7 Very Easy Tips on How to Plan a Vacation That’s Absolutely Epic

7 Very Easy Tips on How to Plan a Vacation That's Absolutely Epic

My toddler-age daughter flew through the air, laughing as she soared and splash-landed in the heated outdoor pool on the Carolina coast. The cool early November temperature didn’t faze her and only mildly affected me as I propelled her with all my might. Those were the days. Our two daughters were young, business was thriving, and we took a couple of beach vacations each year. Then a little thing occurred in 2008 called the Great Recession, and figuring out how to plan a vacation became much more challenging.

My daughters became women, my son born in 2006, sprouted facial hair, and I grew melancholy watching my baby birds spread their wings. I longed for captive times together, playing board games, rushing hand-in-hand into the ocean waves, and watching in terror as the tide destroyed our sandcastles. In a strange moment of sitting alone on the beach in May 2019, I determined to figure out how to plan a vacation for my family each year. We’ve been three years running, and I’ve already booked our September vacation.

I want to encourage men my age to recapture the wonder of planning family vacations. It’s not too late. I also want young fathers to understand the importance of pausing their busy professional lives and learning how to plan a vacation. Yes, it’s expensive, but I’ll explain how you can do it and and give some tips on how to make the most of your time away.

7 Tips on How to Plan a Vacation That’s Absolutely Epic

riding bikes on the beach is one way how to plan a vacation

1 – Set Up an Automatic Savings Plan

Setting up a vacation savings account plays a significant role in how to plan a vacation and it was my first step to ensuring quality beach time with my family. The cliches are true. “If you fail to plan, you plan to fail.” “No decision is a decision.” Hard financial times pounded me into paralysis, and for many years, I stopped planning vacations. But sitting on the beach without my family on my birthday in May 2019 was a humbling, eye-opening experience. Certainly, I could figure out how to plan a vacation if I started a year in advance.

Time is your best friend in mastering how to plan a vacation. I calculated we’d need $2500 for a beach house in the off-season. We never plan a vacation to the beach during high season because of three toos – too hot, too expensive, and too crowded. Not my idea of a vacation. Simple math shows that $2500 is $50 a week for a year. Breaking down an elephant one bite at a time is the best way to tackle big goals.

Fifty dollars a week is skipping a meal out or a combination of things like ordering water instead of sodas or beer when you do go out to eat, shopping for groceries at Aldi instead of the more expensive grocery stores, and switching cell phone service from Verizon to lower-priced carriers like Total Wireless that use Verizon towers.

I made a deal with my family the first year. Since we knew our vacation was a year away, I told them every time they ordered water at a restaurant, I would transfer the cost of sodas over to our vacation savings account. This deal was a sure way of capturing the savings for vacation and helped them join the mission. For more tips on how to save money for a vacation, here are 23 ways to save money easily by financial guru Dave Ramsey.

It’s easy to find $50 a week when you’re focused on your family and figuring out how to plan a vacation. But it’s essential that you create a vacation savings account and automatically transfer the money from your checking account each week.

2 – Get Everyone Involved from the Beginning

This tip is one of the best ways how to plan a vacation. Instead of planning a vacation and dragging your family along, or if your children are adults, and just telling them when and where to show up, let them be a part of the process. Allow them to think and get excited about the vacation a year in advance.

Communication is vital in how to plan a vacation. Create a vacation group text thread. Let your family help you choose the beach, the beach house, and the vacation week. One year everyone voted whether the house would be oceanfront (my choice) or second row with a private pool (my son’s choice). The oceanfront people won. Once the beach town and house are selected, everyone searches for local restaurants and activities, sharing their findings in our message thread. We rode jet skis on the Intracoastal Waters in Surf City two years ago.

saving money to ride jet skis is an excellent way how to plan a vacation

We all know how it is. We unpack our bags on Sunday afternoon at the vacation house, and a few blinks later, it’s Friday afternoon, and our moods tilt towards melancholy. Creating a collective experience allows everyone to enjoy vacation for an entire year and is a thoughtful approach on how to plan a vacation.

3 – Designate Cooking Nights

This tip on how to plan a vacation works exceptionally well with older teens or adult children. Going out to eat every night on vacation is very expensive, and it’s not something we do. We’d have to bump up our weekly vacation savings, and I’d still rather cook at the beach house and use the extra money for jet skis or other adventures. But we do make it a point to share dinner time because breakfast and lunch can be hit or miss.

