Some days prior, Dave had unfolded an old Virgin Islands chart which better showed the whole archipelago for us to use for big picture planning rather than flipping pages in a chart book. He used this chart during his first charter in 1980. He had forgotten it included handwritten notes from the charter company pre-briefing including a description of an anchorage on small, uninhabited Tobago Island, just west of Jost Van Dyke. This description was "Good ON (overnight) anchorage, great!"  Dave had never visited there on that first charter. Tobago Island and its sister Little Tobago Island are the westernmost BVIs. Current guide books don't mention them, but Street describes the same anchorage third hand as a favorite spot of some guy he heard about and large enough for only one yacht in mild conditions.

To us this meant that nobody likely goes there and, in keeping with our “New Destinations” theme, this was all the incentive we needed to go check it out. This decision was made easier by the mild conditions in the forecast and the short distance back to any of several BVI anchorages in case the choice didn’t pan out. So we departed Sandy Spit at 0830 on Thursday, January 12 bound for Tobago Island and the mystery anchorage. Cue Indiana Jones theme song….

We sailed downwind on genoa alone and arrived at the anchorage spot on the west side of the island at 0945 (use Google Earth “Fly to” to find 18 26'44"N 064 49'40"W). Indeed, no one was there and it was a very dramatic setting. This was as Street described – a “small cove close under the cliffs off the sand beach on the western side”. It was more a rocky beach than a sand beach, and “close under the cliffs” could be considered somewhat of an understatement for a boat of our size. Good snorkeling was likely all around and we had already sighted some dive boat mooring balls in the area. Sand beach usually means sand bottom and we nosed our way in.

As the cove was triangular shaped with the small beach at the apex, the surrounding rocky shore got closer on both sides as we went further in. It was still quite deep. The wind was swirling around the enclosed space. We dropped the anchor as close to the beach as we dared in 23 feet of water, hoping to hit sand. The skipping anchor initially told us we hadn’t but eventually we appeared to be holding—the question became, exactly how? The boat was not pointing into the wind where the anchor went down but that could be influenced by winds swirling around the points of land. But wow, what a terrific spot!

With questions of holding paramount in our minds because no anchor watch could alert us soon enough to take evasive action within this closed-in area, Dave dove into the water to view the anchor. He had to zig zag several times along the chain to find it as the chain itself had wrapped along the way around several corners of dead coral and rock. Even worse, the chain had wrapped around a rock and again around the anchor itself 25 feet down below. An attempt to pull up the anchor in this setting could result in it easily becoming fouled and leading to a much more serious problem.

Diagnosing this pattern, we could have still been moving forward a bit when the anchor hit bottom, the chain wrapped around the rock, then back over the anchor as we reversed, somehow getting under the anchor fluke on one side. We knew this was not a situation we wanted to face if we needed to move urgently. Dave swam about to evaluate options for an alternate drop spot for the anchor, which included a very close-in body of good sand. He also saw a large diameter line tied around a big rock creating a loop – a makeshift mooring. Perhaps somebody came here regularly and dove a line to the loop to moor a boat. Conceivably, we could do the same, although it would be tough with only two people and may not be trustworthy.

Dave, still in the water, with Donna at the helm, described the existing scenario and options. We decided the prudent thing to do was clear the anchor chain immediately and depart for a clearer anchorage. Staying in the current situation was just too risky. Dropping the anchor in the obvious close-to-shore sand would have placed the boat too close to the shoreline on three sides. Indie would have made the same decision….   

Free diving, Dave managed to get down the 25 feet to the anchor, lift and move it several feet and unwrap the chain to eliminate the fouling potential. This took three dives. The anchor weighs 66 pounds. Dave had to remain in the water giving hand signals to Donna at the helm for direction to raise the chain with the helm windlass control and/or maneuver the boat as necessary to free the chain from each encumbrance Dave was viewing underwater. He still had to dive a few more times to pull the chain from under rock ledges. One by one, we dislodged the chain until it hung free in the depths. Donna maneuvered the boat gradually and safely away from the shoreline, raising the remainder of the anchor, and allowing Dave a chance to swim back aboard. Whew!

Now, with our first-hand knowledge of this challenging anchorage, it’s curious a charter company recommended it in the first place for anything but the smallest boats. Of course, that charter company went out of business long ago….

We had escaped from Tobago Island by 1030--but it was beautiful while we were there. You might aim to visit there with one of three scenarios: (1) you have a boat small enough to tuck in close enough to anchor in the sand patch and still have enough swing room that you do not smash into the shoreline. Even in this case, we would recommend anchoring with a stern anchor as well which can also be set in the same band of sand; (2) you locate and tie up to the underwater mooring – confirming the line around the rock can be trusted. Lines around rocks usually don’t last long; (3) you find that the BVI National Parks Trust has established a permanent mooring for the location.

We had two pre-identified, backup anchorages picked out as we departed Tobago Island. The first was White Bay (18 26'31"N 064 45'45"W) on Jost Van Dyke – a location Dave hadn’t visited since that 1980 charter. At that time it was the BVI clearing-in point on Jost Van Dyke, which has since been moved to Great Harbor. Dave humorously likes to recall how his 1980 charter party swam ashore with their documents in plastic bags and proceeded to Customs/Immigration in the three-sided, dirt floor, goat-under-the-picnic-table “office” it occupied then. The starched white shirt British Customs official turned them away because they were wearing bathing suits and no shirts…. It has since become well known that you do not present yourself at British Customs without proper attire.

These days, White Bay is very popular. Here you will find the Soggy Dollar Bar, which apparently originally got its name from the dollars carried by swimmers to the beach.   The proprietor there certainly didn’t have a problem with swimmers showing up at his establishment. It is also the reported origin of the Painkiller rum drink. White Bay is a small, narrow anchorage inside a reef with a beautiful beach. As we passed it that morning on the way to Tobago Island, there looked to be plenty of space for anchoring, including along the edges of the mooring field that is located in the eastern half of the bay. We were passing by at an early time of day (around 9:15 am) which for another hour or so is generally the best time to secure an anchorage. So, from unknown, mysterious Tobago Island, we set sail and headed to the popular White Bay, although we would not arrive particularly early.

By the time we got there at 1130, it was extremely populated. There must have been 30 boats in a space that would only comfortably moor or anchor ten. We debated even entering inside the reef to get a closer look, but Donna wanted to give Dave every chance to get to the Soggy Dollar Bar for reminiscing. We decided to drop sail and motored inside along what proved to be a slalom course amongst the way too many boats already there. Driven still by nostalgia, Dave tried to anchor beside the reef, adjacent to occupied mooring balls, and close to an exit channel through the reef. However, this left us uncomfortably close to a moored charter boat. Once again, we found ourselves electing to escape this sardine can (albeit beautiful) bay, heading for our third anchorage choice at Cane Garden Bay, and setting sail for the third time this day at 1145. In hindsight, anchoring outside of the reef is viable and if you HAVE to spend a Soggy Dollar in an overcrowded anchorage, this can be the way to do it….