Who doesn’t love to travel? And sometimes it’s even better with friends! 

This is for all those people who want to go on a trip with a group of friends and they aren’t sure how to pull it off. It’s also for the people planning a celebration from afar and feel uncertain about the outcome. I experienced both of those things on my latest trip to Turks and Caicos and have some insight for those moving forward. 

How to plan a trip with friends

Planning a trip with a group of friends at first seems exciting and magical. You think of all the memories and fun you’ll have when you go on vacation together. But then, you have to figure out who’s going to plan it, keep it organized, and have it go off without a hitch -meaning no one wants to unfriend by the end of the trip!

In my case, I decided to plan our trip for three reasons 

1) because it was my husband’s and my idea, 2) because we were making this trip a celebration for his upcoming 50th birthday, and 3) well because it was his birthday, so, of course, I wasn’t going to make him plan it. 

…Plus, my husband had just planned our trip to Ghana, and you can read more about that here. 

To plan our trip, I handled all the details and made sure to run a few of them by my husband for approval. And since I wanted to get everything set up for our guests, I made all the plans first then shared them with the group.

Things I had to do:

  • Book the house
  • Schedule transportation —I chose to use the same car service the whole trip so we could use it whenever we wanted to leave the house
  • Made dinner reservations ahead (don’t wait until you get there to do so -things are just different these days)
  • Picked out the chef’s menu (for every course, of course)
  • Organized activities (yacht rental and more)
  • Book the party planner (what, a party planner?! I know, sign up for my email list if you want to hear more about it)

Even though these sound like everyday tasks they’re not as easy handled internationally. Thanks to the internet, social media, reviews, and friend recommendations I was able to make all the plans although some reservations still felt a little unsettling knowing I was putting down money deposits with people and businesses I had no real way of verifying because they were so far away. Thankfully, it all worked out!

Planning the trip with the group

If this doesn’t sound quite like your scenario and all your friends will help with the planning for the “big trip”, I still recommend having one person (maybe two) be the main planner or coordinator. While it added extra work for me, having more than one person handling the ins and outs of all the details would’ve been hectic and felt disorganized. Plus, when planning a trip from afar for a large group of people—in another country especially, there are quite a few steps, regulations, and requirements that you need to follow to pull it off. It’s easy to get confused and miss something.

We planned the trip first and then invited the people. So we weren’t all planning together. And since it was my husband’s birthday, he chose the friends who would join us. In doing so, we automatically became the “hosts”. Our vision was that we planned it, and everyone else showed up to enjoy it.

We took charge of all the decisions then asked who wanted to join. Felt good because we didn’t have to wait for people to decide before we made plans, but it also put a lot of pressure on me because, you know… you want it to turn out perfectly for everyone.

However, suppose you included your travel group in the planning. In that case, I recommend having one to two people do the main planning and executing, then run all the ideas through the group via a voting system. That’s worked best for us in past group trips.

When planning with a group make sure

  • Everyone’s voice is heard
  • Talk about travel goals
  • List ideas of activities 
  • Keep a checklist
  • Talk about budget and prepare to pay ahead
  • Discuss the type of identification and vaccination status your destination requires 

Things like budget, room preferences, activities, and dates are great things to discuss as a group. These conversations will weed out who might not be a good fit for the trip this time around.

Should your group book a hotel or rent a house?

We decided to rent a house for the week versus staying in a hotel or resort. I had a friend who traveled to Turks and Caicos in the past and had an excellent experience with a travel company, Rental Escapes. I felt confident with their recommendation, so we decided to use them as well. 

We chose to rent a house together because we never got enough time with the friends we were inviting, and we wanted this trip to feel intimate. However, if we were going to pull off an incredible experience with all of us in one house, I knew I had to be very specific on the type of place we rented. 

Bringing a large group of friends together for a luxury vacation should not include sharing the cooking and clean up —that’s when I head to the hotel.

We had to have a chef, a house cleaner, a pool, and lots of space. We also had to have transportation and reservations for activities. 

If you decide that you and your friends would rather stay in a hotel, I highly recommend an all-inclusive one. There are a million and one benefits when it comes to all-inclusive hotels, but one in particular when traveling with friends is that it’s already paid for. So once you’re there, no one has to feel like they’re short on cash or they need to skip the expensive hotel meal to save a buck. Everyone is on an even playing field in the money department, and that’s super helpful for relaxation and enjoyment.

When you travel with friends does everyone have to know each other

Believe it or not, NO! We’ve done it both ways, but this last trip we took to Turks and Caicos, my husband invited seven other couples, and none, yep, you read it, none of them knew each other. We knew all of them, the friend and their partner, but they had never met each other. That was a first for us but we quickly discovered it could be a fantastic trip when our friends didn’t know each other at first.

We knew these were all great people, and they were there for my husband, but it’s always a risk when people that have never met stay in the same house. So that was an added layer of complexity for me.

Rule of thumb

If you’re planning on traveling with friends who don’t know each other, stick to inviting people you know won’t cause drama or bring toxicity. No one needs that in their life, especially not all the beautiful people who chose to spend their vacation time and money with you.

Introduce the group before you travel 

Put everyone on an email string and (if they’re willing) share their social media contacts. That way, everyone can get a baseline introduction for who they will be spending time with. 

  • Add travelers to an email string
  • Introduce through social media, video calls, or text
  • Send out check-lists and updates to keep people organized

After all, not only did we have to sleep in the same house, but we had to prep for the trip together as well. As the planner, I had to ensure everyone had their proper travel documents and insurance to get into the country and that they met the current covid guidelines —which (as we know) were constantly changing. 

Since many were coming on different flights, we communicated transportation schedules upon arrival to Turks and Caicos. 

And, by the time we all arrived, everyone was super excited to meet in person.

By the end of the trip, the 16 of us were like a group who’d known each other since childhood. It was a really great time, and besides having to organize a ton of moving parts during a pandemic, it was so worth it!

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