Our Trip Sailing the British Virgin Islands on Board Evenstar with Charter Smarter
When it comes to unforgettable vacations, there’s nothing quite like chartering a luxurious catamaran with your friends and family and exploring the breathtaking beauty of the British Virgin Islands. Our week aboard the Lagoon 55 catamaran Evenstar was an absolute dream come true in every way. Think: turquoise waters, iconic beach bars, and hidden island coves all while experiencing the ultimate luxury vacation experience – life on board a beautiful chartered sailing yacht.
Sailing through the BVIs is seriously my heaven – maybe the happiest I’ve ever been on vacation (which is saying something as a travel blogger!) – it is just the HAPPIEST place. With endless sunshine, pristine beaches, and a fun, vibrant island culture, every stop along your charter feels like stepping into a postcard. Whether it’s snorkeling in crystal-clear waters (we literally went snorkeling with DOLPHINS in the wild!!!), enjoying freshly made Painkillers at a beach bar, or soaking in the sunset from the deck of your very own sailing yacht, this destination captures the essence of paradise, perfected. The BVIs are renowned for their unique charm, laid-back Caribbean vibes, incredible sailing conditions, and a sense of exclusivity that makes you feel like you’ve discovered your very own slice of heaven. But lucky for you – I discovered it first so now you can know all the best tips and tricks for planning your own perfect getaway. Here’s absolutely everything you need to know about our adventure so you can plan your group trip to the Virgin Islands! Any more questions after reading this? Leave them in the comments or DM me on Instagram & I’ll get back to you!
Let’s go to the BVI!!!!!!!
but first, WHY SAIL THE BRITISH VIRGIN ISLANDS?
Why sail the BVI versus other places around the world? Well, the British Virgin Islands are quite frankly a sailor’s paradise, offering some of the most protected and calm waters in the Caribbean, and in the world. The consistent trade winds, short sailing distances between islands, and abundance of sheltered anchorages (hello cute Caribbean beach bars!) make it an ideal destination for both seasoned sailors and first-time sailing charter guests. Unlike many other sailing destinations, the BVIs are designed with yachting in mind, featuring countless mooring fields, vibrant beach bars and yacht clubs accessible by boat, and stunning national parks that you can only reach by sea. Whether you’re looking for thrilling water activities, serene beaches, or lively party scene, the British Virgin Islands have it all.
THE BEST TIME OF YEAR TO SAIL THE BVIS
The best time to sail the British Virgin Islands is between December and April, during the dry season when the weather is the most pleasant. We traveled at the end of January and had great weathe. Between December and April offers warm temperatures, steady trade winds, and minimal rainfall, making it perfect for a sailing trip! If you’re looking to avoid peak tourist crowds, consider visiting in late April or early May, just before the off-season begins. Hurricane season typically runs from July to November, and while chartering during this time can be less expensive, many boats are pulled out of the water completely during these months due to weather concerns. Plus, summertime gets verrrry humid, so US-winter and spring is a better time to go.
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WHERE WE SAILED: THE BEST BRITISH VIRGIN ISLANDS SAILING ITINERARY
Our sailing journey through the British Virgin Islands was meticulously planned by our captain after a pre-charter call where we talked thoroughly through our group’s travel style & preferences, the types of days we wanted to have, and places we didn’t want to miss! He then took all that info and planned the perfect week according to the weather to give us the best, smoothest sailing while hitting all of our spots! This itinerary gave us the perfect mix of adventure and relaxation, with plenty of time both on land and at sea. Here’s our day-by-day breakdown and in my opinion the perfect British Virgin Islands sailing itinerary:
Day 1:
We flew into EIS (Tortola, BVI) and started our adventure at Scrub Island Resort, where we had spent a couple nights before our charter to get oriented to the islands. You definitely don’t have to do this and can get straight on your boat! The turquoise waters & island setting set the tone for what would be a spectacular vacation and we were sooo ready to board!!! After getting settled on Evenstar, we spent the afternoon unpacking, having a deliiicious lunch of fresh grilled mahi mahi and a greek couscous salad, and then just relaxed and enjoyed a beautiful sail (with champagne of course!) to Bitter End Yacht Club, where we arrived for sunset cocktails (so good!) and then had dinner back on our boat (the best food in the BVI was on our boat!!!! More on that later!)
