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I design unforgettable travel experiences, always curated for you.
Create Once In a Lifetime Memories
Relax. I'll Handle Everything
See The Best of the World Stress Free
I'm Jessica Oballo, and for over a decade I've been turning travel into something more than logistics. I combine deep industry knowledge, global connections, and a passion for thoughtful design to curate journeys that are as intentional as they are unforgettable.
Africa is close to my heart. From the shimmering channels of the Okavango Delta in Botswana to the vibrant energy of Cape Town, the rolling vineyards of Franschhoek, the Maasai lands of Kenya, and the mist-covered mountains of Rwanda - I plan every corner of this extraordinary continent with care and meaning.
Whether you're celebrating a milestone in Europe, teeing off in Scotland, discovering Japan, or escaping to the Caribbean, I'll plan every detail so that your journey feels effortless - and completely your own.
As an advisor with Departure Lounge, an affiliate of Virtuoso, you gain access to insider perks, exclusive amenities, and a vetted global network of luxury providers - the kind of access that turns a great trip into an extraordinary one.
Follow Jessica Oballo:
Hi, I'm Jessica Oballo!
Navigate the world of international travel with ease. The journey from initial planning to final execution, including handling those unexpected challenges, requires more than just time — it requires expertise. This is where I come in. I have spent years designing tailor-made, stress-free travel experiences for our clients across the globe. Imagine embarking on your dream trip without the burden of anxiety or logistical concerns.
My goal is to create a flawless vacation for you, filled with unforgettable experiences and quality time with the people you care most about. I am here to turn that dream into a reality.
Are you ready to take the first step towards your next adventure?
Follow Jessica Oballo:
My Travel Services and Specialties
Professional Travel Planning
My Services
Top Destinations
Top Travel Styles
1
Dream Trip Planning
Together, we'll discuss your vision for this trip. Tell me everything you'd love to have happen.
2
Personalized Itinerary
I will develop a customized, highly-detailed itinerary for every stage of your trip. Trust me, every detail will be thought through, with some of my signature perks sprinkled in along the way.
3
Seamless Booking and Logistics
Sit back and relax. My global network and I will take care of every detail of getting you where you need to go. You just need to figure out what to pack next - I can help with that too!
4
Bon Voyage!
It's here. Enjoy the trip of a lifetime. You deserve it.
5
Welcome Home!
After you return, we will debrief and start dreaming up your next adventure.
1
Schedule Your Call
Choose the perfect date and time for an in-depth Discovery Consultation that fits seamlessly into your calendar.
2
Craft Your Bespoke Journey
In our collaborative planning session, we'll handcraft every segment of your journey, ensuring an exclusive travel experience.
3
Finalize Your Dream Trip
With the details refined and your approval secured, I'll finalize all arrangements, setting the stage for an unforgettable travel experience.
My connections with premier luxury brands and top-tier travel organizations span the globe, all dedicated to your exceptional travel experience. Whether day or night, my network and I stand ready to ensure every aspect of your trip unfolds flawlessly, elevating your journey to the heights of perfection.
Why Travelers Choose Me
Stories Worth Sharing, Trips Worth Taking
Smooth and effortless! She managed all the details and provided us precisely what we needed to build our perfect family vacation in Japan. 12 days, four cities, multiple trains, cabs, buses...and it ran like clockwork. All of our hotels and ryokans were perfection. Not just the amenities, but the locations were outstanding! And the experiences that she planned were incredible - not touristy, but authentic experiences where we learned about the culture and history that led to the Samurai way of life, or the ancient tea ceremony and the matcha they use in the ceremony, for example. If you're looking for knowledgeable help that will ensure you have a beautiful experience, Jessica is your best choice. 100% recommend.
Christina
Japan Family Trip
Jessica is amazing! While planning our wedding I had nothing to worry about when it came to our Honeymoon. Jessica took complete charge and I am so thankful for her. We have the most amazing South African experience. Outstanding food, views, accommodations and people. I will absolutely never plan another international trip without Jessica. Travel was so easy because she made sure everything was taken care of. Thank you so much Jessica. It was the best vacation of my life thus far!
Lia
South Africa Honeymoon
Jessica Oballo Travel Design has really transformed my traveling from something that was once just a check the box kind of trip to a true experience that has a real impact. From Mexico to Europe and countless trips across the US, I have become more grateful to have the opportunity to travel thanks to Jessica and her impeccable talent in knowing how to tailor each trip to what would make it memorable to me. I look forward to the many trips in the coming years where Jessica will continue to fill my life with more memories and fun as she uses her talent to curate trips I once could only dream of going on.
Jo
Mexico, Europe and US
Jessica Oballo is an outstanding travel agent who provides impeccable concierge travel assistance. Over the past five years, Jess has helped me plan trips to Spain, Portugal, Copenhagen, Denmark, Italy, San Miguel de Allende & Mexico City, and domestically she planned a "big" birthday trip to Telluride and a lovely visit to Carmel Valley for me. Jess really listens to what you want in terms of experiences, price, and comfort in travel. She always has fabulous suggestions on excursions to consider, sites to see and places to stay. And when things go wrong - oh, those Italian trains -- Jess will stick by you to ensure you arrive safely at your destination. I have recommended Jess to many friends who have also benefited from her astute travel planning. If you want a dedicated travel agent with a friendly, can-do attitude, hire Jess!
Velma
Denmark, Italy, San Miguel de Allende & Mexico City
Jessica obviously gets a sense of her clients, what they expect, what they want, and then can provide choices, consistent with my sensibilities to formulate and experience exactly among the lines of what I want even though I didn’t know exactly what I wanted. She is an excellent communicator about planning and then stays in constant communication about logistics up until the time, and even remains in communication during our experience to make sure everything is still going well. It was of the highest quality from start to finish that you could expect from an agent.
Morocco Graduation Trip
My sister and I wanted to surprise my mother with the journey of a lifetime for her 70th Birthday. Jessica made that vision a reality. She created a beautifully organized itinerary that took us through Sweden, Denmark, and Norway — including visits to family and all of my mom’s ancestral homesteads in Sweden, which meant the world to her. Every detail was thoughtful, smooth, and tailored to exactly what we hoped for. Jessica’s care, communication, and expertise turned a special occasion into a truly once-in-a-lifetime experience. We’re so grateful for her and couldn’t recommend her more highly.
Jessica
Sweden, Denmark and Norway
From first contact, Jessica crafted the ultimate 14-day photographic safari: gorilla treks in Bwindi, Mgahinga, and Volcanoes National Parks; chimpanzee and golden monkey encounters; game drives; birding and nature walks; boat safaris; a rhino sanctuary visit; a Batwa cultural experience; and a lecture with a gorilla doctor. In just two weeks, we enjoyed 19 custom activities across six luxurious yet unpretentious lodges, perfectly matching our request for upscale but not over-the-top accommodations. This was my fifth African voyage and ranks among the very best. Jessica’s meticulous planning and seamless organization made it truly unforgettable.
Joe
Uganda and Rwanda
Ready to sharpen your travel tastes and discover the world's best-kept secrets? This personalized travel guide will help you broaden your horizons and get inspired for the journey ahead. Plus sign up to my monthly newsletter for travel inspiration delivered right to your inbox!
Submit your consultation questionnaire, and then we will schedule your free discovery call to begin the trip of a lifetime.
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