I've been to one destination wedding, and had a blast. About 50 of us went, mostly composed of the bride's family, and they were great. I echo the comments above about it being great fun because the prep work is done for you.
The bride and groom asked everybody they intended to invite about a year in advance if we thought we could make it. They booked it and gave us all about 10 months to save up for it and book the time off. Once we were there (a resort on the Mayan Riviera) we had nothing to do, nothing to pay out of pocket for (save for tipping the wait staff to keep the stream of cocktails and cervezas coming), just all the free time in the world to have fun and shoot the ****. My days went like this:
- roll out of bed at 9:30 am
- have breakfast by 10:30
- hit up the pool by 11:30
- have lunch at some point in the afternoon
- meet up at 5:30 pm, decide which restaurant to go to for dinner, go back to our rooms to shower and throw some pants and shoes on
- have dinner
- decide which bar to go to for the evening
- party until the wee hours
- start it all over again the next day
It was glorious. It was a fantastic excuse to take a week off work, and I'd do it again in a heartbeat.
There were a few people who couldn't make it, mostly for cost reasons. It sucked for them but everyone else understood.
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