Join Date: Nov 2009
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kleinlax: Your sailing venue out of Oyster Bay in St. Martin includes St. Barts and Anguilla. All of these places are more "civilized" than the BVI when it comes to night life, so you aren't going to find a Foxy's or Bomba's Shack or loud beach bars like in Cane Garden Bay in the BVI. Rather, you are going to find higher end development and higher end shops and restaurants. Your dress will still be casual, but dressier than Foxy's typical clientele (e.g., collared shirt instead of tee shirt) for dinners ashore. During the day, just about anything (in some cases, nothing) goes, particularly on the beaches in the French Islands. You do want to be covered up elsewhere--particularly on Anguilla--as you should in the BVI.
We've chartered out of Oyster Bay twice--the last time was probably about 5 years ago. Here's what you might do on a 7-day charter. Day 1: sail to Anse de Columbier (St. Barts) and anchor for the night. Go ashore and hike over the hill to Anse des Flamands and have dinner on your boat. Day 2: short hop to the anchorage at Gustavia. Check in with the Port Captain and explore Gustavia on foot and maybe get a taxi tour of the island. Get an original "cheeseburger in paradise" for lunch. Have dinner at a nice harborside restaurant. Day 3: Now that you've decompressed, sail about 35 nm to the Road Bay, Anguilla, anchorage. It's an easy reach to the western tip of Anguilla. Check in with customs and immigration. Get a rental car on Day 4 and explore the island and check out the beaches,using your cruising guide for reference. Dinner ashore at the restaurant by the commercial pier or go more upscale at one of the pricey resorts. Day 5: Depart Road Bay at your leisure for the anchorage at Baie Grande Case. Check out the French restaurants and make a reservation for the best food of the trip. The street barbecue scene would be appealing if it weren't for the great French restaurants (I already said that, didn't I?) Day 6: sail to Baie Orientale and spend your last 2 nights at anchor. While there, you can anchor by Ile Pinel for some interesting snorkeling, but you would probably eat aboard if you stay the night there. Plan on a beach day, by anchoring at the southern end of the Bay and bringing your dinghy in at the southern end of the naturist resort. Walk past the resort to the public area with all the beachfront restaurants and rent a chaise and just chill out at a fabulous beach.
It's a short sail to turn you boat in the final morning of your charter.
Note: You will need to pay attention to the instructions for getting in and out of Oyster Bay and also at Baie Orientale. The charter base will likely clue you in on the approach to Baie Orientale and may advise you to skip it if the conditions are too rough. If that's the case, you might explore Marigot instead.