5 Reasons to Book a Virgin Islands Sailing Vacation

Have you been dreaming of exploring the gorgeous Virgin Islands? Have you ever thought of a sailing vacation on a beautiful catamaran in the Virgin Islands? Well, here are 5 great reasons to book a sailing vacation in the Virgin Islands now!


1. You can experience a sailing vacation without knowing a thing about sailing!

The internet is full of gorgeous photos of sailboats and catamarans skimming the beautiful blue water of the Caribbean… Have you ever wished you could experience that but don’t know a thing about sailing? Well you can! There are several options available when chartering a sailing vacation, including a full charter with a captain and cook, a half-board, which includes a captain and cook and half of your meals (for those that want to enjoy more of the local cuisine) or a captain only charter, in which the guests provision the boat and do their own cooking. Your charter broker can discuss the options and help you decide what is best for your group!


2. You get to experience multiple islands

There are literally hundreds of locations to visit in the Virgin Islands. Exploring this area on a sailing vacation means that everyday you will get to see something new, beautiful and exciting!

You will probably visit at least one new island a day which gives you the chance to see more than a land only vacation.


3. You can go where bigger ships can’t go

On a chartered sailing vacation, you can get to places you won’t be able to reach by a much larger vessel, which means you can see many of the best attractions minus the cruise ship crowds.


You can enjoy your own private beach or cove for the day, snorkel an isolated reef – or, start your own party at a secluded beach bar!


4. Flexibility

A sailing vacation offers a lot in terms of flexibility. Need a catamaran that sleeps 4 or 20? Do you want to snorkel everyday? Do you like to sleep in or get up early? Do you want to check out as many beautiful beaches as possible? Do you have special dietary needs? Do you really want to try a Roti, or a Painkiller?


Are there certain locations you’ve been reading about (perhaps on the Rum Therapy website!) that you’d really like to experience? Are you looking for a quiet family vacation or do you have a group of close friends that likes to find a party? Your charter broker will help to match you with the perfect crew and vessel to maximize your sailing vacation experience.

5. It’s a good vacation value

Regardless of which charter option you choose, a sailing vacation offers a lot in terms of vacation value.


Many things are covered in the price of a charter, including mooring fees, fuel, and cruising permits, as well as meals & beverages (depending on your charter choice), water toys and a crew with extensive knowledge of the area so that you will get to sample the best of the islands!

Ready to go sailing?


This article was sponsored by Certified Charter Broker Laura Jagielski of Denison Yacht Charters. There are many advantages to using Laura as your charter broker.  Because Laura lives in St.Thomas, she can provide an extra level of concierge service.  She knows all the must see spots throughout the Virgin Islands and will arrange your transportation to and from your yacht.  She will be there to personally greet you at the  dock when you begin your charter, ensuring a great send-off.  In addition,  she will meet you at the end of your charter to answer any questions and assist you with your departure. NO detail is too small. She is dedicated to ensuring that your trip exceeds your expectations.

Contact Laura to help you set up your Virgin Islands Sailing Vacation!
Email: laura@denisonyachtsales.com Office Phone: 340-473-0073

The Denison family has been trusted in the yachting community since 1948 when Frank Denison founded Broward Marine in Fort Lauderdale, Florida.  Mr. Denison landed a United States Navy contract, with the first flight of four, 144′ wooden minesweepers, for the Royal Dutch Navy under a NATO contract.  Since then the Denison family has manufactured and sold more yachts over 70 feet than any family in the industry.  The Denison company is not only a powerhouse when it comes to yacht brokerage but also a trusted name in the charter yacht world.  With offices all over the world from Hong Kong to California to Florida to the Virgin Islands, the crew at Denison would be honored to show you how three generations of yachting expertise can be an asset to your yachting experience.

This is a sponsored post. Although we were compensated by the company who sponsored it, the views are solely our own and we only recommend products or services we believe our readers will enjoy.

Cool Signs

As you know, we’re always interested in hearing about people who have been able to make their tropical obsession their profession. We recently heard about the owner of a shop on St. Thomas that manufactures signs and thought that her story was intriguing. Meet Jill Farley, the owner of Cool Signs. Oh, and did I mention, she met Kenny Chesney while doing some boat graphics for him??

1. Can you tell us a little about yourself? I’m actually a civil engineer and was working for the Port of Houston in 2000.  I came down here on vacation with a girlfriend and just decided that I didn’t need to be miserable anymore where I was.  I NEVER planned on staying here –figured a few months would be enough.  Now it’s 12 years later. . .

2. Has it been an easy transition to the islands?  For me, not bad.  I do understand how it would be difficult for most people, however.  I was also lucky enough to meet my wonderful husband down here and he brings a good balance into my life.

3. What do you enjoy the most about your life in the islands?  Sunshine / beach.  After that would be Carnival – I just finished up my 6th year in the Infernos Carnival Troupe and it’s just so much fun.  Parade day is like a day full of joy.

4. What made you decide to start your own business?  It was never my intent to start my own business.  I started working for a lady whose husband had a vinyl plotter and it all just kind of evolved.  It was like I found my niche – after years of not enjoying or being particularly good at my job (as an engineer) I was finally good at something! 

Cool Signs now has 12 full-time employees and is one of the largest sign shops on island.  5. Which famous bars and/or locations have you made signs for?  One of my favorites was going up to Necker Island to put graphics on wind surf boards for Richard Branson.  No, I didn’t actually get to meet him although I did do boat graphics for Kenny Chesney and Sterling Marlin and met both of them.. 

6. What are the challenges of living in the islands?  Living in the islands is a real challenge and hard to describe.  Here’s an example – you find yourself being guarded about making friends b/c it’s such a transitional place.  People come and go for the most part so you don’t really want to let yourself get too attached. 

7. What advice would you give to someone who would like to relocate to the islands?  That’s a tough one because I really don’t encourage people to move here for the most part.  I’ve just seen so many people come and go and know how difficult it is.  Just because it works for me doesn’t mean it works for most people.  I would advise people to practice patience & restraint.  To me, the fact that it’s hard here forces me to remember what’s important.  You just have to let the little things go!

8. Is there anything else we should know about you or your business?  This is my favorite question.  Living here and having this business has given me the opportunity to make people’s lives better and that’s amazingly rewarding.  I get to conduct my business with the highest integrity and standards.  No, I don’t make much money.  I rent an apartment and make car payments and struggle financially but I get to live MY way instead of having to follow a cookie cutter life.

Jill is currently working with photographer William Anthony Torrillo (Old Mango) to publish postcards from the VI’s made from some of his wonderful photos.

Old Mango Postcards will be available in packs of 6 soon on Jill’s website:

Website:  www.coolsignsvi.com

Twitter:  @coolsignsvi


Other posts on Making Your Tropical Obsession Your Profession:

4242 Miles to St. Lucia – The Boiled Frog Guesthouse – Danielle and Steve Unruh

Tears of a Mermaid – Elizabeth Ivy, Glass Jewelry

Searching for Pieces of Eight – Thomas Gidus

Okolemaluna Tiki Lounge, Kailua Kona, Hawaii – Brice Ginardi

Vessels of Freedom – Captain Darrel Hearne

Through the Eyes of a Tropical Soul – William Anthony Torrillo, Photographer

A Pirate Looks at 10 – Fletcher Morton, Trop Rock Musician

I’m Gonna Live My Life Like a Jimmy Buffet Song by Anthony Bjorklund (book review)

Railean Distillers – San Leon, Texas, Kelly Railean