5-Day Catamaran Charter Itinerary in the USVI
Fully crewed catamaran charters are incredibly family-friendly, offering the perfect blend of adventure and relaxation for travelers of all ages. This 5-day itinerary is crafted with families in mind – shorter travel legs, plenty of fun water activities, and kid-approved destinations, all while keeping the luxury and comfort adults expect. From the moment you step aboard, the crew will make sure both parents and children are having the time of their lives. Here’s a taste of a five-day USVI voyage ideal for a family getaway:
Day 1 – St. Thomas to St. John (Maho Bay Turtle Encounter)
Welcome aboard in St. Thomas! After your family is settled and everyone has a cold tropical fruit smoothie (or perhaps a welcome rum punch for the grown-ups), cast off for a short sail to St. John. In under an hour, you’ll reach Maho Bay, a calm, shallow bay on St. John’s north shore that’s a favorite for families. Maho is famous for its friendly sea turtles. The kids will be thrilled to jump in almost immediately and snorkel in the gentle water – within minutes you’re likely to spot green sea turtles grazing on seagrass in 6-8 feet of water (close enough to the surface for even novice snorkelers to see clearly). Noodle floats and life vests are on hand to give little ones confidence as they peer into the blue.
After everyone has had their fill of turtle sightings and perhaps a glimpse of a harmless stingray gliding by, dry off and enjoy lunch on deck. The chef might prepare something appealing to all ages – say, fresh fish tacos with a mild tangy sauce and a side of kid-friendly sliders, so both parents and picky eaters are happy. In the afternoon, you can beach comb on the soft sands of Maho (collecting coral fragments and shells), or take a quick ride over to the next bay, Trunk Bay, so the kids can see the famous panoramic view (and maybe try the undersea snorkeling trail for a bit if they’re up for more snorkeling). Come evening, the catamaran will be anchored in a safe, sheltered spot like Francis Bay. The crew can organize a casual family beach barbecue on St. John’s shore – picture the sun setting as you roast marshmallows for s’mores over a small bonfire (the crew handles all setup and cleanup). Tired from the first exciting day, the kids can snuggle up for an outdoor movie night on the aft deck (projected on a screen under the stars), while the adults relax with a glass of wine, listening to tree frogs chirping from the island. It’s a magical start to your family adventure.
Day 2 – Fun in St. John (Beach Day & Floating Taco Bar)
This morning, wake to the sound of gentle waves and perhaps wild deer or donkeys rustling onshore (St. John’s wildlife sometimes wander near the beaches – a delight for kids to see from the catamaran). After a hearty breakfast, head to Trunk Bay early (if you didn’t visit yesterday) or Cinnamon Bay– both are stunning National Park beaches with powdery sand and clear water. These beaches are great for sandcastle building, shallow splashing, and easy snorkeling along the shore where little tropical fish dart around. Your crew can ferry you in the tender and set up a nice spot on the beach with umbrellas, towels, and a cooler of cold drinks. Spend the morning swimming and playing. Perhaps organize a friendly beach cricket or frisbee game with the crew – they’re often happy to engage and play along with the kids.
As appetite builds, it’s back to the catamaran for lunch, or better yet, a short sail over to Coral Bay on St. John’s quieter side for a truly unique lunch stop: Lime Out in Coral Bay, which is a floating taco restaurant accessible only by boat. This is a hit with both kids and adults. The children will love that they get to swim up or paddle up to a taco boat! With life jackets on or using the paddleboards, they can float next to Lime Out while you place your order for gourmet tacos (don’t worry, the crew will assist to make sure everyone is safe and having fun). Enjoy delicious tacos (maybe fresh mahi for you, simple chicken or beef for the kids) right there in the middle of the bay – a dining experience unlike any other. After lunch, the catamaran will cruise to a serene bay like Hurricane Hole or back toward the west. The afternoon could be a great time for a family-friendly hike if you want to stretch your legs: perhaps the Cinnamon Bay loop trail (easy and short through historical ruins) or the Ram Head trail if your kids are a bit older and up for a stunning view (the hike is about 1 mile each way, with dramatic cliffs and ocean vistas).
