Are you interested in planning a group vacation? You are not alone. Right now, lots of people are researching how to plan a group trip according to Google. And if you have followed me for any length of time…you know that we enjoy group trips with friends every year.
There are links about those awesome trips in this post.
Steps To Plan A Large Group Vacation
So I’d like to share an updated post of my husband’s tips on how to plan a vacation for a group of people (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!
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How It Began And The Planning Process
Friendship: 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.
In fact, these trips were a bonding experience for everyone and we have a text group chat called: Family By Choice.
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 to Lake Tahoe for a ski trip. I asked questions and recorded his tips on how he plans these larger group vacations for us. Here’s how he makes travel plans stress-free and memorable for the whole gang.
Who Is Coming? Your Travel Buddies
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 and flexibility are key.
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Deciding Where To Go For A Large Group Vacation
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 is more economical with the shared expenses and fun than a group of hotel rooms.
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When To Go:
Check the weather! If you don’t mind winter in Paris…great. But if you have children in school and want to go in the summer, the earlier you book in the summer (say May and June) the less expensive. Also, vacation homes normally require a one-week minimum stay.
Trip Planning: How to Organize
- 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 restaurant reservations). 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 trip to Mykonos, Greece) in addition to researching: HomeAway (used for our Sicily trip), Airbnb, and Villas of Distinction (used for our Provence trip).
- Two to three people discuss their findings and submit the best option to the group, including approximate rental costs.
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Now One Person Is In Charge
One person has to be the group leader to:
- negotiate the villa vacation rental cost
- collect the down payments from individuals and make payments
- hire the chef and select menus
- set up local guided group adventure tours, if desired, and pay these vendors
Group Excursions
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.
The Finances
Once you are ready to book, everyone must send in their non-refundable deposit to the group planner. Venmo or Zelle is quick. 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.
You may like Beautiful Farmhouse Manor in Provence which we rented.
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 $1600 to $2600 (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, plane tickets, and rental cars).
Next:
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!
Love your group trips, MA. They always look so well organized and so much fun. I appreciate Howard’s tips and advice … especially the no pain in the ass rule! x
Mary Ann (and Howard) — Thank you, this is a wonderful post that is so helpful! We are going on our first group vacation in May with our 1-year old, and it was a bit hectic to get everyone’s schedule, where they wanted to stay, what they want to do, who needed what amenities for certain aged-kids, and so on. There’s already things we wished we would have known or done differently, and we haven’t even gone yet! But this post will be emailed out to all in our group, as we want to keep the vacations going but without all the confusion next time. Hopefully one day we will be able to travel abroad with our group, too! Thank you again.
Thank you so much, Ann. Bon voyage!!!
I’d love to know how your group decides who will get to sleep in which bedroom. Everyone wants the biggest and the nicest Master Bedrooms. And I don’t want anyone to feel cheated with their payment.
Seems to rotate, who gets what but the organizers usually get the first choice.
Great post, Mary Ann! Howard is a great planner!
Mary Ann, you are extremely lucky that Howard is such a wonderful director for planning these memorable trips. We have done family trips before, but not to this extent and it is a great way to have a terrific adventure. I’m the one who does the planning for any of our trips, unfortunately my husband is totally clueless. Thanks for sharing Howard’s travel tips!
I’ve never traveled with a large group, but can imagine the logistics are complicated. You’ve covered all of the bases so well, and it makes me want to round up some family and plan a group trip in the future!
This is such a helpful post Mary Ann. Please tell your husband thank you for all the great advice. Coming from a real pro that really means a lot! We have a group of friends that have wanted to plan a trip together for ages. Maybe this will be the impetus for us to start planning. Your trip looked fabulous!!
I learned a lot from you post, Mary Ann, and one of the things is that I won’t be the final person in charge. I’ll post the pics to Instagram! What a fun tradition you’ve had and I imagine it has gotten easier and easier. Of course, having Howard in the travel industry is quite the asset. You made me think of lots of things and was actually quite comfortable with the cost you mentioned. To be making memories like you said, it’s all worth it! Now I understand what goes into many of the trips you take. It makes it more fun to follow along!
xx
Thanks, Brenda! I feel the same way and hope Howard keeps being the leader…there are others in the group that are really good too.
