Sailing the Virgin Islands on a Crewed Catamaran

By David Barclay | April 10, 2024

I’m back from my family’s spring break trip sailing on a chartered catamaran in the Virgin Islands and it was a blast.  Today’s blog post will recap our trip, to give you an idea of what it’s like to charter a crewed catamaran for a week.  As a reminder, when you charter a crewed boat or yacht, the itinerary is completely customized for the guests.  I have highlighted what we did, but if you chartered your own catamaran you wouldn’t have to follow the same itinerary or stop at the same places as we did.

Flight to St. Thomas (STT) and the flexibility a charter provides for managing travel complications

We chartered our boat (named Huntress) from Saturday to Saturday for a full 7-days to take advantage of direct flights on American Airlines from ORD to STT. It is possible to charter boats in the Virgin Islands for different trip durations.  While a week is the standard and charter rates are quoted on a weekly basis, it is possible to charter for fewer days (usually a minimum of 4 days, but this is determined by the boat owner).  It’s of course also possible to charter for longer than a week for those with more time to travel.

When I’m helping clients with a cruise booking (on one of my partner luxury cruise lines) I always advise my clients to fly into the embarkation port at least 1 day early, to buffer against any flight delays.  If you don’t get to the port in time for a cruise, the ship will leave without you and then you are trying to play catch-up at the next port, which is not a fun way to start a vacation.  But since we had chartered our catamaran and knew it would wait for us if our flight was delayed by bad weather, we decided to accept the risk of arriving on the same day our charter began (with a direct flight from Chicago we thought there was little risk of a significant delay and we didn’t have to worry about missing a connection).  So we weren’t surprised when we were informed our flight would be delayed, and even though we took off 2.5hrs late, we were comfortable we had made the right decision.  However, about 40 minutes into our flight, the plane altered course a full 180 degrees.  Soon after making this course change, the pilot announced they had discovered a fuel leak, and we were returning to ORD. When we landed, we were informed our flight would not depart again until the next morning, a full 24hrs after the scheduled departure time.  While we were very disappointed with the start to our trip, we had kept our captain informed of our flight challenges.  Two of our guests had flown down the day before and were already on St Thomas, so they boarded Huntress and the crew took them out to a local cove to anchor for the night.  The next day we finally arrived on St Thomas and took a quick pre-arranged (by our crew) cab ride to the harbor.  The crew had already brought Huntress back to the harbor and were waiting for us at the dock.  While we were bummed at arriving a day late, the crew sprang into action to make up for lost time, quickly getting us on board, supplying us with much needed beverages to take the edge off our travel challenges, giving us a short safety briefing, and then sailing out so we could enjoy our vacation.  Although we had lost a day of our vacation, it was by no means ruined, thanks both to the flexibility of a private charter and the incredible service provided by the crew of Huntress.

Huntress:  A Quick Overview

Huntress is a Lagoon 620.  Lagoon is a well-know manufacturer of catamarans and the 620 model is 62′ long.  The smallest catamarans that are available for charter in the Virgin Islands are around 45’ in length and they can range up to 80’+.  As the catamarans get larger, they typically don’t add more guests, most catamarans regardless of size are designed to accommodate either 8 or 10 guests (in 4 or 5 cabins).  Some 50-52’ catamarans might accommodate 10 guests, but even through Huntress is larger than that, she was built to accommodate a max of 8 guests.  What you get as the catamarans get bigger is more space on board, which means larger cabins, bigger baths/showers, larger covered aft areas for lounging & dining, larger flybridges (the 2^nd level above the covered aft section), more space to store water toys, and more room for additional crew members.  That was one of the key reasons we picked Huntress over several smaller catamaran that were available for charter, we liked the larger cabins (with a larger primary cabin for my wife and me that had a larger shower and dual vanities) and that she had a crew of three (Captain, Chef and Stewardess).  On first impression, I was surprised by the beam (width) of Huntress, she was much wider than I expected and both the bow area by the trampolines and the aft covered area were very spacious and could easily accommodate our entire group (and even one night, watching Moana as our entertainment, both our group and the crew fit comfortably in the aft section with good views of the TV).

As I mentioned, Huntress has a crew of three.  Captain Keagan was responsible for sailing the ship.  Chef Olivia plied us with 3 meals and many snacks each day, and Stewardess Haley brought us drinks, tidied up our cabins and generally saw to any needs we had.  But the crew was also flexible and pitched in to support each other, ensuring we were always well cared for.

Our Itinerary

While there is no prescribed route to sail in the Virgin Islands, for first time visitors the crew will generally try to sail a route that hits the highlights of this island chain.  There are two typical starting points for a charter in the Virgin Islands, and where you meet your boat will likely depend on where it’s harbored (though arrangements can also be made in the charter contract to pick up guests at a different location if needed).  Charters may start in St Thomas, in our case we met Huntress at the Yacht Haven Grande marina, but Red Hook Harbor on the east side of the island is another common starting point.  Other charters may depart from the Road Town harbor in the British Virgin Islands.

