1. Have never seen anyone using climbing shoes or know of any place known for boulder climbing.
1.5. There are several good hikes. We like hiking to the Tidepool/Natural Pool near Devils Cupper. You can hike the long way from Guana Bay or a shorter, somewhat easier hike from Point Blanche. Another popular hike is to Petites Cayes. You can hike to it from Anse Marcel or near the dump in Cul-de-Sac. The Loterie Farm offers a hike to Pic Paradis - long hike, hot since you're in a rain forest, but great views. Another hike is to David's Hole. You can get there by hiking from the destroyed La Belle Creole resort or a road near Baie Rouge. The internet has videos on all of these if you want to check them out.

2. The only cliff jumping I've heard of on the left side of Mullet Bay. There is an area there called whale hole where the locals jump. There used to be an area that had a rope to swing out on. Google cliff jumping sxm or whale hole sxm for videos.

3. There are lots of reliable charter companies for both power boats and sailing charters that offer full day, half day, and sunset charters. Would you want a group charter or a private one? We love taking a charter to see the island from ocean.

4. What to do with the charter?? If you want to see turtles, a charter that goes to Tintamarre is popular. Around the island tours that stop at several beaches and the Anguilla charters if you want to visit another country are also popular.

Whatever you do, I'm sure your family will love SXM!