We realized that our friendships were more important then taking any risks of problems so we decided the most important thing was going to be making it as low stress as possible in terms of keeping the activities all in one place and not making a lot of impromptu trip decisions when we were there. Any trips away from the resort needed to be pre-planned and pre-paid. When you have so many different tastes in hotels, food, entertainment, and party life, the best thing to do is find activities that can hit a bit of everyone's preferences. All-inclusive resorts in this case are one of the very best answers and a true friendship saver.
The hard reality of vacations is that money is probably the first thing to cause a rift. Whether it is between husband and wife or one couple being in a tight spot and feeling the pressure of the remaining group to spend more then they are comfortable with. This is exactly why an all-inclusive can keep your friendships intact. Believe me the upfront cost is more expensive and can seem almost unreasonable thinking "I would never spend that kind of money if we just wing it", but you will, and you do. You might save a little on the pocket but you may lose more in your relationships with animosity. Now I am not saying you can't travel to a non-inclusive with your best buds you have always known and would live with, I am talking about that group of your newest best friends or even some family reunions. This way each person can book the room that fits their budget, you can all eat at the same place without fighting over the tab, put your pocketbooks away during the trip for the most part, and enjoy all the entertainment you want as a group or even splitting off.
We chose to go to Turks and Caicos at the Beaches Resort since we were taking the kids along. I also love Sandal's Resorts but that is a resort for couples only, no kids allowed. Our rooms ranged from the beachfront 3 bedroom (not mine of course) to an inside second floor room. The grounds were as secure as could possibly be so the kids had a bit more freedom. We had great food, lots of drinks and fun at the pool bar, a few of us tried the inclusive diving, jet-skis, kayaks and even sail boards. All meals were included and they have a non-tip policy so you leave your wallets at home. Food 24/7 and a good variety of options. In the evening they offered activities for both the kids and the adults so those that wanted to go went out and those that did not relaxed in their room with a good book. No driving, no fuss. There are several all-inclusive resorts especially in Mexico, the Bahamas, and the Caribbean. All of the families and the kids talk about this trip to this day and yes, we all made it out as a group. Sure there were a few hiccups as there is with any big group travel but no one ever had to worry about overspending once we arrived. Remember, movies make it look easy to travel together and heck, even Gilligan's Island they all were stranded together and hardly argued, but that is TV, not reality! Make sure where ever you go as a group you at least try to stay in the groups budget if you can't do an inclusive. Great friendships are hard to come by and it is never worth causing someone to feel out of their comfort level.