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Originally Posted by Julian
What about Sharm El Sheikh m8? I don't know about the nightlife but the diving and snorkelling is the best in the world. 
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Drinking and Diving don't mix. Unless you want to learn how to vomit through a reg and find out how fast fish move when there is lots of food around.
Sharm - good nightlife, but beware of the statement above.
Bali - Kuta - is the Ozzy equivilant of Spain. Nusa Dua is the exclusive bit, but the nightlife is not much - full of honeymooning couples. Bali is still dirt cheap since the bombings scared the australians away. I paid $220 a night for the Sheraton Laguna Nusa Dua back in 2001. Its $95 a night at the mo.
Phuket - Nice - the Laguna area is exclusive, but the nightlife is in town.
Mexico has a lot of Americans.
Dominican Republic has some good deals
Monsoon seeason - don't worry about it - it rains for an hour and is dry in minutes. Rates are better too.
Travel advice - start thinking about getting your immunisation shots. There are a few of them and they should be done a few months before. Most are good for 3-10 years, so with your timing there is no reason not to get them done now.
Airlines - think about what you want from one You'll be on it a while. A charter is cheap but cramped. American Airlines across the atlantic has 35in legroom compared to the market norm of 32, American carriers charge for drinks, european ones don't but the legroom makes up for it. You notice the difference. Thai has good legroom and service but less good in flight entertainment. Singapore has fantastic IFE, and service but is a little cosier and generally full so don't expect a spare seat next to you. Quantus are generally disliked (never used them myself). Again depending on the carrier think about joining their or a member of their alliances Frequent flier program. A flight to Australia or Thailand may well give you enough miles for a free european flight each.
Personally I'd choose Thailand out of the list. Spend a couple of days in BKK also though. The palaces etc are worth a visit. Mexico is somewhere I'd save for when you have kids. The smaller islands you mention (Maldives/MRU etc)are all quieter than you seem to want.