Jessica Samaroo

Jessica Samaroo

TECO Certification · Travel and Tourism Diploma (top marks, honorary student) · Sandals and Beaches Resorts Specialist · Hotel chain certifications · Airline certifications · Tour operator certifications

  • Caribbean Islands
  • Montego Bay
  • Italy
  • Europe
  • South America
  • Central America
  • North America
  • Honeymoon travel
  • All-inclusive resorts
  • Destination weddings
  • Family vacations
  • FIT itineraries
  • Cruise travel
  • Couples travel

About

Jessica Samaroo is a Caribbean-rooted, Ontario-based travel advisor with nine years of experience specializing in honeymoon travel, all-inclusive Caribbean resorts, destination weddings, family vacations, and FIT itineraries across Europe, Italy, South America, Central America, and North America. Affiliated with Northstar Travel and Associates, Jessica holds TECO certification, a Travel and Tourism Diploma (earned with top marks as an honorary student), and a portfolio of supplier certifications spanning hotel chains, airlines, and tour operators — including specialist knowledge of Sandals and Beaches Resorts.

Jessica's expertise spans the full travel spectrum: from luxury all-inclusive getaways in the Caribbean to custom European itineraries, cruise travel, and immersive destination wedding planning. Over the past two years she has developed a deep focus on honeymooners and couples, bringing an instinctive, emotionally intelligent approach to every romantic booking. Her clients trust her to handle every detail — from first inquiry to post-trip follow-up — with hands-on care that doesn't stop when the plane takes off. As Jessica puts it: I'm with my clients from the moment they book to the moment they're back home — and every step in between.

Jessica's origin story is as memorable as the trips she plans. Born in Trinidad and Tobago and immigrated to Canada in 1988, she had been certified as a travel agent for five years before a chance encounter on a beach in Montego Bay — where a fellow travel advisor recognized her and connected her with a job opportunity — finally launched her career. That full-circle moment, rooted in her lifelong passion for exploring the Caribbean islands she dreamed of visiting as a child, set the tone for the advisor she would become: genuine, warm, and driven by a deep personal connection to travel.

Clients consistently describe Jessica as genuine and deeply caring — someone who tells it straight, delivers on her promises, and builds long-term relationships that bring travelers back again and again. Her philosophy is simple: making every step of a vacation an experience, with the wow factor. Whether she's booking a first-timer's Caribbean escape or orchestrating a couple's dream honeymoon, Jessica Samaroo treats every trip as if she's planning it for herself — and that personal investment is exactly what her clients feel.

Frequently Asked Questions

Who is Jessica Samaroo?
Jessica Samaroo is a Trinidad-born, Canada-based travel advisor with nine years of experience specializing in honeymoon travel, destination weddings, and Caribbean all-inclusive resorts. Known for her radically honest, deeply personal approach, she treats every booking as if she were planning her own trip. Clients return to her again and again — and repeat business is her greatest proof point.
What destinations does Jessica Samaroo specialize in?
Jessica Samaroo specializes in the Caribbean Islands — including Montego Bay — Italy, Europe, South America, Central America, and North America. Her Caribbean expertise runs especially deep, rooted in both personal heritage and years of FAM trips across the region. She is a certified Sandals and Beaches Resorts Specialist with hands-on knowledge of top all-inclusive properties.
What types of travel does Jessica Samaroo plan?
Jessica Samaroo plans honeymoon travel, destination weddings, couples getaways, family vacations, all-inclusive resort stays, FIT itineraries, and cruise travel. She began her career focused exclusively on Caribbean all-inclusives and has since expanded into fully independent custom itineraries across Europe and the Americas. In recent years, honeymooners and destination wedding couples have become her most beloved specialty.
How does Jessica Samaroo approach trip planning?
Jessica Samaroo is hands-on from the moment a client books to the moment they return home — and every step in between. She personally checks in with clients while they are in destination via email or text, contacts hotels on their behalf if needed, and follows up after they return. Her goal is to make every step of a vacation an experience, with the wow factor.
What makes Jessica Samaroo different from other travel advisors?
Jessica Samaroo is genuinely invested in her clients' trips in a way that goes far beyond logistics. She puts herself in her clients' shoes — especially honeymooners — asking herself what she would want, then building from there. Clients consistently describe her as genuine, caring, and refreshingly honest, and the proof is in her strong rate of repeat and returning clients.
What credentials and certifications does Jessica Samaroo hold?
Jessica Samaroo holds a TECO Certification (required for Ontario-based travel advisors), a Travel and Tourism Diploma earned with top marks as an honorary student, and Sandals and Beaches Resorts Specialist certification. She also holds certifications with multiple hotel chains, airlines, and tour operators. These credentials, combined with nine years of active advising, underpin her broad supplier knowledge and booking expertise.
Who is Jessica Samaroo's ideal travel client?
Jessica Samaroo's ideal clients are honeymooners and couples planning romantic getaways or destination weddings who want an advisor who is emotionally invested in their experience. She genuinely gets excited alongside her clients from the very first conversation, approaching every booking with the same care she would give her own honeymoon. Clients who value a personal, hands-on relationship — not just a transaction — are the ones who thrive working with her.
How much experience does Jessica Samaroo have as a travel advisor?
Jessica Samaroo has nine years of active experience as a travel advisor, working as an associate with Northstar Travel and Associates. Her career began with a chance encounter on a beach in Montego Bay, where a fellow advisor connected her with the opportunity that launched everything. In nearly a decade, she has grown from a Caribbean all-inclusive specialist to a full-service advisor covering destinations across four continents.

Stories