Here are a few random thoughts on the route.

Provisioning: St. Maarten is a good place to provision, prices are decent and more selection than you will find at most stops on your way south.

Sailing guides/pilot books: Chris Doyles two cruising guides (Windwards & Leewards) are very informative

Keep in mind the yachting infrastructure is pretty sparse on a lot of the islands, access to water and fuel will not be as convenient as in the BVIs also you will be anchoring or taking a mooring just about all the time.

Security: ALWAYS lock the dingy, fuel tank and outboard when ashore and at night. Also since you are traveling in the low season, I would not feel comfortable being the only boat in an anchorage at night.

(My spelling, especially of French language words is not the best so I will apologize in advance for what are bound to be numerous errors)

St Barths: Anse Colombier is a nice overnight anchorage with decent snorkeling. Gustav is a beautiful town, although quite expensive.

Estatia, Saba, Monserate: Never been to these islands so can’t comment.

Heading south you will probably want to choose between Antigua/Barbuda or St. Kitts/Nevis

Antigua: Big yachting community, good nightlife, good beaches

St. Kitts: Haven’t spent much time there, but there are some nice beaches and history related sites.

Nevis: A good stop for a couple nights, this would be my choice between the above. You can rent a car and drive around the island without any problems, they have a Heritage Trail and the stops are identified by signs along the road. Some of my favorite things: stopping at the abandoned sugar plantations, lunch or afternoon tea at The Golden Rock Inn, they also have walking trails where you will probably see wild monkeys, Qualie (pronounced wally) beach is nice for swimming and hanging out, free beach chairs and the prices for lunch at the restaurant are reasonable. Pinneys Beach, fun spot, as Fred warned be careful of the Killer Bees, If you are there on a weekend try the goat waters, the local bar at the ferry dock makes a good one, there is a hot sulfer spring within walking distance of Charletown Nevis also has a large sport fishing fleet if you enjoy that.

You will have a long overnight sail to Guadelope, as Mike has said the Cousteau Park is a great stop. There are two rocks/small islands just offshore with very good snorkeling, but mind the current, it can be quite swift at times. Some nice restaurants, shops and an ice cream stand ashore.

The Saintes are very beautiful but you can see it all in a day or two. A nice beach on the windward side of the island, Plague De Pompierre, it’s an easy walk over the hill from towm, as you approach it there are some snack stands just outside the entrance, the greenish blue one on the right is my favorite. Coconuts in the main town has free wifi, they usually leave it on when they are closed, the password was coconuts last time I was there. In the morning there are women selling some great snacks along the main road, crab in a puff pastry for example. The Doyle guide will point you to some nice snorkeling spots around the harbor. There is also a pizza shop near the dingy dock that had some really good and different pizzas, curry chicken pizza anyone?

Dominica: There’s a good reason it’s called the nature island, absolutely beautiful. We usually spend three nights here to be able to enjoy some great hiking and nature. In Portsmouth take a mooring from PAYS, they provide night time security patrols in the mooring field. The river tour is a nice quite time, a local guide will row you up the river to a bar in the bush. Syndicate Falls is up that way, I haven’t been there yet. Big Papas is a good place for lunch or dinner. South of Roseau you can get a mooring from Seacat, his number is in the Doyle guide. If you need to top up your water tank let him know and he will run a hose out from his house. He can also take you on hikes to Victoria Falls (a nice hike) and Boiling Lake (only for the very fit). The buses run right past his house and you can take one to Champagne Reef or Scots Head (my recommendation for good snorkeling) or into town. Trafalgar Falls and the adjacent hot spring fed stream next to it are not to be missed. You can take a bus from town to get there. There is a shop across from where the buses to Petit Savaun park that sells homemade rum straight out of the barrel, just ask around town. The market in Roseau is small but has some good fruits and veg depending on what is in season. The Ruins Bar, right near the cruise ship port has food and drinks and an interesting assortment of bush teas in the backroom. I haven’t tried the zip line or river rafting yet so can’t comment.

Martinique: I have only stopped there a couple times, I don’t care for Fort De France at all, a large city with elevated highways. The old capital that was wiped out in the volcano, St. Pierre (I think) is a nice spot, they have a decent market right near the dock. We stopped at a restaurant mentioned in the guide, can’t remember the name but it is one or two streets from the waterfront, the food was horrid. There is another restaurant right on the water that was doing a land office business, some kind of crayfish special that night, I would try there if I ever went back. You can rent a car and drive around the island in a day, maybe climb the volcano as you can drive most of the way up. On the Atlantic side of the island there was a popular beach, the sandbar extended far offshore and there were a lot of watersports available there.

Now we’re getting to my neck of the woods.

