

Day 5– Saba Rock to Diamond Cay
We decided to skip the journey to Anegada Island because the winds were predicted to be less than 6 knots all day and most of the next day. The trip to Anegada from Saba Rock is a 23nm journey and you don’t pass anything along the way so it’s a lot of motoring there and back. Instead, we decided to take a slow motor to the western end of Jost Van Dyke and stop numerous places along the way. We started out early (about 6:40am) and stopped at three snorkeling areas. Each one was a little different and amazing in its own way and each about an hour motoring at 6 knots apart.
Our first stop was off was the southern coast of Great Dog Island. The Dogs have many scuba diving spots, but only one that is truly great for snorkeling. It’s along the southern end of Great Dog Island. There are 5 National Park buoys allowing you to moor and snorkel right off the back of the boat. The reef is west of the beach and the day we were there the water was crystal clear and full of beautiful fish. The maps talk of a coral garden and it does not disappoint. The plant life and coral alone is worth the trip, but there are plenty of fish to be seen as well.



We ate a quick snack on the boat before departing for our second spot, Diamond Reef. It is located between Marina Cay –near Scrub Island — and Great Caminoe. There are multiple moorings in this spot but they are close together, so we chose one at the southern end to stay out of harm’s way. Be careful to fully come around the shallows south of Marina Cay before turning in. This area is partially demarcated by buoys but the shallows extend a decent bit to the east of the island so be extra careful if you have a deeper draft vessel. Some people anchor here overnight but one must stay clear of underground power lines when dropping the hook so stay southwest of the mooring field and consult an up-to-date chart if going this route. There is a dinghy line near the reef to tie off to. It is demarcated like all dinghy lines in the BVI’s by a line with several blue and white buoys connected to it and is attached on both ends to the bottom.



After working up an appetite snorkeling, we took the dinghy over to Trellis Bay (basically directly south of the mooring field near Diamond Reef) for a drink and some lunch at The Loose Mongoose. It was just rebuilt following Hurricane Irma and is absolutely amazing. The food was fabulous. We shared ribs, fish tacos, a shrimp roti, some fish bites, and buffalo tempura vegetables. The adults shared the drink of the day, a kiwi gin drink, that was tasty and refreshing. The kids opted for virgin daquiris and painkillers. The servers here were all very friendly and filled us in on a bit about the Bay and gave great advice on food choices. We also picked up a 20 pound bag of ice here to replenish the supply. Feeling full and ready for the next snorkel we headed back to the boat.




The next stop was Monkey Point, a snorkel area that is just around the southern end of Guana Island. We recommend when moving from Diamond Reef to Guana Island to take the inlet between Little and Great Caminoe Islands. It’s narrower than the pass between Little Caminoe and Tortola but has a consistently deep area in the middle where the pass between Little Caminoe Island and Tortola is more inconsistent without local knowledge. We arrived at Monkey Point around 1:30 and found 2 open National Park mooring balls available (if we haven’t mentioned already, all National Park mooring balls we used were day only and not to be used for overnight stays). We moored the boat and rode the dinghy out to the dinghy line which is all the way at the south end of the mooring field. It’s best to approach the line from the west outside the mooring field to avoid snorkelers that are in close to the shore along the reef. The water here was a bit cloudier than the two other spots we hit this day. Not sure if it was the time of day, tides, or if that’s just how it is, but this area made up for it with a far greater number of large fish. We saw a spotted eel and 5 cuttlefish. The current can be strong at Monkey Point (which is another reason why the water is likely more cloudy), so swimming to and from the boat can be more challenging than the other spots we visited. I recommend using the dinghy unless you get a ball close to the point, as that’s where the best snorkeling is.



