A personalized virtual cruising-prep program
A three-month program that takes competent sailors from decided to ready — boat, route, paperwork, and family logistics, handled by people who do this professionally.
You’ve been researching boats, routes, gear, and what it takes to go cruising.
But the questions keep multiplying:
Which boat is right for the way we want to cruise?
What should we do first—and what can wait?
Are we prepared for weather, watchkeeping, and life aboard?
What about visas, family logistics, and all the details we haven’t thought of yet?
How will we know when we’re truly ready to leave?
You don’t need another year of scattered advice.
You need a plan that brings the pieces together,
and experienced people alongside you as you build it.
That’s why we created the Departure Ready Program: a three-month, hands-on program for sailors ready to move from “someday” toward “we’re getting underway.”
Now, get ready to go!
First cohort: January–March 2027. Applications close December 15.
Who it’s for
This program assumes you can sail. It doesn’t assume you’ve crossed an ocean.
We’ll help you buy the boat, outfit it, plan the route, sort the visas, and get you ready for your first overnight and offshore passages. This program takes competent day sailors and weekenders and prepares them to cruise.
This program is for you if
- You’re a competent sailor: comfortable handling a boat, trimming sails, docking, and making decisions afloat
- You’re ready to move from daysailing, weekend cruising, and annual charters to living aboard and going somewhere
- You want standards, not vibes: checklists, milestones, and honest feedback
Admission is by application, for sailors who arrive ready to do the work — we want everyone in the room to succeed.
"This isn’t about making every uncertainty disappear. It’s about helping you make informed decisions, build the skills you need, and turn a daunting departure into a series of manageable steps."
What you get
- A three-month guided sprint, structured like a project — because that’s what preparing to cruise is.
- Six private consultation calls with Teresa and Ben. They are yours to schedule anytime for the entire year. We’ll discuss your program, your boat, your timeline.
- Weekly open office hours – drop in to ask whatever is on your mind.
- Six live curriculum sessions — the project of getting underway: define your mission, find and buy the right boat, outfit it, plan your route, and sort the paperwork — personalized to your plan, your budget, your timeline, with homework between sessions that builds your departure dossier
- Six live skill-building sessions — practical skills for life underway: watchkeeping, radar, weather interpretation, spring fitting out, and more.
- A private cohort community on Slack — your crew for the program and beyond. Membership doesn’t expire when the program does. When you cast off, you stay. Lifelong.
- A departure dossier — the tangible output of three months: your boat criteria, survey and commissioning checklists, documented route plan, visa roadmap, and a final readiness review with Ben and Teresa.
Topics covered include
- Defining the mission: your cruising plan shapes your boat
- Finding and evaluating the right boat
- Survey, negotiation, and purchase — without the mistakes
- Outfitting: what matters, what’s marketing
- Safety systems and redundancy
- Route planning and seasonal windows
Visas, insurance, and international logistics
Family logistics: school, work, and life aboard
Why Us
We were professional mariners before we were cruisers. That's the difference. We came up through the hawsepipe — one of us starting working at eighteen, the other at twenty-two — earning our USCG Master licenses the long way: working deckhands' hours, standing real watches, learning boats by running them. Between us we've delivered yachts offshore, run tugboats, captained a lobster boat, and sailed schooners, square riggers, motor yachts, and everything in between — We’ve sailed from Panama to the sub-Arctic waters of Newfoundland, in the Pacific, the Atlantic, Caribbean, Gulf of Mexico, and the Mediterranean. (Ben has even sailed Billy Joel's boat.)
We've taught for Outward Bound, Sea Education Association, and other ASA and US Sailing schools. Teaching isn't something we drifted into after a good cruise — it's a profession we've practiced for decades, aboard cruising boats and passenger-carrying vessels alike. Along the way, we were trained by some remarkable educators — people who taught us not just how to sail, but how to teach, how to read a crew, and how to keep novices safe while they learn. That's the difference between a sailor with opinions and an instructor.
Only after all that did we become cruisers ourselves: each sailing solo at first, then together. Boats have been the through-line of our adult lives — our own and other people's, lived aboard, owned, worked, and sailed. And once, we tried expeditioning in our own 8' dinghy — just to see if we could hack it.
Recently, we moved our own family aboard and abroad. A year of planning: USCG documentation for a passenger vessel, long-stay visas, a house rented out, a seven-year-old who went from boat school to public school in a foreign country, and international health insurance — all held together through a government shutdown that closed the Coast Guard for weeks. It was a challenging year, and we'd do it again — because everything that made it hard is everything we can now help you avoid, anticipate, or solve.
You're ready to go. We're ready to help.
