The Caribbean via tall ship

By Cindy Shurtleff
This item appears on page 24 of the November 2016 issue.
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The majestic Sagitta. Photo by Cindy Shurtleff

Are you intrigued by cruising the Caribbean on a small ship, visiting small islands and bays that big cruise ships can’t reach, short of arranging your own private charter? It’s possible to do this, and I was delighted to find the Island Windjammers Company, or IWJ (Acworth, GA; 877/772-4549, www.islandwindjammers.com), owner of three tall sailing ships (motorsailers) ranging in capacity from 10 to 30 passengers.

In October 2015, I took a 12-night repositioning voyage on the 120-foot, 24-passenger Sagitta, sailing from St. Lucia to St. Martin, visiting 10 island countries and 11 islands. 

With the exception of one morning and one afternoon’s motor sail, the ship traveled mostly at night, typically anchoring by day in a beautiful sandy bay and occasionally near a town, running dinghies to shore hourly.

The itineraries of most IWJ ships seek out unspoiled, uncommercial islands. It may be different traveling at the height of winter season, but we crossed paths with a cruise ship only once, at Dominica. We mostly had the islands to ourselves. 

My share of a double cabin cost a very reasonable $3,275, which included all meals, snacks and unlimited soft drinks, beer and wine — plus “rum punch hour” — for 12 nights.

Cindy Shurtleff exploring Brimstone Hill Citadel on St. Kitts.

Highlights of my trip were visiting Montserrat, an island that lost its capital city of Plymouth in a devastating volcanic eruption in 1995; swimming the Titou Gorge and hiking through the rainforest on tropical Dominica; touring the compact yet beautiful island of Nevis; snorkeling in the marine park off of St. Barths; hiking to Fort Napoléon in the Îles des Saintes to learn about naval battles from times gone by, and just chatting or lounging on deck or on shore and enjoying the beautiful, warm Caribbean waters.

IWC cruising is very informal. Bare feet and bathing suits are perfectly acceptable on the ship (even at meal times, if you’re so inclined). There are comfortable lounge chairs on deck.

Most of the ships have steep stairs between decks and for getting on and off the dinghy to go ashore, so good mobility is a must. Our group of 21 ranged in age from 46 to near 80. Most were American, but there was one German couple, with a mix of couples, singles and singles without their partners. The convivial atmosphere and close quarters left me feeling like I had made some lifelong friends. 

The staff of 10 couldn’t have been more friendly or helpful.

IWJ offers mostly 6-night itineraries in some very attractive cruising grounds: from Grenada north through the Grenadines; the British Virgin Islands, and out of St. Maarten to the Leeward Islands (St. Kitts, Nevis, St. Barths).

I’ve been to all three areas (the British Virgin Islands nearly 25 years ago) and they’re each very different. My personal favorite, which I visited in fall 2013, is Grenada and the Windward Islands, including Bequia, Union Island and Mayreau, for the charming towns, the conservation marine parks and outstanding snorkeling and diving.

Terre de Haut waterfront on Îles des Saintes, Guadeloupe. Photo by Cindy Shurtleff

My 2013 trip was an independent one. I chartered a catamaran for five of us and hired a captain and a cook. The yacht charter agent Ed Hamilton & Co. (Edgecomb, ME; 800/621-7855, www.ed-hamilton.com) helped me select and book the boat. I’ve used them five or six times and they’re always excellent.

Cruising with Island Windjammers was a delightful way to see beautiful parts of the Caribbean, places typically far too expensive for air-hopping.

CINDY SHURTLEFF

Seattle, WA

Please login or subscribe to ITN to read the entire post.
The majestic Sagitta. Photo by Cindy Shurtleff

Are you intrigued by cruising the Caribbean on a small ship, visiting small islands and bays that big cruise ships can’t reach, short of arranging your own private charter? It’s possible to do this, and I was delighted to find the Island Windjammers Company, or IWJ (Acworth, GA; 877/772-4549, www.islandwindjammers.com), owner of three tall sailing ships (motorsailers) ranging in capacity from 10 to 30 passengers.

In October 2015, I took a 12-night repositioning voyage on the 120-foot, 24-passenger Sagitta, sailing from St. Lucia to St. Martin, visiting 10 island countries and 11 islands. 

With the exception of one morning and one afternoon’s motor sail, the ship traveled mostly at night, typically anchoring by day in a beautiful sandy bay and occasionally near a town, running dinghies to shore hourly.

The itineraries of most IWJ ships seek out unspoiled, uncommercial islands. It may be different traveling at the height of winter season, but we crossed paths with a cruise ship only once, at Dominica. We mostly had the islands to ourselves. 

My share of a double cabin cost a very reasonable $3,275, which included all meals, snacks and unlimited soft drinks, beer and wine — plus “rum punch hour” — for 12 nights.

Cindy Shurtleff exploring Brimstone Hill Citadel on St. Kitts.

Highlights of my trip were visiting Montserrat, an island that lost its capital city of Plymouth in a devastating volcanic eruption in 1995; swimming the Titou Gorge and hiking through the rainforest on tropical Dominica; touring the compact yet beautiful island of Nevis; snorkeling in the marine park off of St. Barths; hiking to Fort Napoléon in the Îles des Saintes to learn about naval battles from times gone by, and just chatting or lounging on deck or on shore and enjoying the beautiful, warm Caribbean waters.

IWC cruising is very informal. Bare feet and bathing suits are perfectly acceptable on the ship (even at meal times, if you’re so inclined). There are comfortable lounge chairs on deck.

Most of the ships have steep stairs between decks and for getting on and off the dinghy to go ashore, so good mobility is a must. Our group of 21 ranged in age from 46 to near 80. Most were American, but there was one German couple, with a mix of couples, singles and singles without their partners. The convivial atmosphere and close quarters left me feeling like I had made some lifelong friends. 

The staff of 10 couldn’t have been more friendly or helpful.

IWJ offers mostly 6-night itineraries in some very attractive cruising grounds: from Grenada north through the Grenadines; the British Virgin Islands, and out of St. Maarten to the Leeward Islands (St. Kitts, Nevis, St. Barths).

I’ve been to all three areas (the British Virgin Islands nearly 25 years ago) and they’re each very different. My personal favorite, which I visited in fall 2013, is Grenada and the Windward Islands, including Bequia, Union Island and Mayreau, for the charming towns, the conservation marine parks and outstanding snorkeling and diving.

Terre de Haut waterfront on Îles des Saintes, Guadeloupe. Photo by Cindy Shurtleff

My 2013 trip was an independent one. I chartered a catamaran for five of us and hired a captain and a cook. The yacht charter agent Ed Hamilton & Co. (Edgecomb, ME; 800/621-7855, www.ed-hamilton.com) helped me select and book the boat. I’ve used them five or six times and they’re always excellent.

Cruising with Island Windjammers was a delightful way to see beautiful parts of the Caribbean, places typically far too expensive for air-hopping.

CINDY SHURTLEFF

Seattle, WA