Your post omits the type of boat and time frame, but I can offer these observations from three different trips to the area (2006, 2009 and 2014). Peacefrog is correct – the Phil he is referring to has a great cruising briefing that used to be available on line at Barefoot Yachts. I think it isn’t posted anymore. If you use the Wayback Machine, you could search for an old version of the barefoot website. You should also look for the great but now defunct website The Usual Suspects. A wealth of knowledge. Also check out TTOL http://www.traveltalkonline.com/forums/postlist.php?Cat=0&Board=southcarib The Doyle Guide is terrific also visit his website http://www.doyleguides.com/ for updates. The last time I sailed the area I did a one way from St. Lucia to Bequia to Mustique to Tobago Cays (Baradel and Jamesby) to Mayreau to Union (Happy Island) to Mopion to Petite Martinique to Carriacou to Grenada. In previous charters I departed from the now shuttered Moorings base at Canouan. Best Practices – Always lock the boat completely including all hatches. Always lock your dinghy, engine and fuel tank. I often would hire a local guy hanging out on the dock to watch the dinghy and the boat when we were away for dinner. $10 EC is less than $4 USD. So $15 or $20 EC basically bought a lot of peace of mind. Conditions – generally breezier than the BVI and at least as breezy as the area around Antigua/Barbuda. Wind was Northerly, which means leaving St. Lucia on the 2014 trip I was on a reach or run the entire sail. Usually saw 15 + knots around the islands and more between the islands and down the west side of Grenada. Since you did not ask about St Lucia, I will omit it from this response. St. Vincent – I have never been there – on purpose. Most of the incidents of crime in the area – both petty and more serious – I am aware of have occurred in St. Vincent. I understand that several charter companies have bases in St. Vincent, but my advice is to be cautious about cruising the island. I am reluctant to paint an entire island as a “bad actor” but I always have a co-ed crew and didn’t want the extra worry. I welcome more recent opposing opinions. Consult: https://www.safetyandsecuritynet.com/ Also check the Noonsite website. Bequia – Bequia is one of my favorite places in the world. Admiralty Bay feels like home. You can anchor along Princess Margret Beach but I usually pick up a mooring closer to the dinghy dock and the Belmont Walkway. The fellow who runs the moorings I have used goes by the name “African.” African is usually in the mooring field; he is hard to miss these days as he had really packed on the pounds. If he’s not in the mooring field, one of his assistants will be … African is a competent, straight forward guy who is a mariner. I trust his moorings and he is a good source of information if you need to source a part or get a mechanic, etc. Belmont Walkway has several great spots for drinks and dinner. Further down the way out of town is a night club sort of place with a dinghy dock. In town, good provisioning, nice out of the way beaches on the other side of the island and a turtle nursery. Visit the model boat shops. Hire one of the local kids to clean and watch your dinghy at the town dock. Best way to make sure it doesn’t “drift off” and is “found” with the corresponding request for a $400 US reward (the deductible on your dinghy). Daffodil Marine is great service to re-water. They come alongside. Mustique – If you’re cheap, stay away. The mooring fee is for 3 day minimum. Few restaurants – one secret local bar called Lisa’s which now may be closed or re-opened and called The View. Ask Slick, he is the Harbormaster and a great guy. Macaroni Beach is as nice a big wave, eastern side beach as you’ll find. Basil’s fun to hang out and people watch. There is a reef called Montezuma’s Reef which is near the mooring field and whose buoy is often off station. Coming from the North (Bequia) motor around West Cay and motor to Isle a Quatre. Fall off between Isle a Quatre and Petite Nevis and sail to Mustique on a close reach. Check charts re Montezuma’s Reef but I believe the way I just mentioned causes you to avoid the reef. Firefly is great for a high end crew dinner. The will pick you up and bring you up the hill. Make a reservation. I really like Mustique. It is the antithesis of most places you will see in The Grenadines and it is a fun and beautiful diversion. Take a tour or rent a mule. Canouan – I haven’t been here in a long time. Once American Eagle stopped flying there the Moorings base closed. There is a guy named Iceman who is useful for re-watering. The Tamarind Hotel had a good bar and good wood fired pizza (owners are Italian). Entry to Charlestown Bay is straight forward. My information here is old and possibly out of date. Tobago Cays – Although I am in no way religious, I usually describe the Tobago Cays as “God’s and Walter Bob’s gift to the World.” Tobago Cays consists of 5 islands and two reefs. Study the charts … if approaching from Mustique/Canouan you will