Addictions spawn other addictions.

My love of southwest Florida and the Keys, pushed me into a love affair of the Caribbean islands, and now the islands have turned me on full force to the art of sailing. Beam reach, who is the give-way vessel, how to trim the sails, reading the weather and sea conditions…I think about all the ins-and-outs all the time.

A new addiction.

Luckily I have a captain friend here that’s teaching me the ropes lines on his 35ft. Lagoon Catamaran. If you’re ever in the Fort Myers Beach area let me know, he charters Old Glory for sails around Fort Myers Beach and Sanibel. Give Captain Bud a call and tell him RumShopRyan sent you for a pirate discount.

The reason I bring all this up is because there’s a great story in this week’s Caribbean Wrap Up about island hoping around Grenada, the Grenadines and Barbados on a four-masted tall ship. If you’ve never been on a sailing you cruise you need to.

No excuses…just go.

Caribbean Weekly Wrap Up

Caribbean Island Hopping Aboard a Four-Masted Ship: I’m sipping a morning coffee on the veranda of my winter rental cottage, overlooking Grenada’s Grand Anse Bay, when I spot a four-masted barque looming over the horizon. Her royals and top gallants appear first, followed by her upper and lower topsails. It’s the 360-foot Sea Cloud, approaching the capital of St. George’s like a vision from an antique maritime painting. As she gets closer, I count more than 20 billowing white sails driving her forward at about five knots under a moderate east-northeasterly wind. –Story

A Food Guide to Jamaica’s West Coast: It’s no secret that we’re big foodies over here, so I was excited to take in the best of what the western coast of Jamaica had to offer. Bear in mind that I visited only a small corner of the country (the coast west and then south from Montego Bay which is where I flew into) and we didn’t dine in 5 star restaurants or hotels every night, so the taste I’m giving you is a combination of local eateries, markets, fresh fish and lobster on an isolated beach that was caught the same day and finer hotel fare. –Story by Huffington Post

Destination – Charlotte Amalie, St. Thomas, USVI: Three things differentiate Charlotte Amalie from other port towns in the Caribbean. First, there are the Danish-style red roofs that dot buildings on the hillsides. The Danes planted their flag on what is now the U.S. Virgin Islands and their influence on architecture remains. Secondly, there’s the U.S. flag waving from public buildings and has been for nearly a century. Nowhere else except Puerto Rico will you see this in the region. Third, several cruise ships, charter yachts, megayachts, passenger ferries, cargo boats, container ships, U.S. Coast Guard vessels and more make Charlotte Amalie’s harbor one of the busiest in the world. –Story by

Caribbean Diving – Top 3 Islands For A Unique Experience: The Caribbean has long been revered for its amazing diving experiences. St. Barths, Nevis, and Virgin Gorda have some of the most spectacular diving in the world, due to a combination of visibility, health of the reefs, quantity of sea life, and variety of fish. That said, let’s take a close look at each. –Story by Caribbean Charter Flights

The best all-inclusive Caribbean hotels: An insider’s guide to the best all-inclusive resorts in the Caribbean, including the top places to stay for ocean-facing rooms, spas, watersports and butler service, in locations including Jamaica, St Lucia, Barbados, Grenada and Antigua. –Story by

If you would like to include any Caribbean stories please leave a comment below or email me your story.


Caribbean Instagram

caribbean bloggers

***Join our Patreon Castaway Crew. For LIVE broadcasts, exclusive content and other perks! Please become a Patron and support our content creation so we can bring more of it to you.

If you aren’t familiar with Patreon, it’s an online platform that allows you to support the work of your favorite creators. Giving them a chance to continue working on their creations without having to worry about where their next meal is going to come from! Thank you so much!