In 2005 we had a group of 5 couples that decided to take a trip together to STT. We had a few planning meetings and gave everyone a responsibility, rent the villa, arrange rental cars, find a big activity, research restaurants, etc. This was everyones first trip to the USVI so we were just winging it. Once we got to the villa we took out a deck of cards and drew for room choices, ace got first choice, 2 next choice and so on. We would take turns paying for food, alcohol, gas, restaurants (we got an itemized check and noted who ordered what) but keep the receipts and settle everything up at our post trip party once we got home.

This worked so well that the same group were all ready to go back in 2007 and rented a villa on STJ. We used the same system and it worked fine for us. We had some minor disagreements but everyone had the attitude that we would just go with the flow and have a good time. We all did everything together (well not EVERYTHING) and had a good time enjoying each others company. Our group all has a good sense of humor and we can really lay the crap on each other and still have a great time. Our group has known each other for several years and have connections through our kids, church, or other groups so we all know each other fairly well. I think that is the key to going in a big group. we would cook out at the villa 2 or 3 times during our trip and everyone would pitch in. We all love going to the beach and snorkeling or just sitting on the beach and soaking it all in. I don't think that I could make this same trip with my family (brothers, sister, nieces, nephews, etc) but I didn't have the option of choosing them.

The best part is that we all truly felt we were traveling with friends and we are planning our next trip in 2009 or maybe earlier.

Eagles Landed,
Even tho you have decided to do the trip "without friends", you certainly started a thread with value!
Thankyou for starting this wonderful thread, I have enjoyed reading everyone's posts!

Thank Sherri, it has been a good read. Very nice to hear other people experiences.

Perhaps I should explain our "closest" group of friends and then you might agree with me that we need to go on this trip alone. 🙂
(please remember that we're landlocked here in CO and even though we have a dive shop in every town, we don't know too many people that know how to swim!) Hubby and I grew up near water, Mich. and Fla.

Couple #1, empty nesters also, travel to the Caribbean once a year. Usually stay at Caneel Bay. Sun God and Goddess...but do not get in the water, never. Love to drink, and be waited on and take day sail trips and never rent a vehicle. To their credit, through their pics, they turned us on to the USVI.
Couple #2, empty nesters, retired techies, travel only to see their kids and grandkids and even though they have a great deal of $, they never spend it on trips for themselves. Have never been to the Caribbean and have never snorkeled.
Couple #3 empty nesters, still working in the tech industry, likes NYC, Napa/Sonoma area, big cities in general. Don't swim, snorkel, etc. Never been to Caribbean.
Couple #4 still working, have a cabin in the mountains and spend majority of their time there. They have travelled around the world, but not to water destinations.

You might be asking yourself, what vacations did we take in the past with these folks? Camping trips, of course!!! And we always gather to cheer the Broncos on! LOL!

Get the picture? 🙂