i just took my girlfriend to st martin in May which is slow season..she loved it, i've been before but enjoyed myself.. though i suppose it really depends what youre into as far as recommendations. from maine so i can understand the getting away from being buried in snowy bullshit.
first off if you're staying a week you'll have to rent a car. get a hyundai hatchback and boobascoot all over the island. driving around is an adventure in itself. the locals drive like assholes so be sure to get insurance..and be prepared to take a crash course on driving like a madman as you'll pretty much have to if you want to get anywhere. avoid driving anywhere if you can from 2-4 or whenever school gets out.. the streets are all narrow and you'll be stuck for hours with no way to pass ( unless you rent a scooter, very dangerous though) and god forbid you bang out of a rotary too soon or too late, good luck getting straightened out!..this ruined an afternoon for us when we thought it'd be a good idea to check out phillipsburg, the capital where the cruise ships come in and its tourist central...avoid like the plague, unless you're into that..shopping, jewelry store after jewelry store etc..
we stayed on the french side in grand case which is the restaurant capital of the island if you're into good meals every night of your vacation. the "lolos", or local bbq pits, aren't very awesome and theres about 5 of them crammed all into 1 little area. they all serve the same type of low quality picnic food out of chafing dishes and they'll hustle you as you walk past to try and get you seated. i'd avoid them. some of my favorites were la tastevin, la cottage, ocean 82... plenty more. outside of grand case i didnt eat much but Pat's roadhouse in simpson bay is where to go. the owner Pat's a funny ass frenchman so sit at the bar if youre into chatting up locals. they make a good homemade ginger rum in a big plastic container you can buy bottles of for $20 or something.
as far as hotel recommendations Hotel L`Esplanade was the best vacation stay i've ever had. possibly due to my proclivity to smoking the reefer, and the ease of procurement afforded to me at said establishment.. though i dont want to blow up anyones spot too much on the specifics of that.. its a little boutique hotel with only 24 rooms, a resident stray cat that will come visit you, or go away if you dont like cats, a tamarind tree on the grounds i happened to use to make fresh vacation pad thai (spicy food is not popular on the island...), aloe plants growing on your balcony in case you burn your cock, pool area has maintained grass lawn and stepping stones so you dont burn feet on hot concrete, free yoga classes, free shuttle down to restaurant alley if you dont want to make the 5 minute walk, beautifully manicured grounds and all up on a hill overlooking the west side of the island for prime sunsets, far away from the 3rd world riff raff aforementioned in the thread. the couple that owns it also have another smaller hotel in grand case l`petit hotel and another in st barths. i wouldnt recommend any all inclusive deals or corporate type resorts. once you get there liqour is dirt cheap at the stores and not worth the added price of an all inclusive that limits food options also.
if you're into nightlife the main spot for that is maho bay. theres a nightclub called tantra which is... a nightclub. if you go during the slow season the bartenders are extra appreciative of tips because they make full wages and i dont think the locals usually tip much or at all and theres not as much tourist action. i was tipping a modest amount similar to how i do back home say $2-3 a drink and the girl started giving our whole party of 4 free rounds of shots all night. the strip club is nearby and outside even is a fine place to find some nose candy that does not disappoint. you can do some bar hopping in simpson bay as well.
