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Lisa Shakespeare

Instagram is a wonderful tool to share photos and videos with but what I personally love the most is its social side. I have made so many wonderful friends through this social app. Lisa Shakespeare is one of those persons that quickly went from someone I followed on screen to someone I got to hang out with IRL. Her bubbly character, zest for life and insatiable thirst for adventure are contagious and the very reasons why she is amongst some of the most popular and well liked travel influencers from the Caribbean.

The few days I had the honor to spend with this firecracker showed me the real Lisa Shakespeare and I am happy to report that the Lisa you see online is the Lisa you will meet in real life. Always happy, always smiling and always up to something.

The Pandemic hit just as her travel career was about to take off. Instead of wallowing in self-pity and disappointment, she turned that frown into a smile and made do with the tools and skills she has. She was giving free reggae fit classes online, started an agency to help other content creators up their game and she started exploring her native Jamaica all while sharing her adventures on social media. I was glued to my phone every single day in anticipation of what Jamaican wonders she would share with us that day.

I am beyond ecstatic that she agreed to put her current adventure on hold to answer a few of my questions. This is my interview with Miss Lisa Shakespeare from Shakepeare Agency, formerly known as Shaespeare Travels.

M: What was your life like pre-pandemic and how has it changed post pandemic?

Lisa: Pre-pandemic, I was about to (and had just started) to truly travel the world! I had quit my fulltime corporate job at the end of 2019 and began pursuing a travel career in January 2020. I moved back to Jamaica then spent a month in Brazil where I hosted a group trip of travelers from all over the world. Then I headed to Nicaragua for a girls trip where I went volcano boarding for the first time! Right after that trip, COVID hit, and everything changed. I lost my full-time travel job, was shut out of Jamaica for four months because they closed the borders, and I went through a pretty rough patch.

However, it propelled me to take matters into my own hands and I ended up launching my own business, Shakespeare Agency, a multi-creative social media marketing, copy writing & travel planning enterprise mixed with dance fitness. So now, “post pandemic”, I’m proud to say that I’m an entrepreneur. Almost a year in as a business owner, I will say it hasn’t been easy and I’ve had my challenges. But I’ve learned quite a lot and I’m excited to announce that I will be rebranding this summer, focusing solely on travel offering content creation for brands as a travel expert and trip planning services for groups and individuals as a travel consultant.

M: You have been showing off your beautiful native Jamaica and, I for one, have been mesmerized by all that your island has to offer. You have opened my eyes to so much and now Jamaica is in my top 3 of places I NEED to visit. 

What would you say is the one thing that most people do not know about your island? 

Lisa: I don’t think many people know that Jamaica is the 3rd largest island in the Caribbean, with a population of almost 3 million. We have 14 incredible parishes, but most people are only aware of maybe three or four because they usually visit the touristy areas of the island like Ocho Rios, Montego Bay or Negril and a few may venture to Kingston.

M: And what is the biggest misconception about the island and its people? 

Lisa: That all there is to Jamaica are our beautiful beaches. However, the island also has so much more than beaches to offer. We have over 300 mountains with the most prominent one being the Blue Mountains where we get our famous coffee. P.S. I’ll share a little secret … I’ve never had Blue Mountain coffee before (I know, I know) but that’s because I’m a tea lover. Gimme a cup of mint or ginger tea and I’m good to go!

Also, not everyone grows, or smokes weed in their backyards in Jamaica.

M: Are there things that you have experienced lately that you yourself did not know existed? 

Lisa: Yes, I discovered the untouched paradise of Treasure Beach in St. Elizabeth. I spent a few weeks out there and fell in love, not only with the area but with the people as well. They were the most genuine and down to earth folks I have ever met and the level of safety and comfort I felt out there was incredible. I also got to experience Pelican Bar, which is a thatched wood bar literally out in the middle of the ocean, where you can stand up because it’s so shallow out there and you can also go swimming

M: What were some of your most favorite Jamaican experiences so far? 

