Adventure Travel Blog

Vacation by Sea and  Vacation by Land

A Combo Vacation Package in the Caribbean

First few days by land next few days by sailing the islands last few days by land

Mix and match anyway you wish for convenience we recommend at least the first night on land (most flights from the states come in mid day to late afternoon)

The best of both worlds St. Thomas’s most reasonably priced accommodations with a view that even the top resorts can’t rival and sailing and exploring the beautiful Virgin Islands with a unique romantic anchorage each evening.

Can’t decide whether to spend your vacation in a Caribbean Mountain Site Hotel or on a sailing yacht? You can have both at the Mafolie Hotel and SailingWithTerry.

Stay at the Mafolie where the hotel clings to the side of Mafolie Hill, overlooking the harbor and downtown. Enjoy pool deck and the canopied restaurant at sunset when cruise ships set out from port, and the lights on the surrounding hillsides flicker on. You can take a cruise ship to the BVI, but you won’t have access to some of the places that SailingWithTerry go too. You can’t even fly in and rent a car on some of these islands. These are places where no one goes, except by chartered yacht or sailboat. Best of all you plan the agenda not the cruise director. The dinghy hitched to the back of the boat is used to disembark and motor to excursions on land.

Guests (sailors) of SailWithTerry.com design their own itinerary upon reaching their embarking place in the Virgin Islands. Unique outings could include a deserted island (Sandy Spit), about one acre in size and with only one palm tree; an island of 200 inhabitants (Jost van Dyke) with native restaurants; fresh-catch 3-pound lobster fests (Anegada); and one-bar outposts with local drinks and native music (the Painkiller at Soggy Dollar Bar in White Bay). Want to change your itinerary during the cruise? No problem, mate.

Captain Terry says, “We teach our guests to sail if they want to you chose the activity level and the amount of participation. As soon as we’re out of the harbor, we switch from motor power to wind power. We put our guest sailors behind the helm and help them put up the sails. Being on the water is one thing, but sailing the boat is part of the experience, part of the enjoyment of the vacation.”

Captain Terry makes sure his guests are aware of all the activities available, including snorkeling, swimming, scuba diving, biking, hiking, wind surfing and kayaking. If you like, he will even take time from his captain duties to lead guide an expedition to a prime snorkeling site (and there are many in the Virgin Islands). Maybe you prefer to find a sunny spot on the boat to loll away the hours listening to the gentle lapping of the sea?

Summertime is off-season for the Caribbean, making it the perfect time of year for a more solitary experience with this combo package. Both the hotel and the boat take advantage of the Trade Winds provide constant cooling and the clear, turquoise salt water is a perfect 81 degrees for no-shock diving and swimming.

Sailing Vacations. Want to get away from it all? Escape all but the welcome distractions, sailing into a small cove dropping anchor, taking off in the dingy to find a new reef to snorkel on, later taking a walk on a snow white beach, and that evening you take the dingy ashore to a small charming beach bar/grill, you have dinner while watching a sunset and listening to island music. 

The trouble is you don’t know much about sailing and don’t know how to handle a sailboat. Her you have a terrific opportunity to experience the tranquility and beauty of sailing in the Caribbean, on your own personalised Caribbean Sailing Vacation, with your choice of sailing vessel, your own captain, your own agenda and for a price less than hotel room?

Caribbean Sailing Vacation

There is always something special about shared family time. A few years ago, my husband and I decided to take our niece (then 8 ) and nephew (then 10 ) on a seven day sailing vacation to the British Virgin Islands. Living in Florida, we wanted to provide them with an experience other than Disney. Although I was excited to share a sailing vacation experience with them, I had three main concerns.

First, would they be bored without their television, GameBoys and Playstations? Second, would the normal sibling spats escalate being in a relatively confined space 24/7? And finally, how would they handle different foods when they primarily subsisted on pizza and buttered noodles? I did not need to worry.

Melody at Virgin Island Sailing, Ltd. made the arrangements through the Moorings to charter a 47’ Catamaran for our sailing vacation. The squeals of delight from Tori and Kacey when we met them at the Redhook, St. Thomas ferry dock, with our dingy, were quickly surpassed by the exclamation, “SWEET!” as we pulled up alongside the anchored Cat. This was the first time they had ever been on a catamaran. After a quick tour of the boat and a head lesson, we all retired early so that we could begin our BVI sailing vacation first thing in the morning.