St. Lucia: I would have to strongly disagree that St. Lucia is not yacht friendly. They have the best yachting infrastructure between Antigua and Grenada and the government is highly committed to promoting yacht based tourism. As examples the Minister of Tourism attends the ARC award ceremony every year and makes it clear they realize the huge economic impact that the yachting community brings to the island. There are satellite C&I offices located in Rodney Bay, Marigot Bay and Soufriere; these exist for the convenience of visitors that travel by yacht. There is even a dingy dock for the malls (with supermarkets) in Rodney Bay. Also when you arrive by airplane you are allowed 30 days on the island, if you arrive by yacht you can stay for 6 months.
Rodney Bay: We like to anchor in the lee of Pigeon Island to avoid the swells when they run from the north. Some boats also anchor in the lagoon, but it is now controlled by the IGY marina; and of course you could take a slip there if you like. The Friday night jump up in Gros Islet is not to be missed. There is a dock right at the end of the street, but for peace of mind I would leave the dingy at the marina dock and take a bus to the party. Pigeon Island has a small beach, some snorkeling, hiking and a nice restaurant. Rodney Bay itself has a wide range of bars and restaurants of all price ranges. This is also a good stop to top up your provisions at either one of the supermarkets in Rodney Bay. You can get a bus to Casteries from there also and go to the market which is quite large and well stocked. My favorite bars in Rodney Bay: The Hairy Clam, Rehab, Delerious, Gravity, Happy Day Bar, Ocean Club, Boardwalk Bar (Last two are in the marina; Favorite restaurants: Fire Grill, Triangle Pub, Rituals, The Lime, The Jerk Pit (food truck), Bread Basket in the marina, Roti Restaurant and Grill across from the marina, Golden Taste in Gros Islet.
Marigot Bay: A nice place to spend the night, quite and not much to do, but well protected from the sea. You can tie up free at Chateau Mygo if you have dinner at the restaurant, probably the most reasonably priced place in the bay. They have decent pizzas but the local dishes are the best. The bar is a fun place to meet other sailors, ex pats and locals.
Soufriere: Anchor in the shadow of Petit Piton, you will smell the sulfur in the wind blowing from the volcano. Harmony Beach Restaurant is right there, call and order ahead of time and arrange for Benny Jr. to pick you up in his water taxi (free). Or you can dingy to town and try one of the local restaurants there. During the day it is possible to walk form the anchorage into town via the coast raod, but I would not attempt it in anything but broad daylight for safety reasons. (you pass through a very poor part of town). The botanical Gardens are a short walk from town and you can get a taxi to go to the waterfall or sulfur springs. The hike up Gros Piton isn’t too bad nature service guides are available (and required) at the trail head the cost is $30 US per person, Petit Piton is much more of a serious hike and should only be attempted by the fit, if you decide to go I can recommend Boomer, just ask for him around town, tell him “his Dad” recommended him.
For me a visit to Soufriere isn’t complete without lunch or dinner at Archies. The menu is chicken, fish or chicken roti, inquire what the fish is and how each is prepared (will be either curry or stewed in Creole sauce). On wed, fri & sat there is a woman selling grilled beef kidneys on the main road, one of my favorite snack foods. The beach at the Humingbird is nice as is the one at the anchorage. The fishermans co-op has a farmers market on Saturdays and everyday except Sunday there will be woman around the town square selling fruit and veg. Sandys Bar is popular with locals on the weekends and the bar by the bridge sometimes has country music jamborees (very popular in St. Lucia). There was a robbery of a bus load of cruise ship tourist at the Botanical Gardens earlier this year, but they were in jail within a few days of the incident due to tips the police received from locals in the area.

Other things to do in St. Lucia: Fish Friday in Anse La Rey, Saturday seafood festival in Dennery, hiking trails all over the island, check the gov’t website for online guide books.

St. Vincent: Try the Captain Bligh rum, one of my all-time favorites. I prefer Cumberland Bay over Wallilabou, more restaurants, less vendors, just a nicer feel to the place. You can dingy over to Wallibalou (or take the bus) to clear in with customs, they are only opened for a short time in the afternoon so check the guidebook or ask around for the schedule. Mama Elma will buy and cook a goat for you if you arrange it the day before, stop at Josephs for some drinks, Mojitos is also a good place for dinner. Things to do, hike the volcano, visit Dark View Falls, hike some of the nature trails on the island, Botantical Gardens in Kingstown, you could try the government website for more ideas they have an online brochure Hiking SVG. We have using Mama Elma to arrange our excursions including guide and transportation. If you are there 3 days after the new moon try to get some tri-tri cakes from old Joseph. The local buses run right past the visitors center, but be aware it is a long crowded ride to Kingstown from there.
Young Island Cut: Take a mooring, the current runs swift through there. Good snorkeling on the back side of Young Island and a good observation point up the top of the small island next to it. Some nice bars along the boardwalk, The French Veranda is probably the nicest they have good coffee there. You can get a bus to Kingstown from there $1.50 EC per person each way. The market in town is very well stocked, there are some small local restaurants where you can get lunch for a couple dollars. There is a big fish market nearby close to the bus terminal, just ask around.

