We've done this many times and it is awesome. We've done it both directions and it really depends on your starting point. We start from St. Thomas on our monohull sailboat and usually go counter-clockwise. The south shore is a low/no charter boat area.

Favorite stops:

- Great Lameshure - excellent snorkeling/diving, trash dropoff at NPS dock, walkable/dinghy to beaches at Little Lameshure and Salt Pond. Maintained NPS hiking trails as far as Bordeaux Mountain and Reef Bay. No villas, but the small VIERS is in the valley onshore, NPS moorings

- Salt Pond - excellent snorkeling/diving, Cafe Concordia is walkable up a hill, Rams Head is a great hike, NPS moorings

- Hansen Bay in Coral Bay - excellent snorkeling, campground/day beach onshore, anchoring, usually a couple of cruisers anchored, you can dinghy to Vie's Beach to access her snack bar

- Hurricane Hole - free day moorings, great mangrove snorkeling in Princess Bay, one of three inner bays with moorings

- Coral Bay Harbor - funky .alt scene with liveaboards, dinghy dock at Skinny Legs, Indigo Grill across the street from Skinny's, longer walkable (1 mile flat) or dinghy to shallow grassy area with no dock in front of Cocoloba Center - Caribbean Oasis, Triple B breakfast, Aqua Bistro, Dolphin Market, Skipper's Brit Pub, the harbor is mangrovey with clay/mud bottom that sticks anchors like glue, odor from mangroves closer in, we won't get in the water here

- Leinster Bay/Waterlemon Cay - excellent snorkeling/diving, Johnny Horn trail hike to Brown Bay/Coral Bay (awesome), walk/dinghy to Annaberg Plantation, NPS moorings (inner moorings do not have cell signal, outer moorings have week signal)

- Frank Bay/Maho Bay - Beautiful large mooring field with two large flat beaches. Maha Bay is a top 10 worldwide beach for us, excellent snorkeling, beaches are busy during the day, but empty in the morning and late afternoon

- Trunk Bay, Cinnamon Bay , Hawksnest Bay - Beautiful beaches, but moorings are more exposed, good day mooring. The concessions are in transition from Caneel Bay operations to a new vendor. The restaurant at Cinnamon Bay may be a decent option. Trunk Bay has a snack bar with frozen drinks and burgers/dogs.

- Caneel Bay - very rolly in a monohull with ferries running from 6AM to 2AM, easy dinghy access downwind (wet coming back) to Cruz Bay with 20+ walkable restaurants and bars, we prefer to play here for early happy hour/late lunch and then move to Maho Bay for the night. Caneel Bay has good sushi at lunch and Zozo's is very popular for dinner, need to use a stern anchor if you use their dock. Caneel Bay is not friendly to folks who want to leave their dinghy their and go to Cruz Bay. Salomon Bay and Honeymoon Bay have great beaches, but many St. Thomas day boats bring trips over.

- Christmas Cove - not St. John, between St. John and St. Thomas at Great St. James island, very nice anchorage with free moorings (poorly maintained) and anchoring allowed, excellent snorkeling, Pizza Pi pizza boat is very good.

Cheers, RickG