Women at the Helm BVI Sailing Immersion
May/June 2027Build real cruising confidence — steering, navigating, anchoring, provisioning, and thriving at the helm in real conditions. This is a hands‑on sailing week designed for women who want more than a casual vacation — it’s for those ready to understand how a cruising sailboat truly operates and gain the confidence that only comes from doing it yourself.
1 Instructor / 2 Students per boat
May/June 2027
7 Days
Caribbean Sailing
What Makes This Trip Special
This isn’t a passive “boat ride” — it’s a working charter experience. You won’t just watch others sail; you’ll be part of a real cruising crew, participating in every aspect from route planning to sail trim, mooring ball pick‑ups, and provisioning for the week’s meals. You’ll live aboard a modern monohull, gaining the practical, real‑world experience that builds confidence and competence on the water.
We keep the program intentionally small: two monohulls sail in tandem, each with an expert instructional captain and just two students per boat. This format means maximum time at the helm, extensive one‑on‑one guidance, and your own private cabin for rest and reflection after a full day on the water.
This is your chance to take the wheel and run the boat — supported every step of the way
This is not a retreat, or a vacation with a little sailing sprinkled in.
This is a hands-on, responsibility-forward, real-world sailing experience designed for women sailors who want to level up their confidence and skills.
If your goal is confidence, competence, and certification — this trip is built for you.
During our time in the British Virgin Islands, you will:
- Log qualifying sailing days
- Practice real-time decision-making
- Learn and practice maneuvering under power skills, picking up mooring balls, anchoring, and day-passage planning
- Build confidence managing crew and vessel
Every day sailed counts toward your goals.
Have Questions?
Send me a message or schedule a time for a call >>
Reserve Your Cabin
May/June 2027- Included:
- Private cabin with private head aboard a Dufour 44’ monohull
- Professional instruction and + onboard captain guidance
- Yacht, fuel, and custom UV shirt
- Pre-trip Crew Planning Meetings
- Not Included:
- Flights to/from the British Virgin Islands
- Airport transfers and hotels before/after the trip
- Provisioning & Moorings
- Trip insurance (highly recommended)
- Crew gratuities
- Personal expenses and optional shore activities
Who This Trip Is For
This week is perfect if you:
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Have some prior sailing experience and want to build cruising confidence in a supportive environment.
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You're ready to take part in an actual bareboat-style charter experience, not just observe.
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Want to develop practical skills like anchoring, navigation, sail trim, and mooring ball handling.
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Love the idea of teamwork, shared decision‑making, and real responsibility onboard.
This trip is not ideal for complete beginners with no prior sailing exposure or for those hoping for a vacation‑only charter.
What You Leave With
√ Logged sailing days in ideal line-of-sight conditions
√ Increased confidence at the helm
√ Foundational charter knowledge and crew skills
√ A clearer understanding of what it takes to charter in the future
This trip is about building the skills, awareness, and confidence that make independent chartering possible. You’re not just learning the mechanics — you’re learning how it all fits together.
Pre-Trip Crew Meetings (3 Total)
We don’t just show up and hope for the best, we run three structured crew meetings prior to departure to ensure everyone is prepared, aligned, and confident.
- Crew Meeting #1 – Expectations & Roles
Trip overview, certification pathways, leadership rotation, and charter responsibilities. - Provisioning Coaching Session
A dedicated meeting focused entirely on provisioning:- Budgeting
- Menu planning
- Dietary considerations
- Coordinating shared costs
- Final Crew Meeting – Logistics & Readiness
Travel coordination, documentation, customs prep, safety review, and final Q&A.
By the time we arrive in Grenada, you’ll already be operating like a charter team.
The Sailing Grounds: Why BVI
The British Virgin Islands offer:
Consistent trade winds
Line-of-sight sailing between islands
Protected anchorages and easy navigation
Short day passages with real-world challenge
World-famous stops like The Baths, Jost Van Dyke, and Anegada
Clear turquoise water and vibrant coral reefs
Lively beach bars and classic Caribbean harbors
It’s the perfect classroom — and an unforgettable place to sail.
Let Me Know About Future Trips!
Proposed Sailing Itinerary
This is a proposed itinerary to give you an idea of the route, stops, and skill-building opportunities. All plans are flexible and may change based on weather, crew decisions, or timing — the goal is a safe, enjoyable, and rewarding sailing experience for everyone.
