Fantastic Flotilla Cruise in the Windward Islands

Leg 1 – St. Lucia to Grenada – February 1-9, 2019

Leg 2 – Grenada to St. Lucia – February 9-17, 2019

Get Away Next Winter and Sail the Windward Islands of the Caribbean

Each of these Colgate Sailing Adventure Flotilla Cruises are special in their own way, with open water passages, and diverse islands and anchorages to explore. Winter winds are usually 10-25 knots from the northeast, providing the kind of flotilla cruise sailing those of us who live on lakes and calm coasts love. With warm Caribbean temperatures, open water passages and short hops you get lots of sailing time in. When cruising south, you are usually on a beam reach. On northward passages, you will likely experience lively closehauled or close reach sailing. You will board the boats at 6:00 p.m. on the first day and you will be off the boats by 11:00 a.m. on the final day.

Choose a One-Way Trip or Sign Up for Both Legs and Truly Get Away

When we did this Caribbean islands cruise years ago, at least half of the group opted for all 18 days under sail. This time around, sailing the Caribbean islands will be just as spectacular and the discount for signing up for both legs even more enticing. See rates on sailing the Windward Islands below.

About St. Lucia

St. Lucia, where we start the first leg of this cruise and end the second leg, is known as one of the jewels of the Windward Islands. While sailing in St. Lucia, you’ll see a gorgeous landscape dotted with banana plantations. Beautiful harbors and picturesque villages beckon cruising sailors from around the world. Volcanic forested peaks, home to many tropical birds, are covered with flora like giant ferns and wild orchards. A must stop is the pair of dramatically tapered mountains called the Pitons which rise out of the sea on St. Lucia’s west coast. Sailing in St. Lucia will be an unforgettable experience!

About Grenada

Grenada, where we end the first leg start the second leg, is known as “The Spice Island of the Caribbean.” For centuries it has been a major source of nutmeg, cloves, ginger, cinnamon and cocoa. Grenada’s mountainous terrain is abundant with fragrant plants and rare tropical flowers, dotted with crater lakes and bordered by white and black and beaches. Its bustling Market Square, historic forts, spice plantations, rum distilleries, colorful coral gardens and beautiful waterfalls in the lush rain forest are just some of the sites to visit on your Grenada sailing trip.

Where Whales, Flying Fish and Dolphins Play


As you sail you just might see whales breach, are certain to catch flying fish as they skirt wave crests. and rush for your cameras as dolphins play in your wake. Each day takes you to a different, fascinating harbor on a fleet of four Moorings and Sunsail catamarans, guided by cruise leaders Nate and Heather Atwater. Exact itineraries are never set in stone, but below is the suggested itinerary that was followed by Steve and Doris Colgate when they lead two Caribbean islands cruises some time ago.
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Where You Will Sail on This Winter Caribbean Odyssey

Below are highlights of the itinerary stops for each of the legs, in no particular order. When you sign up for sailing the Caribbean, you’ll get a cruise book with lots of information on the itineraries for each cruise, always subject to change of course.

Rodney Bay, St. Lucia

Rodney Bay is on the north side of St. Lucia. Once a major British Navy base, it is now a thriving yachting center with a full-service marina, shops and restaurants. If you arrive early enough you might want to explore the Bay’s park with gardens and footpaths marked with plaques, or head to nearby Reduit Beach or Pigeon Island National Park. Board the boats at 6 p.m., then join your cruise leaders and crew mates for a Meet and Greet Party and dinner at one of the local restaurants nearby.

Soufriere and The Pitons

The Pitons, a World Heritage Site, are conical peaks rising more than 2,000 feet from the sea. Just north of Petit Piton (elevation 2,460 feet) is the lovely small town of Soufriere, which shares the name of the nearby dormant volcano, the only one in the world you can drive a car right inside! Soufriere’s charming Creole-style buildings are decorated with gingerbread trim and old-world balconies. Attractions include Sulfur Springs, the volcanic-heated waters of Diamond Baths and its tropical gardens, Maho waterfalls, and the Jalousie Plantation. Join a guided hiking tour in the rain forest near Morne Fond St. Jacques. Climb to the top of Gros Piton (2.619 feet) for an incredible view. In addition to sailing the Caribbean, you have the opportunity to snorkel along beautiful reefs. In the evening, dine aboard or enjoy one of the many restaurants along the shore and in town.

Admiralty Bay, Bequia

The only settlement on the island, Port Elizabeth in Admiralty Bay, is on the west side of the island, where you will find a variety of shops, boutiques, food markets, a bookstore, and lots of bars and restaurants. Bequia has a long tradition of fishing and boatbuilding. Whaling from open sailboats still happens occasionally by special agreement with the International Whaling Commission (maximum four whales per season). There is plenty of room to anchor and moorings are also available. Admiralty Bay is another great place to dine ashore including the Frangipani Hotel for a Caribbean-fare dinner or others listed on the schedule.  Attractions include the Bequia Maritime Museum, Old Hegg Turtle Sanctuary, and the small whaling museum at the home of one of Bequia’s most famous harpooners.