When I went to check on the kids, Tori inquired, “How can you sleep on this thing?” But, I assured Tori that the gentle rocking of the Cat would soon have both children soundly snoring. We cleared the kids through customs in West End, Tortola, and then began island hopping through the BVI.

“I’m bored” was simply not a factor on this trip and my initial concern was a non-issue. Prior to leaving on our sailing vacation, I made journals for Tori and Kacey filled with maps and photos of the BVI.

Each morning we would discuss various topics including the history of the BVI, the culture, music and language. The kids had an opportunity to write down their thoughts and the journals later proved to be wonderful keepsakes for Show and Tell.

The kids loved exploring pirate caves on Norman Island, jumping off the Willie T at the Bight, and snorkeling for hours around the Indians.
They enjoyed the “main drag” on Jost Van Dyke. They decorated and hung a pair of underwear at Foxy’s; Tori had her hair braided and beaded at the beauty shop; Kacey was introduced to Ting ( a carbonated grapefruit drink) at Abe’s By The Sea; and played with Annie’s new puppy.

Both kids became fast friends with Anna’s children and are still pen pals. The crossing to Marina Cay was occupied by learning to man the helm, plotting a course on a chart, and playing hide and seek on the Cat.

The Baths on Virgin Gorda was one of their favorite spots. Climbing through, up and around the boulders without adult supervision was a highlight of their sailing vacation.

I thought Tori and Kacey might appreciate the Bitter End, mainly because I figured they would need a fix at the outdoor big screen television. To the contrary, they wanted to leave because the resort was, “too fancy” and “not islandy enough.” (I think that meant they had to wear shoes and shorts to go into eat, rather than be in swimsuits and barefoot!)

They delighted in playing in the sand at the Beach Club of Cooper Island, chasing goats on Peter Island and swimming with the sea turtles in Great Harbour.

Days were spent snorkeling, swimming, jumping on the trampoline of the Cat, cannon-balling off the aft, telling pirate stories and making up pirate names for each of us. Playing boule and singing with the donkey at Dick’s Last Resort, searching for iguanas, and exploring various coves while learning to steer a dingy were also a great hit.

They learned how to raise a sail and participated in the daily chores of living aboard. Both kids were provided with disposable water cameras and Caribbean fish guides so they could identify what they saw while snorkeling. By nightfall, they were exhausted and often barely made it through dinner.

My second concern regarding sibling fighting was also a non-issue. We were pleasantly surprised to see how well Tori and Kacey got along. The only argument in seven days was a brief spat having something to do with “backwash” in a shared can of Ting.

Overall, the sailing vacation seemed to bring them closer together. My last concern regarding taking the children on a sailing vacation had to do with what would Tori and Kacey eat since their main diet was pizza and buttered noodles. Since this was my vacation too, other than breakfast, I did not cook aboard.

Fortunately, almost everywhere we went had BBQ chicken or ribs, which the kids ate. They tried and liked rice and beans, fried plantains, and a variety of new fruits like mangoes.

We were shocked because they even actually ate triggerfish sandwiches at Foxy’s. Tori did get her buttered noodles on Cooper Island, while Kacey unfortunately developed a taste for fresh Anegada lobster (sorry, Sis!).

Both kids slurped nightly virgin Pina Coladas or Daiquiris – better than any state side slurpee. They thought it was pretty cool to mix their own drink concoctions at Sidney’s Peace & Love. Neither child starved. With all the activity and fresh air, they had good appetites at meal time.

Tori and Kacey were very sorry to see their sailing vacation end. My husband and I have spent many vacations with them, but this was definitely the best. The “BVI” has become as much a normal part of their vocabulary as “pepperoni pizza” and “iPods.”

Recently, my nephew had to write a paper for his sixth grade language arts class about his idea of the most perfect vacation. He did not need to fantasize – he already knew. A sailing vacation on a 47’ Catamaran in the BVI, of course! Since then, we have had several more opportunities to take a BVI sailing vacation with the family.

Luckily for all of us, we are going back again this summer.

For yacht charters and more articles on Caribbean Sailing click here.

Written By Donna Wolfson
Photographs By Donna Wolfson