The Windward Islands include (from North to South, not including outer islands) Martinique, St. Lucia, St. Vincent, the Grenadines (Bequia, Mustique, Canouan, Mayreau, Tobago Cays, Union Island, Petit St. Vincent, Petit Martinique, and Carriacou), and Grenada. 

The Windward Islands are able to offer so many different itinerary options. You can spend an entire trip exploring Martinique, or St. Lucia. You could sail the Grenadines for a week (see here for more info), or if you are able to spend more time and link some of them together and sail the chain! Here are a couple sample itineraries...please feel free to request more suggestions.

Martinique, St. Lucia, St. Vincent, Barbados and Grenada now all have international airports for access. 


*This is just a SAMPLE. Any details are subject to weather and options available to the crew and boat at the time. 

Day 1

Arrive to St Lucia, meet your boat, moored in Marigot Bay. Explore the bay by kayak or paddle board, paddle around the spit to jump in for a swim off the beach and a refreshing drink at Doolittles, or head up to Capella Resort for a walk around their beautiful grounds and a nice swim at their beautiful pool with swim up bar and grill.

Day 2

Enjoy a beautiful morning in Marigot Bay hike to the top of the hill to find local spices and a fantastic view of the bay and the boat. Enjoy fresh mangos falling off the trees and return to the boat for a nice sail down to Anse de Pitons where you will anchor beneath the towering Gros and Petit Piton. Marvel at the fact that these spires plunge straight down thousands of feet into the sea. 

Day 3 

An early morning sail will be a perfect beam reach down to Bequia, SVG where you will arrive with plenty of time to anchor off Princess Margaret Beach, check into customs and walk through the small town experiencing the amazing fresh outdoor markets and handcrafts sold. Continue on along to admire the locally made Bequia sloops, and find the boardwalk that lines Admiralty Bay, which reveals more shops, restaurants and bars and ends at the white sandy beach of Princess Margaret Beach. 

Day 4 

Hire a jeep to take a tour of Bequia and its beauty and be sure to check out the Turtle Sanctuary. 

Day 5 

Sail over to Mustique, a private island of the Grenadines owned by the island’s homeowners under the Mustique company. The island has over 100 villas most of which are rented out, usually to some of the most well known celebrities. Mustique also has two hotels, the Cotton House and Firefly, both enjoyable for a stop while exploring the island.

Day 6 

Sail down Mayreau and anchor in Saltwhistle Bay, behind an idyllic stretch of lowlying land of sand and palm trees that looks out over the Tobago Cays. Here you will enjoy fresh breeze and calm waters. Have fun with a game of horseshoes ashore on Mayreau.

Day 7&8

A short jaunt will take you over to the Tobago Cays, where you will find crystal clear turquoise water, and have the opportunity to snorkel with many turtles in what is protected marine park. Have fun meeting the local boat boys that arrive from Union Island to sell fresh fish, t-shirts or fresh baked bread and opt for dinner as a BBQ made by one of them on the beach of Petit Rameau . They set up a fantastic spread with grilled lobster, fish, stewed lambie (conch), plantains, salad, and much more. Embrace island time in the Tobago Cays and spend a couple nights here.

Day 9

Sail down to Petit St. Vincent. Revel in the quiet anchorage, take a walk around Petit St. Vincent if you like, enjoy their beachside restaurant and bar, or take a dinghy out to Mopion, an ever changing shift of sand in shallow waters on which stands a sole palm frond shade. 

Day 10

Sail back to Union Island, explore some of the most colorful market huts in the Caribbean and savor the taste of the Union Island pineapple, the smallest, whitest pineapple with the tastiest flesh. These ladies sell phenomenal produce, spices and other goodies. Visit Janti “Happy” on Happy Island while your Captain clears out of customs. Janti started Happy Island out of a pile of discarded conch shells lying on the reef, and what was once small enough for just a cooler and a shade, over the years it has been added onto and developed into a friendly bar/ getaway that would make Jimmy Buffett jealous. Relax during an afternoon sail to Sandy Island, Carriacou where you will enjoy a spectacular Grenadines sunset.

Day 11

Set off for a long morning sail, stopping at Ile Ronde for a snorkel and lunch and continuing on to marvel at the sights and smells coming off of Grenada’s west coast. Grenada’s lush green mountainous landscape and colorful towns that line the West Coast of the island are enjoyable to admire as you troll your fishing line before pulling into the anchorage off of St. Georges. The old photogenic Carenage and fort stand in front of you in St Georges and around the corner of the high cliff is a relatively new marina. 

Day 12& 13

Spend two days exploring Grenada’s interior. Options include but are not limited to numerous waterfalls and hikes, cocoa plantation/ chocolate factory, the Mona monkeys and Grand Etang, rum factories, Grand Anse, St Georges outdoor market. Grenada is the Caribbean’s Isle of SPICE and boasts one of the largest producers of nutmeg in the world. Be sure to stock up on fresh nutmeg, vanilla, cinnamon, honey, guava jelly.

Day 14

Take your last dip in the sea and say your goodbyes for departure.