Grenadines Sailing Itinerary: A 7-Day Crewed Week from Bequia

Your week begins at Blue Lagoon Marina on St. Vincent's southwest coast, a short transfer from Argyle International. Your professional crew meets you at the slip with cold drinks and a chart briefing that frames the route ahead, walks you through the boat, and gets your gear stowed. The marina sits inside a reef-protected lagoon with a narrow cut to the open Caribbean—a calm staging point before the first sail.

Around mid-morning, lines off for the easy nine-nautical-mile reach south to Bequia. It's the gentlest leg of the week, deliberately short to let everyone find their sea legs without committing to a long passage on day one. The southwest coast of St. Vincent slips by to port, then the open channel to Bequia, then Admiralty Bay opens up on the bow—a deep, well-protected horseshoe with sailboats at anchor scattered across the bay and the pastel buildings of Port Elizabeth wrapped around the waterfront.

Tender ashore late afternoon for a walk along the Belmont Walkway—the seafront promenade that strings together the boutiques, the rum shops, and the open-air bars of Port Elizabeth. Bequia is the friendliest, most authentically Caribbean of the Grenadines: a working sailing community that built schooners by hand on the beach until well into the 1980s, and still has more salt in its character than any other island in the chain. Dinner aboard tonight—your chef leans into the local catch from the morning fish market—or ashore at Mac's Pizzeria up on the bluff for the lobster pizza that has been on the menu for forty years.

After a slow breakfast aboard, your captain clears Admiralty Bay for the sixteen-nautical-mile run southeast to Mustique. The trades fill in by mid-morning, and the boat reaches comfortably across the open channel with Bequia receding behind and Mustique's low green profile growing on the bow. Most of the morning you'll be on the foredeck or at the helm if you want a turn at the wheel.

Your crew picks up a mooring ball in Britannia Bay on Mustique's west coast—the only legal anchorage on the island, run by the Mustique Company that's owned the place since 1958. Mustique is the private island that Princess Margaret put on the map and the Mick Jagger / David Bowie / Mark Knopfler crowd kept there. There are no resorts in the conventional sense; the island is a private estate of about a hundred villas and a few tasteful infrastructure buildings, kept deliberately quiet. Most guests rent a Kawasaki Mule from the company office at the dock and spend the afternoon driving the perimeter road—Macaroni Beach on the Atlantic side, the turtle sanctuary at L'Ansecoy Bay, the dramatic windward cliffs at Endeavor.

Dinner is the headline. Basil's Bar at Britannia Bay—open-air, on stilts over the water, thatched roof, the most famous beach bar in the Caribbean. The bar took a direct hit from Hurricane Beryl in July 2024 and was completely flattened; Mick Jagger personally funded the rebuild, and it reopened in late 2024 better than before. Wednesday is the long-running Jump Up night when the live band plays late and the island's villa renters and yacht crews end up dancing on the same floor. Other nights are quieter, but the food is excellent on any of them. Tender back to the boat under a star-loaded Caribbean sky.

Today is the day the chain really opens up. A twenty-five-mile downwind reach south takes you past Canouan—a stop you'll make on the way back—straight through to Mayreau, the smallest inhabited island in the Grenadines and the one that holds the prettiest single anchorage in the chain. The morning runs to a long, easy reach with the trades steady on the quarter, the islands of the Grenadines stepping past you on the port beam like a postcard sequence.

Salt Whistle Bay sits on Mayreau's northwest tip—a narrow neck of palm-lined sand barely a hundred yards across, with the Caribbean on one side and the open Atlantic on the other. You anchor in the lee side and the boat sits in flat, clear, sand-bottomed water with the palms a stone's throw off the bow. The beach itself is the best swim spot in the chain after the Tobago Cays—shallow for a long way out, no current, and quiet enough that some afternoons you'll have it to yourself.

Lunch on the hook, an afternoon swimming and paddleboarding, and a late tender ashore for a quiet sunset walk on the sand. There's a small village (Old Wall) about a fifteen-minute walk up the hill on the south side of the island if you want to climb up to the church for the view across to the Tobago Cays you'll sail into tomorrow. Dinner aboard tonight, chef-prepared, the boat barely moving on its chain. This is the rest-day before the marquee day.

A short three-mile reposition this morning brings you into the Tobago Cays Marine Park—the centerpiece of the entire Grenadines charter and one of the great in-water experiences anywhere in the Caribbean. Five small uninhabited islands—Petit Rameau, Petit Bateau, Baradal, Petit Tabac, and Jamesby—sit inside a horseshoe-shaped barrier reef that breaks the Atlantic swell on its eastern edge. You anchor inside the reef in fifteen feet of impossibly clear water, with the open ocean a hundred yards behind you and the cays spread across the western half of your view.

The marine park has been a no-take protected area since 2006, and the result is a fish population and a turtle population that have rebuilt to remarkable density. The seagrass beds between Baradal and Petit Bateau are one of the most reliable green sea turtle viewing spots in the Caribbean—you slip into the water from the swim platform, swim a hundred meters, and there will be turtles. Park rules are strict and well-enforced (no chasing, no touching, snorkel from above), which is exactly why the population is healthy. A guided dinghy tour with one of the park's marine rangers makes the morning—they know which patches the turtles are working that week.

