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ABOUT YOUR SAILING COLLECTIVE JOURNEY Your journey will be crewed by a captain and chef who are not only trained professionals but explorers at heart. With diverse backgrounds as sailors, travelers, artists, gastronomes and academics Sailing Collective crew members offer a wealth of information and life experience to every journey. Your crew will work with you to build a customized day to day itinerary tailored to your group needs, interests, and desired activities. Double and Single cabins are available for you to book and join a one of a kind Sailing Collective experience. You'll make new friends while enjoying the greatest week of your life. Take the leap this winter and join the adventure!

* Price per person | 50% deposit required to book | We encourage you to book your cabin 5 months prior to the departure date

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February 11th — 17th 2024

7 days, 6 nights


British Virgin Islands


2 Double Cabins

1 Single Cabin


$4750 Single Cabin

$7600 Double Cabin



As one of the most regularly sailed itineraries worldwide, there’s no one right or wrong way to plan your voyage. The abundance of islands clustered with such close proximity allows for sailors to sail with the wind conditions in the spirit of the moment. Some skippers will take their crew through a circumnavigate of Tortola while others will zig zag jumping from island to island-Norman Island and then to Marina Cay, North Sound, Virgin Gorda and then sail south to Cooper Island.

The ability to choose your own adventure is one of the pleasures of the BVI. Most of the prominent marinas are located on the south coast of Tortola, which is a common location to start your charter. Roadtown is the main harbor and the capital of Tortola home to most of the provisioning and supplies for sailors cruising the region.

Norman Island

One of the famed islands here is Norman Island-home to the infamous floating bar Willy T’s, which is situated in its largest cove called ‘The Bight’ until the permanently anchored ship sank in 2017 during the unprecedented devastation of Hurricane Irma. Now re-born on a new vessel, the bar is known for its abundance of sailors who can be seen arriving by dinghy and tying up alongside.

Salt Island

One of the lesser ventured activities is hiking around Salt Island, which remains completely uninhabited other than a few families of goats that roam freely around the lush green fields. This island once had a productive salt pond facility that shipped salt as an export until the mid 1970s. Even today during certain periods when the salt pond is dry, you can scrape up the island’s salt which is still harvested in small batches.


The northernmost island in the archipelago requires more sailing time, usually on a pleasant beam reach, depending on which island you set out from. With the trade winds blowing normally leaving from Gorda Sound offers the nicest tack. Anegada is unlike the others.  In a chain of mountainous volcanic islands, Anegada was formed by a coral reef and is just a few meters above sea level at its highest point.

Jost Van Dyke

Sailing southwest from Anegada roughly 25 nautical miles, and just a short hop from Tortola’s west end, is Jost Van Dyke, one of the most emblematic of all the islands in the region. Culture seems to flow from here to the other islands and you’ll see this island’s signature style emulated elsewhere in the form of signed t-shirts and flags hanging from driftwood rafters of the local establishments or signature cocktails but the authenticity of it all here is unmistakable.


Vivian Ho

Vivian Ho


Vivian grew up in a culture where eating well was equivalent to living well, the ultimate expression of care and warmth. From seemingly incongruent beginnings in fashion design to event production to the creation of a pop-up dinner series, she realized that her real passion was for building community through the serving and sharing of beautifully presented meals. She remains curious about various methods of cooking and international flavors, finding constant joy while shopping local farmers’ markets throughout her travels. 

Charlotte Matthews

Charlotte Matthews


Charlotte grew up in New York City sailing on her family's Seafarer 31'. At the age of six, she began sailing dinghies at her local yacht club. She became active in her yacht club's PHRF racing and crewed in regattas up to the national level. Charlotte further pursued her passion by teaching sailing every Summer in New York at Manhattan Sailing School and Hudson River Community Sailing, all while completing her studies in Psychology and Sociology at Hunter College. Charlotte now lives and works full time as a captain in the BVI. She has 17 years of sailing instruction under her belt, over 6,000 nautical miles offshore delivering yachts, and both USCG and BVI Captain's licenses. In her spare time, she can be found island hopping, hiking, reading, racing in regattas around the Caribbean, throwing extravagant dinner parties, diving, and falling off surfboards.

About the Food

The Sailing Collective Travel Co. takes food to a new level. We believe by sourcing local ingredients from local friends we have made throughout our travels pushes us to experience where we are by being engulfed by the regional flavors.