Alternatively, continue the water fun with the yacht’s toys: maybe break out the inflatable tube or big floating mat and let the kids bounce and splash around right off the boat. The crew might organize a little “treasure hunt” in the water, tossing dive toys or shells for the kids to find with goggles on – turning the sea into their playground. In the evening, anchor near Cruz Bay, the main town of St. John, or a peaceful cove. If in Cruz Bay, you could go ashore for some casual live music at a local beach bar (the island often has music in the evenings) or to grab some ice cream as a treat. Back on board, dinner is tailored to please everyone – perhaps a make-your-own pizza night where kids can help the chef sprinkle toppings on personal pizzas, baked in the catamaran’s galley oven. As stars come out, the crew might lead the kids in some stargazing, pointing out constellations (the sky is wonderfully clear here). Another fulfilling day ends with the family bonding and excited for what tomorrow brings.
Day 3 – St. Thomas Play Day (Water Toys & Pizza Pi)
After two days around St. John, it’s time to explore back towards St. Thomas to mix things up. Weigh anchor and enjoy a short, scenic cruise around to Christmas Cove at Great St. James Island, just off St. Thomas’s East End. En route, you’ll pass Pillsbury Sound which often has pods of dolphins – keep those eyes peeled on the bow! By late morning, you arrive in Christmas Cove, a naturally sheltered cove with crystal-clear waters. The setting is like a big ocean playground – perfect for a full water sports day. The crew will bring out all the toys: the kids can take turns zooming around on a tube towed by the dinghy (laughing and squealing guaranteed), older kids or adults might try water-skiing or wakeboarding on the flat waters, and everyone can enjoy swimming and snorkeling. There’s a small coral reef in the cove where you can find colorful fish and maybe a lobster hiding – great for a guided snorkel with the crew helping point things out.
For lunch, you have a novelty that delights all ages: Pizza Pi. This is a floating pizzeria right in Christmas Cove, operated from a converted sailboat. Call in your pizza order by radio or have the crew zip over – and soon you’ll be biting into hot, delicious pizza at anchor. It’s a fun, casual lunch that kids particularly love (“Pizza in the ocean!”). Spend the afternoon at a relaxed pace – perhaps drop a fishing line (some kids may enjoy trying to catch their first fish – small snappers often bite in these waters and the crew can assist with rods and bait), or engage in a friendly family board game or card game in the shaded aft deck lounge. The crew can also set up a craft activity to keep younger ones entertained – maybe creating bracelets or necklaces with Caribbean beads, or a drawing contest of who can sketch the prettiest tropical fish from memory.
Later, take a short hop over to Secret Harbour or Sapphire Beach on St. Thomas if you want a beach change of scenery – these spots have calm waters and possibly other kids around for yours to play with. By Day 3, your family is nicely in sync with “island time,” so the evening is mellow. Anchor off Water Island (back where you started, making a nice full circle). Wednesday and Saturday nights, Honeymoon Beach on Water Island hosts an outdoor family movie night where they project films on a big screen by the beach – if timing aligns and you’re interested, this could be a fun outing where locals and visitors gather (the crew can arrange a dinghy ride over). Otherwise, enjoy a quiet night onboard. Perhaps do a kids’ cooking activity with the chef – like decorating cupcakes or baking cookies for dessert. Meanwhile, parents can steal away to the upper deck for a private sunset cocktail, enjoying a moment of calm as the sky turns dusk-purple. By now, the kids feel at home on the catamaran, and you’ll likely hear them excitedly recounting their favorite parts of the day (probably tubing and pizza!) before drifting off to sleep.
