Exploring Mindset | Miami to Cayman Islands

Exploring Mindset | Miami to Cayman Islands
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£1,990 / $3,220
Feb 19 – Feb 27, 2014

Depart: Miami, FL, USA
Arrive: Grand Cayman, Cayman Islands
Length: 8 days (8 nights)
Focus: Philosophical and Practical Workshops, Sailing and Snorkelling


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We live in a time of constant change where the importance of our actions have a wider reach and impact more so than at any other time in our existence.

Combining an ocean voyage with a programme of specialist workshops designed to stimulate and focus your passions and areas of expertise into an effective future path, join Emily Penn and Dave Cornthwaite on a life-changing 8-day journey across the Caribbean, on S.V Sea Dragon.

We’re offering a special opportunity to experience an environment that provides a true escape from society and the daily distractions of land, allowing freedom to think and develop new ideas with a like-minded crew at the same time as having a unique adventure.

Departing from cosmopolitan Miami, Sea Dragon will trace the length of the Florida Keys before spending 24 hours anchored off Garden Key. Steeped in history and beauty hidden by the shifting sands, the uninhabited desert islands of the Dry Tortugas offer the perfect opportunity to spend a day snorkelling on remote reefs in pristine, turquoise waters and exploring the other-worldly Fort Jefferson, watching the sun set into the Gulf of Mexico.

Experience the joy of feeling Sea Dragon in her element, sailing the wrong way against the wind and the Gulf Stream until she rounds the western tip of Cuba and enters the Caribbean Sea, leaving a final leg of the voyage into Georgetown, the capital of the Cayman Islands.



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Combine island adventures with the chance to learn how to sail and thought-provoking, inspiring personal development sessions, including:

On land
– Setting the Scene: an introduction to the voyage and what to expect
– Safety Briefing & Vessel Orientation
– Why Adventure is Important: why getting out of your comfort zone leads to success
– Getting to know each other

Opening Sessions
– A Practical Introduction to Sailing: seamanship, sail handling, navigation.
– An Insight Into Our Changing World: Environmental (ocean science, degradation and conservation) and Social (consumption, energy, city living and population).

– How to Develop and Maintain a Positive Attitude (saying yes)
– Values: our shifting mindset
– Happiness: what is happiness to you?
– Time: our most precious asset and how we use it
– Discussion: how do we rebuild society?

– Photography & Video Shooting and Basic Editing
– Social Media
– Fundraising
– Ideas on how to avoid procrastination and improve efficiency

– Identifying your passion and expertise
– Creating an Escape List
– One-on-one sessions with mission leaders

Take the Floor
– 30 minute lecture from each crew member (ask them to pre-prepare a presentation, if you want slides (laptop with Power Point/ Keynote will be available)
– Photographer of the Day

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Erin Williams

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Background & Expertise

My background is in youth leadership, cross-cultural dialogue, interfaith relations, and media and storytelling training. I recently traveled to Qatar and Ghana to co-facilitate and document digital storytelling workshops for young people from the Middle East and Africa. I love photography and filmmaking and am involved in both areas professionally and personally.

Expedition Goals

I am going on the expedition to challenge myself physically and mentally. I am also hoping to deepen my understanding of current conservation and biodiversity concerns in order to support conservation efforts more consistently.

Geraldine McFaul

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Background & Expertise

Risk Consultant advising Local Authorities and public organisations on risk and safety including surveys, audits and delivering training.

Sailing experience mainly around West Scotland but also includes circumnavigating Ireland (over 2 trips) and between Vancouver and Vancouver Island. Up to 45ft yachts.

Expedition Goals

I am combining my love of sailing and travel with an increasing interest in photography by joining this adventure. Alongside my more recent attitude to take up more challenges then I had little or no excuse not to say “yes” to this opportunity!

I have been involved in and organised numerous charity fundraising events over the years including ceilidhs, cake decoration and baby buggyblankets among others. Most recently I have taken up cycling and successfully rose to the massive (for me) challenge of cycling London to Paris, 300 miles in 4 days in 2012.

I would like to use the time to identify and consider my next challenges in life, prioritise them and work out how to move them forward!

Giorgio Manenti

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Background & Expertise

Real estate investment banking consultant.

Expedition Goals

Sail, meet new people and be inspired.

Ken Kearney

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Background & Expertise

Construction and Sales

Expedition Goals

Personal Improvement

Matthew Snage

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Background & Expertise

Fifteen years experience in Customer Service, Banking, Sales, Insurance Underwriting, and Telecommunications.
1) Walt Disney World Company, Merchandise or Merchandizing Representative, Orlando, Florida, Summer 1997
2) Language Export Centre, Apprentice, Wales, UK, January 1997
3) Drucks Sporthaus, Sales Representative, Aachen, Germany, Summer 1996
4) Aachener Bausparkasse (German Building and Loans Mortgage Company), Apprentice, Aachen, Germany, Summer1996

Expedition Goals

Learn about Sailing: seamanship, sail handling, navigation, and watercraft safety.
Learn about our environmentally and socially Changing World in our discussions about ‘How do we rebuild society?’
Meet the Expedition leaders, boat crew, and other participants
Personal development objectives
Learn how, and why taking the right adventures stretch your comfort zone
Learn how to properly maintain a positive attitude
Learn about proper Time Management
Learn about creating an Escape List
Learn to how further identify & define my (new) passion to be a professional Explorer
Deliver 30 minutes presentation on my passion –
1) Learning how to create my VISION to be a professional Explorer.
2) Learn how become a professional Explorer – leveraging my skill set and experiences to deliver results in an entry-level position in the right expeditions, adventures and journeys…
3) Learn about the art and expertise of Photography & Video Shooting and Basic Editing, Social Media, Fundraising and decreasing procrastination and improve efficiency.

