“How To” Plan a Group Vacation

Ever since I was 25, I dreamt about how I was going to celebrate turning 30. I know, I am a crazy person. I am the only person that actually looks forward to getting older. I told my close girlfriends that we should go to Italy and rent a villa for our 30th birthday. It just sounded so fabulous, I knew this was something that needed to happen.

As my 30th crept up, the original crew that was supposed to go had changed. Out of the four of us, only three really spoke to each other. So I changed my plan. Instead of four people, I thought, “Let me take my closest friends that are also turning thirty or have already turned 30.” Coining the term, “Year of 30”. My group went from four people to 12! I literally had no idea that I had that many friends.

Planning any vacation can be difficult. Add in a trip that is over seas with 11 other people. People thought I was crazy for traveling with 12 people and planning it all on my own. But it was rather simple. It helps that I have a meeting/event planning background, but anyone can do this. All it takes, is time and patience. Here’s how I did it.

How to plan a large group vacation

  1. Allow yourself enough time to plan for a vacation. Yes, you can wait until the last-minute, but I don’t feel like you are doing yourself service by researching what all is out there. If you are planning a group vacation. start planning 6 to 12 months out. This allows people enough time to figure out their schedules and plan accordingly and even save money.
  2. Determine where exactly you want to travel to. Depending on how large the group is, do not open this up for a group discussion. You are going to hear way too many opinions making it difficult to settle on a location. Have this pre-determined before presenting it to people.
  3. Set the dates of your vacation. When traveling overseas, it is typically better to leave on a weekday, such as a Tuesday or Wednesday. Flights tend to be cheaper.
  4. Create a high-level itinerary for the vacation. Determine what hotel you want to stay at (I will go into further detail later), how long you plan to stay there, and how many cities you want to visit. This is going to set the core of your itinerary. Everything else is just the frosting! You’ll want to have some group activities, but you should also leave some free time so that you can explore and do things at your leisure. Your guests will find this to be important.
  5. Decide if you want to work with a travel agent or plan this yourself. There are many perks of using a travel agent, see my previous post. It takes a lot of time off of your hands and let’s someone else do all the work for you. Just be aware that the prices you are paying for may be slightly increased because you are going through a third-party and they want a cut. The benefit of doing this yourself is that you can collect all the points, which could potentially pay for the vacation itself. If you decide to plan this yourself, continue on.
  6. Decide how many people you want to go on  this vacation. This again will help you determine how much the vacation is going to cost you. The more people we had in our villa the less money it was going to cost us. Once you have an idea, you can start pricing out how much the vacation is going to cost people.
  7. Figure out the cost of the vacation. This is extremely important. You can’t expect people to commit to a vacation without knowing the cost upfront. This is going to require quite a bit of time. You’ll need to contact car service companies to see how much it is going to be to get to point A to B. Or any other sort of transportation. I like to get at least three different quotes from companies. It shows me who falls in line with their prices or who is trying to rip me off. I also love to use spreadsheets to get an idea of the overall cost per person. I used this as a track the entire planning process. One special thing to note is that if you are traveling to another country that is has a different currency, you will need to adjust the cost to reflect the conversion rate. Just like any market, you risk the chance of the currency rate going down or up. Add extra padding for yourself, you don’t want to get caught with your pants down like I did.
  8. Determine how you are going to pay for the vacation. If you are a complete baller and can pay for everything upfront. Good for you! Me on the other hand, can barely figure out my life. I didn’t want to put myself at risk by putting my own money upfront in case someone decided they needed to back out. By asking people to pay for the trip, makes them stay committed and accountable. You will need to determine when money is due to you and how people can pay. I allowed my guests to split up their payment into three installments. They could pay in cash, check, or electronic payments. Set those deadlines upfront. By collecting guest’s money, I was able to put it on my Chase Sapphire Reserve card. I receive 3 x time points when booking and travel or restaurant purchases, this alone paid for my flight to Italy.
  9. Send out invites. We’re adults here, so it’s time to invest in invitations. I prefer electronic invitations, or e-vites because everyone checks their emails 20 times a day. Plus it is a free service  and you can get super creative with it. I like to use Greenvelope–they have all sorts of fun templates you can use for any occasion. You can select Save the Dates, or actual invitations that gives guests the option to RSVP through the email. You can add a plus 1, add survey questions, or even send out thank you notes. When sending  out your invitation, it is imperative that you include all details about the vacation. Your guests will need to know as much information as possible to make their decision. I included a day by day itinerary and then a break down of the cost. Keep it informative but short at the same time. We all know people will stop reading after two minutes if it is too lengthy, therefore can miss a lot of important details.
  10. Create your own personal itinerary. Not everyone is going to want to do the same things as you. Take the time to research restaurants and tours that would be interesting to you. I have mentioned this in several posts, but Viator is great site to use when looking at tours. Condé Nast Traveler is also great when selecting restaurants. Once you have an idea, share it with the group and see if they would like to join you. If so, price out the cost and let them know that this is an additional cost and they can pay by a certain deadline. Your guests will appreciate laying out some options for them.
  11. As you collect money from your guests, start to pay off your expenses right away, especially if the currency rate is down. This will reduce confusion and any awkwardness when traveling with the guests. You will want everything settled upfront before you go.
  12. Share your flight details. It is way easier to have everyone on the same flight as you, especially if you have arranged for a car service to pick you up. Try your best to pick a non-stop flight. You get to your destination faster and you reduce the chances of anyone losing their luggage. Side note: depending on the length, guests should pack a carry-on bag instead of checked bag. Again, this reduces the chances of one losing their belongs.
  13. Send out helpful travel tips. Things to know, how to pack, what credit cards to use (foreign transaction fees), passport checks, and what to wear is always helpful to guests. By doing this, you are creating a concierge service for them and increasing a level of comfort know that you know what you’re doing and that they are in good hands.
  14. Collect everyone’s contact information. It’s important to have this for your own records, but it is also good for your guests to have this prior to the trip so that it is not an issue while traveling.
  15. Create a travel booklet. This booklet should include hotel confirmation numbers, flight info, train tickets, tour tickets, etc. All of this information for your guests, that way your guests can never say they did not receive something. Cover your basis.

There you have it! That is everything I did to plan a 12 person vacation. It is pretty easy and simple for anyone to do, regardless of what your profession is. It took a lot of planning to do all of this, but this is what I love to do. I want to share these experiences with my friends and show them the world that I have seen. Our group had so much fun that they want to do it again in 2018. Check out my Italy Vacation Part 1 and Italy Vacation  Part 2 to read all about our wild and crazy excursion. If you need assistance planning a vacation, I do offer my services for a small fee and be contacted at bordeauxandbubbly@gmail.com. Until next time…xoxo!

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