Bequia: We like to anchor just off the Frangipani, most boats that have problems here seemed to have been anchored in Lower Bay. Lots of bars and restaurants to choose from along the waterfront and in town. Knights Market is a small grocery store with a decent selection and the booze is reasonably priced. There is also Doris’ Store for more gourmet type offerings. Things to do: Sergent Brothers Museum and model boat shop, walk over to Fort Jefferson for some great photos, take a taxi tour around the island or rent scooters for the day, hike over to Friendship Bay and have lunch or dinner at the Bequia Beach Hotel. Jacks bar and the adjacent beach are a nice spot to spend the afternoon, their beach BBQ night with live music is a lot of fun.

Petit Nevis: Small uninhabited island with an abandoned whaling station, the active station is just off Friendship Bay. An easy hike up the hill for great photos of the anchorage, many cairns placed by previous visitors. There is also a small beach on the windward side of the island that you can’t see from the anchorage or the top of the hill (Kim and I have nicknamed it Shaggers Beach for reasons I won’t go into).

Mystique: I could do without stopping here, beaches aren’t any better than anywhere else and the prices in the few bars and restaurants are more in line with a large US or European city. They occasionally close the island to visitors depending on what VIP is on island.

Canouan: The anchorage can be rolly here. You can walk across the island to a nice tree lined beach on the other side, mind the machinell trees, they don’t paint them here.

Tobago Cays: Beautiful, uninhabited, great snorkeling, but mind the currents on the reef. Don’t miss out on the grilled lobster on the beach (if they are in season) we always use Jean Claude, AKA Mr. Fabulous. He can also do a fish cookup if lobsters aren’t in season. We like to eat on shore and time it to coincide with the sunset.

Union Island: Cliffton is the main anchorage, the Anchoraqge Yacht Club has good wifi, Bouganvilla is good for dinner. There is a bank and small fruit market in town. They also have a large trash bin located near the local dock for garbage disposal. There are sometimes dodgy type guys hanging around the public dock that can be quite bothersome, we always use the restaurants dock when we stop there.
Cumberland Bay is a very nice quite anchorage around the backside of the island. Sheckies is good for a drink, but they are a little high priced, 15 EC for a rum punch. From there you can hike over the hill to Ashton, some nice vantage points for photos along the roadway.

Mayreau: Salt Whistle Bay is a nice stop, it can get crowed and the holding can be questionable in spots. Follow previous advice for things to do.

Petit St. Vincent: Private Island, but you can use the dingy dock, visit Goaties the beach bar and use the adjacent beach. The iced cappuchino at Goaties is very nice, the drinks are pricier than other islands, more in line with Mystique.

Petit Martinque: You can dingy over from PSV, not a lot to do there but the people are friendly and you can hike around the island and to the top of the mountain in about 1 ½- 2 hrs. You can also pickup fuel at the main dock.

Carriacou: There is a customs office at the dock in Hillsborough, have all your paperwork in order. The beach, either side of the dock is a good place to look for seaglass if that interests you. In town, there are a few small grocery stores, and an assortment of local bars and restaurants. Lauriena II, just down from Ade’s has good meals cheap. There is a small restaurant across from Ade’s that is good for breakfast, you can get full American, English or Continental breakfast, and brewed coffee. Some of my favorite spots are Petit Carenage in Windward, follow the “Mangrove Trail” (sign on a tree) to a beautiful secluded beach. Anse La Roche is also nice, but requires a bit of a hike you can take the local bus to Bogles and start from there. There is a trail through the mangroves to L’Estere (Paradise Beach) that takes about 45 minutes to walk. At Paradise Beach, Off the Hook is a fun bar, as is the Hardwood Bar at the other end of the beach. Sandy Island is a nice stop, beautiful white sand beach, good snorkeling along the shore; they have installed mooring balls just off the island. Tyrell Bay is a popular anchorage, try the fresh mangrove oysters from a local boat boy if you stop there.

Grenada: My favorite island in the chain. There is a large anchorage just outside of the lagoon. The Port Louis Marina and Grenada Yacht Club offer dockage also. Things to do: Grand Anse Beach, St. Georges, Grand E’Tang Park (arrive early with unpeeled bananas cut in half crosswise to feed the wild monkeys), Seven Sisters Falls, Annandale Falls, spice, cocoa and nutmeg processing facilities around the island, rum distilleries for tours, stop at Creole Shack in St. Georges for a cheap local lunch or dinner. The bus service on the island is very good and you can get anywhere by bus, just ask the driver if your destination is off route, they will take you for a couple dollars more.