Day 1 – Arrival Day at Moorings Marina
3:00 PM – Arrival & Meetup: We’ll gather at the poolside restaurant/bar at Moorings Marina to meet the crew, review the afternoon schedule, and finalize provisioning. This ensures the boat and team are ready for the week ahead.
Welcome Drinks: Raise a toast with your fellow sailors and set the tone for a fun, collaborative week on the water.
6:00 PM – Group Dinner: Enjoy a relaxed dinner ashore, share first impressions, and start building camaraderie with your crew.
Evening – Overnight in Marina: Spend the night aboard the boat in the marina, resting and preparing for the first day of sailing.
Day 1 Skill Highlights:
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Team Introduction & Crew Roles: Get to know your crew and understand responsibilities aboard.
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Provisioning Overview: Learn how to organize and plan supplies for the week.
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Boat Familiarization: Begin familiarizing yourself with the yacht’s layout, systems, and basic operations.
Day 2 – Great Harbor, Peter Island
8:00 AM – Sail Plan Meeting: Start the day with a collaborative sail plan meeting, reviewing weather, route, timing, and crew roles. This helps build confidence and sets the tone for decision-making on the water.
10:00 AM – Depart the Marina: After a light breakfast and final prep, we’ll set off across the Sir Francis Drake Channel, using the passage to warm up helm skills and get comfortable with the boat.
Midday – Skills Practice at Great Harbor: Spend time practicing essential cruising skills, including handling the boat under power, picking up a mooring ball, and building overall confidence in maneuvering.
Evening – Pick up a mooring ball and enjoy a relaxing evening ashore. Explore the local amenities, unwind, and reflect on a productive day on the water.
Day 2 Skill Highlights:
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Sail Planning & Decision-Making: Review weather and route, assign crew roles, and plan the day.
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Helm & Boat Handling: Gain confidence steering under sail and power.
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Mooring Practice: Learn to pick up a mooring ball safely and efficiently.
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Team Coordination: Practice clear communication and crew teamwork during maneuvers.
Day 3 – Sir Francis Drake Channel Sail to North Sound
8:00 AM – Sail Plan Meeting: Start the morning by reviewing conditions and planning the day’s route together. We’ll focus on practical cruising decisions and crew roles.
Morning – Sail to North Sound on Virgin Gorda: While underway, we’ll focus on sail trim, learning how small adjustments improve balance, speed, and overall comfort.
Midday – Lunch stop at Long Bay (optional)
Early Afternoon – Passage Planning: Before heading into North Sound, we’ll review charts, plan our route, and identify potential hazards. This reinforces navigation basics and visual awareness.
Evening – Saba Rock/Bitter End, Gorda Sound, pick up a mooring and enjoy a relaxed evening onshore, watching the sunset and reflecting on the day’s sailing experience.
Day 3 Skill Highlights:
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Sail Trim Practice: Learn to adjust sails for better speed, balance, and control.
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Navigation & Chart Reading: Identify safe passages, plan routes, and practice visual navigation.
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Crew Communication: Continue practicing clear onboard communication and teamwork.
Day 4 – The Baths (Optional) → Marina Cay
8:00 AM – Sail Plan Meeting: Start the morning by reviewing conditions and planning the day’s route together. We’ll focus on practical cruising decisions and crew roles.
8:45 AM – Optional Visit to The Baths: Early risers can explore the iconic boulders, caves, and tidal pools at The Baths before the crowds arrive. Those who stay aboard can enjoy a relaxed morning on the boat.
Late Morning – Sail to Marina Cay: While underway, we’ll focus on sail trim, learning how small adjustments improve balance, speed, and overall comfort.
Midday – Lunch at Marina Cay
Late Afternoon – Dinghy practice
Evening – Stay on our mooring and enjoy a relaxed evening aboard, watching the sunset and reflecting on the day’s sailing experience.
Day 3 Skill Highlights:
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Sail Trim Practice: Learn to adjust sails for better speed, balance, and control.
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Navigation & Chart Reading: Identify safe passages, plan routes, and practice visual navigation.
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Crew Communication: Continue practicing clear onboard communication and teamwork.
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Optional Exploration: Experience boat-to-shore transitions safely while exploring The Baths.
Day 5 – Garner Bay (via Sandy Cay)
8:00 AM – Sail Plan Meeting: We’ll begin with a crew meeting to review weather, currents, and routing options. Together, we’ll map out the day’s passage and assign crew roles, continuing to build confidence in real-world cruising decisions.
