Visiting the US Virgin Islands is a magical thing, but imagine waking up to the gentle sway of a luxurious 45-foot catamaran, the sun rising over crystal-clear waters, and the promise of a new island adventure every day. That was our reality on a recent family journey through the US Virgin Islands with kids aboard The Rapscallion, sailed by Captain Jamie. Thanks to our incredible partner Charter Smarter, our family was able to live out one of our dream vacations in one of our favorite places on earth! From the bustling harbor of Charlotte Amalie to the serene shores of Water Island, we embarked on a five-day voyage filled with unforgettable experiences, breathtaking views, and plenty of family fun.



Charlotte Amalie: The Beginning of Our Journey
Our adventure began in the port of Charlotte Amalie at Yacht Haven Grande in the US Virgin Islands. We had just arrived from the Cyril E. King Airport in St. Thomas, ready to embark on a bucket list adventure when we met our captain at the marina. After some quick pleasantries, we boarded The Rapscallion, a spacious and well-equipped catamaran that would be our home for the next five days. We were given a proper tour of the boat and then shown the grounds of Yacht Haven Grande, including the members pool that the girls used right away! We couldn’t believe that we were finally about to embark on this unforgettable journey in the US Virgin Islands with kids in tow.
Getting Our Families Provisions
After a thorough safety briefing from our friendly captain, we set off to purchase our provisions from the local Moe’s Fresh Market. Although pricing was a bit of a shock coming from the mainland, we managed to get all we needed for our breakfasts, several lunches, and at least two dinners aboard the boat for our journey for under $500. Granted, we did bring some staples with us in our luggage from home to help stretch the budget. Once back on board, Captain Jamie fixed us our first “Painkiller” drink of the trip for a proper toast, then we stayed our first night on the boat right there in the harbor.
Maho Bay: Family-Friendly Paradise
First up on our five day itinerary was Maho Bay, known for its amazing snorkeling. All day we were seeing everything from giant rays to vibrant reefs and colorful exotic fish. There are two shorelines to snorkel here, the Eastern and Western shorelines, that both offer a wide variety of coral and fish species. Maho Bay Beach is great for families, as there’s a narrow sandy beach that has plenty of sun and shade. The sandy bottom extends out a long way from the shore, making it a perfect place for kids to wade, swim, float and play. There’s also plenty of vendors like Maho Crossroads, which is in the area across the road on the west end. Crossroads is a nice place to enjoy music, grab a drink, have some tacos from the food truck, grab some souvenirs, and even rent chairs or floats.



Exploring Water Lemon Cay and The Ruins
Next up was a hidden gem, known as Water Lemon Cay. Water Lemon Cay is renowned for its rich history, fascinating ruins, and stunning underwater scenery. We took the dinghy ashore to hike up to the main ruins of the old sugar mill for a view that was like nothing I’ve ever seen in the Virgin Islands. Though a little hot and rocky on the way up, the hike was very much worth it to see the Cay and the surrounding islands from the viewpoint. After our climb back down, we were all really looking forward a nice dip in the sparkling water. Snorkeling in the cay was definitely a highlight, as its vibrant coral reefs and an array of marine life captivated our entire family for hours.



Story Time: As we came down from the ruins and to where the dinghy was on shore, our youngest found a small spotted ray under a rock. As she approached the ray, a small sea turtle came up to her in the shallow water. She then waded deeper into the water following it out slowly, which quickly turned into a fully submerged swim alongside the friendly sea turtle. Shortly, the entire family joined in and pretty soon we were all swimming in the cay in our hiking clothes, but having so much fun in the process. Such a great family memory!
Saltpond Bay in St. John
Our next stop was Saltpond Bay, a very tranquil spot, perfect for a relaxed day of swimming and sunbathing together. The shallow waters were ideal for the kids to swim and snorkel around safely. A short hike from the shore, was the actual salt pond that was a pretty cool area to explore. The water itself was very shallow and extremely warm, with a super high concentration of salt. Many find it to be soothing, but be careful as it can burn if you have any open cuts or sensitive skin. Spent the rest of the day exploring and snorkeling the entire bay and we must have seen at least twenty or thirty sea turtles. What a great day we had at Saltpond Bay!



Floating Restaurant: Lime Out
After working up an appetite, we made our way back to the boat for a short sail to Coral Harbor, then took the dingy over to Lime Out. Lime Out is a very unique floating restaurant serving delicious tacos right in the middle of the harbor. Dining on the water was a such a fun experience that the whole family really enjoyed. Spent the day floating on these round multi-person seats that were connected to the restaurant, with the ability to swim around and up to more seats at their floating bar. They also make some great drinks and sell some of the coolest merchandise in the US Virgin Islands. All of us left with some sort of souvenir and then we took our small boat back to The Rapscallion to rest up for the evening. Captain Jamie made us another special drink for a nightcap, then we all looked at the stars for a bit before heading to bed and being rocked gently to sleep.



Have you ever eaten at a floating restaurant? Share your experiences in the comments below!
Check out some more of our cool places to eat with kids blog posts here.
Caneel Bay and Honeymoon Beach
Caneel Bay and Honeymoon Beach offered more opportunities for our family to snorkel and enjoy the beautiful beaches. At Honeymoon Beach, we enjoyed a leisurely swim and relaxed in the soft white sand looking for shells and smaller marine life. Caneel Bay was the perfect spot to snorkel and see lots of fish, so many coral species, more sea turtles, and even huge eagle rays up close. Best part about snorkeling here, is that much of the reef is in shallow water making it really easy to glide over and explore.
Safety Note: Be sure to stay close to the reef when snorkeling and keep and eye out for boaters, as it can get busy with those coming in and out. Wear bright colors and put out a flag so you can be seen.



