#MondayInspiration with Angela Eastwick, owner of Somewhere West, Jamaica

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Ever thought about escaping the city rat race and setting up a new life on a Caribbean island? Sounds like a dream right? Well, that dream became a reality for Angela Eastwick, who left a career in TV to set up the delightful guesthouse Somewhere West and tour company JuJu Tours, in Negril, Jamaica.

I stayed at this beautiful place in the lead up to my destination wedding in Jamaica in February and I was so inspired by her story, I just had to feature her in OSL’s ‘Monday Inspiration’.

When I heard Angie’s story, I couldn’t stop dreaming about what life would be like if I travelled to the Caribbean and set up my own business just like her. Read her story – I think you’ll be inspired.

Over to you Angi!

Hi Angie, tell us about yourself and your career…
I’m Angie, I was born in Pearl River, New York where I lived in Queens and worked as a TV production and executive assistant for Manhattan’s Clarity Media Group and I’ve now been living In Jamaica since 2010. I live here with my partner Jermelee and baby Jesse. Together, we run the Airbnb guesthouse Somewhere West, alongside our tour company JuJu Tours.

Monday Inspiration with Angela Eastwick, Somwhere West Jamaica

Why did you decide to leave your career in New York, in TV production?

After almost ten years of living in NYC, I felt my spirit fading fast. NY’s media industry began to suffocate my physical and emotional ambition. Money was tight, the subway ride was long, winters were cold and neighbors remained strangers. I felt like I was living in a black and white television, watching the same show on repeat. I loved the people I worked with and the skills I had acquired, but that wasn’t enough to fulfill my longing for something more purposeful. Jamaica was that for me. I began to see life in color again.

Why did you choose the Caribbean?
I decided to take a vacation with friends, where I’d visited with my family at the age of fourteen and my freezer burned heart began to melt. I saw a vision of an alternative life I could lead intertwined with entrepreneurship and it started from there.

Monday Inspiration with Angela Eastwick, Somwhere West Jamaica

How did you begin to make the transition from NYC to the Caribbean?
Initially, I moved down to the island for three months on my own, which were some of the most profound months of my life. I finally decided to move to Jamaica permanently in 2010 with a close friend – we both wanted to open a business on the island. I’ll never forget my own disbelief, sitting on the plane to Negril with my eight suitcases. I had finally let go of my life in New York, along with all of societal and parental expectations, and truly had no idea what I was really getting myself into.

How did your friends and family react?
People thought we had simply gone mad. “Jamaica’s dangerous!” they would say. Perhaps my track record of being a wild child also gave them reason to believe I had no business running a business.

What did you do?
I began by launching Juju Tours and I sold tours by sneaking into the all-inclusive resorts along Seven Mile Beach to hand out business cards to holiday makers. It was one of the hardest things I’ve ever done but I eventually began to sell excursions and realised it was the authentic excursions that people were longing for. I began taking visitors off the resort and into the true ‘country ghetto’ where I lived at the time.

Monday Inspiration with Angela Eastwick, Somwhere West Jamaica

Was it a culture shock?
Yes. I lived in a true ‘yard’ with a large Jamaican family and there was no Internet, no restaurants, no stores, no car, no TV, sometimes even no running water and electric – just me and the locals. But as I say, it became a large selling point for my company.

When did you realise you wanted to start your own guesthouse?
After three years of running a successful tour business, I asked my father for a loan to buy a small home and the idea for Somewhere West came after that.
My father, a very successful entrepreneur, recommended that we look for a property on the water. He wouldn’t usually spend on something so extravagant and when we looked at Somewhere West (then called Caribbean Dream), even the realtor believed it would never sell. It was shabby, dirty, and had been hit by Hurricane Ivan and then lived in by squatters. My dad’s first words were: “This place is a FUCKIN’ GOLDMINE!”. It turns out his early prediction was very, very right.

Monday Inspiration with Angela Eastwick, Somwhere West Jamaica

How did you transform it from the derelict state it was to a lovely guesthouse?
It was a tough journey and renovations went poorly for the first few months – and I mean very poorly. My partner Jermelee and I knew nothing about construction and we wasted a lot of finances on stupid mistakes. Countertops would go up and later be torn down because they were too high. Tile work would be put down to only later be torn up because too much cement lay underneath. The same followed with plumbing, carpentry, and masonry. It all cost us financially so it was a steep learning curve, along with a lot of blood, sweat and tears!

