All Together Now


A family charter in the British Virgin Islands creates lasting memories and leaves the crew yearning for more  (published August 2014)

Jill, Porter, Russ and Beth at the Moorings base
Jill, Porter, Russ and Beth at the Moorings base

Firmly wedged between the cockpit table and the windward settee, my nephew George napped in his car seat as we healed with the steady trade winds. Down below in the starboard aft cabin, his cousin Porter sprawled out atop a blue and white sheet as a natural sound machine kept him dreaming. And on the leeward cockpit settee, Grandma, or Nana as she’s affectionately known, took a nap of her own.

My dad and I occupied seats behind the boat’s twin helms sipping cold beers as we chatted about nothing in particular—maybe something to do with sailing. And my wife Jill and sister Megan sat to windward shuffling through magazines, enjoying the beautiful combination of sun and breeze.


Our charter in the British Virgin Islands had started just days earlier and with each Caribbean sunset and rise, our crew, three generations of sailors, was falling deeper into the laid-back island life as we experienced it all. As well we should.

Planning a charter for multiple groups of people with appreciably different schedules can prove to be a struggle. But, from the moment our group decided to go and a week was chosen, the cards fell quickly and decisively in our favor. They had to, as the week we had decided upon was in mid-February and it was now mid-November, so we needed to put it together quickly in order to secure a decent price on a boat, and, just as importantly, on airfares.


Since Jill and I had been to the B.V.I. before, and it had always been a twinkle in my parents’ eyes, I began sifting through charter outfits both in the U.S.V.I. and B.V.I. After researching a series of options, we decided to go with The Moorings at Wickham’s Cay II in Road Town. We all wanted a monohull and after talking with a helpful representative at The Moorings, ended up reserving a Moorings 433.

I figured that a boat with a large V-berth and head forward for my parents, and two aft cabins with their own heads—one for Megan and George, the other for Jill and I, and Porter could sleep in the main saloon—would be a perfect fit for our group. It had been just two months prior that the seven of us spent a long weekend aboard our Grand Soleil 39 in the Puget Sound without a problem, so going bigger than 43-feet wasn’t really necessary.

I know that with tight schedules, many people choose to go with a seven-day charter, but I’m a 10-day or more kind of guy, so I lobbied to push the schedule as wide open as agendas would allow. To make a longer charter work we opted for a late start and early finish that would put us on the boat at 6 p.m. and then back at the base nine days later for a noon checkout. I also like this option because it cuts out hotel stays if you can get flights that work with those start and end times.

We ended up getting flights in and out of St. Thomas, which meant taking the Tortola Fast Ferry from Charlotte Amalie to Road Harbour. This is a good option, as flights are usually cheaper into St. Thomas than they are into Beef Island, B.V.I., but the last ferry leaves around 4 p.m. so if your flight is delayed and you miss the ferry, you’ll end up having to grab a hotel on St. Thomas for the night.

Note: When we were there in February there was talk of extending the ferry schedules to later in the evening, but don’t hold your breath.


Russ steering upwind towards the Baths in the Drake Channel
Russ steering upwind towards the Baths in the Drake Channel

Having sailed and taught sailing in the B.V.I. for a number of years, it was up to me to lead the charter party and show them why this beauty of an archipelago is worthy of its moniker, “Charter Capital of the World.” I had a pretty good idea of what our itinerary should include, but stopped short of planning out each day because, quite frankly, cruising just doesn’t work like that.

In December I grabbed a copy of Cruising the Virgin Islands by Joe Russell and Mark Bunzel, which comes with a helpful companion chart, and started to reacquaint myself with distances and to look for some spots that I had never visited before. The loose plan I formulated in my head would accomplish these things in no particular order: visit some places that every first time B.V.I. charterer should go; give us a mix of anchoring, docking and mooring; alternate between eating dinners out and on the boat; provide everyone with some relaxing, family friendly things to do off the boat; and to hit some places that I had never been before. Of course, I also wanted to give everyone as much sailing time as possible without wearing out the crew with too many long sails—read, two 10-month-olds aboard.

Above all else, the reason you come to the B.V.I. on your own boat or to charter someone else’s is the sailing. Sure the other things are there; the beaches, bars, hiking, snorkeling and more, but the sailing is king, and we ended up with perfect 15 to 20+ knot breezes each day. When we set the sails just outside of Road Harbour on our first day I knew it was going to be a great week of sailing. It was Sunday afternoon and as we trimmed for the reach over to Peter Island, the boat leapt forward and charged across the deep blue Sir Francis Drake Channel.

Just like any crew of sailors on an unfamiliar boat, once we learned the lines and got comfortable, it was easy for us to find a groove each day as we reached, ran and sailed close hauled around the islands. On a few occasions we came upon a passing tropical squall where we’d scurry to close any open hatches and to tuck in a reef, only to shake it out soon after the tempest had passed. And my plan to practice a few crew overboard maneuvers was aided when a gust of wind took the hat right off Jill’s head. Vowing to never lose a hat, we quickly went into a figure eight maneuver and after a botched first attempt, got the once ill-fated cap aboard on the second try.

One of my favorite things about sailing in any part of the Caribbean is the plethora of different boats you are sure to encounter—from mile-weary world cruisers and look-alike charterers to grand prix racers, ultra chic mega-yachts and old time schooners, we saw it all. In Gorda Sound we watched in awe as the RC44 fleet raced for two days, and anchored just off the Bight at Norman Island was one of the largest sailing yachts in the world.


