How to Survive Family Vacation as an Adult

Family pic in Aruba

Beachin' with my bro in Martha's Vineyard

Every year at Christmas, my stepdad asked the same question: 

"Ok family, so where are we going for vacation this year?"

My brother and I usually shrug and leave it up to them and they pick an awesome place. That's the easy part. The hard part is figuring out how to do vacation (well) with your family as an adult. Who pays? Who picks? Can I share a room with my boo? We haven't gotten it completely right, but I'll let you in on the evolution of my family's vacation do's and don'ts. 

Our first big family getaway was to St. Lucia in 2009. It was an all-expenses paid trip and it was INCREDIBLE. We stayed at a gorgeous villa, went deep sea fishing and rode horses on the beach. Romantic right? Lol! We also drank lots of delicious St. Lucian rum and ran up quite the tab at every meal. This is probably what made my parents go back to the drawing board about our role in this vacation situation.

How do you get your adult kids to choose family vacation over their trips with friends and significant others AND cough up some cash?

It's pretty tough.

After a similar vacation in Aruba, my parents decided that my brother and I would each pay for a meal for the family. Not too bad for soaking up sun and drinking some sex on the beaches! (I was younger and my stomach could handle those back then). I'll be honest that my brother and I both tried to find the most affordable options, but we didn't complain about the new requirement.

The next year was the straw that broke the camel's back. My parents were over their mooching kids. They chose St. Barth's and my parents told us to pay for our own plane tickets and a meal and our drinks. Dayum! That year, I debated on whether or not I would attend. It wasn't because I didn't love my fam. I was also taking an international trip with friends that year and I hadn't accounted for the new family policy changes. I eventually went and had an amazing time. The house we rented was like something out of a music video and we had a lot of fun together. However, after a long discussion, we realized that our time together was more important than a glamorous vacay. To make things work, here are the steps we now take as a family to keep the peace:

1. Decide on a place that is affordable for everyone to fly to.

2. Set expectations in advance of what we are paying for and what the 'rents will cover.

3. All adults pay for a meal for everyone at least once.

4. Adults pay for their own drinks at restaurants.

5. I promise each year to try my best not to roll my eyes when my mom wants to take the perfect family photo in the hot a$$ sun.

Since we've started our family adventures we've also been to Martha's Vineyard and Naples (Florida, not Italy). What I've learned is that it was never about money to my parents. They just wanted us to take some responsibility and that's completely fair. They actually end up not even enforcing some of these rules. Plus, my mom stocks the house with drinks we like and our favorite food. Although I would love to go on another trip to an exclusive island and gallop on horseback along the ocean, I am looking forward to our low-key, affordable lake cabin trip this year. Jet skis are way cooler on lakes anyway :-)

The horse I spoke of. Poor thing!

Action shot at our pool in St. Barth's

How to Successfully Plan a Group Trip

Old San Juan

In 2013, my line sisters and I finally agreed to do a reunion trip. I knew that planning a trip for 14 girls would be a lot, but I was also excited because I LOVE to plan vacations. It’s kind of like a hobby to me. Eleven out of fourteen ended up going because we are grown and things happen. We are working on a Part 2 so I thought it would be fun to tell you how I approach the planning process.

Find a Robin to Your Batman

My line sister Ashley stepped up early as the one who could speak up when I didn't want my voice to became too obnoxious. This is important because at some point people will get tired of hearing from you. They'll need a fresh face after the 10th reminder email.

Location

We are all over the place in terms of careers and priorities. Keeping this in mind, I wanted to ensure that we had an affordable destination. We threw out a few ideas such as Mexico and Dominican Republic for the all-inclusive deals. We also considered Puerto Rico because the flight was very affordable. After the ladies looked at flight prices, the majority ruled for PR. There weren’t a lot of all-inclusive deals, however, none of us are not huge drinkers so we were ok with it.

Accommodations

I put this after location because once the hotel is booked and paid for, it’s every lady for herself (I mean that in the nicest way possible).  Something will inevitably “come up” with a large group, so if the hotel is paid in advance and everyone is clear on the fact that there are no refunds, it will create less drama if someone is indecisive. I’ve heard of nightmare situations where a lot of people backed out last minute and everyone else paid the difference. Not cool.  Plus, this provides incentive for people to follow through and book their plane ticket. I used BookIt.com and created a deadline to collect the money. Once it was all deposited to my PayPal, I booked the hotel for everyone. There were options to do two per room or 4. I also did a lottery (with my other line sister as a witness) for rooms. Can you tell I was the kid in first grade who said “Hey! That’s not fair!” I looove fairness J

Plane Tickets

This part was pretty easy. Since I booked the hotel rooms 4 months in advance, people had plenty of time to look for tickets. A few people waited until the last minute, but again, hotels were already paid for so if they waited to purchase, it only affected the individual person.  Eventually we all worked it out and we exchanged flight information so that we could share airport taxis.

Activities

This part was so funny. The only thing we all actively participated in was a ratchet “dance contest” in the hotel room. Those videos will remain in the vault. So will our pool music video. Ok that’s it, they’ll kill me if I say more. Other than the contest, we were not always on the same page. I tried to include something for everyone, but everyone didn’t like every activity.

The catamaran trip made some folks seasick. Half of us were basking in the sun while the other half were hiding under towels. Some people wanted to close down the nightclub, while others were ready for bed at 10:30. Get my drift? But all in all, everyone was a trooper and we had a good time.

I created a loose itinerary with information about currency, cell phone availability, taxi costs, etc. The activities looked a little something like this:

Friday

Dinner as a group at La Playita

Relax, Chill

Saturday

Catamaran and Snorkeling

Relax, Pool, Nap or whatever

Dinner

Club

Sunday

Breakfast

Beach

Old San Juan and Dinner

Monday

Hugs and Goodbyes

This itinerary worked because it allowed room for flexibility and options. Other than dinner and the catamaran trip, people did things in groups. I think that’s ok and if someone thinks everyone should do everything together, that will create arguments. The best approach is a couple of large group activities and then multiple suggestions for down time. Of course there were some special little moments where things weren't so seamless, but again…it’s a group trip. It won’t be perfect.

Cost

Besides shopping, most of us left the trip spending less than $300. Flight, hotel and everything included, no more than $700. Pretty good right?

We’re planning our 10 year reunion now and I can’t wait to see where we go and what we do! I’ll be sure to share.

XO!

In the end, we all had a great time.