Alright, time for JC's abbreviated guide to St. John
First of all, I love this place. As I stated above, I got married there and it has a special place in my heart.
Before I get into this too much, let me tell you the types of things I like on vacation because what's great for one person may not be so great for someone else, and my opinions are definately a result of what I like. My wife and I like to stay somewhere nice, but we're definately not the resort type. I don't mind carrying my own bags, and I'd much rather walk through town and experience the "atmosphere" than drive through. We can afford to spend a little money to stay/eat at nice places, but we get very annoyed if we don't feel like we're getting equal value for what we spend.
I'd definately recommend St. John over St. Thomas. St. John is much more slow paced. Getting there from the airport is a bit of a hassle. Frankly, the taxi drivers at the airport on St. Thomas can be a bit rude. Sometimes the ferry guys are great and sometimes not. Also, you'll want to bring lots of small bills for tips to get you from the airport to St. John. From the porters, to the cabbies, to the baggage handlers on the ferries, you'll feel like you're being nickle and dimed to death. Hold on though, it's worth it. Once you get off the ferry in Cruz Bay, everything changes. St. John is much more relaxed and enjoyable. I make it a ritual, as soon as I get off the ferry to go straight to the Dockside Pub and order an ice cold Guiness. Helps me get into "vacation" mode. During peak season, St. John can be a real party town (but certainly not "spring break" crazy). I prefer off-season, when things are much less crowded and more "sleepy". I like having a beach to myself
If you've never been to the West Indies, remember, men need to wear shirts and women need cover ups (if in bikini) while in town, but you can walk around w/ a drink in you hand anywhere you want.
On that note, you can generally find good wine at one of the markets, but it tends to get a little pricey. Beer is a different situation. Beer on St. John is cheap. Even expensive imported beers. If you're a Guiness freak like me, you can get real Guiness, not the stuff we get in the states. Mmmm... Guiness. Also, if you like stouts try Tenant's Milk Stout. Anything w/ rum in it is also cheap.
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Regarding places to stay: (there are lots more that I have no personal knowledge of)
Gallows Point -- My personal favorite. It can get a bit pricey, but the grounds and the sunsets (best on St. John IMO) are wonderful. Classy but not the resort atmosphere. The location is also just a short walk from downtown. If you watch their web site, sometimes you can get an internet special for considerably less than their standard rate. The downside is that you have to wait for the last minute to book it. It's basically a condo with maid service.
Westin -- If the resort atmosphere is your thing, then the Westin is a good place. It's expensive but it's one of the two places that I would consider very upscale. They also keep a tight "command-and-control" on the local businesses that serve their guest (such sailing charters and Cruz Bay Watersports) so you'll typically get good service there. It's a little too far out of town for my tastes though. You'll probably want a car if you stay there.
Caneel Bay -- Very similar to the Westin in terms of its "upscaleness". It's a much older facility and like the Westin, you'll probably want your own car. A nice perk is that they have their own ferry to St. Thomas which makes your arrival a little easier.
Coconut Coast -- I've never stayed there, but I've visited the studio and bought prints there on several occassions. The woman that owns it has always been very nice. It's also convenient to town. I hate to sound negative, but there is one issue that you might want to look into before booking there. Behind Coconut Coast, there's a salt pond. Certain times of year, if the wind is right, a fairly unpleasant smell can permeate the area. However, last time I was there, they were doing some construction and if I understand it, they were planning on opening up the pond to the ocean. I'm not sure what the status of that is.
Tamarind Court -- Never stayed there, so I can only speak of what I heard. It's definatley not a five star, but I've never heard anyone say anthing negative about it, so if you're budget concious, it might be worth looking into.
St. John Inn/Cruz Bay Inn -- unless things have changed a lot in the last year, don't bother. I stayed there one night, and found accomodations elsewhere. They're cheap, but not cheap enough for what you get IMO.
Battery Hill -- Middle of the road price wise. These are condos and not part of a resort per se so there will be no maid service, but they're nice units and have a nice view. If you're thinking about staying there, there's one unit that has an awesome view. I don't remember the unit number, but if you're interested, let me know and I'll try to describe it. They also have a small efficency that's less expensive but still very nice. The only negative I can see is that it's a little farther from downtown. It's still walking distance, but if you don't enjoy a brisk walk, it might not be for you.
There are lots of other places to stay, but these are the one I'm familiar w/. It's probably worth it to call a real estate agent down there. They all do property management and you might find a private apartment or villa that's in your price range. Just remember to account for the cost of a rental car if it's not near downtown.
to be continued ...