Ingredients for a Successful Group Vacation

When approached with the right attitude and planned properly, travelling with friends and family is one of life’s most enjoyable experiences. Here are some tried and true tips to turn your group vacations into some of your best memories ever.


1. Communicate Early
Address the five “W”s plus “how.”
Who is going? A group of people may decide they want to travel together. Or, one person may invite others to join in on a holiday, such as my recent birthday celebration in Tuscany. Make sure all travellers know who is interested in going before they make a commitment.
Where to go? So many choices, so little time.
What does everyone want to do on the vacation? What are their expectations?
Why do they want to go? Find out your companions’ priorities—do they hope to spend time with friends, see the sights or just get away from it all?
When does everyone want to go?
How? As in, how much do people want to spend? Budgets dictate how you travel. Are you flying or driving? Staying in budget accommodations or five-star hotels?
Just because people are on different budgets doesn’t mean they can’t travel together. On one trip, half our group stayed in a luxury resort and the other half (myself included) stayed at a budget hotel. We met up and did most things together and sometimes we hung out as their guests at the resort pool.

Photo: Kimberly Skutt

Related: Don’t forget to save room for travel insurance in your budget! But how much does travel insurance actually cost? Can you beat these guesses?


2. Plan Ahead
Once the basics are decided, set up a meeting. Meeting over dinner, or over appetizers and drinks, is always a fun way to do this. Discuss everyone’s research findings including travel requirements, such as visas, updated passports, travel and medical insurance, and vaccinations. Make sure information is up to date. Have everyone share their findings on what there is to do at your destination. This is especially important on short trips where you may not have as much time. What is on everyone’s must-do list? Each person must have the chance to voice their opinions.

Related: Have questions about travel vaccinations? This article tells you what you need to know.


3. Take Personal Habits and Dynamics into Account
Is someone a natural communicator and up for being the group leader? (That’s “leader,” not “dictator.”) Who is good with directions or finances? It’s best to share the workload. Consider personal preferences. Is someone an early riser and someone else a nighthawk?


4. Track Expenses
This can be done many ways. Divvy up prepaid larger costs, such as accommodations, before you depart. During the trip, have someone in charge of tabulating group costs and keeping track of who paid for them. At the end of the holiday, tally up and promptly pay each other back.


Related: Financial travel tips: Will that be debit or credit?

5. GOLDEN RULE: Everyone Doesn’t Need to Do Everything Together
Be flexible. Find out what people want to do together and then split up for other activities. Plan a time for everyone to meet up. When not together, inform each other where everyone is going and when you are all expected to return Contact the rest of your group if plans change.

By following these simple rules, you have the recipe for a fun and harmonious vacation with your nearest and dearest. Go ahead now. Gather some friends and take the plunge.


For all other podcast episodes of ‘Lily Likes It Here’, check here!

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