Day 1 | Arrive in St.Vincent and Enter the Set of Pirates of the Caribbean

Your Caribbean sailing charter will begin at St. Vincent’s Blue Lagoon. Fully immerse yourself in the culture of Pirates of the Caribbean in these stunning blue waters. St. Vincent is infamous for the start of the Pirates of the Caribbean set, and it will be the beginning of your Grenadines sailing vacation.

Endless exploring awaits you on St. Vincent.

Your first day can be spent making yourself at home on the boat and tasting the local Caribbean seafood. St. Vincent is a picturesque island full of dense jungles and towering volcanic mountains which are surrounded by sky-blue waters.

Day 2 | Set Sail to the Mysterious Mustique Island

Yes, it will be hard to leave the idyllic island life of St. Vincent and its jaw dropping views. Not to worry, the surrounding islands of St. Vincent are equally as stunning (and even better!).

After stocking up on your favorite rum, we’ll sail out of the blue waters of St. Vincent to the crystal waters of the exclusive Mustique, which is known for their “rich and famous” clientele. This sail will take a couple hours, arriving by lunch time to then explore the private island by foot or even horseback if you wish. Snorkeling and beaching go without saying on this tranquil island! And for the evening, let Basil’s Bar take care of your sunset views and local Caribbean music vibes during your vacation.

Day 3 | Get Some Peace and Quiet on Your Charter at the Secluded Beaches of Canouan

On Day 3 of your Grenadines sailing vacation, we’ll continue south towards the old native Arawak settlement of Canouan. This quiet island has a rich maritime history and an extensive barrier reef offering a great platform for water sports. Explore and take in the scenes while keeping an eye out for whales or simply just take in the tranquility on the one of the many secluded white beaches.

Day 4 | Get the Opposite of Peace and Quiet in the Bustling Salt Whistle Bay

A relatively short sail gets you to Mayreau and the idyllic anchorage of Salt Whistle Bay – one of our favorite anchorages and many yachties would also agree. This anchorage is located off Half Moon Bay Beach, which is always bustling and full of life.

Walk to the top of the nearby hill to reach Old Wall Village and enjoy the panoramic views of the Tobago Cays. As the sun goes down, this amazing bay comes alive with local food on the beach and sailors from all over the world sharing beers and swapping stories.

Day 5 & 6 | You Won’t Want to Leave the Water Life on the Reefs of the Tobago Cays

Day 5 & 6 of your Grenadines sailing charter brings you to the Caribbean jewel that is the Tobago Cays. This 1,400 acre shallow water lagoon is surrounded by iles and islets. These cays host one of the most pristine marine environments in the Caribbean Sea.

With amazing scuba diving, snorkeling, crystal clear water with lazy turtles floating by, and sandbars for days – we’d understand if you would want to spend the rest of your time here.

On the outer edges to the east lies World’s End, the world's third largest coral reef where visibility can stretch to over a hundred feet. This also happens to be the spot where Captain Jack Sparrow was marooned with only his rum, and we suggest you do exactly that!

Day 7 | Enjoy the Culture and Bustle of Clifton Harbour, Union Island

We’ll continue sailing south to Union Island. This little hub in the Grenadines offers a vibrant town of endless activities and remarkable anchorage in Clifton Harbour.

Enjoy a meal out and have a walk around this bustling little island. If you want to take it a bit further, put on your hiking boots or your strongest sandals and take a hike up the dramatic 304 meter Mount Taboi. Once you’re finally at the tallest point on Union Island, you can bask in the panoramic views of the Caribbean!

Clifton Harbour features a man-made island called Happy Island. This unique spot hosts a lively bar to sit on the reef with a drink and relish while the kiteboarders put on a show – you won’t want to miss this on your sailing charter! If you’re lucky you can listen to the crazy stories of Janti, the man who built his dream with conch shells on this Happy Island.

Jeremy Tronet, an ex-professional kiteboarder, runs a great kiteboarding school here. If lessons or gear rental is something you wish to try, you won’t find a better place. On the full moon he and Janti host a party at Happy Island, where they kite through the night and sore over the island bonfire! A sure sight you won’t want to miss while sailing in the Grenadines.

Day 8 | Explore the Bays Around Union Island and BBQ with Shark Attack

If you’re interested in scuba diving – Clifton Harbour has plenty of local dive shops we can help set you up with during your charter.

Explore Union Island even more by anchoring in another marvelous anchorage called Chatham Bay. On the leeside of the island, this large well protected anchorage is a place to enjoy boat life and tranquility. For kiteboarders and windsurfers, Frigate Island is also an option with beautiful flat water and less boats.

Despite his name, “Shark Attack” is a friendly local cook on the beach of Chatham Bay. He often comes around to take BBQ orders by boat. If he’s cooking and you sign up – you won't be disappointed!

Day 9 | Sail Back North to Bequia Island and Its Curry Rotis

Today it’s time to about-face and start sailing our way back north to St. Vincent. We’ll stop off at Bequia island just before St. Vincent. With a colonial town overlooked by its fort, still armed with cannons, this spot is a hub for long-term sailors and visitors alike. This is West Indian culture at its finest!

Once tacking your way into the deep-set Admiralty Bay, you’ll arrive at Port Elizabeth. Here you can take a tour of the island enjoying views from Mount Pleasant and the tranquil waters of Friendship Bay.

Bequia is one of the last remaining whaling stations in the world. With strict supervision from the International Whaling Commission, they maintain this culture by using only traditional methods and receiving zero profit. The boats and equipment are all handmade and are almost identical to those in the 1870’s. No whales are killed these days, but they haven’t lost their cultural identity.

Day 10 | Arrive back in St.Vincent & get your last views atop the active Soufriere volcano

On Day 10, we’ll take a leisurely sail back to the Blue Lagoon, where your Grenadines sailing vacation began. Depending on your travel arrangements this could be a good time to explore St. Vincent even more. A taxi ride to the La Soufrière volcano will set you up for an amazing hike and one of the most dramatic views in the region. Another great option is a boat ride to the Falls of Baleine for a cool swim in the mountain waters only accessible from the sea.


This Grenadines sailing charter itinerary is only a sample to what these eastern islands have to offer. Remember that all sailing charters are fully personalized to your schedule, desired activities and destinations. Contact us today to talk about ideas of what your sailing charter could look like in the Caribbean.