turn left at Dry Shingle (its marked), before Catholic Island. I motor sail as I approach the entrance between Petite Rameau and Petite Bateau. You won’t see the range until you are on it. Pass between the two islands, make a right and welcome to paradise. There is now a park charge and moorings available. You can still anchor, I believe. I used to anchor, just south of Baradel Island, but that is now a Turtle Reserve. Tobago Cays is the Headquarters of the International Brotherhood of Boat Vendors. Over the past 15 years, Walter Bobb, aka “Engine,” has convinced the Boat Vendors to cut the crap and actually provide a valuable service. These days a simple “No Thanks” curtails unwanted approaches from the Boat Vendors. I always order a lobster dinner for the entire crew … it is always a highlight of the trip. I am not as up to date on the vendors as some others are, I used to just arrange everything through Walter. Generally, these guys are doing a good job and trying to make a living. Unfortunately, Walter passed away in late 2013 after a mis-diagnosis and short bout with cancer. He was a real giant and one of the reasons the Tobago Cays is a great place to visit. For the entire trip, not just Tobago Cays, make sure when you are getting a price quoted, you are both talking about the SAME CURRENCY – either USD or EC. (You will always get change in EC). I always say to the vendors “I don’t like confusion,” which seems to be a good catch all which means “Hey, I have been here before. I love it here. I know that sometimes there are disagreements between sailors and boat vendors. I don’t want that so let’s work together to know exactly what we are agreeing upon.” Take a dinghy to Jamesby and climb it for the view and to watch the kite surfers. Swim with the Turtles at Baradel. Hire a boat vendor to take you beyond the first reef to Petite Tabac. But bring your own rum since that skinny English bitch burnt all the rum that was already there. Mayreau – Two anchorages. Salt Whistle is the more picturesque but both (Saline Bay is the other) are protected. I find that Salt Whistle can handle about 15 boats, there are often 25 crammed in there. Default to Saline. Robert’s and Dennis’ are both fun places for drinks. Views from the top of the hill are great. Drift diving the Mayreau Gardens on the East side and the wreck by Grand Col Pt. (Be aware of the reef in that area). We used Dive Grenadines – a solid outfit. http://www.grenadinesdive.com/ Union Island – in my mind a “must stop.” In particular, Clifton Harbor. Great for provisioning, getting the feel of a real Caribbean town. Just a fun, authentic place as opposed to Mustique which is fun, but not authentic. I always get a Med Moor spot at the Anchorage YC. They have 24 security so you don’t have to worry about theft. There is a new beach bar/restaurant on the North side of the Island which is getting good word of mouth . I like Lambi’s for dinner. The Bouganvilla is good for breakfast. And of course you need to take the dinghy over to Happy Island. Happy Island is like Café Sport (Peter’s), the IYAC, the Chicken Box, Doug’s Harbor Reef, the White Horse in St. George, etc. If you are a sailor, it is a “Can’t miss.” Check out of Union if you are heading to Carriacou/Grenada. Mopion – I find it to be a pain in the ass to anchor there, but the crew likes it. Petite Martinique – very off the beaten path. Great place to buy booze. Officially part of Grenada, but no place to check in. No one cares. Had to use a stern anchor when there. Only there for an overnight and booze run so I didn’t have a chance to see too much but I had a favorable feeling about the place. Carriacou – my new favorite Caribbean island. I anchored in Hillsborough, but I would anchor in Tyrell Bay. I believe you can clear in in Tyrell. Great restaurants in both places. Make sure you order a shot or two of “Iron.” We dove with Deefer Diving. Outstanding outfit … especially good for the rusty or occasional diver. Really want to stress what a great outfit these guys are. I became a much better diver during my dives with them. The diving itself was phenomenal. http://www.deeferdiving.com/ Favorite bar was a no-name shack on the beach in Tyrell Bay where everyone was sitting around a fire at night on the beach and singing alone with a guitar player. Head also to the north end of the island to see traditional boat building and good hikes. On the sail to Grenada, all the locals give Kick’em Jenny a wide berth. They are serious about it so I decided to follow their lead. You can get updates here: http://uwiseismic.com/General.aspx?id=27 In Grenada, I moored in True Blue Bay at Horizon Charters. Good bar and restaurant in walking distance. Last day motored up to St. George to return the boat to the Moorings. There is a well marked rock/reef in the middle of St. George Harbor … I ran right over it in about 15 feet of water. Just keep it in mind and you won’t feel like a goof as I did ten minutes before I returned the boat. I didn’t hit anything, but I sure felt like an idiot.