Private Crewed Charter
Affordable Luxury - Bespoke Services - Custom Pricing
CONTACT US TO SET UP YOUR VACATION - OPTIONS FROM $11,000 - $20,000 + PER WEEK
The Sailing Collective team personalizes every private 7-day package to match your group's unique vibe and interests, providing customized itineraries and tailored experiences. We will pair you with the perfect Sailing Collective captain and chef to lead your journey through these spectacular islands.
British Virgin Islands private charter season begins in November with pleasant weather though July with February through April being the peak months. We personalize the Sailing Collective 7-day vacation package to match your group's interest. We have a variety of vacation package offerings including:
• Family travel with first-mates and chefs with childcare background
• Private friends charters on monohull and catamarans with up to 5 double cabins
• Honeymooners with private captain and chef
• Corporate retreats and team building regattas
Whether your group is interested in a more rustic DIY-vibe lead by a Sailing Collective captain or a luxury journey aboard a 60'+ premium sailboat with your private Sailing Collective captain, chef, first-mate team, we can match your budget.
Boat options: 40' to 55' monohulls, 38' to 52' catamarans ranging from $10,000 to $25,000 + for a fully crewed charter.
contact: info@thesailingcollective.com / +1 (347) 927 5487
Dayyan Armstrong founded the Sailing Collective out of a passion for connecting people with the world through adventure and sailing. Having been raised with values based on multi-cultural awareness and the importance of global culture, Dayyan combined his enthusiasm for sailing and exploration to create an integrated sailing vacation organization open to adventures, explorers, and sailors alike. With a background in music performance, social theory, and a graduate degree in economics from the New School for Social Research, Dayyan is always excited to participate in discourse in topics of theory, art, adventure, and exploration. Outside sailing and exploration, Dayyan is passionate about cured meats, design, Maine, social theory, Cook’s Illustrated, a good museum, photography, Harper’s Magazine, and various types of cooking over fire or coals.
After graduating with a degree in Outdoor Education, Ross Beane has been relentless about sharing his love of wilderness travel with people wherever he goes. Having worked with programs from Alaska to Maine, he enjoys guiding students of all ages and abilities into beautiful and remote locations to foster technical know-how and an appreciation of the natural world. With multiple certifications in wilderness emergency medicine, he brings with him an understanding of risk management that keeps it safe without compromising fun. An avid sailor since youth, Ross has made many safe crossings and has taught sailing for The Wooden Boat School, New York Harbor Sailing Foundation, and the Manhattan Sailing School before joining Dayyan to help start the Sailing Collective.
Taylor Collins grew up sailing the warm waters of the Gulf of Mexico. He spent his childhood racing Lasers and crewing on Defiance, a C&C 35, and Scorpio, A Creekmore 36. After earning a Masters in City Planning from the University of Arizona, Taylor relocated to New York City and quickly immersed himself in the sailing scene. As as sailing instructor, Taylor has introduced many New Yorkers to the sport of sailing and regularly leads charters in the Caribbean. Taylor is one of the original Sailing Collective captains and has sailed with The Sailing Collective in many locations worldwide. He is a certified diver and a fantastic vacationer. When not sailing, Taylor tends bar at Williamsburg, Brooklyn’s Walter Foods and works on his trucks and motorcycles.
Liz began sailing on the Hudson River when she was eight and immediately fell in love. She soon moved to the Maine coast where she started her education in coastal cruising after obtaining her own boat. Between then and now, Liz has worked at Morris Yachts as a rigger and cruised from Barcelona to London in a seventy-nine foot trimaran, Earthrace (made famous by the TV show Whale Wars as the Ady Gil). She began her captaining career on a privately owned lobster yacht and has gone on to do deliveries up and down the east coast on an array of different vessels. In the summer months she manages the waterfront of The Northeast Harbor Fleet Yacht Club, maintaining the clubs boats and providing private sailing lessons in her free time. She lives aboard her twenty-five foot sailboat and is a USCG certified captain.
Captain Kirk Robinson has always been an incredibly active person both on and off the water. Growing up between Antigua and Jamaica- he spent his early life training to be a professional soccer player. After going on to represent Antigua internationally he came back to the sea where he most loved to spend his time. Kirk started his sailing career as an Engineer with Sunsail working mostly in Antigua and the British Virgin Islands. He travelled to Panama in 2005 to receive his training to become a licensed Captain. For the past 11 years he has been sailing around the BVI and the Caribbean Sea working independently as Captain Kirk.
The British Virgin Islands are comprised of more than 25 beautiful jewels set amid the sheltered, turquoise waters of the central Caribbean Sea. Tortola, Jost Van Dyke, Virgin Gorda, and Anegada are the major isles of the archipelago. The smaller islands, many splendid for day or overnight visits, add to the varied mix of tropical pleasures, which can be as laid-back or as active as desired during a British Virgin Islands yacht charter. White-sand beaches, luxury waterfront resorts, sailor-friendly bars and upscale restaurants, chic boutique shopping, snorkeling and scuba diving on coral reefs teeming with sea life, it is all the perfect blend to create a delightfully rejuvenating experience under sail on a private luxury yacht. British Virgin Islands sailing vacations are one of the top choices among sailors for a terrific and memorable Caribbean adventure.
