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A Refreshing View of The BVI: A 7 Day Itinerary

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Why charter a yacht in the BVI?

There’s a reason the British Virgin Islands are hailed as the world’s top sailing destination. From iconic Caribbean beach bars to breathtaking natural scenery and laid-back island vibes, the BVIs are nothing short of paradise—an ideal cruising ground for sailors of all kinds.

Imagine waking up embraced by lush islands, safely moored in a protected bay, sipping your morning coffee on deck as the sun rises over the mountains. The BVIs offer not just postcard-worthy landscapes but also sailor-friendly conditions: clear line-of-sight navigation, deep blue waters, and plenty of mooring balls. That’s exactly why, when it came time to plan a sailing vacation, my friends and I unanimously chose this stunning destination. As the only one in the group who had previously visited the BVIs, I had the joy of watching their faces light up in awe as they experienced its magic for the first time. While we all had sailing experience of varying degrees, I was the only one who had chartered a yacht before—so everything about this trip was brand new for them.

Although it’s becoming more common, it’s still rare to see women at the helm of charter yachts. My best friend holds her captain’s license, and I bring a long track record of sailing experience—together we co-captained a Fountaine Pajot Isla 40. Arriving at different harbors with two women in their early 30s at the helm always turns heads. People are often surprised to see us managing the boat while the men lounge on the trampoline, drink in hand, enjoying the ride. It makes for a great conversation starter at the bar. Dream Yacht is proud to have women skippers on staff including Lisa who wrote about her experience as a yacht charter captain here.

BVI Base

Getting to the British Virgin Islands

Getting to the BVI is easier than you might think. You can fly directly into Beef Island via San Juan, Puerto Rico, or catch a direct flight from Miami. Another popular option is flying into the U.S. Virgin Islands and taking a ferry across. After months of anticipation, stepping aboard our Dream Yacht catamaran at Hodge’s Creek Marina felt like crossing a threshold into another world. Just a short taxi ride from the airport on Beef Island, the marina was bustling with excitement as fellow sailors prepped their boats, clinking bottles and comparing routes. We checked in with the friendly staff at the Dream Yacht base, completed our walkthrough, and began to settle into what would be our floating home for the next several days.

Find out more about travel arrangements to the BVI here.

Charter options in the BVI

With Dream Yacht, you have plenty of charter options to choose from. Thanks to our experience, we decided to go for a bareboat charter on a catamaran and man the yacht ourselves. For couples, solo travelers, or small groups a cabin charter is a fantastic choice. If you’d rather relax while an expert takes care of the sailing, the skippered charter is a fantastic choice. For the ultimate stress-free experience, you can opt for the crewed charter, where everything is taken care of for you by a captain and a hostess. 

Cooper Island Rum Bar

Day 1 Tortola to Cooper Island

After boarding and provisioning our yacht, we set sail with excitement buzzing through the crew. With the sails up and the sun warming our faces, we caught the perfect angle and reached across the Sir Francis Drake Channel toward Cooper Island, an ideal first stop for easing into the rhythm of sailing life. 

After catching an open mooring ball a few of us grabbed our snorkel gear and dipped into the warm waters off the southern end of the bay. The reef is easy to explore and we were rewarded with sightings of angelfish, large rays, and a school of sergeant majors darting through coral and rocks. 

Cooper Island Beach Club is more than just a resort — it’s a sustainability success story. The entire facility runs on solar energy and features its own on-site microbrewery, a boutique, and a chic rum bar with over 280 rums from around the world. We went ashore by dinghy and explored the resort, enjoying drinks at the bar as the sun dipped low on the horizon. The rum tasting was a hit — spicy, smoky, smooth — each bottle had a story, and the bartender was more than happy to share. It was the perfect way to end our first day in paradise. 

The Baths

Day 2 Cooper Island to Virgin Gorda

We awoke to the gentle sound of water lapping against the hull and the first golden light of dawn spilling over Cooper Island. The stillness of the morning wrapped around us like a warm blanket. Coffee in hand, we stood on the deck, watching the silhouettes of nearby islands emerge from the misty horizon — a quiet reminder that adventure waits for no one. We set sail with a steady breeze and the sun rising higher into the sky, heading toward the mystical island of Virgin Gorda. 

Virgin Gorda holds one of the most awe-inspiring natural wonders in the Caribbean, a place that feels less like a destination and more like a passage into another world: The Baths. We arrived early to secure one of the red National Park mooring balls — day use only — and planned our approach by dinghy. We checked the BVI flag report at The Baths to ensure that swimming to shore from the dinghy line would be safe, it was a yellow flag so we proceeded with caution and a flotation device just to be on the safe side. Strong swimmers or not, respect for the ocean is always part of the journey.

The moment we swam ashore and stepped onto the beach, everything changed. Towering granite boulders rose from the sand like ancient temples, worn smooth by centuries of salt and tide. We followed the winding trail that snakes through the rock formations, crawling, climbing, and wading through shallow pools and golden light. It felt like stepping into a secret left behind by the gods — surreal, sacred, and humbling.