Charters departing from St. Thomas will likely also visit St. John but have fewer days to sail the BVI, while charters starting from Road Town will have more time to sail the BVI but are unlikely to visit the USVI.  Here are a few sample charter itineraries, courtesy of my partner Ocean Getaways.
USVI / BVI Yacht Charter Itinerary
British Virgin Islands Yacht Charter Itinerary

The USVI / BVI Itinerary describes a route that begins along the southern part of the Virgin Islands and then loops back to return along the northern part.  Because of the weather and the direction the winds were blowing during our charter, Captain Keagan had pre-informed us that we’d take a different route. We started by sailing the north side of St. John towards the BVI.  As we entered the BVI, we made a quick stop so Captain Keagan could take our passports and paperwork into the immigration office (we stayed on board and enjoyed the first of many wonderful breakfasts) and then we headed up to Jost Van Dyke to start a clockwise navigation of the BVI.

Our desire for this trip was to spend a lot of time sailing, swimming in the water, and playing with the water toys.  While Captain Keagan offered to take us to the Soggy Dollar bar on our first day in the BVI, and to stop at some of the other well-known bars and restaurants, we opted to skip these and spend most of our time on (and swimming around) Huntress.

About half-way through our cruise, the crew inquired if we would like to harbor overnight in the marina of a nearby resort on Scrub Island, which would allow us to use the resort’s pool and spa.  While we had planned to spend most of the time on the ocean, this was an enjoyable break to take in some time on land and let our kids swim in a resort pool.

Meals

Chef Olivia was incredible, and her creations were both beautifully presented and delicious.  Charter rates for Caribbean charters are mostly all-inclusive, which means all of our meals, snacks, and beverages were included in the charter rates.  If you think that means the crew/chef will skimp on the portions or quality of the ingredients, you would be wrong.  In fact, we felt our crew had gone overboard providing us with incredible food.  We had steak, lobster, crab, charcuterie boards on multiple afternoons, plenty of fresh, raw or partially cured fish (poke bowls, ceviche, lox, etc.), and the best bacon twists ever.  Olivia and the crew also had a gigantic snack basket for us with chips, cookies, popcorn, granola bars and other snacks, and to the delight of our children, the basket “magically” replenished itself anytime it looked more than half empty.

One of the advantages of a private charter is the food can be tailored to the guests’ preferences.  We had completed a charter preferences questionnaire about 2 months in advance of our charter, so the crew was aware of our food likes/dislikes and food allergies.  One of our adult guests is allergic to fish and our children also have several food allergies.  Olivia was able to craft a menu for the week that included meals our kids would enjoy, while still providing more adventurous fare for the adults.  When she made the adults her famous poke bowls for lunch, she substituted watermelon she had marinated herself for the raw tuna in the poke bowl for our friend who is allergic to fish, and we all agreed it was a delicious substitution that satisfied his allergy needs while still letting the other adults enjoy a traditional poke bowl with raw tuna.

The crew also knew our beverage preferences and had stocked Huntress with the sodas and alcoholic beverages we had preferenced on our questionnaire.  Haley was an expert in crafting delicious cocktails for us, and when our daughters learned they could ask for virgin strawberry daiquiris, the daiquiris become a daily afternoon treat for the kids.  The crew was also good at restocking as our week progressed.  When they discovered we enjoyed a particular type of wine on board, or we were getting low on a particular soda, Captain Keagan would make a quick trip ashore to purchase additional provisions.

Activities

You may wonder what there is to do for a full week sailing the Virgin Islands.  I can tell you we were never bored, and it was a most enjoyable vacation.  The experience is like a resort or beach vacation, with periods of activities combined with time to relax (lounging in the sun or reading a book).  And although everyone is on the same boat together, everyone doesn’t have to do the same thing.  Some guests can relax while others are more active, swimming or snorkeling in the water. 

Every one of our days involved some time in the water.  If we were sailing past a good snorkeling location, the crew would anchor, we’d get our gear on and head into the water.  Sometimes it was as simple as just exploring around the boat, other times one of the crew would take us on an escorted snorkel, so we wouldn’t miss the best parts of that underwater spot.  While we sailed, there were opportunities to troll for large game fish, and this was the activity my son was most excited to try on our charter.  

Part of our party getting ready to launch the floating island & my son hard at work trying to catch “the big one”

Snorkeling in the beautiful waters

The water toys on board a chartered boat are very important and can make or break a charter experience, so it’s important to know in advance what the boats have when considering which to charter.  Huntress had all of the more common water toys, but also had two battery powered sea scooters, and the crew was happy to let our kids use them.  Once our kids found out about the sea scooters, our crew was swapping and recharging the multiple battery packs on a daily basis.

Huntress also included standup paddleboards and she carried scuba tanks and equipment.  The crew will take any certified scuba divers on up to 3 dives during a weeklong charter (since I was the only certified diver, I opted to skip doing any dives so I didn’t steal a crew member away from being able to take care of the rest of our group). 

