{"id":1008,"date":"2025-08-08T17:43:16","date_gmt":"2025-08-08T17:43:16","guid":{"rendered":"https:\/\/sailaway-vacations.com\/?page_id=1008"},"modified":"2025-08-21T11:09:20","modified_gmt":"2025-08-21T11:09:20","slug":"sailing-regions-caribbean-sailing-leeward-islands-sailing","status":"publish","type":"page","link":"https:\/\/sailaway-vacations.com\/index.php\/sailing-regions-caribbean-sailing-leeward-islands-sailing\/","title":{"rendered":"Sailing regions \u2013 Caribbean Sailing \u2013 Leeward Islands Sailing"},"content":{"rendered":"\t\t
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Leeward Islands Sailing<\/h2>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t
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Sophisticated sailing through luxury resorts, pristine beaches, and French Caribbean culture. The Leeward Islands offer upscale amenities with perfect trade wind sailing.<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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8 Major Islands<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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Luxury Marinas<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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Nov – May<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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Back to previous page<\/a><\/div>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t
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Island Highlights<\/span><\/h2>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t
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Antigua<\/h4>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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365 beaches and historic English Harbour<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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Nelson's Dockyard<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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Shirley Heights<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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Deep Bay Beach<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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St. Barts<\/h4>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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French sophistication in the Caribbean<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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Gustavia Harbor<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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Shell Beach<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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Luxury Shopping<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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St. Martin\/Sint Maarten<\/h4>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Two cultures, one island paradise<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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Marigot Bay<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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Orient Beach<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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Maho Beach<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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Anguilla<\/h4>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Pristine beaches and world-class resorts<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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Shoal Bay<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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Meads Bay<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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Sandy Island<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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7-Day Leeward Islands Itinerary\n<\/h2>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t
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Daily Schedule<\/h2>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t
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1<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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Antigua - English Harbour\n\n<\/h5>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Charter base departure, explore historic dockyard<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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2<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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Barbuda\n<\/h5>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Pink sand beaches and frigate bird sanctuary<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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3<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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St. Barts - Gustavia\n\n<\/h5>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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French culture and duty-free shopping<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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4<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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St. Martin - Marigot\n<\/h5>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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French side cuisine and markets<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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5<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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BequiaAnguilla - Road Bay\n<\/h5>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Pristine beaches and luxury resorts<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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6<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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St. Kitts\n\n<\/h5>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Volcanic peaks and colonial history<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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7<\/p>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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Antigua - English Harbour\n\n<\/h5>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Return to base via Falmouth Harbour<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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Luxury Sailing\n<\/h4>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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High-end marinas and world-class resorts. Premium dining, shopping, and spa facilities on every island.<\/p>

\u00a0<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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French Culture\n<\/h4>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Experience French Caribbean cuisine, duty-free shopping, and European sophistication in a tropical setting.<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t

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Perfect Beaches\n\n<\/h4>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Some of the Caribbean’s most beautiful beaches with white sand, crystal-clear water, and excellent snorkeling<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t","protected":false},"excerpt":{"rendered":"

