Sailing Lessons

Virgin Islands

April - May, 2014

The Setup

Those of you who have followed some of our past travels may remember that we enjoy getting out and sailing small sailboats such as Lazers and Hobie-Cats. We have done this for many years and both of us had started sailing in Florida before we even met each other. We had always sailed small boats though, probably nothing larger than 18 feet.

For example, below is a photo of us sailing a Hobie Max (18') in the Turks and Caicos Islands. This was typical of our sailing until now.


I had always heard about chartering a boat by yourself, with no captain or crew to run it, called "Bareboat chartering". Someone with the proper experience or training can rent a 40ft sailboat for a week or more, sail it wherever they want to go (within reason), and live on board the whole time. A typical 42 ft sailboat can accommodate 4 people rather comfortably, or 6 people if they are on good terms. A little investigation revealed that there is a sailing association that has defined sailing courses that can qualify a person to bareboat charter. Although we have lots of small boat experience, we had no official experience in sailing larger boats, so we would have to start at the beginning with the first course (ASA-101) and continue with the intermediate (ASA-103) and then bareboat (ASA-104) courses. A number of sailing schools in various locations offer this series of courses, typically running a total of about a week. We chose the "Bluewater Sailing School" because it was in a convenient location (St Thomas, US Virgin Islands) and they offered a 6 day course that fit our schedule. If we knew then what we know now, we might have chosen differently.
We have never been to the Virgin Islands, British or US, so we figured that as long as were going there, we might as well take an extra day or two and look around a bit. Our schedule ended up that we would fly to St Thomas on Thursday and tour around Thursday afternoon, all day Friday, and Saturday morning. Saturday after lunch I would return our rental car to the airport and take a taxi back to Susan at Redhook, where we would start our course about 4:00 PM. The course would be over the following Friday about 1 PM and we had a return flight leaving at 4:45 that day. Our flights on Delta were on time and reasonably comfortable (exit row seats) both ways. We had a Hertz rental car (Ford) that was in good condition and served our purpose well.

Where we stayed

When we started making plans I found that our choice or places to stay on St Thomas would be a little limited; some of the resorts were already full (traveling late April) and others required a minimum of 3 or 4 nights stay, and we were only doing two nights. The sailing school listed a B&B named Two Sandals and said it accepted one and two night stays, so we gave them a try. It proved a bit difficult to find it as their sign pointing down a side road was almost impossible to read. There were 4 or 5 guest rooms in the B&B with a nice common area and a balcony that looked out over the Redhook Bay area. Our room fronted on this balcony and we had a section of it to enjoy to ourselves. Our room was reasonably comfortable with a few idiosyncrasies: the wash basin in the bathroom had no hot water (was not connected) although the shower/bath did have hot water. They asked us to not leave the AC on while not in the room, but the window in the bath could not be closed, letting in plenty of hot afternoon air.

Our view of Redhook harbor from the Two Sandals balcony.

Our room, like another one, were the preferred rooms with the direct access to the balcony but we found out the first morning this was not necessarily a good thing. The sun rises early, about 5:30 AM, and our room faced somewhat east and the window drapes were very thin, so it got very light in the room very early. Also there were a number of chickens and roosters in the area and they do not wait until dawn to start crowing. The morning serenade started about 3 AM. The net effect is that we got up rather early those mornings. The rooms away from the balcony would not be subject to the early morning light or rooster serenade and would probably allow for later sleeping. True to its name, the B&B did provide a breakfast. The hostess baked fresh bread items (scones, pastries) each morning along with good hot coffee and yogurt with granola cereal. Two Sandals was in a convenient location; we could walk about 10 minutes one direction and be at a beach at the Secret Harbor Resort, or 15 minutes the other way and be in the town of Redhook.

Touring St Thomas and St John

Thursday afternoon we walked down to the beach at Secret Harbor and looked around there a while, then went back to Two Sandals, cleaned up a bit and went into Redhook for dinner. After looking around there a bit we settled on an Italian place, Pesce. It was probably one of the nicer places in Redhook, if not in St Thomas. We had a very nice dinner and enjoyed watching some of the other patrons there. Friday morning we got in the car and set out to visit some of the local beaches. We drove through Redhook and a little past and entered the Sapphire Beach resort grounds. There is a public parking area and we toured the rather extensive beach area and marina. There were a couple of people snorkeling in the bay but we didn't see anything that looked very interesting from the beach.