Naomi Jane

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Background & Expertise

My background is in behavioural change, cultural change and project management. I have run my own social enterprise that specialised in creative personal development projects for disadvantaged communities and young people. I am currently a leadership development and employee engagement consultant working for a creative agency but as of the end of March will be a free woman and am planning to re-pursue my passion for behavioural change for underrepresented and disadvantaged community groups., amongst a few other business ideas that I have (including a holistic wellness centre for women).

Expedition Goals

I hope that the trip will give me the head space that I need to build on my plans as I work towards going self employed full-time and move back into the social change sector. I am really excited but quite feel daunted as I haven’t worked for myself for over 2.5 years now and I have got quite comfortable with a monthly salary and a corporate facing role. I know what I need to do, but there is a lot of work for me to do on the ‘how’ and I am hoping this trip will help me gain personal clarity and also helpful insight from other like-minded individuals.

Rowan Wakeford

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Background & Expertise

Born in South African, I have been living in London for the past 7 years. Currently working as a Technical Architect for a city law firm. I am passionate about travelling and experiencing everything this world has to offer.

Expedition Goals

I’ve always believed that I can do or achieve anything…the biggest problem has always been trying to figure out what it is that I want to do and what actually matters in the long run. I’m hoping that this expedition will not only help me figure some of that out, but will also put the things in my life into perspective.


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Dave Cornthwaite – Mission Leader

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Dave Cornthwaite is an adventurer, bestselling author, motivational speaker and founder of SayYesMore. Having travelled more than 16,000 miles under his own steam, his record-breaking expeditions including skateboarding across Australia, stand up paddle boarding the Mississippi River and swimming the Missouri have led to Dave being described as one of the most ambitious and tenacious adventurers around. His entertaining and motivational keynote presentations have been enjoyed on six continents and his passionate advocacy of the word YES has contributed to the sprouting of countless adventures worldwide, big and small. His mission is simple: to motivate people to break down their fears, not be afraid to challenge themselves, consume less, do what they love and enjoy Mondays.

Emily Penn – Mission Leader

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Emily Penn is an oceans advocate, skipper and artist who has extensive exploration experience in the Atlantic and Pacific Oceans. She is a graduate of Cambridge University with a degree in Sustainable Architecture; and Director of global organisation Pangaea Explorations; and the first and youngest woman to be awarded the international Yachtmaster of the Year.

Emily rounded the planet on the biofuelled Earthrace boat; spent 6 months living on a tiny Tongan island organising the largest ever community led rubbish clean-up; and discovered previously unknown oceanic gyres – huge areas of plastic pollution accumulation.

An experienced public speaker, Emily has spoken around the world at conferences, universities and global companies about her adventures and issues relating to our oceans, human mindset and future society.

You can find more information on Emily’s projects at www.emilypenn.co.uk.

Eric Loss – Skipper

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A native of California, Eric has been on the water since an early age. He has sailed more than 55,000 offshore miles, and has sailed everything from windsurfers to 115′ schooners, and recently he completed a single-handed circumnavigation by way of the great capes. He enjoys teaching all aspects of sailing, from boat handling and dinghy racing to navigation and seamanship. He is always eager to share his knowledge of celestial navigation. Eric has been involved in sail training for most of his life, and is an US Sailing instructor. He holds an IYT Master of Yachts Ocean with commercial endorsement and a USCG 100 ton master’s license. Eric is also an experienced diver and PADI Divemaster.

Shanley Mcentee – First Mate

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Shanley was born and raised in San Diego, CA and graduated with a BA in Environmental Policy and a minor in Environmental Science from Western Washington University. Having grown up by the sea, she holds a deep passion for Mother Ocean and our ever-growing need for protection and awareness of the problems our environment is facing. She enjoys anything having to do with the sea, from surfing to scuba diving to sailing, and loves offshore passages. She is PADI Rescue Diver certified and holds an IYT Master of Yatchs Offshore with commercial endorsement.

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February 19: Guest crew will join Sea Dragon in Miami at 4pm. Everyone will have an opportunity to settle into the yacht, and put away their personal belongings. Dave and Emily will give a welcome briefing, followed by some basic safety training.

February 20: Sea Dragon will leave the dock around 10am and sail south along the Florida Keys. Workshop sessions begin.

February 21: Continue sailing along the Florida Keys. Workshop sessions continue.

February 22: Sea Dragon will arrive in the Dry Tortugas to explore Fort Jefferson and watch sunset from the beach.

February 23: Crew will explore the Dry Tortugas with snorkelling during the day, leave in the afternoon and set sail towards Grand Cayman.

February 24-26: Sail across the Caribbean Sea toward Grand Cayman.

February 26: Sea Dragon will arrive in Grand Cayman in the afternoon/late evening.

February 27: After clearing Customs, there will be a morning of snorkelling and activities in the warm Cayman waters. Crew are free to depart the boat by 4pm.

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Travel documents:
Crew will require a passport from their home country that will allow them to travel to the Cayman Islands and the United States. For specific visa information, contact the Cayman Islands Immigration Department or US Customs and Border Protection.

Contribution Includes:

  • 8 nights accommodation on board Sea Dragon
  • All meals, snacks and drinks on board
  • Sailing instruction
  • Safety equipment and foul weather gear
  • All workshops, personal development and one-on-one sessions

Payment does not include:

  • Transportation to Miami and home from Grand Cayman
  • Transportation to and from the dock
  • Personal expenses while in port

Kit List
Please see our Travel Kit List.

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