Lunch is a beach barbecue on Petit Bateau or Baradal, arranged through one of the local boat boys who will set up a table on the sand, grill the lobster (caught that morning, alive in a basket by the table until you order), pour the rum punch, and clean up afterward. It's the most rewarding meal of the trip and one of the most quintessentially Grenadines experiences—you eat with your feet in the sand, the boat at anchor a hundred meters offshore, the reef breaking white on the horizon.

Afternoon is a tender ride out to Petit Tabac—the small palm-fringed islet on the Atlantic side of the reef where Captain Jack Sparrow gets marooned in the first Pirates of the Caribbean movie. It's the most photographed spit of sand in the eastern Caribbean. Back aboard for sundowners, dinner aboard tonight on the hook, and a night sleeping inside the marine park with the reef breaking white in the dark.

After a slow morning swim off the back of the boat in the Cays, lines off for the short twelve-mile run southwest to Petit St. Vincent. The route threads past Mayreau and into Clifton Harbour on Union Island, where your captain clears outbound paperwork (Union has the only customs office in the southern Grenadines) and you have time ashore for an hour or two.

The reason to stop in Clifton, beyond the paperwork, is Happy Island—a small bar that sits on a man-made island in the middle of the harbor's reef. Janti Ramage built the island himself, by hand, by piling up empty conch shells he salvaged from the local fishermen, then poured a concrete top, then built a thatched bar on it. The whole thing is about the size of a tennis court. The drink is the rum punch, and the experience of sitting on a bar built out of seashells with the boats of Clifton anchored around you is a Grenadines moment that doesn't really exist anywhere else.

By mid-afternoon, your captain points the bow east for the short hop across the channel to Petit St. Vincent and Palm Island, the two southernmost cays in the chain. PSV is a private island resort that allows yacht guests on the beach and at the bar; Palm Island is the same setup. Both are reef-fringed, palm-covered, and quiet—the kind of last-stop anchorage that resets the trip after the social energy of Mustique and the marquee energy of the Cays. Anchor off the leeward side of PSV, swim ashore, walk the beach, and have a sundowner at the resort's beach bar. Dinner aboard tonight, chef-prepared, the boat sitting on the hook with the lights of Carriacou (Grenada) twenty miles south.

The first leg of the homeward run—twenty-five miles north back through the chain to Canouan. With the trades on the quarter, this is a fast, dry reach in the typical December-through-May charter window, and your captain has the option of sailing the rhumb line or angling out for a wider tack to extend the day on the water. Most groups vote for whichever puts the boat at the dock by mid-afternoon.

Canouan is the dark-horse stop on the chain. Smaller than Bequia, quieter than Mustique, and home to the Sandy Lane Yacht Club marina on the south end—one of the most polished megayacht facilities anywhere in the Caribbean and the reason a particular slice of the global ultra-high-net-worth crowd has quietly made Canouan their preferred Grenadines stop. You don't have to engage with that scene to enjoy the island. Glossy Bay, the public beach above the marina, is gorgeous. The Soho House Canouan beach club is open to walk-ins for lunch. There's a Jim Fazio-designed golf course on the high ground above the marina if anyone in the group wants to play. Or you simply anchor in Charlestown Bay on the leeward side, swim, paddleboard, and watch the boats coming in and out of the channel.

Dinner is your call. The marina's restaurants are the safer bet for a polished evening; the village tavernas above Charlestown Bay are the local choice. Either way, the boat is a short tender ride from the dock and a quiet night at anchor.

The longest leg of the homeward run, but it's a downwind-quartering reach with the trades doing most of the work—roughly thirty-two miles back north past Mustique and into Bequia. Your captain picks the start time around when the breeze fills in, and the boat rides home on the quarter for most of the morning. Plenty of time at the helm or on the foredeck if anyone wants it.

Late afternoon, you're back inside Admiralty Bay where the trip started, and the bay does the closing-of-the-loop work for you—the same anchorage, the same view of Port Elizabeth, the same boats moored across the curve, but now you've sailed the chain and you know what every island down the line looks like. There's something quietly satisfying about that.

Tonight is the farewell dinner. Two strong options: ashore at Mac's Pizzeria for the lobster pizza and the view down over the harbor, or aboard with your chef pulling out the stops on a three-course plating on the aft deck. Either is the right call. Tender back late, a nightcap on deck, and the last night at anchor in the Grenadines.

A last slow breakfast aboard at anchor in Admiralty Bay, a final swim off the back of the boat, and a short morning sail back across the channel to Blue Lagoon Marina on St. Vincent—the same nine-mile leg you opened the trip with, in reverse. Your crew handles every logistic from the slip: transfer to Argyle International, onward connections to Barbados or direct flights to Miami and the East Coast, a last photo with the boat in the background. Step off with salt in your hair, a week of the Grenadines behind you, and a pretty good idea of when you're coming back.