I collected a lot of info for my trip so I felt I should post our experience in hopes I can help someone.
When: May 18-25, 2014
Where: St. Maarten Simpson Bay Resort on the Dutch side.
Who: I am 37 my wife is 32. We have been married 12 years and have four small children. We are from Utah. We travel as much as we can. We love the outdoors and spend most of our time in the mountains
Why: We have four young children.....duh
In general St. Maarten was much more developed than we expected, we wanted something more quiet. The island is very expensive and we did not see that coming at all, everything was expensive! We rented from a no name local car company and it was not problem. Driving around the island was not a problem and actually quite fun. Finding beaches usually took a little extra time since you had to navigate through shops, restaurants, houses etc. Locals were usually not much help, not because they where unfriendly they just didn't have much experience on their own island (go figure). Tap water on the island is safe to drink, it just tastes nasty so go get some powder mix at the store. The French side of the island is much much nicer than the Dutch side.
Day 1 (Sunday): We arrived with Jetblue from JFK. Airport is small and simple. Our car rental was based in the Simpson Bay area so we had to take a very fast shuttle ride from the airport. Every map we could find was not very detailed so it took us a bit to get our bearings. Check-in at the resort was simple and fast. The resort is great. We took off to find a grocery store and ended up in Phillipsburg because believe it or not a lot of stores are closed on Sunday. The store was ghetto but we got what we needed just 2-3 times more expensive than we thought. If you need to get groceries find the large Grand Marche stores. We ate at the Bucanner Bar and had the Blue Beard Burger and it was fantastic. Off to bed.
Day 2: We went to Mullet Beach. The beach was what we expected and loved it. We spent the day by renting an umbrella and chairs for $15. We ate lunch at the lolo just 50' away and had ribs and chicken for a bargain price of $20.
Day 3: We took off to the French side for the first time. FYI, you do not need a passport to move from one side to the other. We went up to the nature reserve on the northeast side of the island. It was a nice easy hike along the shoreline. It was very peaceful and only ran into 1 surfer on the way out there. We had the beach all to ourselves. After the preserve we went over to Lucas Bay where there are 4 very small islands that we could wade out to. There were urchins in the water everywhere and a great place to collect shells. The french lady with a food shack was very friendly with some great snacks.
Day 4: We are suckers for markets so we had to go to Marigot to the open air market. It was great. My favorite are the spice and produce stands and the few artists with original hand made goods. Make sure you barter with everyone, don't pay the asking prices and don't buy the first thing you see. On our way out we got suckered into going to the Westin at Dawn Beach for their timeshare spill. The resort is nice and our sales woman was very nice and got us right out of there. Since we were on that side of the island we decided to go to Orient Beach which we did not have in our plans. It is everything you would expect. It is nice but very activity and party oriented. The further south you go the more topless women you run into. If you go past the rock outcropping on the south end you will end up in nudist territory, if that is your thing. We bought a bottle of water for $8, did I mention everything is expensive? That night we hit the streets and ended up at Lee's Roadside Grill. It was hopping and the food was great.
Day 5: Excursion day. We hopped on the Blue Beard Heineken catamaran to go to Anguilla. The crew was very friendly and helpful. They worked their tails off taking care of everyone. We were the only couple to stay at Rendevous beach and I'm happy we stayed. There was only two other couples and it was very quiet and relaxing. For lunch we had to fend for ourselves. We ended up at Bankie Banx for ribs and snapper, and yes it came in at $55 not including drinks. The food was good but not near $55 good. The atmosphere and coolness of the place was worth going there. Anguilla is well worth the trip.
Day 6: Lay low. I had the itching for pastries. I found good info on Saraphinas in Marigot. It is a must stop. The food there is not to be missed. The ham and cheese things were to die for and if you were still alive after eating one the coffee eclair sent you straight to heaven on first class. That night we ate at The Stone where they bring dinner out a very hot stone. Great food for sure. Day 6 ended up pleasing our taste buds.
Day 7: What do you do on your last day? Sit on the beach of course. We grabbed a umbrella and chairs on Lay Beach and read our books. We did do some snorkeling which was ok. St. Maarten is not a snorkeling/diving destination. That night we went to Prive for sushi. It is one of the few sushi places on the island and it was average.
All in all we enjoyed our trip very much. We however probably will not go back to St. Maarten, there are more islands to check out.