10:00 AM – Underway: After breakfast and final preparations, we’ll depart Guana Island and set sail for the day’s destination. As a group, we’ll decide whether to end the day at Garner Bay or continue on to Cane Garden Bay, keeping the plan flexible to match the crew’s pace and interests.
Midday – Passage & Anchor Practice at Sandy Cay: En route, we’ll stop at Sandy Cay for hands-on anchor practice. Each student will have the opportunity to approach, set, and weigh anchor, focusing on proper scope, positioning, and clear communication.
Afternoon – Sail to Our Chosen Bay: After practice, we’ll continue on to either Garner Bay or Cane Garden Bay. Upon arrival, we’ll settle into a mooring or anchorage and debrief the day’s lessons.
Evening – Relax & Reflect: Enjoy a relaxed evening aboard, take in sunset views, and reflect on the day’s sailing and boat-handling experience.
Day 4 Skill Highlights:
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Sail Planning & Crew Roles: Collaborative route planning and onboard decision-making.
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Sail Trim & Underway Awareness: Adjust sails for balance, comfort, and efficiency.
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Anchoring Fundamentals: Practice safe approaches, setting anchor, checking scope, and weighing anchor.
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Navigation Basics: Reinforce chart reading, hazard identification, and route selection.
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Team Communication: Strengthen clear, calm communication during maneuvers.
Day 6 – Cane Garden Bay / Garner Bay → Norman Island (Optional Stop: Soper’s Hole)
8:00 AM – Sail Plan Meeting: Start the morning by reviewing weather, currents, and route options. We’ll also consider our starting point—Cane Garden Bay or Garner Bay—and whether to include an optional stop at Soper’s Hole. Crew roles and passage strategy will be discussed to strengthen teamwork and decision-making.
Underway: After breakfast and final preparations, we’ll depart for Norman Island. The crew can decide whether to sail straight there or make a stop at Soper’s Hole for lunch, shopping, and extra skill practice.
Midday – Optional Stop at Soper’s Hole: If we stop, students can practice handling the boat in tighter spaces, approaching a dock or mooring ball, and coordinating as a team in a small harbor environment.
Afternoon – Arrival at Norman Island: Continue to Kelly’s Cove on Norman Island. Pick up a mooring or anchor, reinforcing safe approaches, anchoring fundamentals, and situational awareness in a real-world setting.
Evening – Relax & Explore: Unwind aboard, enjoy the sunset, or explore Norman Island’s famous sights, including The Caves, while reflecting on the day’s sailing, navigation, and boat-handling experiences.
Day 5 Skill Highlights:
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Sail Planning & Team Roles: Review conditions, plan passage, and assign crew responsibilities.
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Boat Handling & Crew Coordination: Practice steering, sail trim, and working together during maneuvers.
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Anchoring & Mooring Fundamentals: Safely approach a mooring or anchor in real-world conditions.
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Navigation Awareness: Maintain situational awareness and identify safe routes.
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Optional Harbor Practice: Gain experience maneuvering in a confined harbor at Soper’s Hole.
Final Day – Return to Base
8:00 AM – Sail Plan Meeting: Begin the morning with a final crew meeting to review weather, tides, and route options.
Underway: After breakfast and final preparations, we’ll depart for the chosen destination.
Final Day Skill Highlights:
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Crew Coordination: Practice teamwork while adjusting sails and managing the boat.
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Route Planning & Decision-Making: Apply real-world cruising judgment to end-of-trip navigation.
- Disembark: Ready the boat and take care of final checkout procedures for an 11:00 departure.
Minimum Sailing Skills Required
To ensure this is a productive, confidence-building experience for everyone onboard, participants should arrive with a basic sailing foundation. This trip is designed to start where you are in your sailing journey and build from there.
NOTE: You do not need to be proficient in the list below, but understand the basics.
Ideal candidates should have a basic understanding of sailing, including:
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Sail Handling: Hoisting, trimming, and lowering sails
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Helm Control: Steering under sail and power
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Essential Knots: Cleat hitch, bowline, and clove hitch
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Safety Awareness: Basic person-overboard procedures
On this trip, we’ll practice these skills in real-world conditions, connecting the pieces to build confidence and strengthen your overall sailing ability.
What airport do I fly into?