Did you ever wonder if you’d taken on too much?
Oh yes. Our work was laughable – any hotel owner who paid us a visit warned us things didn’t look to be going well. One owner offered me his utmost honesty when he said “just quit and go back to what you’re good at.” It was that day where I knew we had no choice but to do better. I couldn’t possibly let him get away with that line.

When did things finally begin to look up?
I met a friendly Canadian man and hired him as our contractor. It was an expensive but wise investment as he taught us how to build the right way. Within a year, Somewhere West was up and running. The guesthouse’s revenue allowed me to continue construction as well as build a house for my growing family at the top of the property. We are still building that house today.

Airbnb Stay at Somewhere West, Jamaica

When did you first start advertising your guesthouse on Airbnb and how has it helped your company grow?
We launched our guesthouse on AirBnB in November 2014 and we are so thankful for it! Airbnb’s mission is to bring attention and business to small property owners and it has significantly helped us sell our concept of private getaways in a truly intimate and serene location. It’s exactly what a business like ours needs to compete with the huge all-inclusive hotels in our area.

Is there anyone who inspires you in the day-to-day running of your own business?
I had never owned a business before but I had spent ample time working close to business owners. My previous boss and mentor, Bill McGowan, taught me to apply excellence in any task, small or big. Everything a business owner does should be executed with perfection. Bill remains one of my major voices of reason. I often ask myself, “What would Bill do?”

What is your typical day like?
My day begins with some morning stretches overlooking the panoramic Caribbean view from our bedroom balcony. Quickly afterwards chaos ensues. I’ll usually check the grounds to make sure it’s presentable and I’ll assist Jermelee, my partner and chef on property, in serving breakfast for guests. I then take a trip downtown for errands and groceries and meet with employees and oversee construction before I spend the afternoon answering emails and taking bookings. There is no task too large or too small that I am above. As a small business owner, you have to do it all.

Why can travelers coming to Jamaica get out of staying at Somewhere West?
Somewhere West allows visitors to see a serene and authentic side of Jamaica, away from the cliché sandy beaches or soliciting souvenirs. It’s a private, family-owned villa, set upon a wave-crashing coast where you can watch the most EPIC sunsets on the island. Now that’s a true getaway.

Monday Inspiration with Angela Eastwick, Somwhere West Jamaica

What are the toughest challenges you face in your job?
The most challenging parts of owning a business in Jamaica is grasping complicated Jamaican taxes, fulfilling necessary and constant red tape qualifications, and managing employees who come from a different culture. Dealing with customers is the easy part!

What are the most rewarding things about your job?
Despite the hurdles I have had to face, Negril has instilled in me a significant purpose. I love seeing my employees improve their quality of life because they finally have steady employment. I love seeing my tour company give back to deprived communities through way of customer donations. I love seeing our Somewhere West customers arrive and leave happy. There’s nothing better than knowing our products have met traveler expectations.

What’s your long term plan for Somewhere West and JuJu Tours?
I would like to expand and improve Somewhere West and JuJu Tours while maintaining both companies’ intimate and specialized experiences. I’d also like to build a basic school. Someone once told me I’m not a stationary person, so maybe they are right. Who knows where this journey will take me. I’m open to any experience.

What advice would you give someone considering this kind of career and lifestyle change?
With a little bit of risk and a whole lot of faith, anyone can achieve a brand new life. But to those looking to uproot their lives for something completely foreign; be careful what you wish for! Often your dreams take on a life of their own and it can be quite an adventure trying to keep up with it all. For me the honeymoon stage of living in Negril has been replaced by the daily tasks of a business owner. But it’s also filled me with purpose and an infatuation for Jamaica still awakens in my heart whenever I step out of my little entrepreneurial world and stick my toes in the sand.

Monday Inspiration with Angela Eastwick, Somwhere West Jamaica

Thanks so much for taking part in this Q&A Angi! For more information about Somewhere West, visit Airbnb.co.uk, follow them on instagram & Facebook and read our review here.

Read: My Caribbean Destination Wedding in Jamaica

Read: A Dreamy Aibnb Stay at Somewhere West, Jamaica


  1. 12th April 2016 / 3:40 pm

    Hi, great article! It reminds me of how I felt after falling in LOVE with Jamaica and staying st Somewhere West in January 2015! I am actually the photographer who took the last image featured in your article! I’d love it if you could give me photo credit and a link back for that image!?
    Inspired Life Photography – available for travel worldwide


    • 12th April 2016 / 3:54 pm

      Hi Brittany, Great to hear from you. Aw, I felt exactly the same after my visit – it’s such an incredible island isn’t it – Angi has created a dreamy little place.
      No problem re the credit – consider it done! Lx