Part of Sapphire beach.

We drove a bit further and, after a wrong turn or two, found our way to Coki Beach. There is a commercial beach enterprise here as well as a bublic beach with a number of vendors ready to provide food, drink, and beach equipment. The beach itself was smaller than Sapphire, but there appeared to be some interesting snorkeling possibilities. I noticed that the vendors seemed very friendly even though we were not buying anything. Across the street some fishermen were cleaning their catch under the shade of a tree.

Coki Beach was not as long as Sapphire, but lots of vendors and avtivity.

Our next beach destination was Vessup Bech, partly because we had seen a vendor advertising windsurfing rentals and small sailboats there. Vessup bay is actually part of Redhook harbor and Vessup beach is on the opposite side of the harbor from the town of Redhook. The beach was fairly long we did find the sailing vendor, but there was no one there. The windsurf equipment we could see was old beginner equipment but they had some interesting sailboats, mostly catamarans, including at least one that appeared to use retractable hydrofoils. Sailing or windsurfing in this area would have been challenging because of all the moored sailboats. We "discovered" the Latitude 18 restaurant which we later heard was a good place for dinner.

Vessup Beach and Bay. Across the bay is Redhook and the marina.

We got back into Redhook about noon and decided to try out Duffy's Love Shack. Despite its reputation as a lively nighttime bar scene, the soft fish tacos were excellent. We really didn't feel like driving into Charlotte Amalie, the main city, and looking around there so we decided to take the ferry over to St John and look around there a bit. We walked to the ferry dock and building, bought our tickets and waited for the ferry's deprture time; it runs on an hourly schedule. At the appointed time we boarded the ferry and relaxed for the 15 minute ride over to Cruz Bay in St John.

The ferry at the dock, prior to boarding.

Upon getting to St John, we took a quick look around the dock area then headed for a hiking trail we had seen on some maps. The Lind Point Trail goes from just outside the Visitor Center in Cruz Bay, around Lind point, and to a beach area called Solomon Beach. We soon saw a sign indicating two paths to take, either a lower trail directly to Solomon Beach, or a higher one that goes to the Lind Point Overlook. Of course we took the higher trail and ended up getting quite a workout, Between the fairly good climb and the hot early-afternoon temperatures, we were sweating pretty well. We did get to the overlook and the view was very nice. During our climb we were surprised to see a deer about 30 feet from the paved trail; it appeared to be used to people and did not run.

A view of Cruz Bay from the Lind Point overlook.

We continued on to the beach and relaxed there for a while, cooling off in the water, before heading back to Cruz Bay via the lower trail. As we got into town we stopped at what appeared to be a local bar/restaurant and got a couple of strong rum punches and two bottles of cold water. After the refreshment we got on the return ferry and headed back to Redhook and Two Sandals. We rested a bit, cleaned up a little, and headed to Latitude 18 for dinner. It turned out to be a friendly, informal place with good food and a local band featuring a singer (Bekka) who was surprisingly good.

Dinner at Latitude 18, with the local band.

The next morning we walked down to Secret Harbor beach again and explored that area for a while. We had to check out of Two Sandals by 11:00 so we got cleaned up a little, packed our bags and headed out. We wanted to get an early lunch so I could get a good start on returning the rental car to the airport. We had seen the restaurant "Fish Tails" along the harbor so went there, only to find out that they only serve breakfast prior to noon on Saturday. We checked the breakfast menu, ordered the breakfast burritos and did quite well. I returned the rental car and took a taxi back and we waited until our 4:00 "appointment".

Sailing School: The Beginning

We had located our boat for the week earlier in the day. Prana is a Benetau (French company) Oceanis 440 (about 44 ft) that is about 20 years old, but in very good condition.

Prana at the dock in Redhook - American Harbor.