After emerging from the Baths, we hiked the winding trail to “Top of the Baths”, a restaurant and lookout that offers more than just food — it offers perspective. From this vantage point, we saw the majesty of the BVI unfold before us: green mountains rising from endless blue, our own boat a speck among the wild beauty of the sea.

Still energetic from our morning’s experience, we continued our journey around the tip of Virgin Gorda into the legendary North Sound — a protected bay surrounded by some of the BVI’s most iconic destinations: Bitter End Yacht Club, Saba Rock, and Leverick Bay where we grabbed a ball for the night. The day ended as perfectly as it began, with soft music, shared laughter, and the gentle rocking of our yacht beneath a star-drenched sky. We fell asleep with the scent of salt in our hair, the echo of waves in our ears, and the knowledge that this was a day we’d never forget.

Woman Skipper Anegada

Day 3 Virgin Gorda to Anegada

We rose before the sun, the world still cloaked in a violet haze as the North Sound quietly stirred around us. The only sounds were the soft creak of mooring lines and the distant rustle of palms. Today’s voyage would take us further than any other — to the wild, windswept shores of Anegada, the only coral island in the BVI chain.

With the breeze at our backs and open water ahead, we raised our sails and pointed our bow north. The passage was long — about 13 nautical miles — and we fell into quiet conversation and reflection, watching flying fish scatter from our wake. As the day unfolded, Anegada slowly emerged like a secret being revealed. Gone were the cliffs and peaks of the Virgin Islands — here was something new. Unlike the mountainous silhouettes of the other islands, it lies low and flat — a whisper on the horizon.

With the sun high overhead, we set out for one of the island’s most famous and remote treasures: Cow Wreck Beach. We could have rented a car, scooter, or moke, but opted for a ride with a friendly local taxi driver from Anegada Reef Hotel, who shared stories of island life as we bumped down the sandy roads.

We found two charming beach bars: Tipsy’s by Ann, filled with character, music, and hammocks; and Cow Wreck Bar, a quirky, self-serve hangout with incredible views and reef snorkeling just steps away. Cold drinks in hand, we drifted between the sea and shade, soaking up the kind of serenity you only find when the world feels a million miles away.

We snorkeled just offshore, spotting colorful reef fish and even two small octopi who changed color and hid when we swam over them. At Tipsy’s, we swung on rope swings, played beach games, browsed the little shop, and enjoyed fruity rum drinks.

As the golden light of late afternoon began to soften the beach, our taxi returned right on time to bring us back to the boat. But the day wasn’t done — not until we experienced Potter’s by the Sea, famous for its legendary Anegada lobster. Pro tip: call ahead or stop by before 4 p.m. to place your dinner order — these lobsters are caught fresh and cooked with Caribbean flair. We dined barefoot, toes in the sand, under a sky turning indigo and silver with stars. The grilled lobster, served with buttery plantains and tropical sides, was heavenly.

Trellis Bay

Day 4 Anegada to Trellis Bay

Morning in Anegada feels like waking up on another planet — one made of light and salt and sky. We lingered longer than planned, sipping coffee in the soft morning sun and reluctantly preparing to cast off lines. The previous day’s adventures at the beach bars had left us giddy and sun-kissed, with just enough of a hangover to laugh about. But the sea was calling once again, and so we pointed our bow southwest, setting out on the longest stretch back toward the heart of the BVI — Trellis Bay on Beef Island.

There’s a beautiful clarity that comes with long sails. With no distractions but the horizon, your mind clears, and your soul settles. We took turns at the helm, giving a few of the men onboard some sailing lessons with a watchful eye. While some of the crew stretched out with books and music, napped in the shade, and let the motion of the waves rock us into a kind of meditation. The yacht felt like its own little world, floating in an endless expanse of blue.

As we approached Beef Island, the landscape shifted once more — mountains rising again, islands crowding the horizon like old friends reuniting. We arrived at Trellis Bay by mid-afternoon, still feeling the dreamy disconnection of the open water. Finding a mooring ball was easy — this bay is well-equipped and sheltered — and we quickly went ashore to explore.

We wandered through Aragorn’s Studio, where local artist Aragorn Dick-Read has created a space full of vibrant pottery, carvings, and his signature steel fireballs — massive sculptures that come to life with flames during the island’s famous Full Moon Parties. Though we missed the monthly celebration this time, the fireballs alone were a sight to behold — intricate, elemental, and almost spiritual in their craftsmanship.

That night, with the sea calm and our hearts full, we watched as the fireballs were lit in the distance for a private event — their glow casting flickering shadows on the water. We didn’t need the crowds or the party to feel the magic. It was there in the quiet. In the sway of the boat. In the soft laughter of friends under a blanket of stars. 

Sandy Cay

Day 5 Trellis to Jost Van Dyke 

The morning light filtered through the hatches in soft bands as we gently woke in the quiet harbor of Trellis Bay. Our planned destination was clear: Jost Van Dyke, home of the iconic Soggy Dollar Bar and the mythical Painkiller cocktail. But the British Virgin Islands are never about going straight from point A to B. They’re about surrendering to the winding path, trusting that the island will reveal what you’re meant to discover. And on this day, it certainly did.

