Project Design is a monthly feature with Annie and Cindy, and THIS one is all about travel planning! I’m sharing my husband’s tips on how to plan a large group vacation (from 8 to 25+ family and friends) without pulling your hair out!
AND at the end of the post, you will find links to essential advice for stylish travel by six experienced travelers! We are so happy they are joining us and I can’t wait to read their tips.
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How It Began
Our group started with these college buddies below and grew to include their wives and children. When the kids were little we rented beach condos next to each other but as they grew up we started taking more elaborate, planned vacations.
My husband, Howard (pink shirt) has had a distinguished career in the travel industry (lucky for me). I trapped him in a four-hour car ride from San Francisco (where we live) to Lake Tahoe for a ski trip. I asked questions and recorded his tips on how he plans these large group vacations for us. Here’s how he does it to it make it stress-free and memorable for the whole gang.
Who Is Coming?
I should say upfront that your group should get along (Howard says “no one should be a pain in the ass”). So, good luck with that. Communication is key.
Deciding Where To Go
In order to have the best options for places large enough to hold your group, you need to start a year or more in advance. Survey the group via email of places they would like to go. Narrow down the list with a vote. Once decided, make sure you have a strong verbal commitment from everyone. This helps define the size of the lodging you will need. We find that renting large homes, villas or farmhouses are more economical and fun than a group of hotel rooms.
When To Go
This depends on the occasion, but if you have children in school and want to go in the summer, the earlier you book in the summer the less expensive. Also, vacation homes normally require a one-week minimum stay.
How to Organize and Plan The Trip
- Designate two to three people to research the destination’s accommodations. This is according to the number in the group and amenity wish list (ie. individual bathrooms, pool, tennis court, maid service daily or weekly, cook, etc). Note: sometimes large properties already come with a cook and if not, the management company can hire one. We often split off into smaller groups for lunch (since really large groups require firm reservations for small restaurants). It’s nice to have casual morning breakfasts together and relaxing group dinners “at home.” Usually, dancing is involved after dinner with our group (we have some music enthusiasts that bring their playlists).
- Google “Villa Rentals in…” to find local specialists (like we did for our upcoming trip to Mykonos, Greece) in addition to researching: HomeAway (used for our Sicily trip), Airbnb and Villas of Distinction (used for our Provence trip).
- The two to three people discuss their findings and submit the best option to the group.
Now One Person Is In Charge
One person has to be the leader to:
- negotiate villa cost
- collect the down payments from individuals and make payments
- hire the chef and select menus
- set up local guided tours, if desired, and pay these vendors
With a large group, you may want to take advantage of organized tours. For example, wine tours, sailing, biking, historical walking tours, etc. Normally, the easiest way to do this is with a local tour operator who arranges a bus to take the group together.
How Much $$$
Once you are ready to book, everyone must send in their non-refundable deposit to the group organizer. After this point, people cannot back out since the total price was based on their participation. It’s unfair to others to make the group absorb the cost.
The villa deposit is usually 50% down at the time of booking (somewhat negotiable). The group organizer sends it. Then, the balance is due about 60 days before the trip. (The final collection for our Greece trip in June is taking place now).
These international trips are not cheap but the prices can vary according to the level of luxury you want. For a week, we find that the price per person including food and tours is around $1500 to $2500 (not including airfare). The splurge is worth it to us for unforgettable memories. Although I would still be happy renting the beach condos like we did when the kids were little.
How To Get There
Everyone makes their own travel arrangements to the destination (including trains, planes, and automobiles).
Planning is complete. You are ready to go to have a fun and unforgettable Large Group Vacation!
Now be sure to check out what these pros recommend!
“How to Pack Your Suitcase Like A Pro” by After Orange County
“How to Take the Stress Out of Packing When Every Outfit Counts” by Brenda Kinsel
“Stylish & Savvy Travel Tips from a Travel Advisor” by Curated Travel
“How to Pack for a Weekend Getaway” by Most Lovely Things
“How to Rock an Over 50 Travel Wardrobe” by Rough Luxe
“Footloose: Shoes For Spring and Summer Travel” by Une Femme D’un Certain Age
Here are some of my favorite things for travel…especially the game-changing, lightweight packing cubes from Amazon!