Day 2:
We spent the next day at the iconic Bitter End Yacht Club, a legendary destination for sailors. Fun Fact: This yacht club used to be coat and tie only dress for men!!! But, nowadays, it’s a casual, luxurious beachy hideaway was perfect for a sunset and overnight stay in their harbor. Their food is also great at Bitter End, if you choose to do lunch or dinner on shore. We loved soaking up the beach, hammocks, and crystal-clear waters, shopping at their island boutique (so cute) and ordering a few painkillers (the delish cocktail made famous in the BVI!).
Day 3:
Sailing to The Baths at Virgin Gorda was a huge highlight of our trip. We arrived just before sunset (thanks to our captain Tim’s guidance) and it was INCREDIBLE- no one was there! During the day the Baths get suuuuper crowded and it’s just not the same experience – so go early in the morning or just before sunset- and time it on a day when it’s “open” which means you can swim in like we did! So so fun! (Also bring a waterproof phone case for pics when you’re there – or if you’re sailing with @sailingevenstar they have one on board – they think of absolutely everything!)
Day 4:
Peter Island was next on our itinerary, and it’s a must-visit for anyone sailing the BVIs looking for a luxe beach day! Access to the pool and beach costs $50 per person, or you can dine at the Drunken Pelican restaurant for free. We opted for a full day enjoying the island’s luxurious beach, pool, floaties, and pickle ball courts!
Day 5:
We overnighted outside Willy T’s, a legendary floating pirate ship bar that’s such a fun, divey spot for drinks. You MUST jump off the side of the bar (known as walking the plank!) it’s a BVI rite of passage!
The next day, we stayed in the Norman Island bay for lots of watersports off of the boat and enjoyed paddleboarding, snorkeling, e-foiling(my favorite!! motorized surfing – they have one on board!) and simply lounging around on the catamaran and having delicious food made for us by chef Zara. It was the best!
Night 5: Cocktails @ Foxy’s Bar
We spent this night doing a quintessential feet-in-the-sand BVI experience with live music at Foxy’s – it was a fab, festive atmosphere. Loooved this spot!
We then hopped back on board the boat for a delicious steak dinner, wine and games! (We brought liars dice – our fav- but the boat also had tons of games on board which was so fun!)
Day 6:
On our final full day, we made our way to the iconic Soggy Dollar Bar at Jost Van Dyke – the best bar in the world. Spending the day sipping Painkillers and soaking up the sun on this famous beach was the perfect way to end our adventure. And Captain Tim knew what he was doing – he got us the absolute best parking spot so we could thoroughly enjoy our day here – it was a DREAM – and I think Jost Van Dyke is my favorite island in the BVI!!!
And, as if the most perfect day could get ANY more perfect. A nearby boat told us that they had spotted dolphins about 500 meters away, and within seconds, we were grabbing snorkels, hopping in the dinghy, and searching for a pod of dolphins. When we saw them, we jumped in!!! And, suddenly, we were surrounded by the most graceful, angelic creatures I’ve ever seen. They swam beside us, twirling and playing in the waves with us. It was a total out-of-body, pinch-me moment—something I’ve dreamed of since I was a little girl, and now, here I was, living it. I don’t think I’ll ever get over this experience. A dream come true, in every sense of the word.
Soggy Dollar Bar continues its magic of always delivering the BEST days of all time – every single time I’ve been there!
We flew out of St. Thomas the next day but if you can with your flight path it would have been easier to fly out of the British side (EIS, Tortola airport) however they have less flights available. I’m pretty sure the crew can tailor your itinerary to where you need to fly out of, whether it’s US VI or BVI, so just talk to them about that in your inquiry!
JETSET TIP: The weather was too windy for us to get to Anegada on our trip, but, if you have time on your charter, I’d highly recommend adding in Anegada to your itinerary. As the farthest island in the British Virgin Islands, Anegada feels like a remote paradise far from the hustle of the more frequented spots. Its pristine beaches, such as Loblolly Bay and Cow Wreck Beach, are stunningly serene and perfect for relaxation. It also has the third largest coral reef in the world!! The shallow reefs surrounding the island are a snorkeler’s dream, teeming with vibrant marine life. Plus, Anegada is famous for its mouthwatering lobster, so be sure to indulge in a fresh lobster dinner while you’re there. Sailing to Anegada is an adventure in itself, with its low-lying coral terrain rising just above the horizon as you approach—a true hidden gem of the BVIs!!!!!
