I just returned from a trip to Sint Maarten / Saint Martin and had the time of my life! Here are some of the best things to do and some (hopefully) helpful tips:
1) Sunset Beach Bar - you can't go to St Maarten and not come here to watch the planes land! Take a seat at the bar and just watch the incoming traffic! The bar offers great drinks and food, that's not expensive.. the views and photo ops are one-of-a-kind!
2) Orient Beach is, in my opinion the best beach on the island. There are both clothing and clothing optional sides, but both offer great sand, sea and views! There are loads of restaurants along the main side, right on the beach and everyone offers chairs and umbrellas! There is also a small area behind the beach restaurants for some finer dining (but still very casual), with about 8 restaurants of varying cuisines (Japanese, French, Italian, etc). There is also a market on cruise ship days for your souvenirs.
3) Nettle Bay - Another great place to go is Dreams at Nettle Bay. Here we had lunch on a practically deserted stretch of beach, with awesome service and great food.
4) For a little night-time entertainment, Cheri's at Maho Beach is a must! We went here on a Saturday night for dinner and a little entertainment - oh boy! What a fun night.. You have to check this one out..
5) Grand Case - This is considered the gourmet capital of the Caribbean and for good reason! We dined at Le Tastevin on Blvd de Grand Case and I would highly recommend it. The views were overlooking the beach and even at night it was amazing! The food was better than expected, great service - and priced very affordably... We went back another night to Le Ti Provencal, and again - this was very good, but not quite as good... Grand Case was a $30 cab ride each way from Philipsburg
6) Anguilla - we took a day trip by catamaran to Shoal Bay and spent the day on the beach. One can never get enough of the white sand and crystal clear water! You can easily see why it's one of the best beaches in the world! Our catamaran crew was fantastic and really wanted to make sure all their guests were looked after... They did a great job!
7) Find a good Taxi Driver! We were super lucky and found Raymond, a driver that was fantastic! We got his phone number and he drove us everywhere we wanted to go (and by the end, was giving us discounts). It can be daunting going to a place you have never been and try to navigate around, so this is a great way to do it. Remember, if you pick up a taxi without calling one, be sure to see their credentials. There are a lot of rogue drivers out there, so just be safe!
8) French vs Dutch?? We ventured out on both sides of the island and both had a lot to offer! The French side is probably better maintained, and who doesn't enjoy a complimentary shot of home made rum after their meal which seems to be the norm? The Dutch side has the shopping (thank you cruise ships) and some lively bars / casinos.
9) Don't let the rain spoil your fun! It rained every day we were there, but it doesn't last long! Just huddle under the beach umbrella for a few minutes or grab some lunch - but unless it's torrential, don't pack up and leave - hang five - it'll clear up pretty quickly!
10) Get out and explore! There is nothing better than stumbling across something cool! We asked for recommendations from our taxi driver and we talked to locals to find out where they like to hang out.. We got some great advice and it made the world of difference. I'm happy to say we went to a different beach almost every day and were able to go to practically every corner of the island.. To me, that's a great vacation that was still supremely relaxing!