Meeting Point: Tortola, marina location determined upon booking confirmation.
Day 1: Meeting time is at 6:00 pm at the front desk, lounge area. If you arrive after 6:00 pm, ask the front desk for the names of the Sailing Collective boats. Look for the Sailing Collective logo on our captain, crew and boat flag - we will be waiting for you. If you arrive early, you can keep your luggage at the front desk and enjoy the marina amenities. We sleep aboard the sailboats at the marina and depart Sunday morning after the orientation detailing safety aboard and boat features After everyone settles in aboard, we dine ashore for our first outing of the journey. Please note that the last ferry from St Thomas to Tortola is 4:30pm and service times are subject to slight changes and delays. Please make sure your flight arrives in St. Thomas before 4:00 pm Day 1 of the journey. Please text your captain if you have any travel delays. We recommend ensuring connectivity to a messaging service such as iMessage, Viber, Whatsapp, or SMS until you reach the boat.
Day 8: We arrive back at the marina at 7:00 am allowing plenty of time to catch the first 9:30 - 10:00 am ferry from Tortola to St Thomas. Please do not purchase flights that depart STT before 2:00 pm.
St Thomas Airport (STT) has the most affordable and frequent flights. After arriving at STT take a high speed ferry (~1 hour; approximately $35/each way - payable with cash or credit) from St Thomas to Tortola.
Beef Island Airport (EIS), take taxi to the marina base, approximately 30 minutes. This is the most direct route but typically more expensive.
Taxis are readily available outside the airport and ferry terminals. Crew will arrange your return taxi from the marina to the ferry or airport.
It is the responsibility of each individual to ensure relevant visas are obtained where necessary. Check BVI visa requirements for your nationality here. U.S. citizens are issued a tourist visa at the airport passport control for a $15 tariff payable in cash only (USD are accepted). Please ensure your passport is valid for the period of travel and for six months after you return with at least 3 blank pages for visa stamps. Your passport name must match the name on the flight ticket otherwise you may not be able to travel and insurance may be invalid.
The Sailing Collective cannot be held responsible for refusal of entry or travel due to lack of visas. If you are in any doubt of your visa requirements, please contact your Embassy for full details.
Accepted Forms of Payment:
US Dollars and US travelers checks are used throughout the BVIs.
Visa and MasterCard are also accepted in most places.
ATMs can be found in Road Town, but it is recommended that you travel with the necessary cash. Travelers preferring to travel with travelers checks can cash them at most banks in Road Town.
The British Virgin Islands bask in a tropical maritime climate. Rainfall is moderately low for tropical islands. Scattered showers are common throughout the year, but all day rain is very rare. There is little seasonal variation in temperature ranging in the 80s during the day and the 70s during the evening. Brief rain showers can be frequent so please bring a light raincoat. Wind speeds vary throughout the year from 5-20 mph.
Sailing Collective stocks each boat with healthy, fresh and flavorful local foods and produce from the region. The provisioning package includes:
Not included in provisioning package:
Cooking Aboard: Passengers and crew cook family style aboard; cooking enthusiasts and foodies are welcomed to add their skills and experience. Sailing Collective skippers and crew are all talented cooks and will prepare meals as well. Collective groups may choose to dine out more times than scheduled if the group or individuals choose.
Dietary Restrictions: Important to notify your Sailing Collective representative of any dietary restrictions ahead of time in your Guest Form: http://thesailingcollective.com/guest-form
*We will have plenty of food to satisfy you for your trip. However, if there are special foods that will make you feel more comfortable for the duration of your trip, please pack or purchase in advance.
Collapsible bags in place of large rigid suitcases are advised for ease of transport on and off the boat.
During days on the water, you’ll want to be wearing light and comfortable clothing. As the vast majority of your time will be spent outside, prepare for elements - bring a light rain coat just in case, a hat to shield yourself from the sun, and a set of warm clothing. Throughout the week we may dine out at a nice restaurant, so bring gear that you’ll look nice in and suits your style. Loading and unloading from the dingy can be a wet activity, a pair of shoes that you can get wet is recommended.
Arrive in Road Town, Tortola via Beef Island Airport or by ferry from St. Thomas by 6:00pm to meet your captain and your fellow passengers at the marina location. Relax by the pool as everyone settles into island time, feel the sun and lounge under the palm trees while the paradise sets in. There will be plenty of time to get situated into your sailboat and make last minute provisions and shopping before we depart the following morning. The front desk will have information for you regarding the location of our boat.