Leeward Islands Sailing Sophisticated sailing through luxury resorts, pristine beaches, and French Caribbean culture. The Leeward Islands offer upscale amenities with perfect trade wind sailing. 8 Major Islands Luxury Marinas Nov – May Back to previous page Island Highlights Antigua 365 beaches and historic English Harbour Nelson’s Dockyard Shirley Heights Deep Bay Beach St. Barts French sophistication in the Caribbean Gustavia Harbor Shell Beach Luxury Shopping St. Martin\/Sint Maarten Two cultures, one island paradise Marigot Bay Orient Beach Maho Beach Anguilla Pristine beaches and world-class resorts Shoal Bay Meads Bay Sandy Island 7-Day Leeward Islands Itinerary Daily Schedule 1 Antigua – English Harbour Charter base departure, explore historic dockyard 2 Barbuda Pink sand beaches and frigate bird sanctuary 3 St. Barts – Gustavia French culture and duty-free shopping 4 St. Martin – Marigot French side cuisine and markets 5 BequiaAnguilla – Road Bay Pristine beaches and luxury resorts 6 St. Kitts Volcanic peaks and colonial history 7 Antigua – English Harbour Return to base via Falmouth Harbour Luxury Sailing High-end marinas and world-class resorts. Premium dining, shopping, and spa facilities on every island. \u00a0 French Culture Experience French Caribbean cuisine, duty-free shopping, and European sophistication in a tropical setting. Perfect Beaches Some of the Caribbean’s most beautiful beaches with white sand, crystal-clear water, and excellent snorkeling<\/p>\n","protected":false},"author":1,"featured_media":0,"parent":0,"menu_order":0,"comment_status":"closed","ping_status":"closed","template":"","meta":{"_acf_changed":false,"_eb_attr":"","_templately_pack_id":"","_templately_imported_at":"","_templately_source":"","_templately_import_session_id":"","footnotes":""},"class_list":["post-1008","page","type-page","status-publish","hentry"],"acf":[],"yoast_head":"\nSailing regions \u2013 Caribbean Sailing \u2013 Leeward Islands Sailing - Sailaway Vacations<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/sailaway-vacations.com\/index.php\/sailing-regions-caribbean-sailing-leeward-islands-sailing\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Sailing regions \u2013 Caribbean Sailing \u2013 Leeward Islands Sailing - Sailaway Vacations\" \/>\n<meta property=\"og:description\" content=\"Leeward Islands Sailing Sophisticated sailing through luxury resorts, pristine beaches, and French Caribbean culture. The Leeward Islands offer upscale amenities with perfect trade wind sailing. 8 Major Islands Luxury Marinas Nov – May Back to previous page Island Highlights Antigua 365 beaches and historic English Harbour Nelson’s Dockyard Shirley Heights Deep Bay Beach St. Barts French sophistication in the Caribbean Gustavia Harbor Shell Beach Luxury Shopping St. Martin\/Sint Maarten Two cultures, one island paradise Marigot Bay Orient Beach Maho Beach Anguilla Pristine beaches and world-class resorts Shoal Bay Meads Bay Sandy Island 7-Day Leeward Islands Itinerary Daily Schedule 1 Antigua – English Harbour Charter base departure, explore historic dockyard 2 Barbuda Pink sand beaches and frigate bird sanctuary 3 St. Barts – Gustavia French culture and duty-free shopping 4 St. Martin – Marigot French side cuisine and markets 5 BequiaAnguilla – Road Bay Pristine beaches and luxury resorts 6 St. Kitts Volcanic peaks and colonial history 7 Antigua – English Harbour Return to base via Falmouth Harbour Luxury Sailing High-end marinas and world-class resorts. Premium dining, shopping, and spa facilities on every island. \u00a0 French Culture Experience French Caribbean cuisine, duty-free shopping, and European sophistication in a tropical setting. Perfect Beaches Some of the Caribbean’s most beautiful beaches with white sand, crystal-clear water, and excellent snorkeling\" \/>\n<meta property=\"og:url\" content=\"https:\/\/sailaway-vacations.com\/index.php\/sailing-regions-caribbean-sailing-leeward-islands-sailing\/\" \/>\n<meta property=\"og:site_name\" content=\"Sailaway Vacations\" \/>\n<meta property=\"article:modified_time\" content=\"2025-08-21T11:09:20+00:00\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data1\" content=\"1 minute\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/sailaway-vacations.com\\\/index.php\\\/sailing-regions-caribbean-sailing-leeward-islands-sailing\\\/\",\"url\":\"https:\\\/\\\/sailaway-vacations.com\\\/index.php\\\/sailing-regions-caribbean-sailing-leeward-islands-sailing\\\/\",\"name\":\"Sailing regions \u2013 Caribbean Sailing \u2013 Leeward Islands Sailing - Sailaway Vacations\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/sailaway-vacations.com\\\/#website\"},\"datePublished\":\"2025-08-08T17:43:16+00:00\",\"dateModified\":\"2025-08-21T11:09:20+00:00\",\"breadcrumb\":{\"@id\":\"https:\\\/\\\/sailaway-vacations.com\\\/index.php\\\/sailing-regions-caribbean-sailing-leeward-islands-sailing\\\/#breadcrumb\"},\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\\\/\\\/sailaway-vacations.com\\\/index.php\\\/sailing-regions-caribbean-sailing-leeward-islands-sailing\\\/\"]}]},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\\\/\\\/sailaway-vacations.com\\\/index.php\\\/sailing-regions-caribbean-sailing-leeward-islands-sailing\\\/#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"Home\",\"item\":\"https:\\\/\\\/sailaway-vacations.com\\\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"Sailing regions \u2013 Caribbean Sailing \u2013 Leeward Islands Sailing\"}]},{\"@type\":\"WebSite\",\"@id\":\"https:\\\/\\\/sailaway-vacations.com\\\/#website\",\"url\":\"https:\\\/\\\/sailaway-vacations.com\\\/\",\"name\":\"Sailaway Vacations\",\"description\":\"\",\"publisher\":{\"@id\":\"https:\\\/\\\/sailaway-vacations.com\\\/#organization\"},\"potentialAction\":[{\"@type\":\"SearchAction\",\"target\":{\"@type\":\"EntryPoint\",\"urlTemplate\":\"https:\\\/\\\/sailaway-vacations.com\\\/?s={search_term_string}\"},\"query-input\":{\"@type\":\"PropertyValueSpecification\",\"valueRequired\":true,\"valueName\":\"search_term_string\"}}],\"inLanguage\":\"en-US\"},{\"@type\":\"Organization\",\"@id\":\"https:\\\/\\\/sailaway-vacations.com\\\/#organization\",\"name\":\"Sailaway Vacations\",\"url\":\"https:\\\/\\\/sailaway-vacations.com\\\/\",\"logo\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/sailaway-vacations.com\\\/#\\\/schema\\\/logo\\\/image\\\/\",\"url\":\"https:\\\/\\\/sailaway-vacations.com\\\/wp-content\\\/uploads\\\/2025\\\/06\\\/sailaway-vacations-original-logo-lichter-blauw.png\",\"contentUrl\":\"https:\\\/\\\/sailaway-vacations.com\\\/wp-content\\\/uploads\\\/2025\\\/06\\\/sailaway-vacations-original-logo-lichter-blauw.png\",\"width\":750,\"height\":300,\"caption\":\"Sailaway Vacations\"},\"image\":{\"@id\":\"https:\\\/\\\/sailaway-vacations.com\\\/#\\\/schema\\\/logo\\\/image\\\/\"}}]}<\/script>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Sailing regions \u2013 Caribbean Sailing \u2013 Leeward Islands Sailing - Sailaway Vacations","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/sailaway-vacations.com\/index.php\/sailing-regions-caribbean-sailing-leeward-islands-sailing\/","og_locale":"en_US","og_type":"article","og_title":"Sailing regions \u2013 Caribbean Sailing \u2013 Leeward Islands Sailing - Sailaway Vacations","og_description":"Leeward Islands Sailing Sophisticated sailing through luxury resorts, pristine beaches, and French Caribbean culture. 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