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There’s nothing like cruising the Caribbean.

I’m not talking about cruising on one of those gargantuan mega-liners that shuttle thousands of people into popular ports-of-call, I’m talking about something more intimate. The experience should be more about the rhythms of sea and the push of wind, it should be more about the relationships with passengers and crew, it should be more about really getting to know an island and not just hitting the tourist traps as quickly as possible.

These are just the opinions of a salty beach bum, but having done both the mega-liner thing and the small sailing vessel experience, there’s no question which one burned a lasting memory into my weathered mind.

Next week I’ll be traveling to St. Maarten/St. Martin to again set sail with Island Windjammers, this time on their second vessel, the 122 ft. Sagitta. Sailing on the companies first ship, the Diamant, was a amazing experience, one hopefully replicated on Sagitta.

Ports-of-Call For Sagitta

We’ll be boarding Sunday (March 23rd) in the afternoon and I’ll be posting live photo updates to the RumShopRyan Facebook and Twitter pages.

St. Maarten

One island, two countries – one side French, the other Dutch. The island with a personality disorder is the home port for the Island Windjammer’s Sagitta. Any ideas on where to go and what to see on island?


Beaches, beaches, beaches…Anguilla has them in spades. Toss in a couple awesome beach bars and some luxury resorts and you get what most people think of when they hear about Anguilla. I’ll hopefully be meeting up with Nori of for an island tour that will peel back the layers of this Caribbean gem.

St. Kitts

I fell in love with this island a couple years ago and am eager to return. Maybe visit a couple legendary beach bars, maybe an ATV tour, maybe ride on the scenic railway–where ever the trade winds blow I suppose.


Nevis Peak has been tempting me for years. A muddy hike to the top of this extinct volcanic crater is hopefully in the cards. Then a lazy afternoon sipping Killerbees at SunShine’s Beach Bar.

St. Bart’s

Millionaires, rock stars and super-models are said to line the beaches of St. Barts. Don’t worry, I’ll bring a stick to beat the super-models away with. Marvelous beaches and French wines and cheeses should fill this day, but other than Le Select, what are some other must visit places?

St. Eustatius

Hopefully this island more commonly known as Statia (Stay-sha) will be on the itinerary. I’ve heard Sagitta hasn’t been sailing to Statia or Saba due to customs hassles, but my fingers are crossed.

If you’ve been to any of these island please leave a comment below and let me know what your “must do” items are.

122 feet sounds like a large boat, it’s really not. You’ll feel the roll of the waves, the shove of the wind. You’ll hear the drop of the anchor, the rise of the sheets. You’ll smell the salt in the air, the aroma of the galley. You’ll experience a real island hopping sailing adventure, you’ll experience something no mega-cruise line can match.


P.S. – Leaving soon? These recommended links below will help you save money and book your trip:

We use all the companies listed here or on the resource page. By booking through these links, the small commission we earn helps us bring you more Caribbean content so that you can save money and have a better island vacation. Crystal and I greatly appreciate any support!

About the Author: RumShopRyan

Just a salty pirate looking to explore and document the wonders of the Caribbean. Professional blogger, rum judge, consultant, marketer, and consumer of blue water beauty. To learn more, visit our About Us Page.