Tobago Cays

There are so many highlights in these five deserted islands, all part of Tobago Cays Marine Park, which also encompasses Mayreau Island. Horseshoe Reef nearly encircles the four main cays, and beyond the reef is Petit Tabac. Pick up a mooring and then set out in the dinghy to look for sea turtles and other fascinating marine life as this is one of the premier snorkeling and diving locales in the entire Windward chain. Dinghy to one of the crystal-clear reefs for amazing snorkeling. No docks are available but you can beach the dinghy for a swim on one of the cays. Perhaps here Heather and Nate will line up a local for a fun beach barbecue. Be prepared to purchase souvenirs as there are many entrepreneurial local boat owners who ply the anchorages selling ice, bread, fresh caught fish, lobsters and of course, t-shirts! Completely undeveloped and uninhabited, the park is a place where time stands still, and stargazing is “balm for the soul,” according to The Moorings website.

Salt Whistle Bay and Saline Bay, Mayreau

Tiny Mayreau is surrounded by crystal clear waters, and bordered by powder-fine sand and lush forests. The fleet will moor in sheltered Salt Whistle Bay, where you’ll find a quaint traditional village. Locals will cook up a lobster barbecue on the beach, and if you want to stretch your legs, head to Salt Pond tucked behind trees bordering the broad sandy beach in Saline Bay.



In 1958 Mustique was sold by its original owners to a wealthy Scottish nobleman, Lord Glenconner, whose grandfather invented bleach. Lord Glenconner bought the island as a present for his wife, a lady-in-waiting to Princess Margaret. For years, the island was an exclusive hideaway for the rich and famous, including Princess Margaret who received a 5-acre peninsula on the island from Lord Glenconner as a wedding present in 1960. Our fleet will moor in Britannia Bay, home of Basil’s Bar, a must stop for yachties where you can sample Basil’s Mustique Whammy and enjoy the Wednesday night Jump Up and Barbecue Night. Basil Charles’s empire consists of his restaurant, a boutique, nearby gourmet shop with fine wines, cheeses and other gourmet treats, and an antique and collectibles store. The island has many more unique shops, a fresh veggie stall next to Basil’s, lots of restaurants including an 18th century sugar mill called the Cotton House Hotel and Restaurant (pricey and exclusive with an exceptional view). To explore the island you can rent golf carts (called mules). Before leaving the next morning, be sure to get fresh croissants, pain au chocolate and fresh baguettes from Sweetie Pie Bakery, Cafe and Boulangerie.

Blue Lagoon, Young Island

Young Island has a variety of good harbors, including one at Young Island Cut at the southern end of St. Vincent. The flotilla will likely head to Blue Lagoon, a well-protected harbor on the southern end of the island. On the main island of St. Vincent are several attractions: At the head of The Mesopotamia Valley sits Montreal Gardens where you can walk along paths lined with fragrant tropical flowers; or visit the Botanical Gardens, the Falls of Baleine, Fort Charlotte and the amazing 3,000’ Soufriere volcano. Yes, it’s a bit of a hike, but well worth the effort if there is time.

Wallilabou Bay, St Vincent

This was the setting for Pirates of the Caribbean with Johnny Depp in 2003 and we hear the lastest version 5! It’s a popular spot for cruisers to see the remains of the original set ashore. Here the fleet may have to work with boat boys, members of the Wallilabou Line Handlers Association – an enterprising group wearing t-shirts and badges denoting their membership. There’s a very nice restaurant and bar ashore, plus water, ice, free showers, internet access, and garbage service. Just up the road you might find a small snack shop and ladies weaving baskets.  To swim, go to the falls about a mile to the left of the anchorage.

Petit Martinque

Grenada’s northernmost island is a great place to go ashore to replenish water, drinks, ice and more. Many residents here make their living building boats, notably plywood speedboats. You can find great snorkeling and exploring at Fota and Petite Dominque which are reached by dinghy. Mopion, known as the world’s smallest island with a structure, is surrounded by reefs, and is a great place to stop for lunch.

Prickly Bay

A popular bay with resorts, restaurants and even a golf club, Prickly Bay is one of the best anchorages with customs and immigration clearance. It is popular! Ashore you can enjoy live steel drum band music at the yacht club’s bar, and if you have time, organize a land tour into the rain forest where you can cool off in one of Grenada’s many waterfalls.

Marigot Bay


This is our last long day of sailing, a great time to reminisce about the week and watch for whales and porpoises along the way. Tucked away at the base of steep, verdant hills on the western coast of St. Lucia is delightful Marigot Bay – a lovely place to unwind before heading back to Rodney Bay. Restaurants here are known for their French cuisine. The new Capella Resort sits on the hillside where the group will enjoy a gala end of cruise dinner. If there’s time, take a sightseeing tour of the surrounding land or head to St. Lucia’s marine park for excellent diving and snorkeling among the numerous shallow reefs near the shore.

St. George’s Bay, Grenada

The Moorings/Sunsail base is in Port Louis Marina in the capital city of Grenada, St. George. It’s colonial buildings ae crowned by orange fish-scale tiles, nestled between multi-colored homes at the forests edge. Narrow streets boast many shops, restaurants and bars. Bay Gardens has over 3000 species of Caribbean plants. The Carenage along the inner harbor is perfect for a scenic waterfront walk. On Saturdays the place to be is in St. George’s Market Square, and the first leg ends here on Saturday!. Fort George, built in 1705, overlooks the harbor to the west and offers spectacular hilltop views.

Dragon Bay

This bay is a nice reach from Port Louis, with amazing snorkeling at Moliniere Point, and an underwater sculpture garden, rumored to be home to a family of black and red sea horses. Government mooring balls are available. The islands palm-fringed black-sand beach is unique.


Tucked away at the base of steep, verdant hills on the western coast of St. Lucia is delightful Marigot Bay – a lovely place to unwind before heading back to Rodney Bay. Restaurants here are known for their French cuisine. The Capella Resort sits on the hillside where you can enjoy a lovely dinner. If there’s time, take a sightseeing tour of the surrounding land or head to St. Lucia’s marine park for excellent diving and snorkeling among the numerous shallow reefs near the shore.

Union Island

After clearing customs and immigration out of Grenada, you can sail across to Union Island which is part of St. Vincent and the Grenadines. Clifton Harbour is where you clear into St. Vincent. The island’s main town, Clifton Harbour is a bustling port full of color and welcoming islanders. Roads and trails offer some of the best hiking and biking in The Grenadines. Enjoy a drink on Happy Island, an island made entirely from conch shells. Union has neat boutiques with clothing, local original art, hand-made jewelry and gifts. Well known for its entertainment and fun restaurants, it also offers superb hiking and biking with great view points at Fort Hill, Ashton, Mt. Campbell and Mt. Taboi. You may want to hire a local guide, familiar with the trails to get to the best view points. Facilities here include the Anchorage Yacht Club, Aquarium and Captain Gourmet Café which all offer free WiFi.


Sunbathing and excellent snorkeling is great around Sandy Island. The town of Hillsborough is Cariacou’s port of clearance, with a tourist office facing the main dock. Built on a glorious beach, the town offers charming seaside dining. A short walk from the docks is a museum featuring an eclectic collection of art and historical artifacts. For local culture, pay a visit to one of the many rum shops and watch local build traditional boats on the beach. Around the corner in Tyrrel Bay is an excellent deep, well protected anchorage. A mangrove swamp, protected by the fisheries department is well worth a visit by dinghy. There is also good hiking including a walk up Chapeau Carre. Businesses and restaurants line the waterfront. Oysters, lobster (in season), fruits, jewelry and calypso music can be purchased from local boat-men. Free bay-wide WiFi is funded by local businesses, based at Tyrell Bay Yacht Haul Out.

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The Offshore Cruising Club Flotilla Fleet

Sunsail 444 Layout

The flotilla fleet for both legs is four 4-cabin boats, each with spacious decks, a large cockpit for relaxing and dining, big main salon with galley area, four private cabins and two or four heads as shown on the layouts. All yachts have generator-powered A/C, electric winches, plenty of storage, and excellent head room for taller sailors on the cruise.

Sunsail 404 Layout

Each of these comfy catamarans can have up to 8 participants aboard, depending on the number of private and shared cabins assigned to each vessel.

Sunsail 454 Layout

Heather and Nate will set up the crews on each boat based on levels of experience, making sure each boat has at least one sailor with US Sailing Bareboat Cruising Certification who can act as “skipper” and another who will be the primary “navigator” (though all should take part in navigating so you know where you are as you sail from one island and anchorage to another).

Moorings 4800 Layout


Just 15 Cabins Available!

Package Rates for Leg 1, St. Lucia to Grenada or Leg 2, Grenada St. Lucia 

  • Single traveler in a private cabin – $3495
  • Two people traveling together and sharing a cabin – $2795 per person

Loyalty Discount for Qualifying Participants

If you have participated in a Colgate Sailing Adventure Flotilla Cruise in the past two years and/or you are an Offshore Sailing School Graduate with US Sailing Bareboat Cruising Certification you are entitled to a 5% discount on the above rates:

  • Grad single traveler in a private cabin – $3320
  • Two grads sharing cabin, both with certification – $2655 per person

If only one grad sharing cabin qualifies for the loyalty discount, or you have signed up yourself and someone else in private cabins and one of you does not qualify for the discount, the non-grad pays regular price.

Package Rates for Both Legs — Round Trip St. Lucia-Grenada-St. Lucia

Sign up for both legs and cruise to your hearts content for 18 days! You are sure to have way more fun than your buddies back home shoveling snow, and you’ll have the time of your life on your St. Lucia to Grenada sailing trip 10% discount on your total package price, plus the 5% loyalty discount if you qualify (see above for details):

  • Round trip single traveler in a private cabin – $6291
  • Two people traveling together and sharing a cabin – $5031 per person.

Roundtrip Loyalty Discount for qualifying past cruise participants and Offshore Sailing School Graduates:

  • Qualifying grad single traveler in a private cabin – $5976
  • Two grads sharing cabin, both qualifying – $4779 per person

Deposits, Payments and Cancellation Procedures

Full payment is required after October 1, 2018, with an additional $300 boat security deposit per person. No refunds are allowed after September 30, 2018. If you sign up for both legs and decide to cancel one of them, your per person rate will revert back to the single leg package rate without the discount for purchasing both legs. If cancelling one of the legs after September 30, 2018 no refund will be provided for the cancelled leg.

Included in Your Package

  • Your shared or private cabin aboard a Moorings 4800, Sunsail 454, 444 or 404 catamaran – assigned by cruise leaders in advance
  • You board the boats at 6:00 p.m. on the first day and the Welcome reception and orientation will be held that evening. You sleep on board at the marina the first night
  • Provisions for all breakfasts, lunches, snacks and three dinners aboard
  • Ice, water and fuel aboard boat when you start out
  • Commemorative Windward Islands Cruise shirt and cap

Other Costs to Plan For

  • Travel to and from St. Lucia and or Grenada
  • Taxi to and from local airports/base – $25-$90 per person depending on which airport you come into or leave from
  • Mooring fees, probably four to five during cruise, cost shared by crew on each boat – $30-$50 per boat per night
  • Drinks and dinners ashore – dinners around $60 per person plus 10-15% tip
  • Customs fees entering St. Vincent and back into St. Lucia – around $35 per person, overtime fees apply after 4:30 p.m.
  • Boat boys tips when they take your lines (sometimes cannot be avoided) – $5-$20 shared by crew on each boat
  • Park fees – around $10 per person
  • Alcohol and other beverages and provisions bought to share or consume on your own aboard the boat prior to and during the cruise
  • Docking fees – if used, not known at this time, shared by crew on each boat

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Who May Participate

Colgate Sailing Adventures Flotilla Caribbean sailboat cruise vacations are for sailors who enjoy the company of other sailors. All participants should have minimum certification at the Learn to Sail level (or equivalent experience) and experience on boats of at least 26’ in length. You also must be in good health with strength and ability to move about a cruising boat easily underway; able to get into a dinghy from the cruising boat and back onto it without assistance. As part of this flotilla sailing holiday, you must be willing to participate with others aboard – trimming sails, steering, helping with anchoring, docking, picking up moorings, and sharing cooking and cleaning up. Minimum age for participation is 18. More information on how the cruises are run is on this page.

Travel to and From St. Lucia and Grenada

St. Lucia Airports: Hewanorra International Airport (approximately 1.5 hour taxi-ride to base); and George Charles Airport (approximately 30 minute taxi-ride to base). Airlines servicing St. Lucia include Air Canada, British Airways, Delta, US Airways and Virgin Atlantic among others. Hotels listed by The Moorings on their website include Bay Garden Inn & Beach Resort, Beau Rivage Villa, Rex St. Lucia, Coco Palm and Palm Haven.

Grenada Airport: Maurice Bishop International Airport is located at the southern tip of Grenada, 5 miles from St. George’s, served by direct and indirect flights from the United States, Canada and London. Direct flights from the U.S. are via Delta, American and Virgin Atlantic Airways. There are many hotels in St. George’s including Allamanda Beach Resort & Spa, Coyaba Beach Resort Grenada Grand Beach Resort & Convention Centre, Spice Island Beach Resort, and True Blue Resort (in Grand Anse).

The Moorings Travel Desk, 866-649-2003 has extensive experience booking flights for charterers to this destination. Call them.

Photo Credits: Most of the photos on from The Moorings and Sunsail websites. Some were taken by Steve and Doris Colgate when sailing the Windward Islands several years ago.