Day 5 · Rite of passage
The challenge they earn
Each child takes on a real challenge sized to their age: canyoning down a waterfall gorge or a summit on the island's high ridge. They train for it, they do it, and the group recognizes it.
Why this isn't a resort holiday
Five moments built into the trip
The island does the hard work of impressing everyone. These are the parts your family brings home.
Days 2 & 8 · Superpower Finder & Ikigai
What is your kid great at?
A guided session where kids name their strengths and parents see them through fresh eyes. Older kids map what they love, what they're good at, what the world needs and what someone would pay for.
Day 6 · Family mission session
Write down what your family stands for
Every family leaves with its own mission statement and values, written together, in your words, on a terrace above the Atlantic.
Day 4 · Parents' evening
A night for the adults
The kids have a hosted night of their own. Parents get a long dinner and a fireside conversation with other families doing this on purpose.
Day 9 · Closing honor dinner
Every child, honored by name
On the last night, each child is recognized in front of the whole group for something specific they did on the trip.
The island
Two coasts, one move
Madeira sits in the Atlantic about 900 km from Lisbon. It's small enough to cross in an hour and steep enough that every day feels different.
Funchal, nights 1–5. The capital. Gardens, the old town, the boat harbor and the levada trails above it.
Calheta, nights 6–9. The quieter, sunnier west coast. Volcanic swimming pools at Porto Moniz and the best sunsets on the island.
What the island feels like
Gardens, markets, waterfalls on the road
Sample itinerary · Subject to confirmation
Ten days in three chapters
I.
Arrive and anchor
DAYS 1–2 · SAVOY PALACE, FUNCHAL
- FriDay 1
Arrival in Funchal
Transfers from the airport to the Savoy Palace. Families meet at a welcome dinner and kids find their crew on night one.
- SatDay 2
Old Town, Monte and the toboggan
The farmers' market and the old town in the morning. Cable car up to Monte Palace Garden, then down the hill by wicker toboggan. Afternoon session for the kids while parents explore.
Superpower Finder, part one
II.
Mountains and sea
DAYS 3–5 · SAVOY PALACE, FUNCHAL
- SunDay 3
Levada walk to the waterfalls
Madeira's levadas are centuries-old irrigation channels with flat paths beside them. We follow one through laurel forest to the falls. Easy enough for a six-year-old.
- MonDay 4
Boat day on the south coast
A private boat along the cliffs with swimming stops. Dolphins are common in these waters. In the evening the kids get their own hosted night.
Parents' evening - TueDay 5
The challenge day
Canyoning with certified guides for kids who meet the route's minimums, or a ridge summit for younger kids. Every child finishes something hard.
Rite of passage
III.
The west coast
DAYS 6–10 · SACCHARUM, CALHETA
- WedDay 6
The drive west to Calheta
A scenic transfer along the coast to the Saccharum. In the afternoon each family sits down to write its mission.
Family mission session - ThuDay 7
Porto Moniz natural pools
Swimming in volcanic rock pools filled by the Atlantic, then a slow lunch by the water.
- FriDay 8
Western Madeira
Cliff trails and lookouts on the island's wild end. Back at the resort, older kids work on their ikigai map.
Superpower Finder & Ikigai, part two - SatDay 9
Free morning, honor dinner
A day for each family to spend as it likes. That night, the closing dinner where every child is honored by name.
Closing honor dinner - SunDay 10
Departure
Airport transfers from Calheta for your flights home.
Activities, order and minimum ages are confirmed with local operators before booking. Every adventure day has an option for younger kids.
Where you'll stay
Two bases, both on the water
Nights 1–5 · Funchal
Savoy Palace
A modern five-star in the heart of Funchal with several pools, family suites and a walk into town. The base for the busiest part of the trip.
- Good for
- Walking to the old town, early starts to the mountains
- Rooms
- Family suites and connecting rooms
Nights 6–9 · Calheta
Saccharum
An oceanfront resort on the sunny west coast, with infinity pools and direct access to the sea. Slower days and long sunsets.
- Good for
- Pool days, the mission session, the closing dinner
- Rooms
- Sea-view rooms and suites
What's covered
Book your flights. We handle the rest.
Included
- 9 nights: 5 at Savoy Palace, 4 at Saccharum
- All group activities, guides and equipment
- All group meals, including welcome and honor dinners
- Every ground transfer, airport to airport
- All five Raising Lions sessions
Not included
- Flights to Funchal (airport code FNC)
- Travel insurance
- Meals on your own and personal extras
Family pricing
Shared first with families on the interest list.
Pricing depends on room type and family size. Add your family below and you'll see it before anyone else.
Your host
"My family is coming on this trip. We want yours there too."
Jay leads Raising Lions, a community of fathers raising healthy, capable, fulfilled, high-agency kids. He and his family travel with the group the whole ten days and run every session themselves.
We've done this before
Families traveling together, kids running in a pack
What happens on these trips
Kids find each other by lunch on the first day. The adults take a little longer. By the last night, everyone is planning the next one.
Hold a spot
Tell us which week works
We take 6 to 10 families. We'll run the week that suits the most of them. Adding your name doesn't commit you to anything.
9 families in. 1 spot left.
OPT 1July 9 – 18, 2027FRI–SUN
OPT 2July 16 – 25, 2027FRI–SUN
OPT 3July 23 – Aug 1, 2027FRI–SUN
Questions
Before you ask
Do we book our own flights?
Yes. Fly into Funchal (FNC). Most US routes connect through Lisbon. We collect you at the airport on Day 1 and drop you back on Day 10.
What if my kids are under 6?
This trip is built for ages 6 and up. If you have a younger child as well, tell us in the form and we'll talk it through.
Is canyoning safe for kids?
It runs with certified guides and full equipment, and every route has a minimum age. Kids below it do the summit challenge instead, and it counts the same.
Does joining the list commit us?
No. The list sets the dates and gets you pricing first. You commit only when you book.
How much free time is there?
Every day has unscheduled time, and Day 9 is mostly yours. The sessions are short and run while the island is too hot to do much else.
Can grandparents come?
Yes, as part of your family's booking. Add them to the adult count.