How to Plan an Awesome Group Trip – 4 Different Options

Traveling with a group of friends or families is a very different dynamic than traveling with a partner, with just your own kids, with a single friend, or solo. I’ve found that the shared experiences this type of travel offers can really deepen friendships and makes all the planning worthwhile!

Whether it’s a group of individuals, couples, or families who want to travel together, it can be tricky to plan a group trip. Where to go? Who’s in charge? What’s the budget? There are a lot of different ways to tackle this (fun) beast and I’d love to share a few options. 

I have done lots of travel over the years in a group. For many years when our kids were young, we went on amazing international summer trips with two other families – 6 adults and 9 kids (Croatia, Bali, Laos, Italy, Switzerland, Iceland, and more). My family would do a family-only trip for the first half of the vacation and then just as the kids were getting restless we’d join the other two families for the second half we were all thrilled with the new company and built-in travel buddies!  Recently I’ve taken some great girls’ trips (Italy, London, New Mexico, Santa Barbara, Bhutan, Rwanda, and Kenya…) and hopefully, there are more of those to come. And now that we are empty nesters it has opened up the option of group couples trips as well (TMB hike, Morocco coming up in March). All of these trips have been smooth and drama-free and I would take any of them again in a heartbeat. 

Here are my four ‘best-of’ overall practices to ensure success when planning any group trip, followed by four options of how to actually organize/plan this type of travel.   

Overall ‘Best-Of’ Practices for Group Travel Planning

1. Consensus: Before planning begins make sure everyone is on board with the same type of trip in regards to budget, ‘type’ of trip (upscale vs casual, active vs loungy, culture vs party) etc etc), duration etc.  You don’t want anyone surprised by that stay in a hostel while hiking the alps, thinking that it’s all going to be 5-star resorts.
2. There needs to be one person in charge. Everyone can participate,  have ‘jobs’ and give input but there has to be a point person. This person coordinates things, is the point of contact for communications, keeps the Google Doc up to date etc.
3. Use a shared Google Doc. Everyone needs to be able to access all the info. At a minimum have one tab for travel info (flights etc) and one for the itinerary. Possibly another tab for activity/restaurant/shopping suggestions that everyone can ‘dump’ into as they come across things to add.
4. Use the Splitwise app. This app lets anyone in the group input an expense and decide how it should be shared amongst the group. At the end of the trip, Splitwise does all the calculations and makes it super easy to settle up with minimal payments amongst the group. 

The 4 Primary Ways to Manage/Coordinate a Group Trip

I’ve been on trips that use all four of the methods below. All of them work well but choosing the best one for your trip depends on who’s going (Do you have a leader willing to put in extra work to organize it? Or is it better to outsource to a professional?), where you’re going (Is it a place you need local knowledge of to plan the best experience?)  and what type of trip it is (Is it a beach vacation that needs only a single hotel booking or a multi-country tour with lots of details and logistics in foreign counties?). The #1 ‘Opt-in, Opt-out’ trip below (introduced to be by my sister-in-law),  is a new favorite of mine, especially for a girls’ trip! It is lower stress on the organizer, lets everyone ‘do their own thing’, and makes for a great trip for all! 

1. Single Leader ‘Opt-in, Opt-out’ Trip: One person plans the trip and invites people to join, giving them the flexibility to do as much or as little of the trip as they choose.  

I went on a trip to London with girlfriends which was arranged like this and it was terrific! We had 10 women, not all of whom knew each other ahead of time (the organizer brought women from different parts of her life together for the trip) meet up in London. Everyone stayed where they wanted to, depending on their desired location/budget/style. I stayed with friends and others were scattered, solo or doubling up, throughout the city.  Everyone was given an activity or meal ahead of time to organize during the week (it was all on the master Google spreadsheet) and people signed up for as many or as few of those activities/meals as they chose to join. The organizer of each specific event then bought tickets/made reservations accordingly. No pressure/judgment to go to anything that didn’t interest you or fit your schedule.  In the end, there were actually very few events or meals that included the entire group. And EVERYONE had a great week!  

