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@ejm1287: My mother, sister and I decided to head south this winter, just for a change of pace. We researched flights, and ended up in Puerto Rico. There are tons of options - from San Juan all the way to the rainforest, and the flights were less expensive there than a lot of other places. Just a thought.
Puerto Rico is fantastic. San Juan is wonderful for shopping and historical culture (the forts are amazing), but if you want to stay in an amazing and relaxing place you should stay outside of San Juan. The Wyndham Rio Mar is about 25 minutes from San Juan and it is like a hidden paradise.
I'm going to share a treasured secret. The Bellavista Bed and Breakfast in St. Thomas is MAGICAL. The best vacation my husband and I have ever taken. http://www.bellavista-bnb.com/
VIEW FROM THE LOVELY SUNDECK

MAGAN'S BAY BEACH

DAY TRIP TO ST. JOHN'S: TRUNK BAY---BREATHTAKING!!!

Tripadvisor has more photos and other reviews. During out stay, many guests had been to Bellavista numerous times. Can't say enough about the food, scenery, and hospitality. Tell Wendy, Doug, and Mocha we said "hi!"
@mwitter80: Thanks for the recommendation, it looks amazing and I'll definitely keep that on my list!
@gvsusara: This is going on my list as well, I love these little places!
st marteen and st thomas are very nice. What about a carribean cruise so you can spend a little time on several islands?
I'd rather not do a cruise, he's graduating with a degree in marine engineering and will be working month-long rotations on a ship starting in May, so I'd like to give him a break :)
Just bumping this up for the evening crowd. Any suggestions, especially those within the US?
Within the US, I would say Key West. Very laid back vibe. It's not really known for it's beaches, though. They do have some good snorkeling trips. Both times I've visited Key West, they were experiencing records lows (January 2000 and February 2010).
I have stayed in a timeshare and B&B, but I would recommend the Orchid Key Motel. It got great reviews on tripadvisor and is at the "quiet" end of Duvall. It's got a great location....near Hemingway House and in between the Southernmost Point and Mallory Square. There are a few other nice hotels near the Southernmost Point, but it's a longer walk down to the square and fishing docks, etc. But they are beachfront property and you can snorkel right off the hotel's dock.
We walked EVERYWHERE and didn't mess with car rental. Some places don't have parking for cars or charge a pretty penny to park. DH and I found the daily parking rates pretty similar to our home area of Chicago. You can easilty rent bikes, mopeds, and these golfcart type things. If you are used to walking, then I would not bother with a rental car if you have a direct flight into the Key West Airport.
**Keep in mind---if you fly to Miami you can drive through the Keys. There are other nice resorts (one on Hawksnest Key and also visit the turtle hospital on Marathon Key) and you could always drive to Key West for the day.
Have you thought about an all-inclusive resort? FI and I stayed at Breezes in the Bahamas around Memorial Day last year. They have a fabulous beach, three pools, a swim-up bar, really tasty food, activities on the resort are included, optional activities off the resort (we did the bus tour around the island). All food, drinks, on-resort activities are included in one price for the hotel. They don't accept tips because it's all-inclusive. It made for a laid-back and relaxing getaway. We spent most of the time just enjoying the sun and water.
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My fiance is graduating from college on April 30, and his birthday is May 6. He starts training for his new job on May 9, so I thought it would be fun to plan a 4-5 night trip somewhere and am looking for ideas. We're from New England, so I'm looking for somewhere out of that area. Mostly interested in the East Coast of the US, Bermuda, or Colorado/Utah/Arizona maybe. No interest in the midwest, major cities (NYC, etc), etc. We could be interested in Europe as well, if we could find cheaper flights (I'd rather spend the money on more expensive international flights when we'll have more time to explore).
Does anyone have any ideas? So far I've come up with the FL Keys, Hilton Head, Bermuda, Grand Canyon area, etc. and am just looking for other fun places that I could research. Thanks!!