Depending on the size of your crew, assign a night for each person or pairs of family members to be in charge of dinner for everyone. They can cook or order take-out, but they choose the menu, and the best part, they pay. My family members usually opt to cook, and they enjoy meal planning and shopping for the ingredients. Sharing the dinner meals takes the load off Mom and Dad, and everyone enjoys participating.

Most people appreciate taking on responsibility (and I mean that in a much broader philosophical sense).

4 – Plan a Meal Out

We plan at least one meal out as a family, usually at the end of the week. Again, it’s a group decision, and we painstakingly choose the restaurant. It’s always one of the highlights of the vacation. Last year, we played karaoke bingo at a restaurant on the pier, and I sucked at music made after the 1980s.

I’m not a “foodie,” but I enjoy eating at local dives on vacation. I’ll ask cashiers in grocery stores or bait shops where the locals eat. I can eat at Ruby Tuesdays anytime. And my go-to most strategic question in the local restaurant is to ask the server, “If I die today and never make it back here, what is the one thing on the menu I’d regret not getting?”

Save money by eating in all week, but punctuate your vacation by enjoying a meal out together. Take plenty of pics!

5 – Take Plenty of Games

The purpose of planning a vacation with family is to regroup after being scattered about all year and to revel in time together. Eating dinners will bring everyone together; we also love playing games. Most vacation spots will have family fun activities such as miniature golf courses, go-kart tracks, amusement parks, and arcades, but if you’re like us and on a budget, these events can be expensive. So, if you want to know how to plan a vacation that’s fun and affordable, let’s talk about games.

We take board games like Monopoly, Codenames, Scrabble, and card games like Apple to Apples and Uno. My niece, Olivia, taught us the dice game Farkle, which has become our favorite family beach game. We’ve laughed so hard sitting around a big table, eating Doritos, Sour Patch Kids, and fun-size Snickers while playing games.

6 – Let the Young Folks Loose

Tip #6 on the list of how to plan a vacation goes against everything I’ve said. Give your older teenage and adult kids a night off by letting them explore the town on their own. Reward them for their willingness to hang out with the old folks all week. My kids and niece love going out. It’s a great chance for them to bond and do crazy (but not too crazy) young people stuff.

This is also the night my wife and I go out. To be honest, we enjoy getting reacquainted over some quiet time. Incorporating downtime into your vacation schedule is an important aspect of how to plan a vacation, allowing for relaxation and rejuvenation.

7 – Buy a Shibumi Sun Shade If You’re Planning a Beach Vacation

I’m not affiliated with the company that makes Shibumi Shades, but I’d be remiss if I didn’t tell you about them. If you want to know how to plan a vacation at the beach, you’ll want a Shibumi sun shade. In 2020, our first annual family beach vacation, we bought an inexpensive canopy-style sunshade on Amazon. We wanted one large enough for the entire family instead of hauling several beach umbrellas – we have a couple of fair skin folks in the family.

The damn contraption took four of us over an hour to assemble! That sucker got packed up and sent back to Amazon.

But while fighting and cussing over our poorly engineered POC canopy, we saw older men quickly setting up blue and teal sunshades up and down the NC beach. The video on Shibumi’s home page is drone footage flying over the beachfront covered in blue and teal. This is true to life. You can watch a young lady set up one in 54 seconds below.

The Shibumi Shade is costly at $270 but easily accommodates six or more people. They have a mini for $190, which covers up to 3 people. Build the price into your first vacation, and you’ll never need to buy another sun shade. It’s worth every penny. The Shibumi website has the tagline, “WORLD’S BEST BEACH SHADE,” and it is. But I’d also include the unique selling point, “Old men can set it up quicker than their wives can sit down and open a Danielle Steel novel.”

Spend less time setting up a sunshade and more time relaxing under your Shibumi. You’ll thank me later.

Wrapping It Up

As time passes and families grow, it’s essential to recapture the joy of family vacations. Despite financial challenges, you can still figure out how to plan a vacation. Fathers can create cherished memories and strengthen family bonds through annual vacations by prioritizing family time and implementing these tips. Your duties as a father aren’t finished just because your kids are too big to launch across a swimming pool. They need your continued leadership and keeping the family together is very important. Serving your family is a wonderful way to enjoy purpose as you travel through midlife and beyond.

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