We set sail from Trellis and cruised westward alongside Tortola. But just as we approached, a gleaming gem caught our eye off the starboard bow — a tiny island oasis known as Sandy Cay. We couldn’t resist. We changed course and grabbed a day ball in the sparkling shallows off Sandy Cay, a deserted island straight out of a dream with sand so white it made our eyes squint. 

We couldn’t stay forever — though we tried — and eventually made our way into Little Harbour, a cozy bay tucked into the east side of Jost Van Dyke. From there, we set out for the Bubbly Pool, a natural tidal formation tucked into the rocky north shore of the island. The hike was part of the fun. Along the well-marked trail, we passed two herds of wild goats, their kids bounding up boulders with carefree joy. It’s no wonder that one of Soggy Dollar’s slogans, “Free as a Goat,” resonates so deeply here.

As we reached the Bubbly Pool, we were once again grateful for checking the flag status — the sea was playful but safe. The waves crashed against the rock wall, and when they funneled into the pool, it created a perfect bubbling noise as if someone was hiding in the rocks with a recording of what you would think the pool would sound like. 

The day had slipped past in a blur of sunshine and discovery, and before we knew it, golden hour was setting Jost Van Dyke aglow. Rather than rush, we decided to pick up a mooring ball in Great Harbour and save our Soggy Dollar experience for the following day.

This is the beauty of a yacht charter: freedom. Freedom from strict schedules, from overbooked tours, from the tyranny of time. Out here, the wind is your guide and your yacht is the key to a different cadence — one dictated by weather, whim, and wonder.

Jost van Dyke, BVI

Day 5 Jost Van Dyke to Norman Island

We took the short sail around the headland into White Bay and dropped anchor just off the shore, swam in with wallets in dry bags, and at long last, stood barefoot at the Soggy Dollar Bar, rum in hand, and huge smiles all around.

Here, the Painkiller is not just a drink. It’s a ritual. Rum, coconut cream, pineapple, orange juice, nutmeg — it tastes like joy and sun and sea. Everyone around us seemed to feel it too: the easy smiles, the slow-dance steps in the sand, the lazy sprawl of bodies in sling chairs.

Then it came time to sail to Norman Island, rumored to have inspired Robert Louis Stevenson’s Treasure Island. It is home to the famous floating pirate ship bar Willy Ts. As we glided into the protected waters of The Bight, Willy Ts was already buzzing with music and revelry. We secured a mooring ball, jumped in the dinghy, and joined the floating party. This night we drank, jumped off the swim platform, and made a host of new friends before finally retiring to our boat. 

The Indians

Day 6 Norman Island to Peter Island

After a slow and much-needed sleep-in, we pulled anchor and made the short sail to The Indians, a cluster of jagged islets off Norman Island known for their incredible snorkeling. The moment we dove in, we were surrounded by vibrant coral and curious fish — a living underwater mosaic that reminded us just how rich and alive these islands truly are. Then it was time to set sail again, this time toward our final destination: Peter Island.

The sail was short, but the sense of arrival was profound. We picked up a mooring ball in Deadman’s Bay, just off the crescent beach framed by the newly reopened Peter Island Resort. The resort’s villas dotted the hills like hidden gems, blending into the lush landscape — elegant, understated, and serenely luxurious.

Although we didn’t go ashore that evening, the view from the water was enough. As the sun dipped low, casting golden light across the quiet bay, we realized we didn’t need anything more than this moment — this crew, this boat, this peace.

Peter Island was our exhale — a gentle, soulful ending to a journey that will live on in memory long after the salt is rinsed from our hair.

White Sand Beach

Day 7 Peter Island to Tortola

With full hearts, we lifted anchor at Peter Island and set our course back to Tortola — where the journey began. Ending at Peter Island made for a smooth, easy sail to the Dream Yacht base. While it’s always bittersweet to say goodbye, we know this won’t be our last time in these enchanted waters.

Why a Yacht Charter is the Ultimate Way to Travel the BVIs

This trip wasn’t a vacation. It was an awakening — a reminder that we can choose a different kind of life, even if only for a week.

Chartering a yacht in the British Virgin Islands is unlike any other kind of travel. It gives you the tools to create your own story — your own route, your own pace, your own private island hop. With a sailboat, you’re not bound by hotel check-in times or ferry schedules. If you fall in love with a bay, stay another night. If the wind shifts, follow it.

It’s complete autonomy with a view — and with a little preparation and teamwork, it’s a style of travel that feels both wildly adventurous and deeply peaceful.

And when you look back, the places become more than pins on a map — they become moments. The view at the top of The Baths. A self-serve rum bar at the edge of the sea. A glowing fireball in a sleepy harbor. Wild goats and waves that laugh. A drink in your hand, your toes in the sand, and nowhere else you need to be.

We didn’t hit every destination. But that’s the thing — we didn’t have to.

There’s always next time.

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