USVI Yacht itinerary Vicarious Catamaran sails you around the Virgin Islands with grace, style, and class.

Thank you to Captain Austen for taking the time to write out this fabulous itinerary and trip report that he just followed with our small group of four guests.

Thank you to Chef Phily for serving a menu that sounds like we all want more!

USVI Yacht Itinerary Vicarious Catamaran
Chillaxin' in the front cockpit of Vicarious

Day 1- Christmas Cove

Our adventure began with a pick up from the beach just outside the airport—no waiting for a taxi, instant shoes off, and toes in the sand.

I (Captain Austen) loaded bags and guests in the tender, then ferried Matt and his group over to Water Island, where the big boat (Vicarious) was waiting with drinks ready to serve.

Once everyone had moved into their cabins and got acquainted with the boat, we set off to Christmas Cove, where we would stay for the night.

Matt’s plane had landed around 3 pm, which left us plenty of time to jump in the water that evening even after motoring up to Christmas cove.

Poke bowls were served for dinner! Complements to chef Phily, they were delicious!

Day 2- Caneel Bay, St. John

Before leaving Christmas Cove, we took off on our first guided snorkel adventure around Fish Cay. We saw many colorful reef fish; angle fish, parrotfish, blue tang, fairy basslet, and many corals too!

Matt had mentioned he wanted to gain experience handling the big boat, so on our way out of Christmas Cove, he took the helm with my guidance. Winds were a bit on the stronger side, so we set sail towards the lee of St. John, Caneel Bay / Honeymoon Beach.

Matt kept the boat on a close-hauled course tacking up the Pilsbury Sound, main with one reef and a full jib.

Rather than just going right to the ball, we passed through the gap at Lovongo Cay and Mingo. Then we sailed around Carvel Rock to head to Caneel bay on St. John.


Once on the ball at Caneel Bay, floats were put in the water, and a round of drinks pass around for some thirsty guests. After cooling off in the water, the paddleboards were deployed, and our four new friends paddled off to Honeymoon Beach to explore.

Upon return, we were happy to hear the white sand, palm trees, and beach bar were still there, lol. A relaxing afternoon of sunbathing and some reading preceded a fun evening in Cruz Bay.

Originally reservations were made for Morgan’s Mango, but STJ was experiencing power outages, so plans changed. We were pleasantly surprised with the generator, menu, and drinks at the Lovongo Rum Bar.

Part of island life is knowing how to pivot and make things into little happy moments!

After all, we are on an adventure.

So, what are the rates for USVI Yacht Itinerary Vicarious Catamaran?

All rates are based on seven nights, fully crewed, and inclusive!

  • 2 guests: $19,000
  • 3 Guests $19,500
  • 4 Guests $20,000
  • 5 Guests $20,500
  • 6 Guests $21,200

Day 3- Maho Bay

Again Matt at the helm, and we took a short little jaunt up to Maho Bay. It was time to stretch the legs! St. John is full of hiking trails with stunning views, and from this day on, we took advantage of that.

I dropped Phily off with our guests at the head of the Cinnamon Bay trail. This one required laced up shoes; 900 ft vertical was considered on the All Trails app as a moderate trail. Phily guided the group from Cinnamon to the top and then down to Maho Crossroads, where a well-deserved drink at an amazing beach bar was waiting for them.

They then ate a beautiful fresh blackened jerk chicken wrap with freshly made Caesar dressing and local Caribbean salad greens.

We explored the beautiful beaches of both Maho and Francis that day. From Francis (the northern part of the harbor), our US cell plans still picked up the towers on St. Thomas.

Sunday night football was streaming; I believe the Steelers won!? Dinner was a hit, and the guests stayed up drinking wine on a candlelit bow.

Day 4- Hansen Bay, St John

This was an action-packed day! Coffee was served in Francis, and Eggs Benedict was served in Waterlemon. Knowing we would end up in Coral Harbor that afternoon for lunch, we walked the Annaberg ruins and snorkeled around Waterlemon Cay.

It was about a three hour stop before we were off again! Passing around the Northeast side of St. John, we motored close to the shore to keep plenty of distance between us and the BVI border.

Momentarily for a period, our phones had all jumped onto the BVI cell networks but once around the corner in Coral Harbor, we were back on US towers.

It was 1 pm, and the group was all hungry for some tacos! Matt helped anchor the big boat right by the famous Lime Out. Lime Out is a floating taco restaurant and bar with floating seating all around. Once stomachs full and a healthy amount of cheer consumed, we relocated from Coral Harbor to Hansen Bay.

Vicarious Catamaran at the Lime Out Bar
Oh you know, just chilling at the floating taco bar Limeout in Coral Bay on St John

The rest of the afternoon was spent relaxing on the floats and paddle boarding around the boat. Rick might have lost a paddle, but the water was so clear Philomena could recover it in minutes.

Out on the east end of St. John, there weren’t very many lights, so that evening, everyone could see the stars really well. Phily served a crowd favorite Shishito Buerre-blanc that all of the guests now have the recipe to. They begged us for more bread and sauce to keep savoring the experience.

