Taking your entire extended family on vacation can be tricky and challenging, but lots of people do it!

Magic Kingdom at Disney World

We’re constantly seeing large groups of folks traveling together in Disney World — it just might mean that you have to plan more intricately and have WAY more flexibility. But after taking my whole family to Disney World and then taking them on a family cruise… I would 100% pick one option over the other.

Large Groups in Disney World

Let’s start by breaking down what you’ll experience traveling with a large group on each type of trip. If you’re doing an extended family (or friend group) trip to Disney World, choosing accommodations is your first hurdle. You can either stay onsite and likely split up between multiple hotel rooms, or you can go the off-site route with a rental house or larger space to share. During my family’s trip, we did a little bit of both — staying a night in a 2-bedroom Villa at Kidani Village on property and then spending most of our stay off property in the same multi-room timeshare (my aunt and uncle already owned the timeshare, so that was a budget-friendly choice).

Disney’s Grand Floridian Resort

Staying off property can be great for having a space to spend time together and cook meals, relax, or enjoy other offerings in the Central Florida area, but there is one big hurdle… getting TO Disney World each day. Piling the whole family into vehicles and driving to the parks takes a lot of extra time, and you must factor in traffic. Plus, then you’re carpooling, and everyone is committing to the same plans for the day. That is, unless someone wants to pay for rideshare.

Rideshare Pick-Up and Drop-Off at EPCOT

The day that we stayed on property was a bit more easy-going. We could use resort transportation to get to the parks on our own schedule and come and go from the hotel room whenever we felt like it. We didn’t have quite as much space, and we spent more money, but there were some definite pros to being in the “Disney bubble.”

Animal Kingdom Lodge

Another thing to consider with your group trip to Disney World is your day-to-day plan. Where will you eat? Will you get dining reservations? Will you purchase Lightning Lanes? With so many options and more people, it can be hard to get everyone to agree on these things, particularly if there are varying budgets. Generally, traveling with a large group to Disney World means that you may have to play to the lowest budget of the group if you want everyone to stick together.

Slinky Dog Dash at Disney’s Hollywood Studios

However, if you’re willing to split up during the daytime, you add a great deal of flexibility to your plans. There’s a little bit of something for everyone in Disney World, so you can divide and conquer — rides, food, live entertainment, characters, etc. Whatever each person prefers! Seriously, our biggest piece of advice for going to Disney World with a group is to split up when you need to. If you try to force everyone to agree on the to-do list all day, every day, then you’ll be miserable by the end of the trip.

Mad Tea Party

Basically, Disney World offers a lot to do across four parks, dozens of resorts, two water parks, and Disney Springs, so if you choose this for your trip, you have options galore. There’s a wide margin of budgets that Disney World can accommodate, and you can customize the trip to your liking. But what about the cruise?

Large Groups on a Cruise

Well, a couple of years after our Disney World trip, my family tried another vacation… this time, a cruise! If you’d like to do a cruise with a large group, I’ve found that most of the decision-making comes on the front end, as opposed to deciding what to do every moment of the day like you do in the parks. We had to communicate quite a bit to decide on a cruise line, a sailing date that worked for everyone, and choose our excursions ahead of time.

Disney Destiny stateroom

However, once you get on the boat, it’s a bit smoother sailing (pun intended). You don’t all have to wake up early to get to the parks or coordinate your transportation and schedule. Depending on the cruise line you choose, you may need to think about dining ahead of time, but for the most part, you can all go to the main dining spaces together and enjoy meals as a group. Even entertainment options are readily available on the schedule — you just need to show up and watch!

Worlds of Marvel on the Disney Treasure

Like Disney World, your family can tailor the cruise experience to fit your needs. If you want to do everything together, you can look at the schedule of events and decide what to do and when to do it each day. If you would prefer flexibility, everyone can split to do their own activities and meet back up for meals, pool time, or shows. It all comes down to personal preference. We found that in general, there were fewer group decisions that had to be made with a cruise.

Royal Caribbean Cruises

Also, if you’re traveling with littles, we found a cruise to be easier. When it’s naptime, or you need a break, it’s much simpler to pop back to your stateroom than it is to leave a theme park, board transportation, and THEN walk to your room. In general, sleep was smoother for everyone. Everyone could just wake up and go to bed whenever they were ready.

Queen Bed in Category 4C Oceanview Verandah Stateroom on the Disney Wish

Now, of course, one of the big downsides to taking a cruise can be the “on a boat” aspect. Some folks may not be comfortable with the smaller confined spaces or may be prone to seasickness. These are things you’ll need to discuss with your group before booking.

Which I Would Pick Again

After doing both types of vacations with my family, it’s clear that the cruise was the winner for us! Our party in particular had a lot of varying preferences. Some of our group liked to stay up late while others were early risers. When we went to Disney World, some people wanted to tap out around dinner time, while others wanted to go from park open to park close. And the majority of my family members didn’t care much about the rides or shows, instead wanting to prioritize experiences, food, and relaxing activities.

©Celebrity Cruises

With all those things in mind, Disney World just wasn’t quite worth the hassle for our group. It required a lot more planning and decision-making, and those who were expecting a vacation left feeling more exhausted than relaxed. The cruise, on the other hand, was right up our alley — the perfect amount of family time, relaxation, and flexibility.

Verandah on a Disney cruise

Of course, this is what worked best for my situation. To decide for your group, you’ll need to take stock of what you know about the people traveling with you and make a decision based on their personal preferences. And though Disney World isn’t the ideal vacation for my extended family, it’s a vacation I LOVE taking with my immediate family, since we’re a Disney family who love the rides, characters, and entertainment.

Pandora in Disney’s Animal Kingdom

So, I ultimately learned this lesson the hard way. Not every type of vacation is made for every group, and planning for multiple people can be much more challenging. If you have a group trip coming up, make sure to be patient and willing to negotiate… and like we say, be willing to split up if necessary. That can definitely minimize arguments!

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What’s your favorite type of family vacation? Tell us in the comments!