Ask For Jess
For all your needs year-round: accommodation, transport, events, experiences, Crop Over & more
What We Do
At Ask For Jess, we make your dream of a perfect Barbados getaway a reality. Whether you’re seeking sun-kissed beaches, luxurious resorts, rich cultural experiences, or exciting island adventures, our personalized vacation packages are designed to cater to your every desire. With a deep knowledge of Barbados, we curate the ideal holiday for you, allowing you to immerse in the natural beauty, vibrant local culture, and unforgettable experiences that this Caribbean paradise has to offer.
Custom Vacation
Enjoy a fully customized vacation experience, uniquely designed to match your preferences, interests, and budget.
Crop Over
Experience Crop Over like a local with curated events, accommodations, and insider access for unforgettable fun!
Wellness Packages
Recharge and rejuvenate with our wellness packages designed to nurture your mind, body, and spirit.
About
About Us
We Curate Memorable Moments
We believe in making life easier by crafting seamless travel experiences tailored to your desires. Founded by travel enthusiast Jessica Reid, our company is dedicated to curating unforgettable journeys that are as unique as you are. Whether you’re dreaming of a custom vacation package, a romantic getaway, or planning a special family trip, our goal is to ensure every detail is perfectly planned.
With expertise in group travel, wellness retreats, and bridal concierge services, Ask For Jess is your trusted partner for creating moments that matter. We handle the logistics so you can focus on enjoying the experience. From start to finish, we make travel easy.
Why Choose Us
We Provide Tailored Solutions
You’ll experience effortless travel planning, tailored exclusively to you. We specialize in creating custom vacations and seamless events, allowing you to relax while we handle the details. Personalized service, unforgettable experiences—Life Made Easy.
Media & Blog
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Latest Updates
Why You Should Book Crop Over 2026 with Ask for Jess
The Crop Over festival 🇧🇧✨ is a cultural explosion of music, dance, art, and vibes. If you’re thinking about joining us in Barbados for Crop Over 2026 (July 29 – August 4), let me tell you why securing your spot with Ask for Jess is the smartest choice you’ll...
The Best Way to Experience Trinidad Carnival 2026: Epic Carnival Cruise
If you’re thinking of doing Trinidad Carnival 2026, but find yourself feeling overwhelmed by all the moving parts (event tickets, transportation, accommodation, spending money?), then let me put you on to the Epic Carnival Cruise. As a seasoned carnival goer (I’m not...
Crop Over for Beginners: Your Starter Guide
So you've finally decided to do it. You're coming to Barbados for Crop Over. First of all...excellent choice if I do say so myself. It's definitely one of my favorite experiences ever, but it can be a lot to process if you're new to it...so don't worry, I got you...
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Celebrate something special
Let Ask For Jess make your special occasion unforgettable! Whether it’s a romantic anniversary, milestone birthday, or family reunion, we’ll design a custom getaway or event that perfectly captures the moment. Celebrate in style, while we handle everything.
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Testimonials
“Our family vacation was a dream! Jess handled everything, from accommodations to activities. The kids loved it, and we had the best time together.”
“Jess curated the perfect wellness retreat for me. From the peaceful location to the relaxing activities, everything was exactly what I needed. Highly recommended!”
“Jess planned our girls’ getaway, and it was amazing! She customized everything to our group’s preferences. We’ll definitely book with her again—such an easy experience!”
Services
Family Travel
Romantic Getaway
Opening Hours
Closed Saturday & Sundays
Monday to Friday
9:00 am to 5:00 pm