Bucket List Family Sailing Trip in the Caribbean

Buck list trips. Do you have one? For us, a family sailing trip in the Caribbean was right at the top. David loves sailboats, I love adventure, the girls love travel in general and beautiful destinations; it checks all the boxes. David and I dipped a toe in, going just the two of us, in 2012 and gained some experience in learning the wrong way to go about planning and implementing a trip like this. We made a lot of mistakes.

When we returned to the BVIs with the kids in 2019, the experience was lightyears more successful and downright magical. And in 2023, we came knowledgeable and prepared in how to make a family sailing trip to the Caribbean an adventurous and breathtaking experience.

I’m so excited to be partnered with The Moorings, the premiere yacht charter company, to share this unique experience with you and am here to answer any questions you have about how to set up this experience for you and your family. Start by checking out my answers to FAQ about the trip, then reach out to me directly if you have additional questions.

Now let’s dive into the highlights of this incredible adventure of a family sailing trip in the Caribbean!

Day 1: Charlotte to Tortola

We left Charlotte, NC midmorning on a Friday and flew directly from Charlotte to St. Thomas. In 2019 we stayed the night on St. Thomas, but this time we knew we wanted to go ahead and get to Tortola in the BVI’s to make a smoother transition to getting the boat the next morning. Once we landed at the airport we took a taxi to the ferry. We had time to get a welcome beverage and some food before boarding the fast ferry for the ride over to Tortola. It took about an hour and we arrived as the sun was setting. A 5 minute taxi ride later and we had arrived at The Moorings base.

The Moorings in unique in that it owns its property on Tortola and has an incredible set up for you to enjoy before (or after) you get on your yacht. We checked into our hotel room, dropped our things, and headed straight to the restaurant. David and I were hungry and the girls wanted to swim, so we picked a table by the pool and all did our thing. It felt like our vacation kicked off right then and there!

fast ferry tortola
The Moorings BVI base

Day 2: Tortola to Norman Island

Can I tell you how nice it was to wake up right where we needed to be? We all slept in, then eased into the day. David and I grabbed coffee from the onsite coffee shop, then breakfast at the poolside restaurant. While they prepped out yacht we tried out our snorkel equipment in the pool for the kids to practice.

Around noon, our boat was ready, so began the onboarding process. The girls and I unloaded our things and put away provisions (the groceries that were delivered right to our boat) while David got the full run through from a Mooring’s captain. He helped navigate us out of the dockage, then hopped off. Then it was just the four of us heading out into the beautiful Caribbean!

We were itching to try out our snorkel skills, so we headed to The Caves on Norman Island. The girls were both super nervous at first and there was quite the process of hopping in, freaking out, getting out, repeat. However, I’m happy to report that with some patience, it turned into an exciting and enjoyable experience! It just took them learning that trying to stay upright is the wrong choice and everything feels super peaceful once you put your face in and go horizontal. So many beautiful fish!

We got back to the boat late afternoon and showered off. Norman Island is home to the new Willy T’s, after the old one sank in the hurricane, and we decided to take the dinghy over and check it out. Watching the kids’ faces as we climbed aboard was hilarious. I knew it was more of a party spot and the kids wide-eyed soaking in of the bumping music and the grown adults jumping off the back of the ship was quite entertaining. We sipped on a beverage, taking in the happy chaos, then took the dinghy back to our boat to grill burgers before calling it a night.

The Moorings BVI base
The Moorings BVI base
kids on boat
Willy T BVI
Willy T BVI
Norman Island BVI

Day 3: The Indians to Salt Island

Sailing is a bit like camping in the fact that we tend to wake up and go to sleep with the sun. We woke early and motored on over to a popular snorkeling spot, The Indians. They made for a beautiful backdrop for coffee and breakfast while David and I waited for the kids to wake up.

After breakfast we headed out to snorkel. There was some of the same hesitancy from the kids, but they worked through it. We all enjoyed the views until noticing some clouds were rolling in and it was time to head out. We didn’t have a mooring ball for the evening so decided to head over to a more quiet anchorage for the night at Salt Island. We pulled in just as the rain started coming down and got set. It poured, so we spent some time indoors, playing cards. I surprised the girls with some Polly Pockets, which helped pass the time, too.

When the rain moved out we felt up for some exploring so we took the dinghy into land. There is nothing developed on Salt Island, but we found a trail and went for a hike. Along it we marveled at the super salinized lake, spotted the wild goats Salt Island is known for, and found about a million hermit crabs. It was such a fun experience and felt like we had the whole island to ourselves (because we did)!

We got back to the boat in time to make some spaghetti, grill some chicken, and call it a night.

kaitlyn boat BVI
rain sail
boat kids
salt island BVI
Salt Island BVI
salt Island BVI hike

Day 4: The Baths to The Bitter End

Our early bedtime worked out well, as we were up with the sun so David and I could motor the boat and grab a spot at The Baths. We knew this was one of the most popular spots and you have to get there early to grab a mooring ball. We weren’t the first ones there but had great success in a beautiful spot. We sipped coffee and made breakfast as the kids slowly woke up, excited to explore their favorite spot.

The Baths, a national park on the island of Virgin Gorda, is world renowned for it’s unique landscape, akin to a giant playground built by nature with boulders to climb over and tide pools to explore. This place is a must on a family sailing trip in the Caribbean. It’s truly incredible and I’ll have to write a breakout post with more details, so stay tuned.