She made a version of the sauce for those who like it hot and like peppers’ flavor. This group liked it hot! They loved how the dish subtly burned their mouths just enough to keep them wanting more.

They were even more pleased how nicely the Flan that followed cooled their mouths and prepped them for more wine. 😊

Let’s carry on the second half of the week with this USVI Yacht Itinerary Vicarious Catamaran

“We had an incredible week on Vicarious, the perfect balance of adventure and relaxation.  Each day different from the one before.  All the meals were incredible and we enjoyed getting to try different cuisine throughout the week.  The service and experience that Austen and Philly provided have us already looking to book with them again next year. We really enjoyed this trip and it met or exceeded all previous charters we have done in the past.” Matt January 2021

Day 5- Ram’s Head, St John

We pulled up anchor and made a quick hop around the corner to Little Lameshure bay. Both big and little Lameshure are beautiful anchorages, but Little Lameshure has a beautiful sandy beach (often unoccupied).

Just around the corner and accessible by dinghy is Salt Pond, an assess point to the Rams Head trail!

At this point, all our guests were becoming experts boarding the dinghy on and off the big boat and beaching it too. This is a huge plus because it meant we could go to more places and see more!

The Rams Head trail is my favorite. It is always a must-see. The views are amazing and not too difficult to hike!

After our successful Rams Head hike, we took the dinghy back to Little Lameshure as a bit of lunch and rest was in order.

In the mid-afternoon, Phily led a snorkel tour right from the big boat to the nearby rocks. Many fish, coral, and a lobster were spotted. We weren’t in national monument waters, so we pursued the lobster. It was a big one and was living in a well-protected hole. This guy proved too difficult to catch, so one day we will return to that special spot.

This evening Philomena’s photography skills were shining! Before dinner, we did a photo shoot on the beach and nearby ruins. One of our guests was so pleased because she finally had great images of herself and her husband.

Their wedding photos did not come out well at all, and she has wanted good portraits of just the two of them ever since.

Beautiful lighting and tasty beverages made the moment magical. The evening got even better after we all experienced Philomena’s cooking too. A white wine pineapple reduction over pork loin with a side of miso, ginger potatoes was a real crowd pleaser!

Vicarious Catamaran
Vicarious Catamaran, Hiking on St. John

Day 6- Lovango Cay

We set off around the corner with the big boat to explore Reef Bay. This was a couple of hour stopovers to get on the Reef Bay Trail, which gains you access to the Petroglyphs and waterfalls.

This was a beautiful hike that wasn’t too challenging but was rewarded with some beautiful lookouts.

After everyone was back to the boat, we planned to stop back into Cruz Bay because the last time we were there, the power outage forced many shops to close. That afternoon our group definitely stimulated the economy at the local boutiques and bars.

Once all were back on board, we set sail for the Lovango Beach club. Lovango Beach club is a brand new resort located on Lovango Cay with private moorings and high-end dining. Matt and the group kindly took Philomena and me out to dinner.

The food was incredible, and we had beautiful views to watch the sunset. The sea urchin gnocchi was a table favorite!

Day 7- Magens Bay St Thomas

From Lovongo Cay, Matt practiced downwind sailing to Magens Bay. We practice jibing the cat and going from wing on wing to two sail. It didn’t take us too long to get to Picara Point and round the corner into Magens.

Magens was a beautiful sight from afar, with its white sand beach stretching from one end to another. We were determined to do another hike. However, it has just rained, and this made the Magens Bay trail a bit slippery.

The dense foliage was beautiful and rainforest-like, but it didn’t allow for many rewarding views. However, at the end of the hike, the local beach bar was found, and the group was happy.

Philomena was back on the boat, preparing lunch, so we left the beach and headed back to the boat. After a delicious meal, it was time for some water sports! The inflatable tube we have is a large pink flamingo that holds two, and after many laps around the big boat, it was time for some rest.

That afternoon, Dolphins were sighted too!

Yacht Itinerary with Vicarious Catamaran. Charter Itinerary
Playing with the water toys on Vicarious Catamaran

Day 8- Crown Bay Marina

Sadly it was time to head back home. Winds were light, so we motored around the west end of St. Thomas to Crown Bay. In a week, we had made a figure eight around St. John and St. Thomas.

We docked at Crown Bay, which is just around the corner from the Airport.

Our guests left by private taxi but not before one more beer was enjoyed, and some plans for the next year were laid.

We can’t wait to see Matt, Sarah, Rick, and Julie again at the same time next year for a BVI adventure!

Vicarious Catamaran does crewed charters for up to 6 guests in the USVI. Your yacht charter can also include stretching down to St. Croix for an exhilarating sail.

I hoped you enjoy this trip report in January 2021. All pictures by Phillomenia of Vicarious and writing by Austen! Booked in cooperation with Nautical Trips 🙂

USVI Yacht Itinerary Vicarious Catamaran