Top Activities in the US Virgin Islands for kids
- Snorkeling in US Virgin Islands: The USVI is home to some of the best snorkeling and diving spots in the entire Caribbean. It’s great for all levels, especially for children.
- Diving: If you are into diving, you have to check out the Diving Charter Fleet from Charter Smarter.
- Historical Tours: Explore the rich history of the islands through guided tours of historical sites and ruins.
- Water Sports: From paddle boarding to kayaking, there’s no shortage of water-based activities. Most of our time in the USVI was spent snorkeling and swimming between the boat and the shore.
- Beach Hopping: With so many stunning beaches, each offering something unique, beach hopping is a must. This was one of our favorite parts of our 5 day adventure, exploring so many amazing beaches. Along with experiencing the beaches themselves, we really enjoyed grabbing drinks and the occasional snack at the beach bars and restaurants.
- Local Cuisine: Don’t miss out on the delicious local food, especially fresh seafood and tropical fruits. Almost all of the islands we visited had a great food scene for us to enjoy.
Cruz Bay: The Heartbeat of St. John USVI
Cruz Bay, the lively hub of St. John, was our evening destination for dinner and music. The bustling town offered a nice mix of shopping, dining, and local culture. We wandered through some charming boutiques on our way to dinner, finally having a seat at the waters edge. We chose The Beach Bar restaurant and enjoyed some delicious island favorites, like Conch Fritters and Grilled Mahi Sandwiches (and of course a Painkiller to wash it all down). We caught a live music performance by one of the local favorite artists at their beachside bar, while playing corn hole in the sand. The vibrant atmosphere was a great contrast to the serene beaches we had visited earlier in the day. We definitely had a fun night out! Back on the dinghy for a dark, but adventurous ride the the catamaran to get some sleep.



Christmas Cove
Up early, we headed to Christmas Cove, which is an absolute paradise. Christmas Cove is a very popular spot with US Virgin Island charterers for the first and last nights, because of the close proximity to Charlotte Amalie and Red Hook marinas. Though we did not stay the night there, we really enjoyed or time and would definitely come back again on our next visit to the Virgin Islands. Kids really liked the name Christmas Island and we had fun dreaming about having one of our own family celebrations here one Christmas.
History Note: In 1614, Captain John Smith is said to have named Christmas Cove when he visited it on Christmas Day.
The Floating Pizzeria: Pizza Pi
Anchoring here allowed us to visit one of the most unique places we’ve ever eaten, Pizza Pi, a floating pizzeria serving some of the best pies on the water. Ordering pizza by boat and enjoying it on your own floating seats in the cove was such a cool experience, especially for the kids! After enjoying a few slices, we took the party back to The Rapscallion to swim a bit from the boat and enjoy our evening with a perfect sunset view from the deck. Christmas Cove was definitely one of our favorite stops!


Water Island: The Final Stop
Our last stop before heading back to Charlotte Amalie was Water Island. This small residential island offered such a peaceful retreat with its beautiful beaches and great hiking trails. We spent our final day exploring the island, stand up paddle boarding around the calm waters, and reflecting on our incredible journey while wading in the warm waters. That evening, we decided to stay ashore and eat at Dinghy’s Beach Bar & Grill. Just as we ordered, a huge storm came through and we took cover under the bar area as we ate our meals. Storms don’t last too long in the USVI, so after it cleared, we all paddled back to the boat to shower up and have our last restful night on The Rapscallion.


One Last Swim
Up early, everyone was eager to get in one last swim, some paddle boarding, and another snorkel session in before we had to head back to Charlotte Amalie. We made the last of the pancake mix and started to pack up our rooms a bit before we jumped in the water. We spent a good portion of the morning and well into the early afternoon back in the water, soaking up every minute we could in one of our favorite places in the world. US Virgin Islands, you will be missed!



How to Plan your own Sailing in The US Virgin Islands with kids
Planning a family sailing trip with kids can seem daunting, but with the right preparation, it can be a breeze. Here are some tips to get you started:
- Choose the Right Charter: Look for a family-friendly company like Charter Smarter that offers all of the things that your family wants and needs for a fun and safe journey through the Virgin Islands.
- Plan Your Itinerary: Research specific destinations and activities that cater to your family and then articulate your preferences when you speak with the charter company about your sailing.
- Pack Wisely: Bring essentials, but be sure to pack light to save space on the boat. Our family only took one small backpack each with simple outfits, bathing suits, flip flops, and minimal toiletries. We did bring our own snorkel gear for the kids, but it is not always necessary depending on the boat.
- Safety First: Ensure everyone knows basic safety protocols for boating and what to do in case of an emergency. Your captain will brief you on the safety for your particular boat, but having prior knowledge is highly recommended.
- Stay Flexible: Be prepared to adjust your plans based on weather conditions and other factors. Your captain will stay up to the minute on all of the weather and marine information and communicate those to you often.
If you have any questions about chartering a boat, check out this great FAQ to get started.
Captain 360 is the program that we chose for our family, as we were interested in having a captain onboard instead of an entire crew. We felt that this was the best fit for our family and our budget. Check out all of the current specials Charter Smarter is running right now to see what fits for your family.
Here’s a map of our charter around the US Virgin Islands:







