Work & Play Vacay: Madeira

4 June – 9th June 2024

In collaboration with

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It’s time to live out the life you’ve always dreamt of

Have you always dreamt of travelling whilst working but you’re a little daunted by doing it alone? 🌊 🌴 

Or have you lost that spark in your business & need to reignite that creative passion you once had? 🔥 


We’re taking business out of the boardroom for a creative business retreat like no other.  Immerse in out-of-this world scenery and be surrounded by a good vibes gang of creatives to inspire, energise & elevate your business to the next level. 


Get a snippet of that dream creative nomad life in the most desirable, up and coming nomad island, without having to do it alone.

The Hawaii of Europe

Sundowners on the beach / sunrise above the clouds / wild beaches surrounded by lush green mountains

Experience the perfect soul-lifting, nature-immersive 5 nights living out the best parts of the “Hawaii of Europe”. You’ll be able to fully relax knowing everything is covered, as each day we explore a new part of the island (and ocean) followed by business boosting afternoons.

We’ve curated the perfect business/living blend. We’ll spend mornings exploring this beautiful island & afternoons putting all the creative inspiration into play.

 Here’s just a snippet of what we’ll be getting up to (everything is completely optional – but we think you’re going to want to do it all).


Watch the sunrise & hike above the clouds on the famous Pico do Areeiro to Pico Ruivo path.

Immerse in the wild beauty of the infamous Seixal Beach & natural ocean pools of the north of the island. 

Take in the beauty of the island & dolphin spot on a boat trip off the shores of Funchal.

Get lost in the chilled city vibes & art trails of Funchal.

Experience the sunset at the infamous digital nomad cliff top party, Purple Fridays.

Morning meditation, sunrise on the beach, volunteer at the local dog shelter & a whole heap of additional extras for you to choose from.

Our very own beachside, white-washed hideway

Enjoy you very own large double room (with ensuite) with views overlooking the wild Madeira coastline. We’ll be staying at a dedicated beachside co-working hotel, fully equipped for the perfect work & play vacay. 


Hang with everyone in the light and airy co-working space, or grab some quiet time with your own desk overlooking the ocean if you need to take a quiet call during your stay. 


The hotel is located in the up and coming digital nomad village of Ponta Do Sol. A village etched out of the coastal cliffs, with a chilled vibe for the perfect creative recharge.

Business impact

✨ Breathe new life into your business ✨


Allow your mind to wander beyond the confines of daily routines, unlocking creative ideas you never knew existed.


By stepping back & immersing in creative conversations in idyllic scenery you’ll gain clarity on long-term goals and can envision the bigger picture. This newfound clarity can translate into more streamlined processes, innovative solutions, and a strategic roadmap for the future.


You’ll spend 5 nights reigniting the flame for your biz, working on bigger picture plans & come away with a support network for life.


What can I expect?

You'll experience the ultimate work/play trip with everything covered (so you can sit back,  recharge & reignite your creative clarity). 


This is a group trip of solely for founders and freelancers (max 15), so you will meet so many likeminded folk on the same ride as you.


Everyday we have arranged an epic activity/adventure; from sunrise hikes, to ocean boat tours. These will usually happen in the morning. You will then have free time from 2pm/3pm to work on your business or go and explore more of the island (perfect if you need some downtime).


During the day we will have open creative business conversations around various topics, helping you gain clarity, elevate your business & build an unstoppable mindset to take on the rest of 2024.

We will then all meet for a local dinner in the evening (and watch the sunset from our ocean-side accommodation 🥺). 

Everything is optional, but it's the perfect chance to be surrounded by likeminded people but also have solo time if you need it.

What value will it bring to my business?

This retreat can have immeasurable impact to both your business & life. 


The power of stepping away from the everyday,  immersing in awe inspiring scenery, and being energised by creative souls who are completely aligned is something you can't put a price on. 


We will be supporting you to work on bigger picture visioning, to find clarity on your journey ahead, and work though the barriers you may be facing. 


You will leave energised to elevate your plans even higher than you could have dreamt of, as you get a reminder of the life you are working towards. 


Obviously, you get out what you put in. We cannot guarantee direct impact but we've set up a line up to skyrocket your creative energy & go full power in the ride ahead.

Will I get my own room?

Yes! You will have your very own large double room, with ensuite, balcony and beautiful sea view.
I scouted the accomodation in 2023 and can confirm it's stunning!

I'm thinking of going solo, will I be OK?

Yes! Almost everyone will be coming alone and won't know anyone (some may have met before but it'll mostly be all solo people!).

Going solo is the best way to come on a trip as you can be completely yourself, and come away with 14 other new pals!

We will make sure you have enough space to be immersed in the group and have your own time (if needed). Myself and Vicky are on hand to make sure you have the best time!

What sort of people will be on the trip?

The trip is for creative and wellness founders and freelancers. You will meet folk just like you who are doing their own thing and up for new adventures. 

Do I have to do all the activities?

No, not at all. We have a core set of events/activities everyday and then you will have free time or the option to hang out with smaller groups for optional activities (extra hikes, chilling on the beach etc.).
Everything is completely optional. We would love to have everyone involved in the core things, but totally understand if you want to dip out.

We will also make sure everyone is accommodated for as much as possible.

Will there be a lot of "work"?

The work bit is completely down to you. The daily activities will usually run in the morning and finish by 3pm at the latest (some earlier). You will then have time between then and dinner to do work, or just have a sweet holiday around some epic folk.

What sort of work should I plan to do?

This will be a trip of a lifetime and we don't want you to miss anything. You can plan what work is best for you, but we advise to not book too much client work, and leave the time to big picture work and creative work (as the scenery and people should get the ideas flowing).

Do you offer a payment plan?

Yes, you can either pay in full or pay via instalments. 

A £200 deposit will secure your booking. You are then able to pay in three instalments of £255, £200, £200 (members only).

All payments are non refundable due to accommodation confirmation. If you need to cancel, we will do out best to fill your place and you will get a refund of all previous payments. 

You must ensure you have travel insurance to cover any additional payments (flights etc.).

Price & Member Discounts

Pay in full or via a monthly payment plan


Full retreat price for non-members
£ 1055
  • Full retreat experience
  • Double room with sea view and ensuite
  • One year Outsite membership
  • Daily activity planned to see the best of Madeira
  • Experience the digital nomad village of Ponta Do Sol
  • Live the digital nomad life without having to go solo
  • Secure your place for just £200 (deposit)
  • Monthly payment plan available at no extra cost
  • Uncommon Club membership discount available


£ 455
  • The full retreat experience, including all activities and socials
  • This option does not include accommodation. You are able to secure your own accommodation in Ponta Do Sol.


All the deluxe rooms for the work:play retreat have now sold out. We have opened a limited number of experience-only spaces, so you are able to experience all the features of the work:play vacay, but have the freedom to choose your own accommodation.

Please email to enquire (and ask any questions you may have) and we will send you all the booking details to confirm your space.

The details


5 nights | Tuesday 4th June (arrival) – Sunday 9th June (departure)


Private ocean view hotel room with en-suite


Max 8


Tuesday 4th June 2024

What’s included:

What’s not included: