Join the waitlist for the Azores, July 2027
Fill out the form below or if you have more question, connect with your hosts, Richard and Devon.
A retreat designed for your next chapter
We are finalising dates and the venue for Faial Island in July 2027. This is the list we will come to first.
The world's a weird place right now, and it might not be obvious what your next move will be. There's a good chance you have already been successful at something, but the journey feels unfinished. You're not alone. There's a whole community of people just like you doing the work to create something better for themselves and the people they care about. We've lived through big changes ourselves - the death of a spouse, divorce, starting and running great businesses, shutting down failing ones and even exiting them. We've switched careers, moved countries and raised children to adulthood. We've learned that change is easier when you've got good people around you.
Limited spots— apply now
Add your details and we will be in touch as soon as the dates are confirmed, before this opens more widely. Nothing is committed at this stage - it simply means you hear first.
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Prefer to talk to us?
You can book time with either Devon or Richard to discuss details or get to know us
Why do I need to apply?
Get answers
Get real, candid insights into what to expect, directly from the hosts
Meet the venue
Find your fit
Limited spots
As much as we'd like, not everyone can be accommodated
What people say after they leave the retreats
New retreats, but
seasoned leadership—
Guided by a team with 60+ years of collective experience and an expert local team
What we'll cover on the calls
- What makes Second Harvest different from other events?
- How do I get there from where I am?
- Who will be hosting the sessions?
- What activities will be included?
- Can I bring a spouse/partner/friend?
- What kind of people will attend?
- What’s the investment, and what’s included?
- What can I expect to leave the event with?
FAQs
Because the ocean makes the point better than any workshop can. The waters off Faial and Pico are a Mission Blue Hope Spot, one of the few places on Earth where the biggest animals in the sea come up within a breath-hold of the surface. Horta is a real working marina town, not a resort, so boats leave from the door. And the island itself, remade by a volcano within living memory, is a standing argument that renewal is the far side of loss. It is the rare place where the setting is the curriculum.
No scuba, no certification, no experience required. Everything happens on snorkel and breath-hold, at the surface or a few metres down. The one real prerequisite is that you are comfortable swimming in open water. Certified free-dive safety staff are in the water on every outing. Alongside Roger, Richard is a trained Divemaster and Rescue Diver, and the boat team includes two to three certified members. Roger guides and films; safety is separately and professionally staffed. Snorkelling is encouraged but every water activity is optional. You set your own edge.
Everything except your flights to the island. Your investment covers accommodation in Horta, all meals and drinks, every boat expedition and in-water session, free-dive guiding and safety, breathwork, yoga, meditation, and all ground transport to activities.
Click Apply on this page. Once we receive your application we will set up a short conversation to make sure it is a great fit, for you and for the group. If it feels right on both sides, we will send a private payment link to secure your place.
You are welcome back. The structure will feel familiar, but the experience is wholly its own. New experiences, new people, new encounters, new ground to cover. Many Harvesters return as part of a seasonal rhythm.
The underwater cinematographer behind My Octopus Teacher, along with Blue Planet II, Our Planet and Netflix's Our Oceans. He has spent fifteen years earning the trust of wild animals on their terms, and he will be with us in the water the whole time, choosing the sites, reading conditions, and bringing the encounters.
Moderate and self-paced. Expect early shoreline swims, breathwork, gentle yoga, and boat days that can run long. The offshore seamount trip is a full day on the water, six to seven hours in total. Comfortable open-water swimming is the baseline; everything beyond that is optional.
Swimwear, light layers, a light waterproof jacket, hat, and reef-safe sunscreen. If sea water irritates your eyes, pack swim goggles too. We will advise on wetsuit thickness once dates are set, and we can arrange exposure gear. We provide journals, but bring your own if you prefer. And leave a little extra room in your bag, because you will go home with more than you arrived with.
The honest answer is that wild animals keep their own schedule and nothing in the ocean is guaranteed. What we can tell you is the calendar. Mobula rays (late June to October), blue sharks (mid-July to mid-October) and barracuda are a summer story. The great migratory whales, blue and fin, pass through in spring. You are very likely to see the resident sperm whales and dolphins that are here year-round. We plan around the animals, not the other way around, and we build in flexibility for weather.
Pricing is $8,750 for a single room and $12,275 for a double room (plus one guests, like spouses or partners). A payment page is shared once you’ve applied and we’ve had a short alignment call. This helps us keep the experience tailored, intimate, and intentional. Pricing includes all lodging, food, drinks, programming, and local experiences.
The ocean sets the terms. If conditions close the water on a given day, we adjust, and there is always more than one way to spend a day on Faial. For guest cancellations: cancel 60 days or more before the retreat and we will refund your payment minus a 35% fee to cover advance booking costs. Within 30 days we will do our best to transfer your spot to a future retreat if openings exist, but no refund is provided.
Second Harvest is for people in the middle of life who look successful on paper but feel misaligned inside. They have built careers, businesses, families, reputations. They have done what was expected of them, and done it well. What has changed is not their ability but their relationship to how they are spending their time. It is an exhaustion rather than a crisis. Motivation still exists, but they are after meaning. The old goals do not pull like they used to. They do not want another productivity system, self-help framework or motivational push. They are not broken and they are not looking to be fixed. They value depth over hype, real conversation over performance. They are not trying to escape their life, they are trying to redesign it.