Relaxing at the Soggy Dollar
Relaxing at the Soggy Dollar

To show first time B.V.I. sailors around the islands and not include stops at places such as Foxy’s, The Soggy Dollar Bar, Sandy Cay and Spit, the Bight at Norman Island, the Baths, the Indians, Marina Cay and many more would be cruiser’s blasphemy.

Our lunch stop at the Baths on Virgin Gorda was fun and stunning as usual, but unfortunately turned into one of those situations where you find yourself outside of the usual charter cruiser scene and instead, enveloped by throngs of cruise ship passengers. I never like to miss the Baths, though; Devil’s Beach is just too good to pass up and the walk through the immense catacomb of granite boulders is always humbling.

I could talk about any number of bars or restaurants that made our list and deserved at least a stop for one drink, but The Soggy Dollar Bar in White Bay on Jost Van Dyke was one of the most memorable on this trip. After grabbing a mooring ball close to shore in Great Harbour, we headed ashore and found an always-friendly cab driver to give us ride up over the hill. With beach chairs procured and the boys playing in the sand, it was time to enjoy the Soggy Dollar’s claim to fame—the Painkiller. There is not much left to say after that.

But we also had to spend time exploring the underwater world of the B.V.I., which meant snorkeling at about every anchorage or lunch stop we made. Snorkeling is a favorite pastime of most cruisers and the B.V.I. offers a variety of great places to look below the surface. A favorite of many is certainly the Indians. Near Pelican Island, the Indians are red pinnacles of rock that jut out from the Sir Francis Drake Channel. The wind was up when we stopped by, which made the mooring uncomfortable, but the snorkeling around the rock formations was some of the best we saw all week. The bright sunshine illuminated the water surrounding the Indians while schools of colorful fish pecked at the coral, and sea fans waved to us as the current pulsed through the rocks.


Just some of the water toys available at Bitter End Yacht Club
Just some of the water toys available at Bitter End Yacht Club

With a crew of seven, two of which were under the age of one, I figured a relaxing mid-week stop at the famous Bitter End Yacht Club would do everyone right. We were not disappointed.

After sailing from our anchorage at Marina Cay and stopping for lunch at George Dog to do some snorkeling—and to make sure George got to see his island—we continued on to Gorda Sound. At the Bitter End’s Quarterdeck Marina the welcoming dock master, Carine, helped us into a slip next to a gorgeous, 100-foot red Swan that made our 43-footer seem like a dinghy. When we were tied up and squared away Carine gave us an introduction to the property before we hit the refreshing showers ashore.

Started in the mid-60s as a rustic bar and outpost with five small cabins for charter captains and adventurous sailors alike, the Bitter End is now a full-service resort with cottages, restaurants, pools, moorings, a marina, a small market, a fleet of sailboats and more. My goal in stopping at the Bitter End for two nights was to give us a full day to relax and use the resort’s amenities before taking off refreshed for the latter half or our week.

That morning, while I worked on Cruising Compass at the pub by the marina, the ladies enjoyed a pool-side yoga session then set off with the rest of the crew for a two-mile hike on Guy’s Trail and came back with stories and photos of nearly getting lost before coming upon a breathtaking panoramic view. The afternoon was spent lounging by the pool and getting out for some watersports. Jill and Megan decided to try their hand at standup paddleboarding and my dad and I determined that we needed to do some more sailing, so we took out a couple Lasers from the BEYC’s fleet. We hadn’t sailed Lasers in years and had a blast slaloming our way through the protected mooring field in an excellent breeze.

For sundowners we took the dinghy over to Saba Rock where we sat on the shaded deck and then walked out to the bluff overlooking Eustatia Sound and Reef. It was a perfect end to the day.

IMGP1633 While a charter vacation typically has a schedule and list of things to do and see, one of my favorite parts are the unplanned events that happen in between. For our crew, some of the most memorable moments were created when we weren’t doing much at all—just lounging in the cockpit or cooking and eating meals at anchor.

During the busiest seasons of the year, the B.V.I. has any number of great places to head ashore for drinks and dinner, but we found those to be some of the best times aboard the boat. From grilling out while stern tied in Little Harbour, Peter Island on our first night, where the excitement of the first day kept us up laughing well into the night. Or while eating lunch and pouring over our charts and cruising guides to plot our next few days. These little moments are the ones that always stick out.

There is nothing quite like chartering with your family. Though Jill, Porter and I live-aboard and my parents have a 40-foot cruising sailboat of their own, being able to leave it all behind and come down to the Caribbean together for a charter was a one of a kind experience. And while some may bristle at the thought of bringing a pair of 10-month-olds along for the ride, they were nothing but a pleasure and enhanced the trip in every way.

As with every charter, the last sail back to the base was somewhat solemn as we all knew, but didn’t want to acknowledge, that the week was coming to a close. Instead, we recanted personal highlights, laughed at inside jokes that were produced throughout the week and talked about where our next charter would be. Because, while trips like these are sometimes referred to as “vacations of a lifetime,” I think this crew would concede that we are just getting started.

IMG_0428Our itinerary:

Day 1: Arrive in St. Thomas, ferry to Road Harbour, and spend the night on the boat at the Moorings base
Day 2: Road Harbour to Little Harbour, Peter Island
Day 3: Little Harbour to Marina Cay via the Baths
Day 4 & 5: Marina Cay to the Bitter End via George Dog Island (2 nights)
Day 6: Bitter End to Sandy Spit
Day 7: Sandy Spit to Great Harbour, Jost Van Dyke via Sandy Cay
Day 8: Great Harbour to the Bight, Norman Island via Soper’s Hole
Day 9: The Bight to Road Town via the Indians and Great Harbour, Peter Island
Day 10: A night at The Moorings and home