All in all, three great spots to snorkel. For those of you who can’t visit all three, we will summarize to help you choose.
- For those with small children who aren’t the greatest swimmers, or not experienced at snorkeling: Diamond Reef is the most accessible and protected. It has great fish and some shallow areas where fish can be seen easily near the surface especially if snorkeling with a noodle or life jacket.
- For those looking for beautiful underwater scenery, especially coral, sea fans, etc., the area south of Great Dog is by far the most beautiful of the three locations
- For those looking for a wider variety of fish, eel, etc., Monkey Point is the best. Additionally, the spot has the added bonus of White Bay Beach being right next to the snorkel area allowing those who choose not to snorkel to sit on the beach instead of the boat.
Tired and satisfied from a long day, we made the 9 nm motor, as there was still no wind, to Diamond Cay between Jost Van Dyke and Little Jost Van Dyke. We had reserved a Boaty Ball to make sure we had an anchorage as we were coming in less than an hour from dark. That said, and likely because we did reserve one, there were plenty of balls to be had. We cleaned up a bit and took a dinghy ride to Foxy’s Taboo, Foxy’s sister bar, for a drink. The wind was light, but the no-seeums were not, so we left quickly and headed across to try the B-Line bar on Little Jost Van Dyke. It was far less buggy and they had cornhole out for the kids. We had a drink there and met the husband and wife owners, lovely people who moved to the BVIs from Jamaica shortly before Irma and are still recovering from the hurricane that decimated these islands. They also have moorings available. We were having a great time and ordered some delicious honey stung wings. Foxy’s Taboo has the name, but the B-Line is where it’s at. Anyone in this neck of the woods should definitely make a stop at the B-Line for a drink and a snack. Both locations had Wi-Fi available, but the B-Line could be used on the boat, especially if moored on the B-Line balls. Movie for the night was Cruella, but we were so tired only the oldest child made it to the end.





Day 6– Diamond Cay to Cane Garden Bay
We woke up to a beautiful sunrise and started slow, letting everyone sleep in as we all needed it after a long day in and on the water. We left the boat around 9 after some egg, ham and cheese bagel sandwiches and headed out for the famous bubbly pool. It’s a pool that has a small opening to the ocean that affords the waves entrance, but in a controlled way that makes it nature’s jacuzzi. The weather was predicted to be colder than usual and very windy, so we wanted to get to the pool prior to the wind really kicking up. The trail to the pool starts behind Foxy’s Taboo through the back gate. You head right down the path that runs along the edge of Diamond Cay. There is driftwood and debris that obscure the path, but if one looks hard enough the trail can be seen and followed. As you come around the top of the bay a sign that says “up da rock” can be seen. These orange lettered signs help guide you the rest of the way to the pool. When we arrived, a few wild goats were by the pool. We guess humans aren’t the only ones who appreciate this interesting natural phenomenon. The pool is awesome, but if it isn’t high tide or there aren’t any waves, it’s a bit underwhelming. We were lucky to get a few huge waves and therefore the full effect of the pool. A quick note: the walk there does involve climbing rocks, narrow paths and uneven terrain. Those who are less coordinated, older or very young, or not in reasonable shape may find this a challenging hike. The entrance to the pool is over numerous slippery rocks and the pool is quite deep in the middle (5-6 feet) with a strong rip current when the larger waves come in. Those who are not great swimmers should be careful to stay in the shallower end of the pool and/or wear a life jacket.









