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Tobago was one of our favorite stops in the whole EC. We spent about 10 days there after spending the bulk of hurricane season 07 in Grenada. Very few cruisers make it there. All the anchorages are exposed to the north which isn't really a problem in the summer months when you don't have to worry about northerly swells. But this is no place to be if a storm comes through, so you'll need a plan to either run back to Grenada or down to Trinidad if the weather turns ugly. You can supposedly anchor in Bon Accord Lagoon if a storm threatens and your draft allows entrance.
It has some incredible beaches, a nice rainforest, great snorkeling and diving, cheap and good restaurants, cheap taxis, free diesel (well almost), and cheap provisioning. Groceries here will cost you about half what it does in Grenada. It is a very clean island and the residents seem to take a lot of pride in this, it's a completely different world from Trinidad. The Pigeon Point beach is one of the best in the Caribbean.
There aren't any boat services here though, the anchorages are deep so you'll need a lot of rode, and the clearance procedures are a bit of a hassle. There aren't really any dinghy docks so you'll have to beach the dinghy when going ashore. It's worth the inconveniences to get off the beaten path though.
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