We sailed a one way from St. Martin to BVIs May 2014. We sailed 6 days around St. Martin and area, then overnight to BVIs for 7 days. We rented a cat from Sunsail/Moorings and stayed at Captain Olivers.

My suggestions as follows:
IF you feel comfortable driving have a rental car company meet you at SXM with a car. We used Golfe Car Rentals. Very friendly company, nice cars etc. 2 persons from Golfe met us outside departures. They gave us the car then they drove in their car to Oyster Pond so that we would follow them. You drive right past the Grande Marche so we knew where it was for provisioning the following day. I requested Golfe to pick up the car at Oyster Pond in which they did. Talk about convenient!!

Regarding delicious meal on Friday night, as others mentioned the Dinghy Dock is bar/pub food. If you arrive late and are tired, this is a good option. Another is Mama Pizza that serves both pizza and Italian dishes within walking distance from Captain Olivers. Very nice Italian, casual and not too expensive. They take cash only. If you want a foodie type dinner, then I suggest driving to Grande Case or thereabouts. We had 2 wonderful meals at Sol E Luna (on the way to Grande Case). A reservation is definitely recommended.

Regarding sailing itinerary. We spent our first night on Tintamarre, beautiful uninhabited island for exploring, swimming and simply enjoying nature. Caveat our trip was based in May, I haven’t looked at wind patterns and exposure for January so you will need to check for optimal anchorages and also be aware of north swell.

After Tintamarre we sailed to Grande Case and anchored overnight. Enjoyed exploring the beach, beach bars and dined on lobster at Shambala. The following morning we sailed to Marigot Bay to check out before we heading to Anguilla. Found a little place to have coffee and breakfast crepes – La Vie En Rose. Then while gathering a few more provisions found a wonderful Boulangerie-Patisserie in which to purchase amazing baguettes/sandwiches to eat underway.

Sailed to Anguilla for a 2 night stay. It is expensive to stay in Anguilla, if I recall correctly is was $450 EC to stay 2 nights including permit to visit the outer islands. In hindsight though we should have stayed one more night and rented a car in which to tour the island as it is stunningly beautiful. We dined at Elvis Beach Bar and a tapas restaurant in the area, but I cannot recall the name. Also I recommend Blanshards or Blandshards Beach Shack if you are able to go to Meads Bay.

Day 2 in Anguilla we sailed to the out 2 of the outer islands for a day trip as overnight anchoring is not permitted; Sandy Island and Dog Island. Dog Island is a beautiful uninhabited island that we had to ourselves. It has a beautiful stretch of brilliant white sand that merges into the stunning turquoise water. Probably one of the most beautiful beaches I have been to in my life. It is approximately 10 nm from Road Bay to you need to give yourselves ample time to get there and back to Road Bay for the evening. We did not go to Prickly Pear Cays, which I would like to see – next time!

When we checked into Anguilla we also checked out at the same time as we were only staying 2 nights. Up early the day we were departing, we headed for St. Barts. We were a little nervous about finding a mooring in Gustavia and took the first one we found in Anse Du Corossoil. It was a long dinghy ride in to check in but at least we found a mooring. We checked in and out at the same time as we were only staying 2 nights. Our biggest mistake about arriving in St. Barts was that it was a Sunday. Practically everything was closed. We found a little bar in which to have a cold drink, but were out of luck for anything else.
If you feel like splurging on a spectacular lunch and magnificent people watching take a cab to La Plage Restaurant in Tom Beach Hotel. What an experience. If you are lucky on the way back to Gustavia you may be able to watch a plane land at the St. Barts airport. Quite the feat and quite entertaining!

From Gustavia we headed to Il Forchue, our last stop in the Leewards. Nice secluded spot/marine park. This island was our staging point before going heading out to the BVIs on an overnight sail. We barbequed lunch then had naps until it was time to set off for the BVIs, departing about 6:30 pm.

All in all a fabulous vacation and are planning on going back in 2017, perhaps staying in the Leewards next time and sailing to Barbuda and back. Too many places to see and too little time. Hope this helps in your trip planning!!!