Consisting of three main islands: Anguilla, St Barthelemy, and St Martin; the northern leeward islands offer amazing sailing to pristine islands. Marine life lives here in an abundance that is thanks to an extensive marine eco park system that keeps the coastline and the reefs unspoiled. The smallest territory in the world divided between two nations, France and Holland, this sail offers a cultural tour between islands that feel like worlds apart despite being so close. From the pristine and deserted beaches of Anguilla to the finest gastronomic restaurants of St Martin and to the exciting night life of St Barth, there’s something here for everyone. With more than 100 nationalities on less than 25 square miles, St Maarten is a unique island that deserves her nickname: the friendly island.
Premier package includes:
An incredible 7-night voyage
Collective captain and chef (for a week of the best food of your life)
Journey Coordinator travel support to help guide you on your journey Onboard family style meals with 7 breakfasts, 6 lunches, 3 dinners and snacks
Marina fees and dockage
Boat incidentals including fuel, water, bedding, towels, etc.
And of course 7 days of unabashed adventure and epic memories...
Before booking, please review CANCELLATIONS/CHANGES, INSURANCE, AND CONDUCT policy on the booking page.<p>
Location
St. Martin
St Martin
Season
Winter 2025
Marigot, St Martin
Road Bay, Anguilla
Prickly Pear, Anguilla
Anse Marcel, St Martin
Ile Fourche, St Barth
Gustavia, St Barths
Tintamare, St Maartin
Provisioning Sailing Collective will provision your journey with local foods and produce. Cooking Aboard: Your Sailing Collective chef will thoroughly review your guest form with your culinary preferences and will customize a menu specifically for your departure.
Included in provisioning package*:
6 breakfasts, 6 lunches, 3 dinners*, snacks, water, coffee & tea
* Subjected to change, 3 meals will take place shore.
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.
Beverages You can choose to bring your own beverages aboard or request for your crew to provision beverages on your behalf to be billed at the end of the charter. Select locations will have online ordering options. If you would like your crew to purchase beverages, we ask you be specific with quantities and quality (for example: we prefer light red wine in the $20 - $30 per bottle and scotch no pricier than $50)
ADDITIONAL COSTS We recommend planning on having at least $300 – $1000 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 10% to 20% offering)
GRATUITY Tipping your captain and crew is welcomed. If you are satisfied with your service, the industry standard for yacht charters ranges from 10-20% 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 is recommended.
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.
We also encourage that people 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 (unless previously discussed boarding time change). We return back to port on the final evening by 5:00pm and disembark between 8-9:00am on the final day.
Terms & Conditions By booking this journey, you agree to comply with the stated Terms & Conditions 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.
REALISTIC DISCLAIMER ABOUT BOATS Boats can break. Charter boats are like a rental car, they are checked before and after each charter. The engineer team is required to check the vessel for maintenance issues and make repairs during the half-day turnaround. Vessels require constant attention like any other complex mechanical system. If you are particular about your exact vacation requirements, we recommend booking a yacht charter with a higher price point allowing for three-crew and we are happy to assist brokering a luxury yacht charter for you and your group.
Stay Updated
For news on upcoming journeys, events and more sign up for our newsletter
© Sailing Collective Travel Co. 2025