrades” and optional excursions. We planned a few extras that were paid and traveled between resorts when we just wanted a change of scenery.

 

Find Kid-Friendly Activities (if they’re coming)

If you’re bringing the kids, you’ll want to make sure they have fun too. If not, skip this part (for real this time) and head to the next section. As all parents know, if your kids aren’t happy, you aren’t going to have a good time.

Even if your trip isn’t focused solely on your child’s happiness – there are a ton of fun things you can do to ensure they have a great time. For instance, in Amsterdam, there is a Legoland. While I wouldn’t assume that many people are choosing Amsterdam as the top location of choice for their kiddos – if you’re there, you might as well head to Legoland and ensure they have fun.

We love looking for Zoos, aquariums, or interactive museums in cities we’re visiting. We have a two-year-old and this ensures that we have a special activity to bribe promise we’re visiting with good behavior.

 

Scour the internet for flight/hotel/tour deals OR work on planning your vacation via travel miles

As if the first few phases of this process weren’t enough manual labor, now it’s time for the hard work of actually stalking down those deals. You can sign up for flight alerts or just pop over to your favorite sites daily.

Here are a few of my top tips:

1. I would recommend starting far in advance and checking on the baseline cost before you click on the “buy” button on anything
2. Google coupon code for “x” before you buy anything. So many sites will give you 10% off if you sign up for their email list, or they just have coupons floating around
3. Look up off-season specials. We try to hit a hotel every year during the winter that there is NO WAY we could afford during the summer. It’s nice to pamper yourself with a resort’s low season

This is outside the scope of this article, BUT I have started getting into travel rewards. If you’re interested in traveling for FREE by putting your normal spending on credit cards, take the Travel Miles 101 Course to learn more.

Grab your passport and go!

Finally – after the hours and hours (and probably months) of planning, you’re ready to go. After all the hard work you’ve put in you probably only need to grab your passport and your travel folder (you have one, right?) and go. Don’t forget documents for your kiddos if they are tagging along.

If not, enjoy traveling with ⅓ of the bags and grab a cocktail on the flight. You deserve it!

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