Lisa: Pelican Bar is definitely a fav! I loved the “Tiki Pon Da Sea” experience which is another thatched hut bar on a boat that takes you out to sea in Negril and stops at a small uninhabited island with the most beautiful clear water and white sandy beach, which is just absolutely breathtaking. They cook fresh fish and lobster on an open fire grill … some of the best seafood I ever had! I also love off the beaten path and not so popular adventures, so my favorite waterfalls are Benta River Falls in Westmoreland and Nanny Falls in Portland.

M: Let’s talk about local food? Most of us know about akee and sailfish. I myself had it for the first time not too long ago and loved it. What other dishes are classic Jamaican? 

Lisa: Oh food … my absolute favorite topic ever to talk about! A few classic Jamaican dishes are rice and peas with jerk chicken, jerk pork or oxtail. We also love white rice with curry chicken or curry goat and for me, my personal favorite is stew peas with pig tail. Oh man, my mouth’s watering right now! Escovitch fish is also popular with festival and bammy.

M: Which parish is your favorite for romance, which for adventure and which for fun and bacchanal? And why? 

Lisa: Oh wow … uhm… for romance, I would probably say Westmoreland (and not because it’s one of the more popular parishes) but because I think it has a lot to offer in the romance department from hotels and private cottages, dedicated to adult couples only, with intimate and quiet surroundings, along dramatic seaside cliffs, with spectacular views over the ocean and some of the most beautiful sunsets you’ll ever see.

For adventure, I would say Portland, which is on the northeast coast of the island, and it’s great for off the beaten path adventures where you can find some of the most beautiful waterfalls like Nonsuch Falls, Nanny Falls, Reach Falls and Somerset Falls. Part of the Blue Mountains is also in Portland so it’s great for hiking.

M: You have been showing some super nice places to stay around the island. Do you have a personal favorite?

Lisa: Oh, that’s a hard one … I like different places for different reasons. For example, I loved my time in Treasure Beach and Katamah Beachfront Guesthouse was my favorite place to stay because it was a tropical oasis by the sea. I loved my little cabin with the outdoor shower. The simplicity, lush surroundings and genuine hospitality from the owner left a deep impression with me. I would go back in a heartbeat!

For a more “in the scene” vibe, S Hotel in Montego Bay is my favorite because it’s located right on the hip strip and directly on the beach. It’s a beautiful and modern hotel with two really cool pools, one of which offers stunning views of the ocean. I was also obsessed with the free-standing bathtub in the room, where I soaked for a few hours, uninterrupted.

M: If you were to set up a marketing campaign to get visitors to the island, what would you focus on?

Lisa: I would definitely focus on off the beaten path adventures and hidden gems. So, I would highlight the more unknown parishes like St. Elizabeth, Portland, St. Thomas and others where most people are unaware even exist. The campaign would showcase Jamaica in an authentic, cross-island journey tapping into our deep history, cultural roots, delicious food, unspoilt waterfalls and rivers … the REAL Jamaica.

M: We cannot have a conversation about Jamaica and not talk about its beaches. Which beach is the one beach you think is totally underrated? 

Lisa: Boston Beach in Portland! Omg, it’s absolutely stunning! The water is warm all year round (okay, you might want to fact check that lol) but honestly, the water feels amazing and it’s crystal-clear. It’s also one of the few places in Jamaica you can go surfing. Plus, another perk is that it’s close to the infamous Boston Jerk Center. Definitely a must visit when in Jamaica!

M: What are your future plans? Will you be going to your regular programming of traveling the globe with organized group trips or will you be concentrating more on showing off your homeland? 

Lisa: So, as I mentioned earlier, I will be rebranding Shakespeare Agency to focus solely on travel and that will be a mix of both local and international travels. However, as a proud Jamaican, I want to showcase my island more than ever, so I will be focusing a lot more on local accommodations and excursions. One of my future goals is to work with the Jamaica Tourism Board as the island’s brand ambassador to highlight and represent all that Jamaica has to offer! This doesn’t mean I’m giving up international travels … I definitely plan to visit at least 10 more countries before the year is over and a few will be group trips that I organize. I couldn’t be happier that travel is slowly coming back, and people are opening up to the idea of getting back out there. So, I want to be on the forefront of that wave and be a person of authority and expertise in the field of travel, as well as inspiring others to see the world.

You can follow Lisa’s adventures on Instagram or Facebook and of course her website is a must visit for more information about her services:

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