We have always wanted to take the family on a big trip for Spring Break. We always saw other families doing this — going to Europe, going to the mountains for skiing — and we haven’t really done that. It was always due to some other priority like getting a new job and having to move to another state, Scouting activities, school sports or not wanting to spend money. After taking some sailing courses, buying our first boat and putting it on the hard for the Winter, we were craving for some Winter sailing. So we saved and found the perfect opportunity to go on a charter sail in the BVIs. Unfortunately, that was right during COVID.
We first thought of going during Christmas 2020, but with borders being closed, we quickly put our sights on Spring Break 2021. At that time, we thought for sure the borders would be opened and we could travel freely. Then we changed the trip to be Christmas 2021. Then we canceled that one for various reasons and we lost our down payment which was around $3,000. Ouch! By early 2022, we felt ready to go to the BVIs and booked the charter again. Mind you that we were already on our 2nd and much larger sailboat. That was a roller coaster of planning and cancellations, but we all lived in that period of time where nothing was certain but facemasks and travelling restrictions.
I want to thank also our sailing trainer and broker, Captain Rick from True North Sailing out of NYC. What a great guy and with so much experience in chartering in the BVIs and elsewhere. We could not have done this charter with Sunsail without his support and guidance along the way. With both of us working and kids at home at the time (10, 15, 17), we had no time to study up and organize this ourselves. I highly recommend anyone doing this for the first time to take this similar approach.
Traveling by Car, Plane, Ferry, Taxi (Sunday)
We flew into St. Thomas and reserved a ferry. That trip went fairly smooth. The plan was to fly in Sunday morning, take the ferry from St. Thomas to Road Town, get on the boat and then take off that evening for our first stop.
Road Town and The Moorings Marina, Tortola (Sunday-Monday)
For whatever reason, we only wanted to charter a 38 foot monohull. Maybe it was due to cost (?), but I cannot recall as it was so long ago. We arrived late at the marina well after dark. There was almost no one working at the marina. After checking in and walking to the boat, we were pleasantly surprised that the 38 footer that we chartered was like new. We hunkered down and had a simple night of eating and card games.
It was a calm night at the dock.
Before we turned out the lights we had discussed needing to ask for a larger boat. We were now well-accustomed on the HR46 to 3 cabins and plenty of space for everyone, but this Sunsail 38 with only 2 cabins was tight. So we awoke the next morning and found the marina to have a few more staff running around. At the desk, I asked if they had larger boats available and how much would it cost to upgrade. To my surprise, they did have larger boats available. To upgrade to a 42 footer with 3 cabins was only $500. I was so excited, I had paid for the upgrade no questions asked.
Little did I know that this would turn out to be a 6-7 hour adventure. The larger boat was a bit older, and we had to reschedule a new safety walk and briefing. We are now on island time, and the person assigned was already walking other boats for arriving customers. He had to squeeze us in. The larger boat was missing a few things that needed to be addressed like a replacement anenometer. That involved calling for maintenance and the instrument crew hadn’t arrived yet. All of these things and plenty of other details I felt that I had to micromanage, because, again this was island time. We could not even put our belongings on the boat that I just paid for because we were waiting for a new certificate from the government with our names on the paperwork. This required a “runner” to drive all over the island to the terminal and print a new certificate. This is our first experience working through the process that these island put in place. There seems to be a good amount of “special fees” required to get processes to move quickly, and I wanted nothing to do with that.
Customers were now returning boats that they themselves had chartered, and one of the families that we befriended gave us a lot of excess food that they no longer needed. They gave us advice where to shop, and so we took a walk to RiteWay Pasea Estate. It was a well-stocked grocery store. We loaded up on a $few hundred in food and got mauled by taxi drivers, and we escaped their greedy hands by walking back. I think Rachel carried 10 bags and I had 15; the kids all had bags to carry as well, but we were surely not going to be taken by local taxis.
The Boat
After several more of my nudging requests and what seemed like an eternity, finally by 2pm Monday, the boat was officially ours and we moved in and on. And we ended up on a 42.1 or 41.1, it seemed that the vinyl lettering on the side doesn’t match the nameplate. It didn’tt matter to us, we were much happier. Or so we thought.
This boat only had 1 cabintop winch with only a total of 3 winches. We could not furl the headsail unless we were on a port tack. We felt that we were somewhat experiences sailors and that anyone that was not experienced could have been in a dangerous situation. We enjoyed the fold-down/walk out transom on this trip. Other than that, it was just a boat.
Norman Island (Monday-Tuesday)
We left the harbor with a partial plan for the week, but we were supposed to start much earlier than 3pm on Monday. As it goes in boating, you have to be flexible. I set the course for Norman Island and we arrived there after a few tacks.
Pulling into the anchorage before dusk, we had time to test the water. Since this is our first charter, none of us can believe we are here and that we actually made it happen. The reality has set in…we are on vacation.
