My SO and I got in on the US fare mistake/sale to STX for the first week in Dec, and I am trying to figure out where to stay...we are in no way locked down to STX, and I have been looking at STT, St Kitts, and even San Juan...My problem is that we, and myself in particular are very picky about hotels and places to go to...I want to go somewhere where we can still be in some civilization, but nice...I'll give an example. I loved Waikiki Beach, and wasn't all that crazy about Kauai, because I like being able to go to a mall or shopping, as well as being able to see natural beauty. So heres my question...since I want to stay at somewhere thats 4 or 5 star, and don't want to pay more than $200/night, from my searches that sticks me in San Juan. I don't get the feeling that any of the Virgin Islands will keep my interest for 7 days, and my SO can't sunbathe due to a skin condition, so just sitting on the beach isn't really an option. Can anyone make a suggestion, or at least push me towards something? Is Puerto Rico a good idea, maybe staying in the Westin? Or would STT have enough to keep our attention?

Sounds like you picked a bad destination.

LOL. Try Miami.

I say this not out of malice, although I am a bit incredulous, but if you liked Waikiki, there aren't many places in the Caribbean that you'd like. If you hated Kauai (wow!!?!), I'm guessing that natural beauty means looking at Diamond Head from the air conditioned restaurant. There just isn't a lot of that in the Caribbean -- ESPECIALLY for cheap. High-end properties in the Caribbean are targeting very wealthy Americans and Europeans. Look at the new Starwood property in Anguilla. Look at the resort on St. John's. You'd have to spend two or three times your $200/night. Even the new resort in St. Maarten, if it opens, is going to be several hundred dollars in the off season.

Why would you buy a ticket to a small, relatively undeveloped Caribbean island if you 1) like lots of commericial crap; 2) can't sunbathe; 3) very picky about hotels (as long as they're under $200/night)?

I would seriously consider cancelling. Or getting on the first flight to Miami.

I didn't say I hated Kauai at all...just thought it was all about done in 3 days...in fact I loved Kauai...Maui on the other hand...

PS - I hate Miami. :-P Gimme Orlando, Tampa...even FLL...
And I only bought the ticket because it's first class for amazingly cheap, and I can use the miles...but I thought I could find somewhere to be...is San Juan at all commercial?
LOL. Try Miami.

I say this not out of malice, although I am a bit incredulous, but if you liked Waikiki, there aren't many places in the Caribbean that you'd like. If you hated Kauai (wow!!?!), I'm guessing that natural beauty means looking at Diamond Head from the air conditioned restaurant. There just isn't a lot of that in the Caribbean -- ESPECIALLY for cheap. High-end properties in the Caribbean are targeting very wealthy Americans and Europeans. Look at the new Starwood property in Anguilla. Look at the resort on St. John's. You'd have to spend two or three times your $200/night. Even the new resort in St. Maarten, if it opens, is going to be several hundred dollars in the off season.

Why would you buy a ticket to a small, relatively undeveloped Caribbean island if you 1) like lots of commericial crap; 2) can't sunbathe; 3) very picky about hotels (as long as they're under $200/night)?

I would seriously consider cancelling. Or getting on the first flight to Miami.

San Juan feels to me like a combination of Miami and the rest of the Caribbean. It's commercial, but not like Waikiki. Don't remember a Cheesecake Factory.

Do you speak Spanish?

San Juan feels to me like a combination of Miami and the rest of the Caribbean. It's commercial, but not like Waikiki. Don't remember a Cheesecake Factory.

Do you speak Spanish?

Nope...I didn't think I NEEDED to...do I? I know Spanish is the main language there, but can't I get by with English and odd hand movements to explain my odd gringo ways? :-P

My best advice, based on your postings, really would be to consider cancelling the trip. I've been to a lot of the Caribbean and seen a lot of miserable Americans who thought it was going to be like Tampa or Honolulu.