Since this was to be a course in bareboat chartering, I expected the boat to be equipped and supplied as a charter boat would be, but such was not the case. It turns out that Prana is basically Captain Bill Mile's personal boat. Well, not completely, but he is a partner in the company that owns Prana and other boats and Prana is his home; he lives on board during the sailing season, about 7 months a year. This means, among other things, that his clothes and other gear was stored in lockers and other storage areas that we would normally (on a true charter) use for our own stuff. There was no manual or operating instructions for any of the on-board equipment, so Captain Bill gave us a quick tour or "check-out" on some of the equipment. On a true charter you would either go shopping and provision the boat for the week of sailing yourself, or hire a provisioning company to do so, and they would provide you with a list of the provisions and probably some sample menus. Instead Molly, the captain of the other Bluewater boat, Weatherbird, did the shopping Saturday morning and we had no idea just what food and supplies we had on board.

Manny at the helm of Prana.

We met our fellow student sailor, Manny, a very pleasant middle aged man originally from Brazil who has lived in the US since 1984. He is basically a "nuclear physicist" at a research facility near Chicago and he has been doing some sailing on small and midsize (32ft) boats for the past year or so. Manny was fairly quiet but a good guy to have around and he made the week much more pleasant than if he had not been there.

The "Floor Plan" of Prana.

Saturday afternoon Captain Bill gave us a tour of the boat and overview of what we would be doing for the week. He assigned sleeping quarters and we got the relatively roomy (for a sailboat) forward "V-Berth", Captain Bill got the aft "cabin" which had very limited (almost none) headroom and poor Manny got the dining table. The table dropped a little and got some added cushions and made into a bed, joining with the cushions of the seating area. We had a head (very small bathroom ) in our forward cabin while Manny and Captain Bill shared a head in the rear of the open area. The features and operation of the shower and other "facilities" in the head is worthy of a story in itself, but we'll let it go at that for now.

Inside Prana. Our cabin is through the door and Manny slept on the table.

Our cabin had two large hatches that opened to catch the wind at night and there were several electric fans that helped move the air. We were reasonably comfortable at night, but I'm not sure I'd want to do this in much warmer weather. Manny and Captain Bill probably had less ventilation than we did but Manny reported that he was reasonably comfortable.

We had purchased a couple of bottles of wine and Captain Bill pointed out the cooler on deck to put them in and where we could get some ice. Manny normally joined us working on the wine while Captain Bill had his own stash of liquor and he seemed to favor his Gin. That first night Manny joined us for dinner at Molly Malone's in Redhook before we got on board Prana and settled in for the night.

The mornings generally followed the same pattern as we figured out that first morning on Prana. As mentioned previously, the sun came up early and the ventilators did not block much of the light, so we were awake early. Manny tended to sleep a little later so we tried to wait until 7:00 or so prior to opening the door and starting breakfast proceedings. The first morning we saw that there were large bags of cereal; raisin bran and plain cheerios. We reached for the raisin bran but Captain Bill said no... the cheerios had been opened so he didn't want to open another bag until the first was finished. Of course Bill didn't eat cereal, so he didn't care about eating the same bland cereal each morning. So the standard breakfast for most of the week was cherrios with bananas. After breakfast we did the housecleaning, including cleaning the heads and carrying off any accumulated trash. We were also instructed to "swab the decks" each morning. We used a bucket to lift seawater to the deck, and broom/brush to clean. I doubt that you would do this on a real bareboat charter and the other Bluewater school boat students did not so this, but Prana was Captain Bill's boat, so we washed it every day.

After getting everything in shape, we would plan the day's sailing. After the first couple of days it was our responsibility to lay out the course and figure out how long it would take to get where we were going. This required getting the weather forecast for wind and sea conditions. Of course Captain Bill had special phone service that allowed him to get good information "online" while we tried to listen to the NOAA forecast, which was almost unintelligible. After a couple of days I found that I could usually pick up enough of a wireless signal to pull the Wind-Guru site which had about the best information available.

Then Captain Bill would tell us what we were really going to do for the day: what sailing exercises or drills we would do and where we were to anchor or moor for the night. This first morning there was apparently a lot to cover as Captain Bill went through many details of the weather forecast, keeping logs, maintaining the boat's systems, and such so we didn't actually leave the dock until shortly after noon. Although leaving the dock and docking the boat were both on the list of things we were supposed to learn, we only did each twice, and all times Captain Bill was at the helm; after all, we didn't want to take a chance of putting a scratch on his boat. That Sunday afternoon we left Redhook and sailed to Francis Bay, on the Northwest coast of St John.

