Thanks so much to everyone who posts. I've spent a lot of time reading on this forum and gathering great information, so I thought I'd share our experience.
This was our 3rd trip to St. Maarten, but our 1st time venturing out on our own. We have stayed at Flamingo Beach each year and have always had a wonderful experience there. We were a group of 4 girls in our 20s-30s, so we were a little nervous about renting a car and going off on our own. We really didn't have any trouble, and were so happy with the decision to try something new this year.
Our 1st day was cut short due to travel issues, so after getting in late, we decided to just stay close by the 2nd day. We rented the car from Hertz at the resort and headed down to Sunset Beach for lunch and to watch the planes land. That was a really fun experience! We spent the rest of the day at the resort and then walked across the street for dinner at a French restaurant. I'm not even sure what the name was, but it had a cute outdoor seating area with lights in the trees, so we decided to try it out. The food was really good and reasonable. I got one of the specials which was a puff pastry with crab and shrimp in a cream sauce for $14. There was live music and we enjoyed the atmosphere. We were told about some sort of party at Bliss that night, but we weren't interested in driving down there, so we walked over to the Red Piano. I guess everyone really was at the party because it was pretty empty, but we had a good time.
Day 3: We drove to Marigot to catch the ferry to Anguilla. We got a little turned around trying to find the main road. There was a sign that looked like it was pointing us to turn left, which we did, but ended up in a more residential type area. There was a security guard standing in front of one of the buildings, so we stopped and asked him, and it ends up we should have just stayed straight on the road. So we turned around and were on our way. It was a Sunday, so traffic wasn't bad, but you really do have to be a defensive driver. The main roads were fine, but as we were driving through the towns, we had dogs and people just walking out in front of us, cars cutting us off, etc. We just took our time and didn't let it bother us. We had a map, but couldn't really find many street signs, so just kept driving toward the water to find parking for the ferry.
When we got to the place to buy the tickets, there was a really nice man named Nell who helped us out. He asked if we were going to Shoal Bay, which we were, so he told us he'd take us there and gave us his card. His business is Nell's Taxi and Tour Service. There was a ferry that was leaving in 5 mins, so he walked us through the process of paying the tax, filling out the form, and making sure we made the ferry. The ride over was about 20-30 minutes and was a little rough. Once we got there, he told us he'd wait for us on the other side of the customs area (make sure you bring your passport). There were about 12 of us that he loaded up in his van and drove us over to Shoal Bay. The ride was another 20-25 minutes. He gave us a tour and pointed out interesting facts on the way. He asked what time we all wanted to go back and was right on time to pick us up and take us back. He charged $20pp and we didn't pay until he dropped us back off at the ferry.
The beach was really beautiful! Just a handful of people, so it felt really private and secluded. I'll post a more detailed report and pictures of the beach in the Anguilla forum. We chose Sunday to go so we could hear the band at Gwen's. The atmosphere was perfect and the food was really good! I'll also post pix and a review in the other forum. We spent a good amount of time in the hammocks and just enjoying the incredible view.
No issues on the way back. We had a calm ferry ride and were able to enjoy the views of St. Maarten from an upper deck. No problems finding our way home. We got back to the resort around 6pm and enjoyed the sunset and then headed down to the Boathouse for dinner. We had eaten there 2 yrs ago and remembered the food to be good. This time we had a bad experience and ended up leaving without getting dinner. It was close to 10pm when we found out that they hadn't put our order in (got there at 8:30pm). At that point we weren't hungry anymore and just wanted to go to bed. We understand "island time", but that was ridiculous. The servers were all outside, only 4 tables with people in the restaurant, so I'm not sure how we got missed.
Day 4: We went to Pinel Island. It was a Monday morning, so traffic was bad, but we were heading in the opposite direction from everyone else, so it wasn't bad for us. We drove over to Orient Beach for breakfast and then took the boat over to Pinel Island. They really pack the people on those boats! They squeezed us in, so we didn't have a wait. $7 for rt. We sat in front of "Up on the Key" and enjoyed the day. I'll post pix and a review under Things to Do. We waited for the last boat to take us back at 5pm. No problems with the drive home. It's really only one main road, and we followed the signs to get through the towns. Again, we were going against the traffic, so it wasn't bad for us. We went back to the French Restaurant for dinner and then the Red Piano.
It was a quick trip, but we really packed a lot in and felt like we had a nice getaway. We never had a moment when we felt uncomfortable or unsafe. Like many others have said, use common sense and be aware of your surroundings. We used the safe in our room and didn't leave anything in the car. We took turns getting in the water so someone was always watching our bags. We didn't drive around after dark, and were lucky to be able to walk across the street for nightime entertainment. I'm a planner and like to know what to expect, so thanks again to everyone who posts here. I think I enjoy the planning process as much as the actual trip! :)