Sunday morning before we depart Road Town, The Sailing Collective captains conduct informative sailing and boat tutorials before departing and sailing the Sir Frances Drake Channel on our way to Marina Cay and Nanny Cay. Shake out the sails and learn the ropes as we sail the afternoon passing paradise island after paradise island. We cook aboard in the evening with an optional night out at the famous Pusser’s restaurant for a relaxing evening nightcap.
Spend the morning in the famous Baths on Virgin Gorda's western coast, enjoy the most beautiful beaches of the Virgin Islands and spend the morning snorkeling throughout the crystal waters. Sail north past Spanish Town and The Dog Islands to the north side of Virgin Gorda Islands and anchor in the famous North Sound just past Necker Island, Sir Richard Branson’s private island. Go ashore to rent Lasers and Hobie Cats for an afternoon of dinghy sailing or take a hike to Gorda Peak to view the best sunset in all the islands. This evening we cook aboard before going ashore to the happening Bitter End Bar.
Sailing due north to the BVIs flattest island, Anegada will appear out of the ocean about 4 miles from our end destination. Anegada is one of the BVIs largest and flattest islands with the highest point only 30 feet above sea level! This unique island is perfectly lazy and beautiful, recently voted one of the top beaches in the entire Caribbean by The New York Times, there will be plenty of opportunity to experience the Anagada way of life by enjoying a rum cocktail along white sand beaches. In the evening a lobster BBQ dinner will be prepared for one of the most authentic Caribbean meals in all the islands.
Cooper Island Beach Club is set on the pristine shores of Manchioneel Bay, on the northwest corner of the island. The beautiful surroundings, white sandy beaches and turquoise waters are perfect for relaxing, swimming and snorkeling. Relax on our unspoiled island and make friends with the local wildlife. Golden sands, palm trees and turquoise waters. Discover some of the best dive and snorkelling sites in the world: Our beach is renowned for amazing snorkelling and at its southern-most tip, Blue Tang, Queen Angelfish and schools of Sergeant Majors congregate at ‘Cistern Point’.
Arriving in Jost Van Dyke by the afternoon, we will pickup mooring in Great Harbor and enjoy our last boat cooked meal of the trip. The famous Foxy’s Bar has live music and claimed to have the best traditional BVI rum drink, the Painkiller. During the day we will stop by a beautiful small uninhabited island named Sandy Cay where we will enjoy a short hike with a fantastic view of Tortola's north shore.
Wake up early to motor to the near by Sandy Cay for an amazing morning at the BVIs primer uninhabited islands. Take a nice walk around the parameters of Sandy Cay or lounge on this idyllic beach and take in the palm trees and blue Caribbean water. Setting sail to Norman Island, we will take up mooring on the west side of Norman Island where we will spend our last night at the infamous Willy T’s Restaurant, this floating bar/restaurant/boat is a must for BVI visitors.
The Beneteau 43.3 was designed with sailing performance firmly in mind without sacrificing comfort. A full-batten mainsail and roller-furling genoa easily drive the sleek hull in all conditions. All sail control lines are led aft to the cockpit for safety and convenience, and the mainsail has a self-stacking system and lazy jacks. The yacht also has an electric windlass, and aft is a generous swim platform. The galley is sensibly laid out along the port side and has all features. Forward is a large double cabin with en suite head with shower, and aft there are two double cabins and two heads with showers. All cabins have plenty of storage and hanging lockers, and opening ports and hatches as well as fans.
Understated luxury: design, space and seamlessly integrated functionality, beauty of the wood, and soft colors. The mineral architecture, with elegant taut lines of the 4-cabin versions is an invitation to quiet relaxation. The premire versions surprise with their level of comfort, and make no concessions to either space or functionality.
Now the largest chartered monohull by the Sailing Collective in the BVIs, the 53 built by Jeanneau, is perfect for larger groups and families, looking for a combination of sailing performance and comfort. Above and below deck, her layout allows for plenty of room for socializing, but also offers practicality and performance where required. Headroom: Entry to Cabins: 6' 1" Galley and Cabins: 6' 5" Headroom at helm: 6' 6" The Jeanneau 53 is a pleasure to sail and is responsive to touch, her electric winches and bow thrusters make her surprisingly easy to handle.
A symbol of the new generation. With its sleek design and luxurious features, the Lagoon 40 is a good sailing comfortable catamaran that will be your home at sea.
The Lagoon 450 has everything you could want in a cruising boat: Incredible performance under sail, wide open deck space for lounging, and an incomparable comfort in the saloon and the cabins. The wide hulls of Lagoon 450 offer comfortable cabins with larger floor space than other catamarans of the size. An airy saloon contains an open concept modern galley (kitchen) and comfortable seating all with stunning panoramic visibility of the natural beauty that you came for. The aft deck is covered by a hard top bimini so that there is always plenty of breezy shaded space for lounging when you are taking a break from the sun drenched foredeck. Up front the netted "trampoline" between the hulls is the ultimate place to enjoy this boat under sail with the sun beaming down and the water rushing below you.
Explore photos from our past journeys
