I highly recommend that you do a one-way starting in St. Vincent for a 10 day itinerary. They will deliver the boat to St. Vincent for a fee. The most we have paid was $700 but that was not for a cat. This is a much more enjoyable trip (you won't be beating your brains out going into the wind for half your trip) and you get to see more. Bequia is an island that really is not to be missed...it is beautiful, has tons of cute local bars and a ton of history. The people are amazing!

Leaving from St. Vincent my suggestions are:

1st night: Bequia (I would do 2 nights here but that is how much I love this island): We have had some of the best lobster pizza ever at Mac's Pizzeria. The Whalebone is a fun place to check out for the whalebone decorations. The Frangipani has been there since I was a child (it was my parent's favorite place to go, so we went there a lot) so we like to go for a drink here. Last time there we went to Jack's Beach Bar because my oldest son's name is Jack. Might be a good place to hang during the day because of the beach. We went for happy hour.

2nd night: Mayreau, Salt Whistle Bay: Do the lobster beach BBQ here as it is much cheaper here than in the Tobago Cays. Make sure to barter. We paid $400 EC for 5 of us in 2016. Also check out the cute town by walking up the hill. Beautiful church at the top of the hill that has gorgeous views to the Tobago Cays and then reward yourself with a beverage and a swim in the pool at Dennis' Hideaway.

3rd night: Tobago Cays: Such an amazing place to just explore by dinghy. Tons of turtles to snorkel with off of Baradel. Great beaches everywhere. I would stay here for 2 days too if you can do it.

4th night: Petit St. Vincent: Goaties beach bar is a favorite. Gorgeous beach.

5th night: Clifton Harbor, Union: check out of St. Vincent and the Grenadines here. Cool bar is Happy Island. We really liked Sparrow's Beach Club. They have a shuttle that will pick you up in Clifton and take you to their place on the Northeast side of the island. Beautiful beach with the bar/restaurant right on the beach.

6th day: Sandy Island, Carriacou: Clear in at Hillsborough first and then hang for the day at Sandy Island.
6th night: L'Esterre Bay: There are several cute beach bars here.

7th night: Tyrrel Bay, Carriacou: We really liked the Lazy Turtle here. Just don't eat the manchineel apples that are abundant on the beach here. They are highly poisonous. I would actually add a day in Bequia instead of doing Tyrrel but thought I should leave it in as an option.

8th night: St. Georges, Grenada: We like to leave a couple days at the end of the trip to explore Grenada. Port Louis marina is a great place to be based out of. Easy to get places and they have a very nice facility along with a pool. St. Georges is not to be missed. I always make my kids walk up to, St. Mary's church which used to house the school I attended as a kid. Last trip we rented a car and drove to Annandale Falls (chose these because it was easy to hike into right off the road and we only had the car for the day). We also toured the Chocolate Factory and River Antoine Rum Factory (which was really cool) and then drove back along the east coast for a totally different view of the island. We wanted to end the day at Westerhall Estate for another tour of a rum factory but they were closed by the time we got there. I would suggest dropping the chocolate factory in favor of another rum tour.

If you do end up leaving out of Grenada there is a great grocery store (they even had veggie burgers) right by the marina. I think it is a Foodland. You can even take the dinghy to the little dock right by the store and have someone wait there for you.

Things are very different in this part of the Caribbean compared to the BVI's where we also frequent. The sails are longer, the seas are usually a bit bigger, wind stronger and you kind of have to act like less of a tourist. Absolutely lock your dinghy at all times. Take it out of the water at night and lock it. Make sure the outboard motor is locked as well as the gas can. Try to take as few valuables as possible. That being said, you will need a bit more cash as there are places that don't take credit cards. Whenever you leave your boat, lock it up tight (as in hatches and portholes as well as the cabin doors). When in town just be aware of your surroundings and don't leave bags unattended. This is not to scare but just to make you aware. The locals are amazing people and so kind and helpful. Just a few bad apples cause unnecessary reputations. The boat boys can be a bit annoying but also super helpful, especially if you are in the Tobago Cays and realize you don't have enough ice! LOL! I recommend being polite and telling them no thank you if you don't want them to bother you.

Enjoy! We are going back this December/January and are getting our boat out of St. Lucia, which is a first for our crew and I haven't done this sail since I was a kid so I'll have lots of questions for the forum!