Yacht Charters: Chartering A Catamaran In The Caribbean

A Virgin Islands Charter Vacation

If you’ve never chartered a yacht before and are thinking about what the next vacation should be, seriously consider chartering a catamaran in the Caribbean. Now I’ve done many charters with friends, family, colleagues, etc., and there are always a few worries that creep into my head. Will everyone get along? Will someone get sick? Will we have enough space? Will we be bored?

But I recently chartered a luxury catamaran with my husband, my parents, my sister and her fiancé. We did a full week, 7-night / 8-day charter in the Virgin Islands. It was such an amazing experience, I thought I’d share more about our itinerary with you. 

Day 1: We left St. Thomas and headed over to Waterlemon Cay in St. John. We left the dock out of Frenchtown around 1pm and had a beautiful sail over to St. John, with a perfect temperature of 80 degrees + lots of sun. Once we grabbed a mooring ball, everyone was super eager to feel the water. Some of us swam ashore to walk around the beach. Some of us hopped in the dinghy and went to check out the rocks for snorkeling. While snorkeling, we saw a couple of green turtles, a variety of tropical fish and spotted an eagle ray. We enjoyed the anchorage as it was quiet and calm, giving us a great starting point for the following day. As the sun went down, we enjoyed a round of Painkillers and cheers’d to being blessed with a week in the Virgin Islands.

Day 2: We woke up early the next morning and decided to do a hike. There’s a great walking trail from the beach up to the impressive Annaberg Ruins, so we took the dinghy ashore. The ruins are one of the best preserved and well-maintained sugar plantations on the island. The walk itself is about 2.5 miles roundtrip and it’s an easy stroll along the shoreline. We were the first ones there for the morning, with a family of deer still enjoying the peace and quiet. It was a bit eerie walking through the ruins, just the six of us, reading the informational placards and imagining what a difficult life it was for the slaves there. The ruins are on top of a hill, offering a fantastic vantage point, where you can see St. Thomas, Jost Van Dyke and Tortola.

We left the anchorage and headed up to Soper’s Hole, Tortola, BVI to clear through customs. From Sopher’s Hole, we made it over to The Indians, one of my favorite snorkeling spots in the BVI’s. It has so many purple fans, fish life and the mooring balls are so close, it’s an easy swim to the rocks. From there, we sailed over to Great Harbour, Peter Island. I was super excited to see the new, infamous, Willy T’s, a floating pirate ship bar (the previous one was destroyed in Hurricane Irma). The Willy T’s is known for its fun, party atmosphere. The thing to do is to grab a drink (some liquid courage) and jump off the top deck of the boat with a friend or two. Actor Vince Vaughn, even made an appearance, so you never know who you’re going to run into in the Virgin Islands.

Day 3: We woke up early the next day to hike around Peter Island, only to find that there are “No Trespassing” signs and lots of construction work being done. Since Hurricane Irma hit in September 2017, the resort hasn’t reopened. But it’s still a great island to spend a night at. The other great anchorage off Peter Island is Deadman’s Bay, where there’s a great beach to walk. We decided to leave Peter Island and head over to Salt Island, where we knew we could get a nice walk in.

Once anchored at Salt Island, we swam ashore to check out the Salt Ponds and walk the trails. The trails aren’t that difficult to walk, sandals worked great. The trails wound us up to the Southwest side of the island. It was a fantastic vantage point and we saw a few goats off in the distance. Unfortunately, at this time of year, it’s still not dry enough for salt to be collected. I’ve been to the island when there’s so much salt, it first looks like the ground is covered in snow. We also went over to the Wreck of the Rhone, which is just off the south side of the island. This site is a great dive site, but when the water is clear and calm, you can see the entire wreck via snorkeling. The most impressive thing is the massive bronze propeller.

We finished the day by sailing up to Leverick Bay, Virgin Gorda to spend the night. Before the sun went down, we went ashore to attend The Michael Beans Pirate Show. I will admit I was a little hesitant at first, thinking it’s more for kids but everyone in our group thoroughly enjoyed his corny pirate jokes,  the singing, the rum penalty shots and the conch blowing contest; it’s definitely an audience participatory show and worth stopping by.

Day 4: We rented a safari truck so we could spend the entire day on Virgin Gorda. The family decided to hike Gorda Peak, to get the blood flowing. It was a great hike and I would definitely recommend it, but make sure to bring sneakers (sandals were a bit difficult). After the hike, we drove over to The Baths and spent some time climbing around on the giant granite boulders, swimming at Devil’s Bay, doing our best Tyra Banks’ poses at ‘The Cathedral’ and looking for souvenirs at the gift shops at the National Park’s entrance. From The Baths, we drove up to Hog Heaven, a great BBQ restaurant with epic views of Mosquito Island, Leverick Bay, Necker Island, Prickly Pear and Saba Rack. That day was so clear you could even see Anegada! We enjoyed lunch and PainKillers and got back into our rental safari to head over to Savannah Bay to spend the rest of the afternoon on the beach. It’s a great beach to end your afternoon on, as it’s a shallow and calm bay with a nice long beach to walk.