The main airport for the British Virgin Islands is Terrance B. Lettsome International Airport (EIS) on Beef Island/Tortola.
Most travelers connect through St. Thomas (STT) in the U.S. Virgin Islands, as flights from the U.S. are more frequent and affordable. After arrival, it’s a short taxi or ferry to our marina, where your BVI sailing adventure begins. Detailed arrival instructions and local transport options are included in the Trip Guide you’ll receive after booking.
Do I need to get local currency, and what's recommended?
The official currency in the BVI is the U.S. dollar, so there’s no need to exchange money before your trip. It’s still a good idea to carry a small amount of cash for tips, small purchases, or island fees, but credit and debit cards are widely accepted at marinas, restaurants, and shops.
What if I need to cancel?
We understand that plans can change. Please review our cancellation policy carefully: 90 Days or More Prior to Embarkation: If you cancel your booking 90 days or more before the embarkation date, you'll receive a full refund of your deposit, minus a $200 administrative fee. The refund will be reimbursed to your original payment source. 45 to 90 Days Prior to Embarkation: If you cancel your booking between 45 and 90 days prior to the embarkation date, your deposit is non-refundable.
However, if a replacement can be found for your cabin, you'll receive a full refund minus a $400 administrative fee. Less Than 45 Days Prior to Embarkation: If you cancel your booking less than 45 days prior to the embarkation date, no refund will be allowed unless a replacement can be found for your cabin. If a replacement is found, a full refund will be issued minus an $800 administrative fee. Reservation Transfers: A reservation can be transferred to another student, upon approval, with a $200 administrative fee.
Can I transfer my booking to someone else?
Of course! Reservation Transfers: A reservation can be transferred to another student, upon approval.
When is the final payment due?
Your final payment for the trip will be due 90 days prior to the embarkation date.
If you'd like to set up additional, smaller payment dates between now and the final due date to help manage your budget, please don't hesitate to let us know! We're happy to work with you.
Do I need a hotel before or after the trip?
Not required! Our provisioning meeting is at 3 PM, and we stay docked that day. Hotels are optional if you want to arrive early or rest before sailing. Recommendations are in your Trip Guide after booking.
What should I pack for the trip, and what kind of luggage is best for a boat?
We recommend packing light and using soft-sided bags or duffels that are easy to stow onboard. For a detailed list of what to bring — including clothing, gear, and personal items — check out the complete Packing Guide in your Trip Planner, which you’ll receive after your cabin booking is confirmed.
Can I bring my own food, and can my allergies be accommodated?
Yes! All provisioning is planned, purchased, and managed by the students, so there’s flexibility to accommodate dietary needs. If you have allergies or special dietary requirements, you’ll be able to include foods that work for you when organizing provisions with the crew. Bringing a few personal items is also fine, but most meals will be prepared from the shared provisions on board.
What happens if there's a medical emergency?
Your safety is our top priority. All BVI trips carry a comprehensive first-aid kit, and the captain and crew are trained in basic first aid. For more serious situations, we have onboard communication systems, including VHF radio and cell phone if needed, to contact local emergency services immediately.
If onshore medical care is required, we can transport you to the nearest appropriate facility in the BVI, such as Peebles Hospital on Tortola, or other local clinics. In extremely rare or severe cases, medical evacuation to a larger hospital in a nearby territory (such as St. Thomas in the U.S. Virgin Islands) may be necessary.
This is why it’s highly recommended to have comprehensive travel and health insurance, including emergency medical evacuation coverage.
Is there an emergency number my family can use to reach me?
Yes, absolutely. Before the trip begins, you will be provided with a dedicated emergency contact number for the trip leaders, our local sailing base in BVI, as well as the local VISAR (Virgin Island Search and Rescue) contact information to share with your family and emphasize that it is strictly for genuine emergencies. For non-urgent communication, they can try to reach you directly on your cell phone, keeping in mind that coverage can be intermittent while underway.
Will I have cell phone coverage?
You will generally have cell phone coverage while in BVI. The primary local providers are Digicel and Flow. However, please be aware that coverage can be spotty or non-existent when we are further offshore or sailing between islands. While international roaming is an option, it can be quite expensive, so many participants choose to purchase a local SIM card upon arrival for more cost-effective communication. Be prepared for periods of limited connectivity – many find this a welcome opportunity to disconnect and fully embrace the sailing experience!