Day 4 – Magens Bay and Pirate Tales
Get ready for a highlight day at one of the most iconic spots in St. Thomas: Magens Bay. After breakfast, cruise around to the north side of St. Thomas (about an hour’s journey). Entering Magens Bay, you’ll see why it’s often heralded as one of the world’s top beaches – a graceful curve of white sand lined with palms, with calm, crystalline waters extending far out. Anchor in the bay and spend the day enjoying this natural playground. This is a great day to deploy any remaining water toys – try out the stand-up paddleboards as a family (Magens’ waters are typically flat, ideal for even beginners to paddle around without waves). You can have kayak races, or the crew can set up an inflatable trampoline or floating mat if your catamaran carries one, turning the sea into a personal water park. On the beach, the kids might enjoy running around; Magens has a lovely shallow entry perfect for toddlers to splash safely and for bigger kids to practice swimming. The crew can bring sports gear for a beach frisbee toss or even a soccer ball for a quick kick-around on the sand (Magens has plenty of open space).
For lunch, enjoy it picnic-style on the beach or back on board – whichever the family prefers. If onshore, there’s a beach bar that serves burgers, sandwiches, and the famous “Painkiller” cocktail (a must-try Caribbean drink for adults – a creamy rum punch topped with grated nutmeg). Don’t worry, there are virgin versions for the kiddos, essentially delicious smoothies. After lunch, perhaps take a short family nature walk to explore. Magens Bay has a nature trail at the far end of the beach that winds through mangroves and forest – it’s an easy walk and a chance to possibly spot birds, hermit crabs, and lizards. Another option: visit the nearby St. Peter Great House & Botanical Gardens on the hill above Magens (a quick drive the crew can arrange). There, besides gorgeous views, kids can feed koi fish and see parrots, and parents can enjoy the panoramic lookout.
By late afternoon, head back to the catamaran and start a leisurely sail downwind along St. Thomas’s coast. You’ll likely return to the Charlotte Amalie area to overnight, but before you do, one more adventure: a stop at Buck Island, St. Thomas (not to be confused with Buck Island at St. Croix). This small island near the entrance of Charlotte Amalie harbor has a protected reef known as Turtle Cove and even a shallow shipwreck of a WWII-era vessel called the Cartanza. It’s a superb snorkel spot for all ages – lots of fish and typically several turtles about. Do an early evening snorkel here (the sunlight angle near sunset can actually make it easier to spot sea turtles as they ascend for breaths). With that final snorkel, you’ve kind of come full circle – ending with more turtles just like you began on Day 1. As the sun sets on your last full day, cruise into Charlotte Amalie’s harbor. For a grand finale, how about a bit of pirate lore?
St. Thomas has a swashbuckling history, and your crew or a local guide can regale the kids with pirate stories as you sail past Blackbeard’s Castle on the hill. You might even arrange for a fun “treasure hunt” on the yacht, where earlier in the day the crew hides some small trinkets or souvenirs and draws a treasure map for the kids to follow around the catamaran – ending in discovering their “loot” (perhaps little pirate figurines or island keepsakes). It’s an entertaining way to tie in the history with your final night. Enjoy a sumptuous farewell dinner on board – maybe the chef creates a menu of everyone’s favorites from the week – and then indulge in a decadent dessert. As the stars wink on and the harbor lights reflect off the water, the family can gather for one last evening of togetherness on the deck. The children might present a “show” (kids often love performing, and a yacht makes a great stage – who knows, maybe a talent show or a thank-you song for the crew). Laughter and maybe a few tears of joy will cap the night, as you prepare to say goodbye to this floating home that treated you so well.
Day 5 – Farewell to the Islands
Your final morning on the catamaran has arrived. Wake up in Charlotte Amalie with cruise ships perhaps pulling into port nearby – but you feel a world apart, having experienced the islands in a far more intimate way. This morning, there’s time for a relaxed breakfast – the chef can whip up everyone’s favorite items (banana pancakes for the kids? Eggs Benedict for the adults? Fresh mango smoothies all around!). It’s also a time to snap those last family photos on the bow with the St. Thomas skyline in the background, and to exchange warm goodbyes with your crew. The kids give high-fives (and maybe hugs) to the captain and crew who have been their adventure leaders all week, and you express gratitude for the extraordinary service and attention to detail. If your schedule allows, you might do a quick walking tour of historic Charlotte Amalie before heading to the airport – climbing the 99 Steps up to Blackbeard’s Castle or visiting the open-air market for souvenirs (the crew can help organize a short excursion). Or you may simply transfer directly to the airport, which is conveniently only a 15-20 minute drive.
