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.