All of the North Shore beaches are fine for children as there is no 'surf' to be concerned with. Hawksnest offers close reefs if the 4 yo wants to snorkel.

Selecting hiking trails for kids that young is a tricky. Depending on the 4 yo, you may be carrying both before too long. Most trails follow natural slopes of the island so some steady climbing is involved where ever you go. Perhaps the trail to Salomon and Honeymoon beach is short enough not to tax your group. You might ask the Parks Department in Cruz for suggestions.

Starfish Market in Cruz Bay is a great grocery store.

Mongoose Junction may have a decent selection of beach toys, but for the selection and price, I would bring them from the mainland (if you can still find them out of season). An option is to buy them on STT (K-Mart) before you come over.

Prepared food: No experience here so I pass to others for suggestions.

Depending on the winds, both can have 'rough' moments. The Red Hook ride is 15 minutes shorter and my daughter felt that ferry was a 'smoother' ride.

One of the nice things about USVI is the conditions remain fairly constant all year round(unless hurricanes are around). The temperatures are pretty much the same and so are the bugs. They are really only an issue when breezes are calm or non-existent (early morning, dusk and in secluded grottos).

Hello,

For hiking with the children perhaps Cinnamon Bay self guiding trail through the plantation ruins and the forested area around it.

The Simple Feast is a good choice for carry out food.

--Islander

The Annaberg ruins are not a 'trail' but would be nice for the family. I believe several trails include the ruins so you could go out and come back along one if a hike is what you want without commiting to the entire trail.