We swam into shore at Devil’s Bay midmorning and had the entire place to ourselves. It’s one of those moments where to only word you can come up with is- wow. It’s breathtaking. We played there for a bit before decided to take advantage of the morning quite and wander through the baths. I was worried it wouldn’t feel as exciting to the kids being their second time, but I was wrong. They lit up with adventure as they scampered up, down, and in-between the giant rocks.

Late morning, it began to get busier, so we took the trail up to The Top of the Baths, a beautiful open air restaurant overlooking the Caribbean. They have a small pool on the back deck, but the kids love it, so we spent time there eating lunch and splashing around. Afterward we walked through the gift shop then headed back down to The Baths. We snorkeled and climbed more boulders and made our way through the caves again. It truly is the most unbelievable spot.

Late afternoon we returned to the boat and did a little jumping off and playing before heading north towards The Bitter End. We had made reservations with them in the weeks prior for 2 nights, so it was lovely not having to worry about having a spot. When we arrived we went right ashore to explore. The new build since the hurricane is absolutely gorgeous. I’ll do a breakout post about this spot, too, because the attention to detail is beautiful.

We wandered, explored, then showered up and took the dinghy to adjacent Saba Rock, another newly rebuilt destination that is truly just a giant rock with a spectacular restaurant and a few hotel rooms. Island luxury at it’s finest! We ate on the deck, explored both levels, and returned to the boat happily satisfied and exhausted.

The Baths
The Baths Virgin Gorda
Top of The Baths restaurant
Kaitlyn boat
hailey Kaitlyn boat
Saba Rock
Saba Rock BVI

Day 5: Oil Nut Bay and The Bitter End

How relaxing it felt to wake up on day 5 with nowhere to go. David and I took the dinghy to shore to get a latte from the Bitter End’s Coffee Shop. We set on the deck, relaxing and soaking in the vistas, trying to decide what to do for the day.

The kids love riding on the dinghy and I had heard things about Oil Nut Bay, which is just around the corner by water. So after breakfast and covering ourselves in sunscreen, we set out. The water was calm that day, which was good because you do head out into the Atlantic Ocean for a short bit while you make your way to Oil Nut Bay, but it’s worth it to see this incredibly luxurious resort! Especially because it’s a spot most people might not see on a family sailing trip in the Caribbean.

We started at the more private end, where guests stay, accidentally, but the staff member that met us was incredibly gracious and gave us a tour of the pristine property and rental homes before directing us one cove down to their more public restaurant.

We had lunch at Oil Nut Bay’s Nova, a stunning combination of function and design. The kids LOVED the pool overlooking the water on the dock and David and I loved the spicy margarita. We explore the boutique and enjoyed our lunches and the overall high end vibe.

After lunch we returned to the boat, did a little kayaking, then enjoyed some down time. Jimmy Buffet came by with his dog to offer us some rum, and we accepted. Ok, ok, there are some people saying it wasn’t really Jimmy Buffett, but in my mind, I met the man himself because “Jim B.” had me completely convinced!

We washed up and enjoyed dinner that night on shore at Bitter End’s restaurant on the deck with the most phenomenal sunset. Perhaps I’m bougier than I like to admit because it was one of my favorite days: exploration and delicious food!

Oil Nut Bay
Oil Nut Bay
Oil Nut Bay
Oil Nut Bay Nova
Oil Nut Bay Nova
The Moorings yacht charters

Day 6: Bitter End to Anegada

I woke up this day sad to leave this beautiful spot, but excited for the “long sail” to Anegada. It’s the furthest away island and takes a couple hours to sail to. It’s also unique in its topography. All the islands are super mountainous, except for Anegada, which is completely flat. It makes it a fun one to sail to because it seems to appear out of nowhere.

At 7:00 AM I hopped onto BoatyBall and was able to secure us a mooring ball for the night, which took the pressure off of us to have to get up and go early. So instead we went ashore to enjoy one last meal at The Bitter End.

From there we headed out, put up the sails, and enjoyed a completely peaceful crossing… minus the moment when David almost lost the drone in the middle of the sea! Luckily he was able to drop the sails quickly, and captain the boat back to retrieve the drone and it’s footage!

We arrived at Anegada after lunch and immediately headed to shore. David thought it would be fun to rent scooters to explore the island. Hailey cried immediately, thinking it looked dangerous. I kind of agreed, but not wanting to say no to adventure, Hailey hopped on board after a short test drive, and I hesitantly agreed.

Well, I should have stuck to my gut, because long story short, I ran my scooter into a prickly bush with Kaitlyn on the back. It scared me to death, thinking I might have hurt her, but she was just fine. I had some scratches on me, but thank goodness I only went as slow as the scooter would go.

We shifted gears (pun intended), returned the scooters and got a taxi ride over to Anegada Beach Club on the far side of the quiet island that is home to only about 300 people. The pool and the walk along the beautiful beach revived us all. If we were to do it again, we’d get to Anegada earlier to enjoy the beach for longer. It’s so beautiful!

We played at Anegada Beach Club for an hour or two before heading to The Lobster Trap, where we enjoyed the most delicious lobster dinner with a heck of a view to match!

The Bitter End
The Bitter End
The Moorings yacht charters BVI
Anegada beach club
The Lobster Trap, Anegada
The Lobster Trap Anegada
Hailey boat

I’ll continue our family sailing trip in the Caribbean adventure in part 2!


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