Don't Just Vacation.
Become a Crew.
Private sailing adventures that transform families and friend groups into certified skippers. Return home with a skill for life.
A minute to ask · your proposal within a day · no obligation
What Families & Friends Are Saying
“Our teens didn't look at their phones for 7 days. They were too busy learning to sail. That alone was worth it.”
“I organized this for 4 couples. Everyone's still talking about it a year later. Best thing I've ever planned.”
“My 14-year-old parked a 45ft catamaran by Day 5. The confidence she gained will last a lifetime.”
Your Captain Makes the Trip
We don't just rent you a boat. We match you with a mentor who becomes part of the family for a week. Ex-Yacht Week skippers with RYA Yachtmaster certifications—they know how to win a regatta and make your teen put down their phone.
Every captain is hand-selected for their sailing expertise, teaching ability, and—most importantly—their personality. We match you with someone who fits your group's vibe.
5-Star Accommodation That Moves
Forget cramped boat stereotypes. Our catamarans are floating luxury villas with the space of a boutique hotel—and a new view every morning.
Space for Everyone's Pace
While teens learn to sail on the foredeck, grandparents can read in the shaded cockpit. Parents take the helm while kids explore on paddleboards. Our catamarans offer simultaneous adventure and relaxation—something no resort can match.
“But What About Seasickness?”
We hear you. Here's the truth: catamarans are fundamentally different from traditional sailboats. Their wide, stable platform means gentle motion—even in active sailing conditions.
- Catamarans are 50% more stable than monohulls
- Wide beam means virtually no tipping
- Your coffee won't spill—guaranteed
- Perfect for non-sailors and first-timers
The Transformation
Watch your crew transform from passengers to skippers in just one week. It's not magic—it's methodology.
Nervous Beginners
Ropes look like spaghetti. Wind seems unpredictable. The boat feels foreign.
Building Confidence
You're raising sails, understanding wind, starting to feel the rhythm.
Taking the Helm
Navigating between islands, reading the weather, making decisions.
Certified Skipper
Parking the boat. Leading the crew. You did it.
What You Take Home
ASA Certification
Official credentials that let you charter boats worldwide
Practical Skills
Navigation, weather reading, boat handling—skills for life
Team Dynamics
Communication, leadership, problem-solving under pressure
Confidence
The knowledge that you can handle something challenging
For Kids: Stealth Education
They think they're on an adventure. They're actually learning:
- 🧭Navigation — Math in disguise
- 🌊Weather patterns — Science in action
- 🪢Knot tying — Problem solving
- ⛵Sail trim — Physics they can feel
“My son learned more about physics in one week than a semester of school.”
— Jennifer M., BVI Trip
You're the Alpha Planner?
We've Got You.
We know you're the one who makes things happen in your group. You deserve tools that make you look like a hero—not a travel agent.
😩 The Usual Experience
- ✗Herding cats to agree on dates
- ✗Awkward Venmo requests for deposits
- ✗“Can you send me that link again?” x47
- ✗If it fails, it's YOUR fault
✨ The Sailing Virgins Way
- Polished proposal you can share in seconds
- Individual payment links—no collecting money
- Concierge handles all questions
- You get all the credit for an amazing trip
Shareable Proposal
Drop our beautifully designed proposal PDF right into your group chat. Instant credibility.
Clear Per-Person Pricing
No awkward money conversations. Everyone sees exactly what they'll pay upfront.
Flexible Date Options
We'll give you 3 date options to present. Let the group vote.
Easy Sign-Up Link
Individual payment links so you're not collecting money from friends.
Choose Your Trip Blueprint
Not sure what style fits your group? Pick a blueprint and we'll customize from there.
The Classic Adventure
Balanced sailing, snorkeling, and exploration. The crowd-pleaser.
Party & Sail
Epic beach bars, sunset parties, and social sailing.
Wellness & Wind
Morning yoga, healthy meals, mindful sailing, hidden anchorages.
Full Send
Maximum sailing, certifications for all, skill-building intensive.
Ready to be the hero of your friend group?
Get a Shareable ProposalTakes 2 minutes. We'll have it ready in 24 hours.
Frequently Asked Questions
Everything you need to know before setting sail.
Absolutely not! Our private courses are designed for complete beginners. Most of our guests have never stepped foot on a sailboat before. Our ASA-certified instructors will teach you everything from scratch, and by the end of the week, you'll be confidently handling the boat yourself.
Still have questions? We're here to help.
Ready to Become a Crew?
Tell us about your dream trip and we'll create a personalized proposal with handpicked yachts and a custom itinerary — within 24 hours.
Join 500+ families and friend groups who've set sail with us