cAfter returning from the bubbly pool, we decided to motor down to Great Harbor on JVD to try and score a mooring ball. We got there around 10:30 and drove between Great Harbor and nearby White Bay for an hour or so but could not get a mooring ball. The winds for the night were predicted to be strong, so the moorings and prime anchoring spots filled up quickly. A quick word: When looking for a mooring early in the day ask people if they are leaving. We tried to be polite and lurk a bit away from the moored boats, as a result, we had not 1, but 2, moorings stolen from underneath us because less polite souls drove right in front of us. After an hour or so of searching, we took this as a sign that we weren’t meant to be at Jost Van Dyke for the night. This is also the most common spot for pre-departure Covid testing, making it the place to be on a Thursday for folks leaving Saturday or Sunday. (This may change now with the US testing window moved to 24 hours before entry back in the States.) We headed out to Cane Garden Bay because we brought antigen tests we could do from anywhere with Wi-Fi. This is a tip we recommend to all as long as the pandemic rages. These tests allow you in about 20 minutes to do a rapid antigen test (good right now for fully vaccinated folks — which we all are) anywhere where you have Wi-Fi and it’s quiet enough to hear the person guiding you through the test. We used the Abbott Binax Now Covid-19 home test (6 for $150). After a beautiful sail where the wind cooperated, we arrived in Cane Garden Bay and headed straight in to do our Covid tests. We went to Paradise Bar Restaurant. This quaint beach bar is great and right along the swimming area of the beach. The staff were so nice and when they saw we were doing our tests and struggling a bit to hear the telehealth folks, they turned off the music and left us alone without being asked. What great people and a great place to see a sunset. We were all negative for COVID and ready to apply for our visas. The boys went swimming and the adults enjoyed a drink and some music.







It was Thanksgiving and one restaurant had a full Thanksgiving spread (something we didn’t expect but will take advantage of in the future if we do the BVI’s again for Thanksgiving) but we had already planned and purchased steaks, potatoes and shrimp for our Thanksgiving feast. We got back to the boat fired up the grill and made a feast to be thankful for. The movie for the night was Home Sweet Home Alone and both adults fell asleep again before the end. Honestly we are not sure we have ever gone to bed as early as we did on this vacation.
Day 7– Cane Garden Bay to Norman Island (The Bight)
Glad we got a mooring ball last night, as the wind and waves were significant and it was nice to not be worried about an anchor slipping. We didn’t sleep great because the boat was rocking and rolling. Although we don’t get sea sick, it is hard to sleep when the boat is banging around. The kids, typical teenagers, slept through almost all of it, but Mom (and therefore, Dad) was up every 30 minutes or so making sure nothing fell off the boat. We loved Cane Garden Bay but would advise against mooring there overnight unless the wind is calm or from the south/southwest. Also, we would recommend mooring as close to the western shore as possible as it seemed better protected from the more typical westerly winds.
We got up around 8:00 and headed over to White Bay where we anchored to try the Soggy Dollar. The swell was 3-4 feet so it made for an exhilarating ride over to Jost Van Dyke. Once you’re through the channel and the reef here there is an excellent sandy bottom for anchoring with great holding. Having known this, we would have been comfortable anchoring here the night before. Live and learn as they say. We beached the dinghy and drug it the whole way above the surf at the Soggy Dollar. The Soggy Dollar lived up to the hype with an incredibly soft sand beach and great adult beverages. They have a ring game, cornhole, and a ton of umbrella tables. We had a drink, a swim, and some games then headed back to the boat.






Then it was time for a great sail at 7-8 knots (with a reef in) over to Norman Island (The Bight). The Bight has a protected marina (except form northwesterly winds) with 100 mooring balls. We grabbed a ball and headed out to the Caves around the westerly tip (Treasure Point) of the Bight for some fantastic snorkeling. We recommend buying a dive flashlight or two to explore the Caves as they are dark but full of interesting fish. This area has shallows and deep areas so there are multiple ranges of size and species of fish. There is a strong current in certain areas, so a noodle or strong swimming abilities are recommended near the changes of tides. If not staying over in The Bight, one can moor at the National Park mooring buoys and either swim or use the dinghy line as we did. It can be a bit cloudy in some areas but is full of great fish.



After a great snorkel we made our way back to the boat to drop off the gear and head to Willy T’s, a boat moored in the west end of the Bight, which features great drinks, merchandise, and food as well as the chance to jump off the top deck into the water. This is an experience appreciated by all. We even saw a few grandma and grandpas jumping off with their families! After a few hours, and a lot of flips and jumps, we headed back to the boat.