Our “Non-playing Bunco Group” goes on a trip every year. We haven’t done any international travel, but our trips are planned much like yours. A destination is decided upon, a commitment from each person in the group, a VRBO or hotel booked and then money is collected monthly to pay for cabs, Ubers, a “last night” dinner out, groceries and tours. Airfare, lodging and spending money is paid for individually. We’ve been to NYC, Boston, Nashville, Seattle, Sedona, Chicago and then, locally, Los Olivos/Solvang. This year is also local: Palm Springs. We’re considering Vancouver and British Columbia in 2020. We have between 6-12 people go every year. It’s so much fun and something we girls look forward to every year. Thanks for your excellent tips and new location inspiration!
Sounds like so much fun, Suzanne!
I LOVE seeing all these happy faces and beautiful places in your images, Mary Ann. What amazing travel adventures you have shared with these longtime friends. Your husband is quite a pro and I have to agree with his mantra on travel planning. 😉 It can be daunting putting all the details together for a large group and clearly, he has the process down! You mentioned Villas of Distinction which is one of our preferred companies with my agency, CADENCE, in La Jolla. Was the villa in Provence a Villas of Distinction property by chance? Having just returned from France that first image is swoonworthy!
Wonderful post and thanks so much for coordinating our group posts today.
Merci!
Heather
Curated Travel
Yes, it was Heather. Bastide St. Martin. Thanks so much for participating with us. Love following you on Instagram!
I am constantly amazed at Howard’s wonderful skills. I have been so impressed by the size of people who are, I now know, not pains in the asses. I always enjoy your travel posts—armchair, vicarious—because the reality of me traveling with a group of people on purpose is highly unlikely…like break out in hives impossible. But you and co make it look blissful. Does your group have a name? Perhaps a logo and shirts to follow? My favorite pic was the one in Italy that looked like a promo for an opera!
HAHAHA…YES lucky for us that we all get along! The name of the group text changes with the destination. Right now its: “Mykonos Beach Club.” 🙂
IF ANYONE BACKS OUT CALL ME PLEASE!!!!!!!!!!!!!!!
I would LOVE TO BE A PART OF YOUR FAMILY/FRIENDS VACATION!
I have always wanted to do this in TUSCANY!Maybe its time to start planning for my 60th!
I cannot wait to see your GREECE photos!!!!!
WHAT A WAY TO ENJOY LIFE!
BRAVO HOWARD!
XX
You SHOULD plan it for your 60th! It really is amazing how it all comes together with advance planning.
Those trips must be so fun! But you left out the part about the bonus spa recuperation weekend for the organizer and ONE person responsible. 😂 That’s a lot of work and worry. I’m always happy to be that person and I think I have a knack for it, but few people recognize the amount of work involved.
Yes…just taking notes while Howard was talking fast in the car made me think “man, this is a lot of work!”
This is so helpful as we are planning a family reunion in Italy. Thanks, Howard and Mary Ann!
This is great advice. I have only done a big trip with family, and since it was in Europe, I organized it all. I had a list of possibilities, and in the evening we would choose which thing to do the next day.
Cooking lessons were one way to do something together that involved local culture and allowed us to eat in, but a chef would be a real treat–restaurant quality with the convenience of home. It’s also a great idea to have a tour operator with a bus–I rented a full-size van and drove, which was not so fun for me.
Pay attention to the photos on different sites–places list on several platforms. The platforms take different cuts, so you might find quite a variance in prices for the same place. You have to notice that the photos are of the same property.
Good point! Howard did say that different sites have different prices for the same property. Good to research. Thanks.
This was so informative (thanks Howard!). I am amazed at how reasonable the cost is per person. Makes me want to invite a group and go! How fortunate to have a pro like Howard take the helm and go with it. Everyone must be so grateful to have him take charge. Thanks for organizing this little pd venture. Great job!!
Thanks, Cindy. I DO feel lucky to have Howard. I don’t think the per person cost includes lunches and cocktails out. But yes, it does seem pretty reasonable for the great fun.
Mary Ann (and Howard)!
This is so fun! I adore the photos and especially the one with Howard in the pink shirt! These trips are amazing and what fun to travel with your families and friends. The best way to stay connected and shared past and present experiences! Love all the tips and I’m sure this is giving people tons of ideas for planning one of their own!
xo
Annie
Thanks, Annie! Can’t wait to ready your post!