Each voyage, both group & private, has a private culinary artist aboard preparing some of the most unique, interesting, and thoughtful food you may ever enjoy in your life! From breakfast to dinner each day of the journey, we are blessed by beautiful meals by one of the most talented culinary teams in travel anywhere in the world.

General Information

Provisioning Sailing Collective will provision your journey with local foods and produce.  Cooking Aboard: Your Sailing Collective chef/crew is incredibly talented and can handle the group's needs with ease. We are all about participation and learning, so if you'd like to help, just ask and we'll get you involved! Collective groups may choose to dine out more times than scheduled if the group or individuals choose.

Included in provisioning package*: 

  • 6 Breakfasts, 6 Lunches, 3 Dinners (or similar), Light Snacks, Water, Coffee & Tea

* Subjected to change

Dietary Restrictions We can accommodate as long as we know in advance! It is important to notify us of any dietary restrictions ahead of time and include full details in the Guest Form that you will fill out prior to the start of the trip.

Sailing a group journey is a collective experience calling us to ebb and flow with the tides of the group. While alcohol and soft beverages are not included, we find a well curated bar shared across the group works out best. We offer two beverage during group journeys packages during the course of the week*:

• $150 for wine, beer, spirits and soft beverages • $75 for soft beverages and under 5 alcoholic drinks. *Private charters, beverages are billed to the charter

Private Charters: Pay as you go

You can also choose to bring your own beverages on board at no cost. Beverages through our package options will be provisioned for by your crew based on the preferences shared in your guest forms. Alternatively, if you plan to purchase your beverages separately, it is best to stock up before we depart the marina! Morning beverages and water are included for all guests.

Please confirm your package choice within your guest form so your crew can plan accordingly!

ADDITIONAL COSTS We recommend planning on having at least $300 – $600 in spending money depending on spending habits. You will be responsible for paying for:

  • All expenses on shore including meals and drinks

  • Flights and transportation to and from the marina location

  • Onboard beverages

  • Gratuity (a 15% to 20% offering)

GRATUITY Tipping your captain and crew is welcome. If you are satisfied with your service, the industry standard for yacht charters ranges from 15-20% of the cost of the charter. Gratuity is split evenly between the crew and can be paid via cash, check, Venmo, or PayPal. Please contact your Sailing Collective Journey Coordinator if you have any questions.

  • 10% - Standard good time on holiday with good service.

  • 15% - Exceptional service on your holiday with exceptional service!

  • 20% - Extraordinary experience and your crew sent the voyage to the moon and back!!

PACKING LIST Collapsible bags in place of large rigid suitcases are advised for ease of transport on and off the boat. Loading and unloading from the dingy can be a wet activity, a pair of shoes such as flip-flops that you can get wet if we are landing on a beach.

As the vast majority of your time will be spent outside, prepare for elements - bring a light raincoat just in case, a hat to shield yourself from the sun, and a warm layer.  Throughout the week we may dine out at a nice restaurant, so bring an outfit looks nice and suits your style. Loading and unloading from the dingy on beaches can be a wet activity, a pair of shoes that you can get wet is recommended.

We also encourage guests bring ecologically appropriate products into ocean environments. You can read more about those recommendations on the Sailing Collective Journal here: Packing for a Healthy Ocean

The Journey Schedule Meeting time is at 9:00am on Day 1 of the charter. Our last night is spent back at the starting marina before we disembark by 9:00am on the final day. Select locations allow for the vessel to return on the final morning, which we will opt for when available.

Terms & Conditions By booking this journey, you agree to comply with the stated Terms & Conditions and Covid Considerations, available on our website. Please contact info@thesailingcollective.com with any questions. 

Travel Insurance We recommend purchasing a travel insurance policy that protects you in case of general and covid-related trip interruptions. If you choose not to purchase travel insurance, you forfeit the right to a refund or credit in the event you have to cancel your trip with Sailing Collective.

PASSPORTS AND VISAS Please ensure your passport is valid for the period of travel and for six months after you return. The Sailing Collective cannot be held responsible for refusal of entry or travel due to lack of visas. If you are in any doubt please contact your Embassy for full details.

WEATHER Daytime temperatures will generally reach highs of around 27°C that's about 80°F. At night the average minimum temperature drops down to around 20°C, that's 68°F. The average daily wind speed in June has been around 11 km/h, that’s equivalent to about 7 mph, or 6 knots. In June, for the nearest coastal location, the temperature of the sea averages around 22°C, that's 72° Fahrenheit.


Lagoon 45

Lagoon 45



British Virgin Islands


February 11th — 17th 2024


British Virgin Islands

Only 3 Cabins Left

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