Dinner tonight was on Norman Island at Pirate’s Bight. In one word, the food was spectacular. As we had been doing all week we ate family style. We ordered octopus and potatoes bravas as our appetizers and both were spectacular. The octopus was perhaps the best we have ever had. For the main course, we shared a seafood jambalaya (with lots of fresh seafood), grilled wahoo (again fresh and amazing), an Anegada lobster (which was incredibly meaty, tasty, and different than the Maine lobsters we are used to), and a chicken roti. Of the six dishes, not one was bad. We had wanted to ride over to Willy T’s for one more drink but we were absolutely wiped and all hit the sack by 8pm.




Day 8-Day in The Bight
We decided after a great night’s sleep in a still harbor to stay in the Bight for the next day and overnight. This was the second spontaneous change of plans during this vacation and part of what makes sailing so great. We headed out after a small breakfast aboard the boat to the Indians by dinghy. As the seas were relatively calm and they sit less than half a nautical mile from the Bight there was no reason to move the boat off its mooring. If the seas are rough, your dinghy not as seaworthy, or you are just passing through for the day, there are also National Park mooring balls here that can be used as a home base. The dinghy line is to the north of the last rock (Indian) off Pelican Island. The whole area around the Indians, and between them and Pelican Island, is a reef, so there are so many places to snorkel. This was the most well-rounded of all the places we snorkeled and absolutely worth a stop. There were shallow areas with deeper crevices, plus a large deep area in the inlet, as well as off the west cost of the Indians which would be a great place to scuba as well. We saw one huge school of fish as well as many kinds of fish including a few we hadn’t seen yet on this vacation. The plant life and coral were also beautiful with very little reef destruction or bleaching.







We decided we would hit Willy T’s again for some flips, dives and some lunch. Dinner was on the boat with chicken, shrimp, and rice and beans.
All in all, a relaxing last day before an early wake up call to get back to the Moorings base ahead of a ferry to a plane to home.
Day 9– Trip back to Moorings Base and sad ride Home

We awoke to a beautiful sunrise and set off back to the Moorings base to drop off the boat and prepare for the long journey home. James met us right outside the marina and helped us dock the boat. Thank God he did, as the slip they put us in was a really tight squeeze in between a catamaran and the concrete wall of the marina.
We washed off the boat and had a post charter run down with a staff member. We then jumped on a cab for a ride back to the ferry terminal and to pay the multiple fees to leave the country. We used the Road Town Fast Ferry on the way back to the USVI and it, like the Smith’s Ferry, was air conditioned and well appointed. Upon arriving in the USVI we cleared customs and took a cab to the airport to await our flight. American Airlines as they are want to do recently, had cancelled and rescheduled our flights a few weeks prior, turning our 6 pm direct flight arrival into Philadelphia into a layover in Miami leaving hours later and a midnight arrival at home. The airport is nice and has a few areas for food and snacks but is small and our wait felt long. The flight home was nice but the cold air upon arriving in Philly was a shock to the system.

