Vacation Ideas - May
 

My husband and I are planning a 5-night vacation over Memorial Day weekend and are looking to spend ~$2K. Does anyone have any ideas? We like AIs, but not a must. We're looking for a resort with good food (a la carte options), nice pools and a nice clean beach (without too many hagglers). We are looking to relax but would also like to do a little sightseeing too, so the island will need to be safe. The other caveat is we do not like little planes or prop planes and will be flying from BOS.
My husband would also like to rent a moped (Bermuda maybe?) and have a drink at a beach bar while listening to live music.
Any ideas??

That's also a holiday weekend in Bermuda, as well as high season - is your airfare included in that budget? It's a short flight from Boston, but you might need to consider different options for that kind of money here.
You sure could rent the moped, though!!

No, airfare is not included in our $2K budget...we have points we can use. Do you think Bermuda is a good idea? We're also looking at Barbados. Any thoughts?

Both are fairly expensive islands, but you could probably find something in that range. There are no AIs in Bermuda.

But your bigger problem is going to be flight availability. Flights during Memorial Day have already booked up solidly, and I'm not sure you'll be able to use your points regardless of how many you have.

American still has a few award tickets for Barbados that include Memorial weekend. (30K miles each, more options for 60K) May have some luck with Northwest using American Eagle connections.

Sorry if you have Delta or Continental.

Looks like most are through Miami and may include overnight flights for your return.

Been doing some faily extensive Hopefully someone can benefit.

I think you would like "Villa Rolandi" on Isla Mujeres..... small island off of Cancun. you fly into Cancun and the hotel sends their private yatch to pick you up and take you to their resort. Service is aweseome, rooms are all suite-look over the water, and the food is gourmet! Breafast and very nice dinner are included - breakfast is delivered to your room whenever you want it. Read reviews and see traveler pics on www.tripadvisor.com (search villa rolandi) for what you get, its a deal and the place is a gem! I went last Sept and am going again in May! the island is quaint and safe and the seafood is FRESH and awesome!