Either way, the crew handles your bags and ensures your transfer is seamless. As you travel home, the family will be brimming with stories: from swimming with turtles and eating pizza at sea, to the night of the treasure hunt and spotting dolphins off the bow. This 5-day family itinerary packed in a lot of adventure without ever feeling rushed, and more importantly, it provided countless moments of family bonding. You’ve shared experiences that will become cherished memories – and perhaps sparked a passion for the sea in your young ones. The USVI, with its calm waters and mix of activities, proved to be an ideal setting for a luxury family charter. Until next time, you’ll carry a piece of the islands (and maybe a new stuffed turtle souvenir) in your hearts, and you’ll know that Boatcrowd stands ready to welcome you back for your next catamaran rental USVI vacation whenever you’re ready for more.
Featured Experiences
A fully crewed catamaran charter in the USVI unlocks a menu of exclusive experiences that simply aren’t possible with other types of travel. Here are some featured experiences that our guests love to include in their itineraries:
Snorkeling & Underwater Exploration
The USVI offers world-class snorkeling right off your catamaran. Dive into calm bays to discover colorful coral gardens and a rainbow of tropical fish. Swim through the famous underwater trail at Trunk Bay or float above a sunken shipwreck teaming with marine life at Turtle Cove. One minute you could be snorkeling with sea turtles at Maho Bay, and the next, marveling at a school of blue tangs weaving through a reef.
Your crew will provide quality snorkel gear for all sizes and even guide you to the best spots. The water is warm and clear year-round – perfect for novices and kids, yet still exciting for experienced snorkelers. From starfish beds in St. John’s Leinster Bay to the vibrant reef of Buck Island (St. Croix’s protected marine park), every snorkel stop is a new adventure beneath the surface.
Scuba Diving for the Adventurous
For certified divers (and even those who want to try diving for the first time), the USVI has some spectacular dive sites. Many crewed catamarans carry dive equipment or work with rendezvous dive companies to offer onboard diving experiences. Explore the dramatic wall off St. Croix’s north shore, where the sea floor drops off into the blue abyss, adorned with huge coral fans and sponges. Investigate the wreck of the Cartanza Senora off Buck Island, St. Thomas – an accessible shallow wreck that’s home to schools of fish.
St. Thomas and St. John have numerous reef and ledge dives where you might encounter barracuda, sea turtles, and reef sharks in their natural habitat. If you’re new to diving, your crew can arrange a Discover Scuba session in a calm bay, so you can experience breathing underwater in a safe, supervised setting. Diving from a private catamaran means no crowded dive boats, flexible schedules, and personalized dive plans. It’s just you, the deep blue sea, and an unforgettable underwater world.
Private Beach Picnics & Island Hopping
One of the most romantic and relaxing experiences is having a deserted beach all to yourself. With your own catamaran and tender, the crew can whisk you to any number of uninhabited cays or secluded coves for a bespoke beach picnic. Imagine stepping ashore on a tiny island like Sandy Cay or Lovango Cay, where it’s just your group under swaying palms. The crew sets up a luxe picnic with blankets, pillows, and a gourmet spread – perhaps a chilled lobster salad, fresh tropical fruits, and a crisp wine – all arranged just for you.
Spend the afternoon swimming in the shallow waters, beachcombing, or simply napping in the shade with the sound of gentle waves. No one will disturb you – it’s true island bliss. For families, the crew can turn it into a fun “castaway” adventure, maybe even setting up a treasure hunt for the kids on the beach. Each day on a charter, you can hop to a new island or beach, so every lunch can have a new stunning backdrop. It’s the ultimate island hopping, minus any hassle – your crew handles all the details while you soak up paradise.