Last Thoughts
What made this a great family vacation:
- We spent a lot of time off devices and disconnected from the internet which allowed us to bond and make memories truly as a family while all present.
- The boys got to grow closer as there wasn’t as much competition but instead, shared experiences.
- We had adventures as a family with tons of inside jokes and funny memories to remember.
- We shared almost all our meals family style allowing us all to experience several different flavors everyday and often try things we wouldn’t as individuals.
- We ate together and talked about the day and what we were looking forward to the most. This is something our busy lives often don’t afford without some disruption.
What the kids thought?
- The eldest’s favorite things were:
- All the snorkeling (Monkey Point was his favorite)
- Willy T’s- flips, dives and good times with new friends
- The B-Line bar with cornhole and fast Wi-Fi
- The youngest’s favorite parts were:
- Willy T’s
- Snorkeling at The Caves off the Bight
- B-Line Bar
Would we do this again? Absolutely. We already have a Bahamas charter vacation on the books this year, but we think another trip to the BVI’s is definitely in the cards in the next 2 years.
What would we do different- Not much really, but when we come back we definitely want to get out to Anegada. Other than not getting to Foxy’s, we really did most of the highlights otherwise (and didn’t feel rushed doing them). We would probably skip Salt and Cooper Island which were both fun and the Cooper Island Beach Club was beautiful, but having the lay of the land and being there once, a longer sail on day 1 is something we would definitely do. We definitely would do Jost Van Dyke on less crowded days and skip Cane Garden Bay as an overnight as it was the only night we really had trouble sleeping. We would also fly directly into and out of the BVI’s. We didn’t do this for Covid purposes, but without those restrictions there is no need to fly through the USVI.
Final Recommendations: A few things to remember when planning and going on a charter sail trip in The BVI’s:
- Allow yourself some extra time and allow for planned flexibility as you don’t decide where the wind comes from and how much wind there will be. Spending too much time motoring and racing to locations without time to enjoy the sail and scenery defeats the purpose of this type of vacation.
- If you’re not sailors, or don’t want to be bothered, consider a captain. But if you’re up for the adventure, the BVI’s are a very approachable place to sail even for those without years of experience. Consider taking a course (we used US Sailing for our training and you get 10% off with the Moorings if you complete your bareboat cruising with US sailing) and set off for adventure.
- Do not miss The Bight, The Baths, Diamond Reef, Monkey Point, The Caves, and the Indians.
- Places to go if you’re near by:
- B-Line bar (Diamond Cay)
- Bubbly Pool (Diamond Cay)
- Pirate’s Bight (The Bight-Norman Island)
- The Loose Mongoose (Trellis bay)
Fascinating trip full of adventure, fun facts, and good advice for traveling during the time of Covid. Emphasized the advantages of a well – planned vacation and the importance of being able to adapt and go with the flow. Traveling with young folks close in age with a spirit of adventure and independence seems valuable to the adults also having a relaxing enjoyable time. The photo spread enabled you to visualize the various places and made you feel like you were there. Snorkeling and other outdoor activities in abundance, good food and endless vistas, and friendly professional staff at all the venues added to the total package that this trip provided. There is a certain admiration for the tenacity of the people on an island that has been devastated so recently by tropical storms. The Wandering Keller’s hit a grand slam on this one.
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Glad you enjoyed it. It was really a great trip. Really approachable place to sail and explore.
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I did a double take and had a good laugh while reading about your kids’ selections at the Loose Mongoose. I hadn’t heard of a Painkiller cocktail. At first, I just thought they found a way around the virgin aspect of their daquiris. A really loose mongoose indeed……
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Definitely a great experience had by all. The painkiller is definitely a great cocktail to sip and the frozen version at the soggy dollar is definitely my favorite.
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What an incredible trip! Your family will treasure these special memories forever!
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I’ve always wanted to sail through the BVIs. You make the trip seem so easy, even with teenagers. You stopped in so many wonderful places and fantastic reef destinations. I can’t wait to see where you go in the Bahamas!
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wow what an amazing experience for you all. Hubby dives and we enjoy snorkelling so sailing through the BVIs would be a bucket list item for us.
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A very interesting journey! You have such varied and busy days. I think you saw a lot of new places and got positive energy from this trip!
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You squeezed so much into your trip and still it sounds like you had a very relaxing time, well done there..!! Sailing around the Caribbean is definitely a lifetime goal of mine. The BVIs look very attractive, because you’ve got the beaches and diving locations but all looks pretty well organised.
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I have to say it is really the ideal place to sail as everything is close, all the mooring areas have dingy docks ashore, there are lots of different places to eat and dive as well as the water is deep nearly everywhere so not too much worry of running aground. It’s definitely a very friendly place to visit for your first charter sail.
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