Day 5: We left Leverick Bay early in the morning, so we could enjoy a full day on Anegada. After anchoring in the main harbor, we picked up our safari rental to spend the day exploring Anegada, the “drowned island.” With its highest point of approximately 28 feet, it’s understandable where its nickname comes from and is unlike any of the other British Virgin Islands. Anegada reminds me of The Bahamas, with the endless powdered sugar beaches and beautiful turquoise blue waters. Our first stop was the viewing platform, overlooking Flamingo Pond, a giant salt pond that hundreds of flamingos call home. I’ve decided my new favorite spot is at Flash of Beauty Restaurant on Loblolly Beach. My family and I spent quite a bit of time walking the beach there, enjoying a couple of drinks, but we all agreed the best part was the snorkeling.

The reefs, coral and sea life were the best I’d seen in the entire Virgin Islands. From Loblolly, we headed over to Cow Wreck Beach to enjoy lunch. This is another great beach to walk and there’s a cute gift shop as well. We ended the day with sundowners on the boat. Anegada is one of my favorite islands as it’s a great spot to watch the sunset, with unobstructed views of the sun disappearing into the horizon. For dinner, we went ashore to enjoy delicious lobster at Wonky Dog. There are several other restaurants that will do lobster dinners, but I prefer Wonky Dog as it’s lower key and you can enjoy dinner with your feet in the sand. We called the restaurant ahead to make a reservation and ordered six lobsters. When you arrive for your reservation, the staff will grab your drink order and then a few minutes later your dinner is served! Talk about service. Anegada is known for its lobster and for the past three years, the Lobster Festival has taken place here in November, where multiple establishments around the island create their best lobster dishes.

Day 6: We pulled up anchor to start making our way to Jost Van Dyke, which was about a 3 ½ hour sail. We made a pit stop at Sandy Cay to have lunch, go for a swim and stroll around the island (there’s a short walking trail on the island). From Sandy Cay, we went over to Great Harbour, Jost Van Dyke. We grabbed a mooring ball, dinghied ashore, bought some local banana bread and then took a short taxi ride over to White Bay. You can also walk from Great Harbour to White Bay, it’s not super long, but it’s quite the workout, with steep hills; the taxi ride is only $5 per person. We spent the afternoon at Soggy Dollar, Hendo’s Hideaway, One Love and Gertrude’s. My must-have is the Razztherapy PainKiller at Soggy Dollar, as my husband’s is the NillaKilla PainKiller. We were going to spend the night at Jost Van Dyke, but made a last-minute change and decided a sunset sail would be much nicer. We made our way over to Maho Bay, St. John, with an epic sunset as our backdrop. When we got to Maho, we went swimming one last time before it was too dark, taking turns jumping off the bow.

Day 7: Two people in our party had to fly back to the states on Day 7, so we left Maho Bay and grabbed a mooring off of Honeymoon Beach, just around the corner from Cruz Bay, St. John, where they could catch the ferry to St. Thomas. Cruz Bay is great to grab some souvenirs, a bite to eat, listen to music, but it’s most known for its crazy Happy Hour specials. There are some businesses that haven’t reopened since the hurricanes, but there are also new shops/restaurants that have opened. In fact, the Tap & Still (best burgers in the USVI) has opened up their third location in Cruz Bay. My favorite shops are Bamboo Studio (for jewelry), St. John Spice Shop (for spices, tea, coffee, candy), St. John Scoops (for local, freshly made ice-cream), and Big Planet (for t-shirts, sandals, sundresses, bathing suits). After shopping and grabbing an ice cream, we decided to walk the Lind Point Trail. It starts out of the Virgin Islands National Park Building parking lot and takes you over to Solomon and Honeymoon Beaches. It was an easy stroll, but I would recommend wearing sneakers, as there are lots of rocks and tree roots to step over. However, when we were walking back to Cruz Bay, a family was making their way to the beaches and all the kids were barefoot! Solomon Beach was super calm and not very crowded. Honeymoon Beach is a bigger beach with watersport rentals as well as a snack bar + cocktail bar, so if you wanted to grab a Rum Punch, rent a beach chair, or use a stand-up paddleboard, Honeymoon Beach is the perfect spot.

We made our way back to Cruz Bay, grabbed one more PainKiller from Cool Desires and then headed back to the boat. We left that mooring ball and went over to Christmas Cove to spend our final night. Christmas Cove is a super calm anchorage, on the west side of Great St. James Island. There, you can snorkel, swim, paddleboard and even order pizza! Pizza Pi is a pizza restaurant on a sailboat, anchored out in Christmas Cove, that is open from 11am to 6pm, and they’ll even deliver by dinghy! We spent the evening watching the sunset and reflecting on what our favorite stops were from the week.

Day 8: With it being our last day on charter, it was definitely a sad day. But we had a great sail over to Yacht Haven Grande, St. Thomas, where we disembarked. Our flight wasn’t until late afternoon so we spent some time walking around Havensight and eventually had lunch at Smokin’ Rooster, a great BBQ spot. There’s air conditioning seating as well as a large outdoor garden space to enjoy drinks/food while on certain nights of the week, they have live music.

My sister and future brother-in-law both left the boat saying, “Laura, you’ve ruined any future vacation we take after this, because how could anything else compare?” And that’s the message I’ll leave with you. This vacation is unlike anything you’ve done before. With a different view to wake up to every morning, chefs preparing you five-star meals, having the captain be your own personal tour guide, it’s a vacation everyone needs to experience at least once, if not make a tradition of going annually with your friends and family.

If you need more information about a Caribbean catamaran charter or would like to book a one-of-a-kind vacation, please don’t hesitate to contact me. Happy chartering!