Gourmet Dining Onboard
Prepare to indulge in five-star dining at sea. Fully crewed charters come with a private chef who crafts menus tailored to your tastes. This isn’t standard cruise buffet fare – these are gourmet meals often rivaling the best restaurants, served in the most exclusive setting: your own catamaran. Every day, you’ll be amazed by the culinary creations coming out of the galley. Wake up to the smell of freshly baked pastries and rich Virgin Islands coffee. Lunch might be a spread of ceviche made from the catch of the day, vibrant salads, and homemade conch fritters with tangy dipping sauce.
Dinners are elegant affairs under the stars – perhaps grilled Caribbean lobster with drawn butter one night, and filet mignon with a local twist (seasoned with island spices) another. The chef will incorporate local ingredients – like sweet mangoes, passionfruit, or perhaps the famous spiced “Bush Tea” flavors – to give you an authentic taste of the USVI. Have dietary requests or a child who only eats pasta? Menus are completely personalized, whether you want healthy spa cuisine, a vegetarian feast, or a special birthday cake. Many crews also excel at setting the scene: expect beautifully set tables with fine china, creative garnishes, and maybe even a surprise beach dinner with tiki torches one night. And best of all, you don’t have to lift a finger – it’s all-inclusive pampering. Each meal on board becomes an experience in itself, often accompanied by breathtaking views that no restaurant can offer.
Exclusive Land Excursions & Cultural Immersion
Beyond the beaches, the USVI is rich in culture and history, and a crewed charter can connect you with insider experiences on land. Want to explore historic downtown Charlotte Amalie? We can arrange a private guided walking tour that delves into the pirate lore, Danish colonial history, and iconic landmarks like Blackbeard’s Castle and the 99 Steps. Interested in the culinary culture? Take a guided food tour through St. Croix’s Christiansted to sample West Indian curries, johnnycakes, and Cruzan rum cocktails at local haunts. If you’re a nature enthusiast, your captain can hire a National Park guide to lead you on a hike in St. John’s lush forests, pointing out exotic plants, petroglyphs, and maybe even introducing you to the island’s wild donkeys.
Consider a trip to St. Croix’s rainforest to see the beer-drinking pigs at Montpellier Domino Club – a quirky local tradition! For the adventurous, we can set up a day of sport fishing or a scuba diving charter with experts, or even a helicopter tour above the islands for a bird’s-eye view. On St. Thomas, you might enjoy a round of golf at Mahogany Run or a spa day at a luxury resort – whatever your land-based interests, Boatcrowd’s network will make it special. These are not cookie-cutter excursions; they’re tailored to your preferences and often private. It’s all about immersing yourself in the local vibe – be it dancing to steelpan music at a local carnival, visiting an art gallery opening on St. John, or meeting a local historian for coffee. At the end of the day, you return to your catamaran enriched by authentic experiences many visitors miss, with plenty of stories to tell.
Sunset Moments & Nightlife Afloat
Some experiences defy category – they’re simply the magical moments that happen when you have a catamaran at your command. One such moment is the sunset ritual: each evening, find a beautiful anchorage, let the world slow down, and watch the tropical sun melt into the sea. Perhaps you’re perched on the sundeck with a Painkiller in hand, or floating in the water beside the catamaran as the sky turns gold. No two sunsets are the same, and the tranquility of those minutes is often a trip highlight. Conversely, if you crave a bit of nightlife, a charter can accommodate that too. On a couple of nights, you might decide to dress up a bit and step ashore for some island nightlife – maybe hearing live reggae music at a beach bar on St. John or trying your luck at the casino on St. Croix (the USVI’s only casino is at Divi Carina Bay, St. Croix).
But many guests find the nightlife they love most is on the catamaran itself – stargazing from the flybridge, enjoying a movie under the open sky, or even having a spontaneous dance party on deck with your curated playlist thumping over the catamaran’s sound system (your crew might show off some dance moves too!). And let’s not forget the simple joy of night swimming – some catamarans have underwater lights that attract fish, so a midnight dip can feel like swimming in an aquarium of glittering plankton and curious tarpon. Whether you want serene or celebratory, the evenings aboard offer something truly special. Every experience – day or night – is elevated by the fact that it’s just for you. That’s the beauty of a crewed charter: total personalization of experiences, creating memories that will last a lifetime.