1. Pros:
   1. Lots of flexibility. 
   2. Great for individuals/girls/guys trips. 
   3. Great for city trips. 
   4. Lets people accommodate their own desires/budgets for lodging and pay for it directly themselves. 
   5. Lets people do only part of the trip if can’t do the whole thing. 
   6. The organizer doesn’t have to coordinate every activity.
2. Cons:
   1. Not as good for non-city trips or for people who aren’t independent travelers. 
   2. People have to commit to activities ahead of time (also a ‘pro’!)

NOTE: My friend Beth has started organizing women’s hiking trips in this fashion after hearing about my London trip and has had great success. She tells people where/when the hikes are, and where she’s staying/dining and simply asks the invitees to let her know who will be hiking with her on what days – brilliant! I am going on another trip of this style to Santa Barbara this spring. The organizer is giving options of where to stay (I’ll stay with a friend) and we can join as many or as few of the organized meals and activities as suits us. Can’t wait!

2. Group Planned Trip: Plan the trip as a group, with one person the ‘primary organizer’

The many international multi-family trips we’ve been on were done this way. The three families traveling discussed where we wanted to go and once a final option was decided upon I researched/shared/discussed the hotels and activities (others would contribute ideas as they wanted to) and made the bookings. People were in charge of making their own travel arrangements to get there/home and I booked the hotels and activities for the trip itself. 

1. Pros:
   1. Everyone gets a say in what the trip is like. 
   2. Can be customized to exactly what your group is wanting to do (lodging/activities/dining). 
   3. Can be less $$$ going direct. 
2. Cons:
   1. More work for the organizer as lots of research is needed to choose hotels, activities, restaurants, etc, and to make the necessary bookings. FYI – This is part of why I started JamboGuides as I was spending hours upon hours in research and I wanted to share the results of all the planning with others!  
   2. If something goes wrong, it’s up to you to fix it – no agent to call. 

3. Travel Agent: Use an outside travel planner/operator for logistics

A travel agent can coordinate the itinerary (with input), the bookings, and the payment. The group must decide where and when to go, for how long, what activities they want to do, etc. and then the agent will make the arrangements. 

3. Pros:
   1. Takes the legwork away from the group planner. 
   2. Lets everyone have input as needed on what the trip includes. 
   3. Payment can be handled by the agent directly with each participant.
   4. If changes need to be made the agent can efficiently manage it. 
   5. Works well in a country where you have to go via an agent (Bhutan) or where researching/orchestrating arrangements may be more difficult (Safari), as well as when you need local transportation booked. 
4. Cons:
   1. You often only get the recommendations of hotels etc that the agent may have connections to. 
   2. You have to have a trusted travel agent who knows how you like to travel.

Note: We are going on a trip to Morocco in March with 3 other couples and are using a Travel Agent. When Covid caused us to postpone the trip last year she was able to make all the changes necessary to push it back a year quickly and efficiently – a huge time savings for us, beyond the savings of her booking the entire trip in the first place! 

4. Tour Operator: Use a tour operator with ‘pre-done’ trips to join. 

You can choose a pre-arranged trip like a hiking/biking excursion with Backroads or a cruise where you join a larger group, or ask them to prepare a private trip for your group. Once you pay you don’t have to plan a thing and once you arrive at the destination you also don’t have to do a thing as they take care of all logistics. 

5. Pros:
   1. Takes all the pre-travel and on-the-ground logistics away. 
   2. Everyone can manage their own booking/payment.
   3. For kids, it gets them up and doing things without prodding from you! 
   4. They are equipped to handle any emergencies or change of plans. 
   5. They provide the bikes/equipment needed for the adventure. 
   6. They have already done the research and have chosen the best places to stay and things to do. 
   7. You just pay once before you start, and then the tip at the end.
6. Cons:
   1. Lack of flexibility. 
   2. Often $$$.

NOTE: We did a multi-generational family cruise which made it so easy for everyone involved. Many people use Backroads or similar types of organizations as a way to get multiple families or friends together for a stress-free active planned trip as well.

Enjoy the wonders that group travel can provide!