Moored in Francis Bay, St John. The boat on the right is Weatherbird, the other Bluewater school boat.

It only took a couple of hours but it did give us a chance to get to know Prana and how to operate all the lines and the winches. We moored in a good spot in Francis Bay, where the northerly swells should not affect us much during the night. That evening we broke out the propane powered grill and appointed Manny the grillmaster to cook some chicken. We had our wine and watched a nice sunset that evening.

Sunset in Francis Bay.

Monday: School continued

We slept surprisingly well for the conditions, with no real ill-effects of being moored in an open bay. As usual, the sun got us up early and we went through our normal morning routing, including cheerios with bananas, checking weather, keeping logs, cleaning, and collecting trash (there was a trash bin on the beach). I will say that Captain Bill was good about getting a pot of coffee going in the mornings. Any coffee that was left one day would be reheated the following day for the first round of coffee while the fresh pot perked.

Today we would mainly stay in Francis Bay and do some drills, working on tacking and a few jibes (some people prefer to spell them gybes). Besides learning how to handle the larger boat, we also had to learn to work together as a team and each person had to work each position for a while.

Susan at the helm doing the drills.

As with most days, at lunch either Captain Bill would take over while we made sandwiches or we would take turns going below to fix our sandwich. About midafternoon we left Fancis Bay for the short sail around a large point and into Leinster Bay to the east. Again we tied up to a mooring for the night and studied for a while. We had to take three written tests during the week, based on three books, so we had to study quite a bit to make sure we got the required 80% passing grade. Manny went snorkeling around a small island named Watermelon Cay. For dinner we again appointed Manny the grillmaster and this time he prepared some hamburgers.

Snorkeler's view of Prana. (And Prana has never been to Key West).

Tuesday: an interesting day

Tuesday morning was the normal routine, breakfast (more cheerios), cleaning, checking the weather and planning the day. Today we would do a bit more real sailing, leaving Leinster Bay, sailing north across the "Narrows" between St John and several islands of the British Virgin Islands. We were headed for Diamond Cay on the eastern end of Jost Van Dyke where we would do some drills and then sail over to Cane Garden Bay on Tortola.

A ferry passes just in front of us in the Narrows.

It was nice just sailing for a while although Captain Bill would quiz us frequently on just where we were and where we were headed. Crossing the Narrows was a little interesting as the wind tends to funnel down the relatively narrow passage, stirring up some waves and there was quite a bit of boat traffic. On the way to Diamond Cay we passed Candy Cay where there were quite a few boats anchored at a sandy beach. In the Diamond Cay area we practiced "circle drills" which are quite challenging as it involves almost constant trimming of the sails and alternating between doing tacks and jibes. This is one drill where the person at the helm really has it the easiest, but again, we all took turns at all positions. When we got tired of going in circles, we headed toward Cane Garden Bay on Tortola. It was almost straight upwind so we were tacking a lot and we didn't have full sails set (to make the drills easier) so it took a while to sail the couple of miles. Cane Garden Bay turned out to be rather interesting in several ways. Manny wanted the experience of anchoring rather than mooring and Cane Garden offered some good anchoring sites as well as moorings. We anchored with no major problems and, as usual, Weatherbird ended up close to us again.

Captain Bill, Manny, and Susan up forward, Weatherbird close by, in Cane Garden Bay.

There is a small town here so Captain Bill took Manny, Susan, and I in the dingy to a dock and dropped us off. (Apparently he did not trust us with the dingy.) Our mission was to get ice for the wine and perhaps some more wine as it was running low. We found a store and got the wine and Susan found a box of Granola cereal. Finally, we could have something other than cheerios for breakfast! We picked up a block of ice for the cooler and headed back to the dock. It was about 6:00 but Captain Bill was not to come pick us up until 6:30, so Manny walked down a road to find an old rum distillery and Susan and I headed to the dock and watch the world go by. About 6:10 Captain Bill apparently saw us on the dock and came over in the dingy to pick us up. I suspect that he had been enjoying his gin during our absence as he soon started giving us a hard time about poor planning because we had left Manny on the shore (Bill had to go back and get him at the appointed 6:30) although if Bill and come at the agreed-upon time of 6:30 to start with, all would have been right.