STX makes Kauai look like Waikiki; however some of the towns are 2 blocks long (though not many) and there is some interesting shopping (aimed at cruise ships, mostly jewelry and junk). You won't find any nice accomodation at under USD 200/night in December. San Juan would be cheaper and with more to see, but not necessarily nicer. You are going to a beach/scuba/golf and horse-riding destination where all the food has to be imported (so limited availability and high prices); it does sound like the anti-thesis of what you are looking for. Still, the virgin islands are charming and it might grow on you.

Aside from private condos, The Buccaneer is the nicest place on STX. Great views, beach and great beds/pillows (why are these so hard to find nowadays??). I completely doubt that there is enough on STX --AND-- STT to keep you occupied for a week if not interested in relaxing. STX has about 3 shops worth walking into and a 4x4 block area of trash. The other side of the island (F'Sted) is not worth the gas money. STT has cruise ship shopping- tons of duty free, but it could easily be done in a day.
Do you scuba dive? if so, bring your C-card and get to work, lots of great places to dive in VI, although you are subjected to not really knowing if where you want to dive will have vis that day.

If you bring your passports, you could go over to Tortola for a day, but you would need to rent a vehicle to get around, or pay some expensive taxi rates.

You could go to SJU and do tourist stuff or take some day trips to various areas (Ponce is pretty, but no "great" hotels there...although that HoJo is much nicer than most HI's I've been in recently). SJU has shopping, but if you're looking for Rodeo drive, forget it. Walmart and cheap stores reign in PR, aside from a smattering of "Polo" level stores in Old San Juan, it's mostly trash and trinkets. Most areas there is someone able to speak enough English to get by.

Any specific questions, let me know.

I think we may do the Buccaneer for 2 nights, then hop over to SJC for 5...If I could only get the Marriott or the West in SJC for a bit cheaper...everything I can find ends up being about 200 a night at least when you add the ridiculous taxes...

Aside from private condos, The Buccaneer is the nicest place on STX. Great views, beach and great beds/pillows (why are these so hard to find nowadays??). I completely doubt that there is enough on STX --AND-- STT to keep you occupied for a week if not interested in relaxing. STX has about 3 shops worth walking into and a 4x4 block area of trash. The other side of the island (F'Sted) is not worth the gas money. STT has cruise ship shopping- tons of duty free, but it could easily be done in a day.
Do you scuba dive? if so, bring your C-card and get to work, lots of great places to dive in VI, although you are subjected to not really knowing if where you want to dive will have vis that day.

If you bring your passports, you could go over to Tortola for a day, but you would need to rent a vehicle to get around, or pay some expensive taxi rates.

You could go to SJU and do tourist stuff or take some day trips to various areas (Ponce is pretty, but no "great" hotels there...although that HoJo is much nicer than most HI's I've been in recently). SJU has shopping, but if you're looking for Rodeo drive, forget it. Walmart and cheap stores reign in PR, aside from a smattering of "Polo" level stores in Old San Juan, it's mostly trash and trinkets. Most areas there is someone able to speak enough English to get by.

Any specific questions, let me know.

Wow this is a tough one but here are a few recommendations:

St. Kitts - St. Kitts Marriott Resort & Royal Beach Casino. One of the best Marriott branded properties I have ever visited. St. Kitts is a lovely island but the shopping is very limited (no malls) but sure you will find lots to do outside of just sun bathing

San Juan - Another very god bet. Lovely city. The Condado area has great nightlife and Old San Juan is even better. Shopping is also excellent and some of the best malls are within the City or just on the outskirts (USD20. away) Plaza Las Americas and Plaza Carolina. No need to speak Spanish, I don't but that never stopped me from having a blast.

St. Maarten - You never asked about this island but IMO it is your best bet for shopping, activities, night life and the "island experience". You get the best of two countries wrapped in one vacation (French St. Martin and Dutch St. Maarten). You will be amazed by the culinary experiences at the restaurants on the French side of the islands as well as the fashion houses. On the Dutch side, shopping for diamonds and electronics will take your breath away - St. Maarten is a duty free port. Finally its close proximity to Anguilla, St. Barths, Saba and St. Eustatiaus means that you could see a new island each day. Definitely worth checking out.

Hope this helps you out a bit.