Everything’s Better With Friends: Planning a Group Trip


Although I have been known to do solo travel, I have also done a lot of group travel through leading group tours in Cuba, Spain, Hawaii, and many other epic destinations. When I ask for feedback post-trip, most of the comments are about the friendships that were made rather than the itinerary nor the destination. Knowing this, I asked a peer travel blogger from the U.K., Jim McDonald, to share his approach to planning a group trip.

I hope you enjoy Jim’s suggestions!


There’s much to love about taking a trip by yourself, or just with your significant other, but when it comes to all-out fun, it’s hard to look past heading on an adventure with friends. It seems like we see our core group of friends every day when we’re growing up, but when we get older those get-togethers seem all too infrequent! By taking a trip as a big clan, we can look forward to rekindling those relationships, have fun, and see the world all at the same time. Sounds pretty perfect, right? Below, we run through everything you need to do to make sure the trip goes off without a hitch.

Look Far In Advance

There’s a reason why we don’t have a chance to see all of our friends as often as we’d like: everyone’s so busy! People are off getting married, working on being awarded a promotion, looking after the kids, and so on. As such, people’s schedules are usually booked up pretty far in advance. So when it comes to planning a trip, you’ll need to give people as much notice as possible. Let people know that you’re planning a trip for, say, six months into the future, and most people will be able to get it into the diary before other plans make it in there.

Pick Your Activity

It’s easy to fall into the habit of just sitting around, a glass of wine in hand, and catching up, but it’s not very adventurous, is it? As such, think about building the trip around an activity. What you choose will depend on your interests, age, fitness levels, and so on. Will you decide to go on a hiking trip, and out there all on your own? Will you decide to go full on culture vulture, and spend time exploring a cosmopolitan city? Or will you just choose a beach destination, and let the sea and sand take care of the hard work for you? There’s no shortage of exciting options out there.

Where To Go?

There’s a lot of exciting adventure options out there because…it’s a big and beautiful world, with great destinations in all corners. So where will you go? You could look at staying in the United States, but for a true adventure, look at traveling overseas. There are plenty of flight options to Europe, South America, Asia, and well, everywhere. This, of course, should be a group decision. Have a chat with everyone who’s part of the clan, and see what they can come up with. It’s a good opportunity to tick a destination off the bucket list, but only if everyone’s on board with the suggestion.

Accommodation Options

The traveling and activities will be fun, but the star of the show will be the accommodation. This is your opportunity to go big! You probably won’t be able to stay all under one roof, but you can take a look to see if there’s a luxury studio apartment for rent, and then divide people up into groups. So long as you’re all nearby, you’ll be able to enjoy evenings all together in your accommodation before everyone goes back to their own spaces. And in fact, it’s probably recommended that you’re not all under one roof, even if it’s an option – while you’ll enjoy all being together, everyone needs their own space from time to time.

Delegating Responsibilities

When you’re traveling by yourself, you can usually just wing it, and do your own thing – but this isn’t the case when there’s a big group. There’s a lot to take care of when you’re planning a trip for multiple people! But just because you may be leading the charge when it comes to the trip, that doesn’t mean you should be in charge of everything. That’ll be unnecessarily stressful! Instead, delegate the responsibilities so that everyone is contributing. One person can be in charge of organizing airport transfers; another in charge of booking activities; another in charge of researching accommodation, and so on. Many hands make light work, remember!

Separate Needs

Everyone who agrees to go on a group trip will adopt a “group” mindset, but that doesn’t mean that you need to do absolutely everything all together. While you’ll share many similarities, you are not all the same! If there’s an art gallery you want to visit, but no one else is interested, then you should still go. When it comes to scheduling activities, it’s important that things aren’t overly scheduled; make sure that there’s some “free time” thrown in there, so people are able to do their own thing for a while. Plus, if you’re going adventuring for a week or more, then you’ll almost certainly want some time for yourself anyway. You love your friends, but you can’t be around them twenty-four seven – go hit that art gallery, and enjoy your own company for a while.

Learn to Compromise

While it’s important to keep in mind that people are going to have separate needs, keep in mind that part of traveling with a group is knowing when to compromise. There are times when you’re not able to get things all your own way. The key thing is to keep the group together, enjoy other’s company, and if the rest of the group have their heart set on a particular restaurant, then you might have to suck it up and go along with it – even if it wasn’t your first choice. Learning how to work with other people is a good life skill to have, too!

Group_of_friendsTake the Lead

It’s easy for things to get fall by the wayside when you’re traveling as a group. When there are many people, but no leaders, then it’s easy to find things more disorganized that you’d like! As such, someone needs to take the lead to order taxis, make decisions, and so on. Of course, taking the lead doesn’t mean being overly controlling. But if everyone’s just sitting around, then it’ll be time to shout “let’s assemble!” and get the adventuring underway. If you’re an experienced, pro traveler, then it’s reasonable that you handle the issues that other people might not be able to handle quite as well.

Sensitive to Financial Issues

When you’re younger, the differences between you and your friends were slight; you were all in the same boat more or less. Now, there will be differences – and the biggest, most obvious one will be different financial circumstances. You might have a friend who earns big bucks, while another has much less disposable income. On your trip, you’ll need to be sensitive to the needs of the people who don’t have as much money. Don’t automatically suggest going to the area’s most expensive restaurant, or ordering champagne or anything else, unless you’re sure everyone can afford it.

Know Thyself

You’ll want to bring the best version of yourself to the trip and to do that, you’ll have to be aware of what sets you off. If you get angry when you’re hungry, then make sure you’re not going for hours without food. If you get ratty when you drink gin, then don’t drink gin! Know thyself, and you’ll be able to be the best you on your travels.

Planning the Next One!

There’s no doubt that you’re going to have a terrific time when you’re on your travels! Plan well, get everyone involved and enjoy yourself. Who knows, this might be the beginning of an annual tradition – there’s nothing better than traveling with friends!

**Post contributed by U.K. based travel blogger, Jim McDonald. He is a lover of all things craft beer-related.**


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