Dinner was fantastic and the restaurant was packed. I wish we would have arrived a couple of hours earlier. Matt was picking the best menu items for the whole trip, and he kept that crown almost the entire week. The next morning we awoke and Rachel took the boys for a hike up to the ridgeline and I stayed on the beach with Audrey watching her swim. Not long later, we unhooked from the mooring and headed for Marina Cay.
Marina Cay and Scrub Island (Tuesday-Wednesday)
After all, we are chartering a sailboat so we decided to sail and sail hard we did. The weather was still blowing 20-25 knots in the exposed sea on the Southeast side of Tortola. This is where we learned the limitations of the boat, because everytime we had to tack, we were missing an extra winch. The boat held up to the wind and our pinching and pushing, so we had a nice spirited 3.5 hour sail.
We landed at the Scrub Island mooring area and took the South side of the Marina Cay motoring in slowly with the sun directly in our eyes. It took us a couple of attempts to get on the mooring ball, due to the wind and poor picking on my part, so we circled around and chose a mooring ball that was farther out with fewer neighbors. It was stunning to look around the anchorage at the land jetting up from the sea.
While safely anchored we realized looking just to our South was the shallow reef that we missed on entry. It was turning dusk and we were so hungry, so we took off in the dingy for a damp ride to shore from Marina Cay to Scrub Island.
We dropped into the restaurant for dinner. It was fine, the service was good — but Norman Island had much better food. After dinner we found some cornhole boards and started to play a family tournament. I don’t recall who won, but it was very relaxing. Back to the boat we go in the pitch dark with only a flashlight. It was a bit dicey as we were in some swell with chop, but nonetheless, the boat was waiting for us upon safe return.
The Baths (Wednesday am)
We got to bed early, because we knew we had to get to The Baths very early to beat the crowds. The Baths is the must-do part of the trip, and there is a strategy to visit either early in the week, later in the week or in the middle of the week. But one thing for certain is: You have to get there early in the day to get a mooring. Nothing would be more frustrating than to sail there and not have a place to tie up.
Best of all this trip other than the sites and the family time is to have uninterrupted time to sail and listed to the water rushing past us.
OK, we landed at The Baths and took the front mooring. I mean the very front mooring. We were very lucky. But we are newbies, so we didn’t know how to get to shore. We weren’t sure if we could use our dinghy or where to tie up. So we decided to risk it and swim all the way in. That was a crazy move with the swell wrapping around the South end of Virgin Gorda. We took our time and got to the swimming area. But being so inexperienced at beach landings, we didn’t really know how to actually get to the shore without being bashed into the rocks. Matt and Aaron went ahead of us and took the wrong route which put them right into submerged rocks; ouch! A quick hike up the mountain gave us spectacular views alongside breakfast.
We hung out a little bit, but it was starting to get crowded with other tourists flocking in so we decided to get back to the boat to let someone else take out mooring. The swim out was a little chaotic again with the boys out in front — and not listening to our screams. By now we have a handful of people driving dinghies up and down the mooring field to drop off members of their crew. But some of these people have no common sense as they sped through us swimming. We had more chance to get run over by a dinghy then drown in the ocean! Rachel’s famous quote from the entire trip was “Hey dummy!”; that was the only way we could get Mr. Dinghy guy to pay attention to us.
Great Dog (Wednesday lunch)
We left our mooring at The Baths as there were several boats waiting in line like they would wait for the close spot in a Walmart parking lot. We had plenty of time on our hands and wanted to find a spot to anchor for lunch. We chose Great Dog, and boy, the water was so clear and we were anchored very close to shore. Scary, though, that we had a lee shore behind us and a rocky bottom. I was nervous the whole time, and could take my eyes off the shoreline and visual markers. But the views were spectacular and the few boats that were there left.
To give you an idea about our anchorage at Great Dog, look at this anchor drag map. Now you know why I was nervous with a lee shore behind us.
Rachel was wasting none of her vacation away from the commotion back home. She snorkeled everywhere she could, and her excitement to explore was showing strong. After a quick lunch someone came into the anchorage and got pretty close to us. So, we picked up anchor and motored away from Great Dog on track for Saba Rock.
Saba Rock (Wednesday – Thursday)
The sail from Great Dog to Saba Rock was uneventful and felt more like a task. As they say, any day on the water is a good day.
This anchorage felt a little different. Sure there were catamarans everywhere, but these boats were noticably larger and there were even some cruiser boats here. It was evident to us that this anchorage and surrounding area had several large yachts and people with larger budgets than we had. We jumped in our dinghy and went ashore. Saba Rock itself was beautiful in its post-hurricane rebuild state. We walked around the small island and scored a water edge table for dinner. We watched all of the yachties come ashore with their crew dropping them off, and other groups arriving in dinghies that cost well north of $50,000.
