Grenadines: Best Sail Itinerary

From the April/May 2010 issue of ISLANDS magazine, available now in the ISLANDS Store.

Day 1: Start Relaxing on Canouan
The Moorings cruise of the Grenadines departs from Canouan. So first I flew to Barbados (you can stay overnight at the Crane, if you like). Then I took a ferry to Canouan, famous for Raffles Canouan and its spa with glass-floor treatment rooms set over the water. Linger there.

Day 2: Set Sail for Bequia
Board the Moorings cruise, where Capt. Simon Goodhead and fiancée/first mate Louise Cole take care of everything. First stop: Bequia, perhaps the Grenadines most socially vibrant island. There are enough bars along the waterfront of Port Elizabeth for a proper pub crawl; the bustling fruit market is a must-shop — and a must-eat is the lobster pizza at Mac's.

Day 3: Drink Up Mustique
The sailing cruise continues farther south to Mustique and legendary ­Basil's Bar. I'm still dreaming about the frozen Mustique drinks. But after, you'll find yourself drawn to Macaroni Beach, with a long stretch of white sand. It's walkable, but you're better off buying a ride from one of the taxi drivers by the dock. Climb the hillside at the south end of the beach for a bird's-eye view. If you want to spend the night, Firefly is a great treehouse-style ­boutique hotel on the more lively west side.

Day 4: Eat Up the Tobago Cays
Upon arrival here, there's a good chance that Romeo, a boat boy, will show you the fresh lobster you'll have for dinner that night. You can be sure to work up an appetite by snorkeling along the reef and in the protected sea-turtle lagoon.

Day 5: Get to Mopion Early
Here's the thing about Mopion — it's almost too awesome. Essentially a hump of pure white sand in the sea, it has just one permanent thatched umbrella that's set near its highest point. If you want Mopion to yourself, make sure the captain plans to arrive just after sunrise. It's your only chance. Take it.

Day 6: Settle into Union Island
As you enter Clifton Harbor, Janti's Happy Island greets you. It looks like a floating patio. You should stop by for a beer. On Union, look for some hand-painted signs on the main road poking out of the bushes just past Evergreen Cafe. This is the entrance I found to Costello Paradise, the confederation of bars and art that culminates with the hilltop Pelican Bar and the best happy-hour view in the Grenadines.

Day 7: Swim off Mayreau
With a population of 300, Mayreau barely feels inhabited. Climb to the church at the island's highest point to see the wide-open view. Say goodbye to the Grenadines with a swim in Salt Whistle Bay.