Whether you’re getting your besties together for some theme park fun, rounding up the extended family for an Alaskan cruise, or relaxing beach-front in a rented house for a week, traveling with a group can be equal parts fun and stressful haha. But now that I’ve traveled with 16+ people two summers in a row, plus played a part in planning a number of adventures for both my family, friends, and others, I feel like I have some suggestions to offer up that might help!


BEFORE YOU GO
My first piece of advice before you even think about budgets, trip expectations, or even location, is assigning some type of designated “leader” (or better yet, reaching out to a travel professional). It can really help with the “too many hands in the cookie jar” concept, so there’s someone to handle all the nitty-gritty details, while gathering input from others. Ideally this person should be organized, detail-oriented, is able to take everyone’s opinions into consideration without only concentrating on their wants and needs, and can make time to research, follow up, and follow through. But, I’ve got you if you’d rather leave it up to someone else and just kick back (it should be a vacation after all) 😛
GATHERING DETAILS – Once you’ve found your travel advisor or designated planner, then you start asking questions. I use a form and both formal and informal conversations with my clients to craft the perfect trip (bit.ly/travelingwithcat), but at minimum you should focus on the Who, What, Where, When, and How:
- WHO is going on this trip? Will it just be adults or will kids be included? And if kids are coming, will you be bringing Grandma along to help?
- WHAT kind of budget are we looking at per person/group? Try to think about transportation, lodging, food, and any excursions or activities that you want to participate in, as everything adds up. And be sure to factor in the number of beds… if no one wants to share, it might be better to get a suite or even two connecting/adjoining rooms.
- WHERE do you want to go? Does your group like sun and sand, cold and snowy, mountains and lakes, cool ocean breezes, roller coasters, water parks? Do you need all-inclusive or some type of dining plan so you don’t have to make too many daily decisions? Or will you have access to a kitchen and want to make every group responsible for dinner one night?
- WHEN would you like to go? Ideally, beach vacations take place in warmer months but if you’re going south you may not necessarily need it to be in the summer. Hurricane season (June to November) can affect some cruises, but not if you’re talking Alaska, the Mediterranean, etc. Do you need to work around school, job, and holiday schedules?
- HOW will everyone book, pay, plan? Will your designated person do all the legwork and deal with everyone’s details individually? Is a travel advisor your best bet to make sure deposits are collected, payments are made on time, and no one is dragging their feet with decisions? Whenever money is involved, there’s ultimately some risk…
PLANNING PLANNING PLANNING – After everything is booked and you’re approaching your departure date, there are a few things that can help make everything run smoother once you go.
- Dining – If applicable, make dining reservations in advance so you aren’t trying to bring a large party on a whim. Even if you have more than 6-8 people, it can be difficult for restaurants to accommodate with less notice, so unless you feel like waiting with cranky, hangry friends & family, call ahead or see if there are online reservation options. (Psst, this is also something your travel professional can help with!)
- Arrival – If you’re all flying in, try to arrive around the same time so that you can share transportation or merge car rentals or shuttle reservations to where you’re staying. It can keep costs down, and oftentimes there are discounts for larger parties if you do private versus shared. If you’re driving but others are flying, you can also try and coordinate pickups/dropoffs! Be sure to compare parking costs at your location (if you decide to rent) versus ride-share services like Uber or Lyft, as it might be cheaper if you don’t need a vehicle once you arrive at your final location.
COMMUNICATE!!! – I cannot stress how important communicating with each other before, during, AND after is to a successful adventure. I’ve had clients come to me because the experiences they had with their last travel advisor or designated planner were less than ideal. It can be a make or break scenario, and you don’t want to lose money, time, or relationships over something that should be fun and fulfilling!
- Be sure to share information and updates frequently. Start a group chat or Facebook group to share ideas, make lists, and plan.
- Delegate tasks if necessary, especially if deadlines are involved. Just because you have a “leader” doesn’t mean the rest of the group can’t step up at one point or another.
- Talk about concerns and ask questions as they arise, as it may be “too late” later. If you think something might not work for the good of the group, voice that concern and offer up suggestions for something better. And always keep an open mind.


DURING
For this first segment, I’m just going to touch on a few of the things I feel are most important when it comes to traveling with a larger group. I’ll dive into more in a future edition 🙂
- Don’t try to stay together the entire time. Let me say it again in a different way and all caps so it really hits home haha… DON’T EXPECT TO STAY TOGETHER FOR EVERYTHING YOU DO. Everyone is different and may not want to do the same things. Some of your group might have kids that don’t meet height requirements, or someone may have a disability or fear that keeps them from doing a particular activity. And while some people are okay with sitting and watching others live out their bucket list items, there may be something equally thrilling and satisfying for that person to do instead.
- Overscheduling is a thing… DON’T DO IT! While you may want to experience everything you can together, and by all means take your party’s needs and wants into consideration, but it’s unrealistic to expect things to be planned out from sunrise to sunset. I always suggest trying to plan for a few meals together, a group photo at minimum, and maybe some other smaller group activities. It makes for a better experience for everyone, and you’re not stuck to a rigid schedule when an opportunity might arise for something else.
- Don’t expect anything, but don’t be afraid to ask. Many places will do their best to accommodate large groups, but you’ve gotta advocate/ask! I highly recommend not going into something expecting YOUR best outcome, as that’s not always possible, and always have at least one suggestion up front that can help your group while taking limitations into consideration. For example, some restaurants may not have a table that can fit 16 people, but they have two tables of 8 next to each other that can accommodate your party. Or they may not be able to get you all on the same helicopter tour, but can try their best to land both helicopters in the same place so you can enjoy parts of the tour together.
- Be thankful and complimentary whenever necessary. Large groups can be daunting for some locations, especially if they’ve dealt with less than ideal situations before. You set the expectation and reaction from your first interaction all the way until you leave. If you start out negative and condescending, you can’t really expect people to bend over backwards if/when you need something, can you? Many locations have comment cards you can fill out when something goes well and I encourage you to voice the GOOD (Disney even allows Cast Member compliments in the app, which is super convenient)! If you do have concerns that aren’t time sensitive, you’ll likely get a survey to fill out after your departure, so you can share them then. But if there’s something that needs immediate attention, reach out to a manager or concierge… with the right attitude haha. You know the phrase “you can catch more flies with honey than vinegar,” right?
- It might be listed last in this section, but this is really the most important… BE FLEXIBLE! Don’t expect everything to go 100% smoothly with a larger group. Something is likely to go wrong, and you’ll just have to pivot! Have a backup plan in place if possible, but also know your non-negotiables. It will likely be stressful at times, but work together to find applicable solutions. Above all, cherish the time you have and memories you’re making together. That’s the part that you’ll remember in the long run ♥️


AFTER
I really only have one piece of advice in this first segment for after the vacation has completed. Well, two actually…
- Create a shared photo folder! It is impossible for any one person to capture everything, so this way everyone sees and can outwardly experience what everyone else did! Especially if you take my advice and do some things apart from the whole group, it can be interesting to see the different perspectives and experiences. We tend to use Google Photos, but Amazon Photos also has an option, and we’ve used Snapfish and Shutterfly in the past. Find what works for you and your group!
- WHERE TO, NEXT?! Unless something went terribly wrong, chances are you’re already trying to decide what your next group adventure will be. Go back to step one and begin again!
(Or fill out my form and I’ll make it happen 😃)


Loved it! I can see where a lot of your advice has been put to the test.
Thanks for always going along with my crazy plans 🙂