That evening we agreed to meet up with the students from the Weatherbird for dinner at a local restaurant that is well known in the area, Quito's. Although outwardly cordial, I suspect there was some animosity between Captain Bill and Captain Molly; I think they each thought the other would be joining the group for dinner, so neither showed up. This worked well for us students as we could freely compare captains/instructors. The consensus seemed to be that Molly had her faults, but she was not as far off in left field as Bill.

All the students enjoying dinner without the captains at Quito's, Cane Garden Bay.

When we got back to Prana Bill apparently wanted to continue the discussion of our earlier "poor planning". (Perhaps he had continued enjoying his gin?) It turned into quite a discussion of our poor attitudes (from his viewpoint) and his poor teaching techniques (from our viewpoint). I very seldom get angry, and I don't think I ever raised my voice, but let's just say I was rather firm in stating my opinions. Manny was rather quiet during all this and although Manny was generally quiet anyway, I suspect that he didn't want to anger Bill too much as he very much wanted to successfully complete the course. On the other hand I had already figured that we were unlikely to ever use our certifications if we did pass, so I was not concerned about that. In the following days Bill seemed to mellow a little. I'm not sure if it was because of our discussion or perhaps he realized that we really were learning to sail his boat reasonably well.

Wednesday: Crew Overboard!

Wednesday turned out to be an interesting and mostly fun day. Captain Bill seemed mellower, we successfully did some interesting drills, and our overnight mooring and dinner was definitely different. After the normal morning routine of breakfast, cleaning up, and planning the day's activities, we raised the anchor and headed back over to Diamond Cay. I was at the helm on the way over and, according to the moving-map GPS we were heading directly where we needed to go when Captain Bill instructed me to "turn a little to starboard", so I turned about 10 degrees right. He was quiet for about 15 minutes then as it became clear that we were headed for a small island and very shallow water, he asked where I thought I was going. Oh well....

We did frequently have "picture postcard" views of the ocean and islands.

Once in the bay behind Diamond Cay we did Crew Overboard drills. We took a life preserver that we named Bob and would throw him overboard and then we would maneuver back around so as to be able to pick Bob up with a boathook off the bow of the boat. This is a bit more difficult than it sounds; even just getting Bob successfully back on board when properly positioned was tricky. In this maneuver the success depends mostly on the helmsman steering the boat properly and when all three of us successfully completed the exercise, Bill didn't have much to complain about. We even did the exercise a few more times for fun; we were having a good time throwing Bob overboard and retrieving him. We even did a few more circle drills for good measure. Through much of this there was a local fisherman in a very small skiff in the middle of the bay so we were sailing in circles all around him. We wondered just what he thought was going on, although perhaps he sees this kind of behavior all the time.

Prana, Weatherbird and Keremeos moored Mediterranean style at Sydney's Peace and Love Bar and Restaurant.

After we finished throwing Bob in the water and doing the other drills, we sailed around the corner of Jost Vay Dyke to Little Harbor and "Sydney's Peace and Love" bar and restaurant. This gave us the opportunity to do a "Mediterranean Mooring" type of docking: we put the anchor out about 100 ft in front of the boat and tied the stern securely to the dock in multiple places. It turns out that you have to do this right, or Strawberry, Sydney's daughter who runs the place (Sydney died several years ago) will tell you to do it all over. Apparently this is a regular Wednesday night thing as both Weatherbird and Keremeos, a very nice catamaran that is part of the Bluewater sailing fleet, showed up there also. After getting tied up properly we had time to look around and shop in the boutique, which was an experience in itself.

Sydney's Botique: The women running this were fun and very effective salespeople!