Marinas and Ports of Call
The U.S. Virgin Islands has excellent marina facilities mostly on St. Thomas and some on St. Croix. Your journey will probably begin at one of St. Thomas's top marinas, such as Yacht Haven Grande in Charlotte Amalie (a full service, luxury marina often hosting superyachts, with shops and restaurants adjacent) or American Yacht Harbor in Red Hook (on the eastern end of St. Thomas, great for quick hops to St. John). These marinas offer such amenities like provisioning stores, boutiques, and sometimes even spas or pools that you can use before departure. On your charter, you will be mostly at anchor or on mooring buoys in beautiful bays, but you may dock or visit smaller harbours as part of the adventure.
St. John has no large marinas – the town of Cruz Bay has a small dock and moorings, and otherwise you'll use the National Park mooring balls provided in many bays (your crew will handle this; moorings protect the coral by preventing anchoring in sensitive spots). St. Croix has a couple of marina options like Green Cay Marina or the St. Croix Yacht Club, if needed, but often visiting yachts will anchor off Christiansted or Fredericksted as the harbours are big enough. Boatcrowd will plan all these logistics in advance, so you don't have to worry about securing dockage or moorings – it’s arranged or expertly handled by your captain. If you have any land-based plans (like dining ashore or exploring a town), your crew will get you as close as possible, be it tying up to a dock or using the tender to ferry you in.
Insider Tip: In popular spots (like Maho Bay or Caneel Bay on St. John), the Park Service moorings can fill up in high season. Your captain’s local knowledge is key – they often arrive a bit earlier or have alternative anchorage spots ready. Trust their timing; if they suggest leaving a bit early from one spot to snag a prime mooring at the next, it’s worth it to ensure you get the best location. All in all, the USVI is a very yacht friendly place – you'll find the infrastructure reliable and the sailing distances short and sweet.
Sea Conditions and Weather
The USVI is beautiful for sailing because the sea conditions are normally gentle. The islands are protected by the Caribbean Sea on one side and warmed by the steady tradewinds from the Atlantic on the other side. Most of the time, you’ll enjoy smooth sailing with moderate breezes. The trade winds come from the east/northeast in winter (Dec–Mar) and from the east/southeast in summer (Jun–Aug), blowing at around 10–20 knots, a perfect speed for a fun catamaran or sloop ride, but rarely too heavy (except for the odd Christmas winds or weather fronts).
The seas between St. Thomas, St. John and their cays are usually calm, often just small waves (1–3 feet). The sail to St. Croix is a longer sail across open water (~ 35–40 miles) and can be choppier, with swells of 4–6 feet depending on the wind – your captain will do this leg in the morning when it is calmer, and most larger yachts manage it fine. During the peak hurricane season (Aug–Oct), as noted, most yachts will steer clear of the area, but early summer can still see afternoon thunderstorms or the occasional tropical disturbance. The crew is always on the lookout for weather on the satellite and local knowledge, so you will probably avoid any bad bits.
If a squall pops up (quick rain showers are not unusual year round), it usually passes in 20 minutes and the sun comes out again – it’s actually quite nice and often produces a rainbow. The sea temperature is warm (79–84 degrees F) so you can swim and snorkel for hours without getting chilly. If anyone in your party is prone to motion sickness, let the crew know – they can advise on best cabin choice (mid-ship is most stable) and will navigate to the most protected anchorages each night (there are plenty of coves where the water is lake-like). For most, seasickness is unlikely in these gentle conditions, but just in case, it is a good idea to bring some motion remedies (pressure bands, ginger candies, or medication) – the crew usually has some on hand too. All in all, expect a nice ride throughout; the USVI is known for its lovely sailing conditions that are perfect for beginners and experienced sailors alike, which is why it is one of the most popular charter destinations.
