How to Actually Enjoy Your Group Vacation

Taking group vacations is one of my favorite ways to travel, and I’ve had some amazing experiences with group travel over the years. I’m actually more of a homebody, but my friends have helped me to step out of my grid!

Several years ago, I participated on a choir trip to the Czech Republic and Israel. There were about a hundred of us on the trip, which included singers, leaders, and the band. It was a multi-generational group, ranging in age from 14 to 80 years old, so getting everyone onto planes and loading luggage, equipment, and bags onto busses was a complicated logistical experience!

By the end of that choir trip, we had all become like a big family. We supported each other through fatigue and illness, shared cell phones to call home, interpreted in conversations with the locals, and helped each other figure out how to pay for things in foreign currency.

On the other hand, I once went on a trip that went horribly wrong…but it was still a bonding experience for all of us. On a group trip with some friends, we were going to travel on their yacht for ten days of good food, wine, snorkeling and sunshine. Instead, about 5 days into the trip, everyone came down with the flu! We all suffered together, sharing updates on our symptoms.

Because I’ve done a number of these group trips, I’ve got some good tips for how to actually enjoy traveling with your friends and family members. But before we dig into those tips, let’s talk about the pros and cons of traveling with a group. After all, group trips aren’t for everyone, and you’ll want to figure out if they’re a good fit for you.

The Pros of Group Vacations

Here are some of the biggest advantages of vacationing with a group:

1. Often, the itinerary is planned for you. If you’ve been invited to travel with someone else, it’s likely that most (or all) of the itinerary for that vacation will be planned for you. That can be a big plus if you hate vacation planning and don’t care for doing research about your destination.

2. You may be challenged to try new experiences. Because someone else is planning the itinerary, you probably need to be open to trying new things on a group trip – including participating in new activities or experiencing new culinary adventures.

3. You can create amazing memories with people you know. You’ll have wonderful stories and shared experiences with the friends and family members you know before you go on the trip – and you’ll also bring home some incredible photos!

4. A group trip is a great bonding experience, so you can expect to meet new people along the way – and those folks will often feel like close friends by the end of the trip.

5. When someone else plans your trip and leads you through new experiences, you can see the world through that person’s eyes. You can learn a lot about other cultures and countries by going with the flow on group trips.

6. It’s easier to accept help from people you know. Ever notice that it’s easier to call a friend and ask for directions than it is to stop strangers and ask them? When you’re lost, confused about currency, or baffled by local customs, it’s far easier to turn to someone you know and ask for guidance.

7. Group vacations can be cheaper. You can often get discounts when you travel with a big group, so that can help when you’re on a budget.

8. Guided tours are often included in group trips, which can be a big plus if you’re worried about speaking a foreign language, navigating through a new city, or driving on the wrong side of the road!

The Cons of Group Vacations

1. As I mentioned above, you’ll probably meet new people on a group vacation – and that can be rough or meeting new folks isn’t really your thing. When you meet new people, you’ll probably find yourself making a lot of small talk on your vacation. If you’re really introverted, small talk can feel exhausting and crowds may feel overwhelming.

2. You may be limited in your travel choices. There are certain places where a large group is going to have trouble traveling, so you may need to compromise on your vacation choices in some cases. It easy to navigate a new city with 4 to 6 people, but there if you’ve got a group that can’t all fit into one car, you’ll need to coordinate carefully.

3. When you travel with a group, there will likely be times when you lose your authority over your decisions – like when you’d like to wander freely in a new city, but the tour guide tells you that you need to stay with the group. If you always want control of your time, group travel may not be for you.

Other Questions to Ask Yourself Before Going on a Group Vacation

Factors like the length of the trip, how familiar you are with the people in your group, and your level of travel experience can all affect how much you enjoy yourself on your group trip – so it’s important that you ask yourself some critical questions as you’re planning your vacation.

Ask yourself:

How often do you travel?

Having experience with traveling on your own is helpful if you’re going to travel with a group. Traveling puts you out of your comfort zone, and adding more people to the mix can complicate things in some ways (but make them easier in others).

Along the same lines: Consider whether your destination a new place for you, or if you are returning to somewhere familiar.

How well do you know the people you’ll be traveling with?

Have you travelled together before? Have you spent much time together? Spending time together for shorter periods of time (like for dinner, or doing activities together) is different than waking up with people every morning for a week.

On a group trip, you’re likely to see some annoying habits –  especially if you share bedrooms and bathrooms – and people can sometimes get under your skin. It helps if you know what you’re in for in advance.

Do you have similar interests to the people you’re traveling with?

If everyone on the trip has completely different tastes and preferences, you’ll be more likely to have conflict on your trip when you’re trying to make decisions.

My husband and I went on a 10-day sailing trip around the British Virgin Islands a few years ago. We were traveling with five other couples, and we were sailing with a crew who managed the boat and cooked and served all the food.

The majority of our time was spent on the boat, and we only made a few stops every couple of days. Most the people on the trip were happy with that, but a few people felt a bit confined.

We were given the details of our itinerary in advance, so we should have known what to expect. Those of us who felt some cabin fever came to the realization that we do better if we got to disembark more often. But since many of us had never experienced a vacation like this, it was a learning experience – and we learned to speak up when it was possible to make an unplanned trip ashore.

Would you mind being on a sailboat for seven days, or would you prefer to disembark more often?

What’s the situation going to be with food?

Will food be provided on the group trip, or are you sharing the cooking? If you’re sharing the culinary duties, do you like to cook for large groups – or do you prefer to eat out and try new types of food when you’re traveling?

If you have dietary restrictions, you’ll also need to plan for that in advance. I’m gluten intolerant, so I need to be careful and always understand exactly what I’m eating. I’ve discovered that whoever is preparing the food for the group appreciates knowing about any dietary restrictions ahead of time. For the most part, most people are willing to accommodate most dietary needs if given some advance notice.

How long will you be gone (or more importantly, how long do you like to be away from home)?

Do you like to be away for extended periods of time, or do you prefer short trips, like a long weekend or an overnight excursion?

What’s your preference for accommodations?

Do you like camping, or would you rather stay in a 5-star hotel? If you’re not really an “outdoor person,” camping for a week with your friends might be kind of miserable. Ask yourself what types of accommodations you prefer, and take that into account when you’re planning your trip.

I’ve found that sometimes it’s possible to make adjustments. For our annual Great Sand Dunes family camping trip, some people camped in tents. Since I’m not much of a camper, we rented a pop-up camper that provided shelter from the elements. This proved handy when there was a rainstorm – our 3 children were thankful they could retreat to our camper!

Does everyone in the group have the same budget?

Figure out in advance if you’re on the same page, as far as your budget expectations are concerned. If the people in your group have budgets that are vastly different, are there options for those who are more frugal to opt for a different experience than those who are want to spend more?

Will you be traveling to a foreign country? If so, does someone in your group speak the language?

Will you need an interpreter? If so, who will be in charge of acquiring those services? It’s helpful for everyone in the group to understand the plan for handling language issues, when these situations arise.

My family went on a trip to Europe, and we spend part of the trip in Germany, visiting Tom’s family. The vacation was amazing, and we had a great time seeing Hamburg through the eyes of locals.

The trickiest part of the trip was when we all went on a tour with a guide who spoke German the entire time. Tom speaks German, but it was really tough for him to be our interpreter (it’s a lot harder than it looks!) The kids and I nodded off several times because we were so jet lagged.

I felt awful about it, and we didn’t mean to be disrespectful, but hearing the German speaking tour guide lulled us to sleep. In hindsight, it would have been helpful to have an English version of his talk, so that we could follow along.

My Top Tips for Planning and Enjoying Your Group Vacation

1. Plan ahead. The more people you’re coordinating, the more schedules you have to juggle. If you plan your trip a year or more in advance, the members of your group can plan accordingly and block off the time on their calendars.

2. State your needs. I don’t like to plan vacations, so I’m happy to have someone else handle the details – but I do have opinions about how busy each day is. I don’t like to have every single minute of every day scheduled for me. Consider your individual preferences in advance, and make sure to communicate with your group leader about your biggest needs and concerns.

3. Decide who’s in charge. It’s easier to have one or two people be the “go to” authorities for questions and decision-making. Making decisions by committee can be tricky, and conflicts can detract from your vacation experience. If the itinerary is planned ahead of time, it’s also easier for the leaders to keep track of confirmation numbers, reservations, travel plans, etc..

Even if the person in charge makes a bad decision, at least you’re all in it together. It’s much easier to change course together when everyone is on the same train!

4. Whenever possible, have separate sleeping quarters per person/couple. It’s good to have a bit of distance from each other, and getting a good night’s sleep makes little annoyances easier to deal with. No one wants to deal with someone snoring in group sleeping quarters, and keeping everyone awake every night – and no one wants to be THAT person, either!

5. Go into the trip with patience and a sense of humor. Things will go wrong on your group vacation, and recognizing that fact can help you cope. Keep in mind that sometimes those spontaneous, unplanned experiences are more enriching and fulfilling than the planned ones.

The Magic of Traveling as a Group

I know some of my all-time favorite travel memories have happened while I’m on group trips. It’s a fantastic way to travel, as long as you plan ahead and speak up about your own needs.

Now I’d love to hear from you – do you have any fun group trip experiences (or any group travel nightmare stories)? Share them in the comments below!

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