One of the other important aspects of picking a boat is getting the right fit between the crew and guests, and for us, we definitely picked the right crew.  In addition to a stellar chef and having a 3^rd crew member to ensure prompt and pampered service, we had wanted a crew that was good with kids.  The crew of Huntress hit it out of the park in this department.  Olivia & Haley happily played cards and other onboard games with our kids (Uno became a favorite for the charter).  Captain Keagan oversaw the water sports and was very good and patient with our children.  He took them tubing behind the tender multiple times, and even tried to teach our kids to wakeboard.  He was always optimistic and encouraging even though for most attempts they didn’t get up out of the water and the few times they did, they only stayed balanced for a few seconds.  But rather than be discouraged, they were invigorated and kept wanting to try again, and we know that only happened because Captain Keagan is so good and patient with children.

Another wonderful part of our charter, for us as parents, is it also provided us with the opportunity for one-on-one time with our children.  This may sound like a paradox, that we enjoyed good one-on-one time while in a somewhat confined area, but it’s true.  I could sit with my son while he fished, at the same time my wife might be at the bow of the ship chatting with one of our daughters, and our other daughter might just be lounging by herself, enjoying the wonderful weather.  There were also many times when our kids were swimming and would convince one of us to jump in.  That parent would get quality time with all three of our kids (of course that only lasted for so long before the other parent would hear all of the laughing, giggling, and splashing and jump in to join the fun).

The Custom Touches of a Private Charter

Any charter crew will tell you their goal is to create an unforgettable experience and life-long memories.  On the pre-arrival call I had with the crew about a week before our charter, I asked if they could arrange a special surprise and activity for our kids.  That request was to design a treasure hunt, where our kids would find an initial clue on board Huntress and it would lead to an adventure/hike on land, culminating in finding a “treasure” at the end.  I can’t recall where I had heard of the treasure hunt idea, but I knew crews of other yachts had planned similar surprises for their guests.

Again the crew of Huntress knocked it out of the park and exceeded every expectation I had for this activity.  They had picked Norman Island for the treasure hunt and given our clockwise route, that meant the treasure hunt was be on our 2^nd to last day, just before we crossed back into the U.S. Virgin Islands.  Captain Keagan and Haley departed Huntress early in the morning, on the pretense that we needed more supplies.  They hid the clues along a path leading to the top of the island and then returned.  As our kids were getting their swimsuits and sunscreen on, the crew put an empty bottle with a message inside by the ladder used to enter/exit the water.  When our kids went to go swim, they found the bottle and opened it to read the message.  Of course, they were a little skeptical when all of the adults (including the crew) feigned ignorance at how the bottle got there, but they were quick to read the clue and start on the treasure hunt.  Haley even pulled out pirate hats for us to wear on our adventure.

Reading of a clue and hiking up to the top of the island

The clues took us to the top of the island where we enjoyed incredible views.  Our kids expected to find the treasure at the top of the island, but as they found and read the last clue, they learned that the treasure was “back where the tenders are docked”. 

Views from the top of Norman Island

They raced back down the hill (with the adults following at a more moderate pace) and after a little searching, discovered that the crew had hidden the treasure under the dock.  The crew had somehow located a very cute Melissa & Doug treasure chest, and upon opening our kids found the best treasure ever, a huge pile of chocolate coins, ring pops, and candy necklaces. 

We returned to Huntress, having thoroughly enjoyed our adventure and our kids proceeded to devour their newfound spoils.

Wrapping up our charter

The afternoon of our last full day on Huntress, we crossed the invisible boundary between the BVI and USVI and anchored once again off St. John.  This time everyone (including the crew) had to go ashore to go through U.S. immigration, but the process was quick, and we were soon back on board for our last dinner aboard Huntress. 

The next morning, we sailed back into the Yacht Haven Grande marina.  It had only been 6 days since we first departed from this marina, but it felt a lot longer, our days and nights packed with a ton of fun.  We finished our packing and Chef Olivia took a few of us to the local grocery store so we could procure lunch and snacks for our flight home.  Then it was time to say goodbye with lots of hugs and a few tears from our children.  It felt like we were leaving behind good friends, and it was hard to believe our time on Huntress was really over. 

The charter after ours was another family that had previously sailed on Huntress and were returning for another week of fun.  After our experience, I can see why chartering can become an annual tradition, an opportunity to bring family and friends together, while reuniting with the crew who also became friends.

The verdict

Our experience on Huntress was exactly what we needed for our spring break, a combination of activities and relaxation, quality time with family & friends, warm weather, and lots of being pampered by the crew.   In the taxi to the airport, our kids asked if we were going to charter Huntress again next spring break and when my wife and I said that was a possibility, they quickly started petitioning for that outcome and haven’t stopped since we’ve returned home.  I must admit, I periodically daydream about being back on Huntress, and if we don’t charter her again for Spring Break 2025, I’m confident it won’t be too long before we are back onboard, creating even more wonderful memories.