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Help me? I've never planned a trip before.
My SO and I have never really traveled together. Four years ago, we went to Daytona with a group of friends over Christmas break. It was a bust. I went with my Mom on a cruise and it was fun, but we (SO and I) have never been anywhere together.
It looks like we will have 7-9 days in late June where we can plan a trip somewhere. We would be flying out of Chicago. I don't want to waste a lot of time on a plane, so I'm thinking something close (as opposed to Europe) might be better.
Things we'd enjoy:
- jet skiing (we've never done this)
- beach lounging
- lots of eating and drinking
- no driving if we are outside of the continental US (so I'd want to stay in a resort and have everything we need on that resort)
- entertaining nightlife
This all sounds like a cruise, but I don't think I want to go on another cruise before I actually try a vacation somewhere. Does anyone have any suggestions? Hotel recs if you have a specific location we *must* go to?
We'd like to keep the cost reasonable, but this is our first splurge so I think if we can keep it at or below $4k for the week we should be good.
Thanks in advance! I really appreciate the help! 
Re: Help me? I've never planned a trip before.
It sounds like you would be happy at an all-inclusive resort. Mexico, the Dominican Republic, Jamaica, Turks & Caicos, Aruba, St. Lucia, a bunch of other Caribbean islands would be good places to look. I've never been to an AI, so I can't give you suggestions, but does any of those countries sound most interesting to you or have better flights from Chicago?
Keep in mind that while an AI could be a good fit, it's really not hard to organize a non-AI vacation. H and I went to Aruba for our HM, and we stayed at the Bucuti, which was great. We didn't need to drive - we took taxis to the other hotel area a couple times (like $10 a ride) and took the bus into town once. That for us is a lot more interesting than staying at the same resort the whole time. Just don't want you to think that the options are either driving or never leaving the resort.
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Maybe L.A.? Plenty to see, do, eat there, plus the beaches you're looking for.
Personally I am not a fan of AIs. We did it once for just a couple of days as part of a bigger trip and it just felt so...I don't know...sterile? We could have been anywhere in the world and there was no real feeling of local color, cuisine, culture, experience. I couldn't wait to get out of there and really see the area.
What was disappointing to you about your trip to Daytona? (might help with ideas...)
If you want to stay in the U.S., I'd recommend Florida or the area around Charleston, SC (Folly Beach, Kiawah, John's Island).
We're headed to Aruba on Saturday - for a first timer the high-rise (AI resort area) might be up your alley. It's unthreatening.
Or Mexico.
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I agree with pp that an All-Inclusive might be up your alley, especially where it sounds like your looking for an easy and relaxing vacation. With that said, I've never been to an AI and I usually cruise in the carribean. Bermuda, Bahamas, DR, and of course Mexico (even though I avoid Mexico), I would say would probably be the cheapest, but there's so many other beautiful spots too in the Carribean. If you want U.S. L.A., San Diego, Hawaii, Hilton Head SC, Key West, would all be great spots. For flights Hawaii and Key West will probably be a little more, but you never know
Good luck!
You can always set up price alerts using Kayak, Yapta, etc. so you know the cheapest time to book a flight. Tuesdays and Wednesdays are generally the best days to book! Good luck!
we went for late December and New Year's, and except for Jan 31, the place was dead. We seriously sat in a bar with one biker guy one night. I need more to do and see, and the beach was too cold (although we kind of knew that).
It sounds like the majority of you think an AI would be best for us, and you're probably right.
I'm thinking either an AI outside of the US or a Florida town, which also would be less intimidating. If anyone is familiar with FL, where is a place that would be fun for a couple in their early twenties, but doesn't feel like Cancun on spring break?
ETA: thanks for the tip on booking Tues or Wed!
I don't know anything about travel.