WHAT’S INCLUDED IN A SAILING CHARTER IN THE BVI
Chartering Evenstar was ALL-INCLUSIVE which was amazing – it came with so many things include in the charter rate that made the experience seamless and stress-free:
All-Inclusive Meals and Drinks: 5-star meals (3 meals a day!) tailored to your specific preferences and an open bar with premium spirits (that the crew will use to make increeedible cocktails) and wine and beer. Picture yourself sipping on freshly blended strawberry mint margaritas or creamy piña coladas while you take in the island breeze as you sail. Chef Zara can even set up an island rum tasting, sampling the best of the Caribbean. And every morning, you’ll be in heaven with breakfasts complete with Captain Tim’s homemade sourdough avocado toast and Zara’s breakfast burritos, paired with delicious lattes crafted to perfection using the onboard espresso machine! This is LUXURY, y’all. I was in absolute paradise with the food & drinks on our yacht.
As far as types of food you’ll experience on board Evenstar, one of my favorite lunches was Zara’s homemade poke bowls, and dinners ranged from freshly grilled mahi-mahi and gourmet couscous salads to the most delicious steak and veggies one night, and a shrimp pasta that I will dream about forever! Every meal and drink is an experience, designed to elevate your time on the water.
Watersports Equipment: From snorkeling gear and paddleboards to kayaks, fishing equipment, and an e-foil surfboard, everything you need for fun on the water is onboard.
Fully Crewed Charter: The experienced crew, Tim and Zara, take care of all the sailing, cooking, and cleaning, allowing you to fully relax.
Luxury Amenities: The yacht features air-conditioned cabins, spacious common areas, and Wi-Fi so you can stay connected while enjoying paradise.
ALL ABOUT THE YACHT
The Lagoon 55 catamaran Evenstar is a floating oasis of luxury. Here’s what makes this yacht so special:
Accommodations: Evenstar comfortably sleeps up to 8 guests in its 4 beautifully appointed cabins. Each cabin features an en-suite bathroom, air conditioning, and plenty of storage.
Design: The Lagoon 55 is known for its spacious layout, with ample room to lounge both inside and out. The flybridge offers panoramic views, while the aft cockpit is perfect for al fresco dining.
Crew: Tim and Zara are the heart and soul of Evenstar. Tim is an experienced captain who ensures smooth sailing, while Zara is an incredible chef who prepares gourmet meals tailored to your tastes. Every meal on board is a 5-star dining experience. Tim even bakes his own sourdough bread, while Zara creates homemade ice cream. They cater to all dietary needs and preferences, ensuring every meal is a highlight of your trip. Imagine waking up to the smell of freshly baked bread, indulging in a seafood feast for lunch, and ending your day with a decadent dessert under the stars. Tim and Zara’s passion for hospitality shines in every detail, creating an unforgettable culinary journey at sea.
Extras: The yacht is equipped with all the water toys you could want, including paddleboards, snorkeling gear, fishing equipment, and the show-stopping e-foil surfboard for gliding effortlessly over the water. There’s even a tender for exploring nearby coves and beaches.
If you’re interested in more details on the. yacht, shoot an email to [email protected] and I can help get you the best rates and book you!
HOW TO BOOK A BVI CHARTER
Booking your dream vacation aboard a sailing yacht in the BVI is simple – shoot me an email to [email protected] and I can help connect you with the team for a charter.
PRICING OF A BVI SAILBOAT CHARTER
Charter prices typically start on the low range of $20,000 to $30,000 for 6, 8, or 10 guests, with high-end pricing on $50,000 to $70,000. Yacht prices vary based on factors such as size, year, number of cabins, and crew requirements! For a 7-night, all-inclusive charter, per person rates generally range from $2,600 to $6,000 depending on the yacht and specific offerings. Which is a GREAT price for everything you get (and is about equal to what you’d be paying at a luxury hotel, but with so much more included). For exact pricing quote, contact [email protected]
PACKING TIPS FOR SAILING THE BVI
Packing for a sailing trip in the British Virgin Islands is refreshingly simple—you really don’t need much for a BVI vacation! That’s the minimalistic, rejuvenating beauty of living on a sailboat for a week. You’ll find yourself living a very simple life of swimsuits and cover ups on board.
But there are a few essentials you’ll definitely want to bring along to make your trip as smooth and enjoyable as possible!
Clothing for the BVI’s:
Pack lightweight, breathable clothing for sunny days and casual evenings. Think swimsuits, cover-ups, shorts, and tank tops. I did not need a jacket or sweater for nights when we went (January) but I did buy a long sleeve ‘boat shirt’ at Bitter End Yacht Club’s boutique that I liked wearing at night!