Sydney's bar is unique in that it is a "honor bar". It is completely open; you help yourself to whatever drinks you want to fix and write it down in a notebook on the bar. At the end of the night they figure out what you owe for the food and drinks and you pay that. The dinner is done in groups, such as a boat or two at a time (there were several other boats there besides our group). They set up a buffet style serving line with BBQ, chicken, and pork. They also offered optional items like lobster. One of the guys on Weatherbird got the lobster and they served him what had to be the biggest lobster I have ever seen in a restaurant. He definitely got his money's worth. During the evening I found out that the boat captains get their dinner free if they bring in several people on their boats. No wonder this is a regular stop for the Bluewater Sailing boats.

Dinner at Sydney's: The guy in the blue cap has the large lobster in front of him.

Thursday: on the home stretch

Thursday morning we went through our usual routine, enjoying the granola with the cheerios and a fresh pineapple that needed to be eaten. We did our cleaning, took the trash to a dumpster on land, released the lines and headed out. We only had one maneuver that we were supposed to master to complete all the objectives, heaving to. This is a simple process that puts the boat in a state that it will slowly go forward but will not turn either direction very much. This can come in handy of you need to leave the helm for a while. Bill said that Francis Bay was a good place to practice this, so we made the pleasant 90 minute sail from Little Harbor to Francis Bay. Heaving to is actually a simple maneuver after the other things we had been doing, so we each did it a couple of times and Bill declared us done and asked if there was anything else we wanted to do. Manny suggested doing some "figure 8"s that were described in our textbooks, but Bill had not heard of it. We explained that the idea was to pick to markers in the water and sail around them in a figure 8 pattern. We had trouble finding markers that would work but finally I almost completed a full figure 8, but had to cut it short to avoid possibly getting tangled in the lines from a mooring buoy. When we were done in Francis Bay we sailed down to our overnight stop in Christmas Cove, between St John and St Thomas and a short distance from Redhook Harbor. After tying up to a mooring, Manny, Susan and I went snorkeling before studying for the final test which would be Friday morning.

Manny got back from snorkeling first and welcomed us back.

That evening we worked on leftovers (chicken and veggies) for dinner and Captain Bill took some time to go over the subject matter of the upcoming test. The third test was the most difficult of the three, but not just because the material was more difficult. The "textbook" for the third course/certificate was relatively old, unorganized, and poorly written and it turns out the test was similar. Apparently this is a known problem because as Manny, Susan and I were sitting in the cockpit studying just before sundown, Captain Molly came swimming by, stopped for a while, and gave us some good "hints" for the test.

As usual, Weatherbird moored close to us in Christmas Cove.

Friday: Final test and headed home

After the normal breakfast routine Friday morning we took the final test. Although the test had some very "rough edges" all of us passed and Captain Bill said we had all demonstrated the required sailing skills, so we had earned our course certificates. Christmas Cove is only about 2 miles from Redhook so we did not even bother raising the sails, instead I took the helm under power and managed to get us into the harbor, where Captain Bill took over to actually dock Prana. We had set lines and bumpers ahead of time and several guys on the dock helped out, so the actual docking process turned out to be a non-event, other than watching the huge catamaran that was tied up at the end of the dock.

We had a 4:45 PM flight out and Bill had called a taxi driver he knows to meet us at the dock about 2:00. About the time we got tied up at the dock, around 12:00, the driver called back and said that Carnival was in process in Charlotte Amalie and since we would have to drive through it, we should get started earlier. Bill, however, wanted an extra good cleaning of Prana, including vacuuming the interior floors and a very thorough scrubbing of the decks and all fittings with fresh water from the dock. With the driver standing waiting for us, we did the cleaning as quickly as we could and waited as Bill completed the "paperwork" for our certificates. Finally Manny, Susan and I loaded in the taxi and headed out. (Manny was staying overnight in Charlotte Amalie so we would drop him off at the hotel on the way through town.)

It turned out that Carnival did not cause any traffic problems so we dropped Manny off and got to the airport with lots of time to spare. The driver dropped us at a small restaurant just across the road from the airport so we could get some lunch. Now that all the stress was over and we didn't have to rush any more, it was one of the most enjoyable meals we had that week. After lunch we walked over to the airport terminal, got checked in, through customs and security, and still had almost two hours before our flight was scheduled. The flight was on time, reasonably comfortable, and we got home about 10: PM that night. It had been an "interesting" week, and it was good to be home.

The St Thomas airport greets us as we leave.

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