Steps To Plan An Unforgettable Large Group Vacation | Classic Casual Home (2024)

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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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.

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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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

1. 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).
2. 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).
3. Two to three people discuss their findings and submit the best option to the group, including approximate rental costs.

See Also

Heading home for the holidays? Here are the cheapest days to book your flight.

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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.

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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!

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