Saba Rock felt safe buit we could hear the wind and waves just on the North side of the Island. If the island was not there, we would have had quite a rolly night on the mooring. Neighbors had their above- and underwater lights on all night and were playing some music with lots of kids and dinghies motoring past us going to and from the restaurant as well as from boat to boat.
Anegada (Thursday-Friday)
This was the big day. Let’s get our sail on and make a run up to Anegada. We have been waiting for 2 years to make this particular trip by sailboat. We would be met with consistent Easterly winds almost the entire distance.
Anegada was my absolute favorite place from the entire trip. It felt very natural with it’s own culture. We traveled by car rental around the island.
We hung out at the restaurant at Loblolly Bay and practices on the slack line. That was kinda fun for a while with some ice cream.
Then we ventured into the water to snorkel the reefs. Although we spent money on snorkel gear, the kids were being kids and throwing a fit about having to use them or how to use them. As parents, we couldn’t teach them and they wouldn’t listen. The boys took off unaware and mindlessly pursuing the reefs not paying attention to the swell coming in. Matt got himself into a nasty situation, which sent Rachel running down the beach screaming. Such tourists! But he was in a situation where he could have gotten hurt because he didn’t have the gear and wasn’t using what he had correctly. Rachel and I snorkeled out and around and had a great time.
We drove up to Anegada Beach Club and walked around the place. We watched some folks trying windsurfing and foiling. Then we walked through the property and sort of half-played on the volleyball court. Then we got back into the car, drove around a bit then ended the night getting our lobsters.
Great Harbour – Friday – Saturday
The next morning, we tried to unhook from the mooring ball and leave the anchorage. Instead of looking like pros, we looked like a bunch of rookies by getting the keel wrapped up by the mooring lines. We couldn’t go forward or backward. At the helm, I somehow got the rudder turned enough to kick the bow sideways and we got free. Others in the anchorage were a little nervous that we would hit their boats, and for good reason. Nonetheless, we were free and ran out of there with our tails between our legs.
We left Anegada with another monohull apparently with the same destination or route in mind. They went directly for the rumb line. After looking at the wind direction, we elected to point North for a bit coming out of Anegada to get a better wind angle. We pinched all the way to Great Harbour as far as we could get. This would be our last big sail, and our decision turned out to be the right decision as we won the race.
Once we got to Great Harbour we again found a great mooring ball. We snorkeled and walked the shore and tiny little town. We spent a while and some money in the dive shop. Then we hopped in the dingy and went over to White Bay to see what all the fuss was about at the Soggy Dollar Bar. It was a bumpy ride, but once we got into White Bay, we saw so many boats and many dinghys up on the beach. Wall-to-wall people in the water. So we went back to Great Harbour and snorkeled more. It was our best experience for the whole week with snorkeling and water fun. Everyone was relaxed and thinking about the journey home tomorrow.
The next morning we got up early and motored all the way to Road Town. We took Thatch Island Cut which was wild with the current and eddies; it was a bit spooky, but the house on the very West end of Tortola up on the mountain is amazing. We fought our way into the marina by waiting in line and forcibly entering the breakwater; otherwise, the marina folks would not have gotten to us. We struggled with the ways of the island and marina — lack of order, lack of process.
St.Thomas (Saturday-Sunday)
We planned to take the ferry back to St. Thomas Saturday and stay in a AirBnB hotel (The Green Iguana; highly recommend) for the night in order to catch our return flight. That turned out to be a fun choice. That night we were pretty exhausted, so we walked in and around the area of the hotel and near the main harbour to get dinner. Dinner was fantastic, but I forget the name of the place. Then we jumped into the rooftop pool for quick dip. Here is the view that we had from the pool.
We walked around St. Thomas in the morning all the way around to Crown Bay Marina and had breakfast at Tickles. The food was decent and the marina view of all the boats was fun to drool at.
We walked back into town and rented a car there and drove around. We should have done that sooner in the day. The car is highly recommended with so many hills and windy roads. But the rental place was a little sketchy.
We got to the top of St. Thomas and soaked up the breathtaking views.
That is the end of such a wonderful trip. We had an incredibly enjoyable time — a once-in-a-lifetime experience for our family. We also achieved our goal of getting some Winter sailing in; we sailed about 98 nm this trip.
For background, we took this trip with all of the following going on:
- Me ending a job in NJ
- Me starting a new job in MD
- Rachel traveling to Europe for work
- Rachel coordinating a move of her job from NJ to MD
- Selling our NJ house
- Buying our MD home
- Finishing all Winter refit work on Skyward in Connecticut
- Launching the boat in Connecticut and sailing it down to Annapolis
- Planning an Eagle project for Aaron (to be done in May)
Needless to say, April 2022 was one of the most hectic times of our lives, and the trip was the perfect break from that hustle-and-bustle. We would do that trip again in a heartbeat.
The Loxodograph 