How long are you going for.

More than a weekend and it is really hard in my experience unless you are all completely on the same page.

I will only travel with people who are completely 100% fine doing things separately as well as together. I do not share a room any longer. I do not eat at expensive restaurants. I am happy to travel with people when the general idea is we plan a day and whoever wants to do it comes along and everyone else does whatever they want. And no sensitive, criers, feelings get hurt, offended / insulted easily people.

I don’t do this. I prefer traveling with DH so much more than a handful of woman. To much compromising/discussing etc. Also I am not wasting energy on all of the things mentioned. I am adult not sharing a room with another adult. And definitely traveling with people where, compromising on accommodations/dining, accounting, playing banker or splitting costs “fairly” is required .

Yuck. I would not do this for more than a long weekend, and a place I can drive to and back. I only travel with immediate and close family who I know I enjoy traveling with.

We do a group trip every other year so have it pretty down at this point. Other than the big stuff like location and cost

Sleeping arrangements. Some people are fine sharing and will assume others are too
What are the expectations as a group? Breakfast/lunch/dinner/all excursions together or can people come and go and pick and choose? .
If you're doing an Airbnb, how are you dividing food, cleaning, cooking?
Once something has been booked, there are no refunds. It gets too complicated.
No transferring your spot to anyone else unless it's someone the group knows and okays
Budget while there. No one wants the friend who wants to go to expensive restaurants every night when other people can't afford it.
No "rules" like phone free zones or things like that. Don't put restrictions on what other people can do unless it's a safety thing or something that's really rude (like bringing people back to the Airbnb to sleep with)
If you have single people on the trip, can they bring people back to sleep with?

Know yourself. Do you know if you like to travel with others. A lot of others? And these people. Start by making peace with what you know about yourself. Then, you'll be able to tweak the experience, set boundaries when you need to, and thoroughly enjoy what parts are most important to you.

Know that you and everyone will need downtime, even when together -- putting in earbuds, tuning out the world, for example. Respect and expect a wide range of behaviors, that are a way of coping with all the togetherness.

agree with where you will stay and how you will split costs. if you get a house, decide how to divide up meals/cooking and eating out. are you expected to do everything together? or will you go your own ways sometimes? what things does everyone really want to do - build a schedule from that. agree with pp about the cruise - some people hate them, but I have found a cruise and disney world to be awesome for a group of adults with varied interests.

I have only done trips as a family with others - we shared all the food expenses evenly as a family even though some families were larger than others - some couples, some with 4 kids.

When we booked houses we made sure every family/couple had a bedroom and the kids were sleeping wherever they could.

Definitely have group calls and discuss sleeping arrangements.

Keep the food expense separate from lodging expense

From our trips we realized first come first serve for rooms causes issues so we now do a lottery pick for the rooms

We all had various interests so we decided to pay for activities on our own.

Destination and sleeping arrangements. Unlike a PP, I'd poke myself in the eye with a sharp stick before I'd go on a cruise. No shared sleeping. Hotels are preferable. Budget. Expectations as in do we do everything together all the time? Or can we split up/opt out. Always go in even numbers, never three.

Don’t travel as a group of 3 women.

https://www.vogue.com/article/the-white-lotus-three-person-girls-trip

Also make sure people know they are still on the hook if they cancel. It is NOT ok for one person to front the expense for a rental, etc. then have people drop out and the arranger have to eat that loss. You commit, you pay!

Echo above. Cost/payments splitting are important, especially if you’re looking to share a house or room. Also itinerary— what do they want to do? What do you want to do?

Do not go on a trip with people that you feel you cannot be upfront with. What I mean by this is, if you need your own room (and I do, now that I’m older!), don’t let yourself get talked into a sharing half of a bed with someone. Or if you need to keep to a certain budget, you need to communicate that— and have it respected.

I travel a lot with friends and the only bad trips I’ve had are when I felt too insecure to say something or if I felt that someone was domineering the trip. I had one trip where one person was very clearly trying to get out of paying for things and we all ended up working around them/paying for them, as they were kind of a difficult person— but they were also difficult here in the U.S. That was an aggravating situation.

Maybe that’s my other piece of advice— make sure you really like the people you’re traveling with, or have the ability to break off and do your own thing if not!

Definitely not a White Lotus hotel. Way too high a body count.

Key are dates and destination.

Then accommodations (rental or hotel), sharing rooms or each gets a room; traveling alone or with significant others / kids… these are the basics, then other things based on destination like activities there, food sharing (if staying in rental), etc… a beach house rental with families will be very different things to consider than flying to a resort for a girlfriends weekend.

Money - payment, sleeping arrangements, bathroom, activities, food.

Tbh, do a cruise. Everyone pays the same amt. You take care of your own payment. It's all inclusive.

No headaches about who is eating your food, shared bedrooms/bathrooms, no short end of the stick, etc.

Group of 40 year olds - I never have traveled with friends before. First time. A few of them have traveled together years ago.

What do you always want to know before agreeing on a destination, or group trip?