Matching Swimsuits for the Group!
If you’re sailing with a group, it’s so much fun to have matching group swimwear from Kenny Flowers! There are cover ups too and cute, great quality matching swimwear and resort wear options for men, women, and kids too! Imagine showing up to Soggy Dollar Bar like this:
Shoes:
You’ll mostly be barefoot on board, and even when you go to shore!!!!! It’s amazing. but bring one pair of comfortable sandals/flip flops. If you plan on hiking, tennis shoes (but we did not hike so I didn’t need anything except these easy travel sandals!)
Sun Protection:
The Caribbean sun is no joke! But the boat has you covered with reef-safe sunscreen! I like to pack my own face sunscreen (I love this one), and a wide-brimmed sun hat (or few if you’re like me and love a good hat! here are my favorites), and don’t forget your sunglasses!
Snorkel Gear:
Don’t worry about it! Evenstar has all the gear you need onboard!
Reusable Water Bottle
While I would normally say to pack one (and I like to have it for the airport/flight, you will actually have these on board Evenstar to help you stay hydrated and eco-friendly!
Camera or GoPro
You’ll want to capture every moment of your adventure, from the turquoise waters to breathtaking sunsets. I like this GoPro for underwater shots!
Makeup, Seasickness Medication & Toiletries:
Pack any personal medications and travel-size toiletries. I didn’t wear much makeup on our charter! But I do like having this tinted sunscreen, a little blush, and some mascara! While we never felt sick on our boat, don’t forget motion sickness remedies if you’re prone to seasickness, just in case! I personally like to pack non-drowsy dramamine as well as these ginger drops – they work wonders! I prefer to take the non-medication ginger drops before doing dramamine because dramamine can make you sleepy (even the non drowsy version!)
Chapstick
Your lips will get dry in the BVI! I love this lip balm.
WHAT I WORE:
bikini linked hereJETSET TIP:
Leave some room in your bag! Each stop along the way offers incredible local merchandise, from Soggy Dollar Bar t-shirts to handcrafted jewelry. You’ll definitely want to bring home a few souvenirs to remember your trip.
FREQUENTLY ASKED QUESTIONS
How customizable is a sailing charter? Your charter is all about you and your group!! Every day is designed to reflect your preferences, from the destinations you visit to the food and drinks served on board. A detailed preference sheet and pre-charter discussion help tailor your experience. Plans are also flexible to accommodate weather conditions or last-minute changes.
What’s included in the charter rate? The rates are all-inclusive unless specified otherwise. This includes the use of all onboard amenities and water toys, crew services, taxes, cruising permits, licenses, and specified food and beverages. Contact Charter Smarter here (and let them know I sent you!) for an exact pricing quote.
What’s not included? Rates exclude flights, onshore meals or excursions, and gratuities (a standard gratuity ranges from 15% to 20% of the charter fee).
Can I book a shorter or longer charter than a week? Absolutely! While 7-night charters are standard, shorter charters (4-6 nights) and extended charters (10-14 nights) can be arranged to suit your schedule.
Will I feel cooped up on a sailboat? No!! You can design your itinerary to spend most of your time on land, if that’s what you like. I never once felt cooped up on the boat – it’s spacious and beautiful and becomes your home! But we did go somewhere every day and we made land-time a priority!
Did you get seasick? No and I think this has to do with the captain!! Our captain was so skilled at making it a smooth sail for us – even in windy conditions. I didn’t get sick once. However, I never go into the inside cabins while the boat is moving (that’s a sure-fire way to feel sick). I also avoid looking at my phone if the seas are rocking, and always get out into the fresh blowing air. We had smooth sailing though and I never felt it. I personally like to pack non-drowsy dramamine as well as these ginger drops – they work wonders if you do start to feel it. I prefer to take the non-medication ginger drops before doing dramamine because dramamine can make you sleepy (even the non drowsy version!)
Where does all my stuff go? Is there storage on the boat? There is plenty of room to put all your clothes & belongings away on the boat – it’s designed so beautifully!!! They also were able to store our suitcases below deck once we had unpacked which was nice.
What types of charters are there? From romantic getaways and family vacations to flotilla-style group adventures and scuba diving charters, there’s something for everyone. Whether you’re celebrating a milestone or exploring as a family, Evenstar provides the perfect setting.
Let me know any other questions and I can answer! This was seriously our DREAM trip, and I’m already wanting to plan another one back!
xx
Christina
