(301) 875-8251 | moc.yspyglabolgym%40ofni

The Trip of a Lifetime Awaits You

I design unforgettable travel experiences, 100% done-for-you. 

Create Once In a Lifetime Memories

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Relax. I'll Handle Everything

See The Best of the World Stress Free

You deserve more than a "trip." You deserve a world-class travel experience.

Good news... those just happen to be my specialties.


Unforgettable Vacations Done-For-You

Hello, my name is Lolita!

International travel can be complex. From planning to logistics to booking, to dealing with the inevitable problem...doing it on your own is not an option for those who want to see the world without stress. Since 2017, I've been creating unforgettable travel experiences for clients around the world. So you can enjoy the trip of a lifetime without an ounce of traveler’s anxiety.
I know you want a flawless vacation filled with amazing moments with the people you love. I'm here to make that happen.
Ready to start planning your next journey?

  • About Me

    I started my hospitality industry career in the 1980s, working as a Front Desk Receptionist at the Grand Hyatt in Washington, DC, and later as a Call Center Reservationist for Delta Airlines. While working my way through college as an undergraduate at Howard University, these experiences fostered my love of travel, luxury, and exceptional customer service. I started Global Gypsy Travel in 2017 to provide sophisticated travelers with handcrafted, personalized, iconic travel experiences.

    Travel is essential to living a life filled with purpose and meaning. It enables you to venture beyond your small pocket of the world and experience beauty in the unknown. It is also an avenue to connect with other travelers, whether you are a seasoned traveler or new to traveling the world. The experiences and travel packages I curate are all about opening up to new cultures, expanding our understanding of ourselves and others, and supporting local communities.

  • Luxury Expert

  • Planning Professional

  • Satisfaction Guaranteed

My Travel Services and Specialties

Professional Travel Planning

My Services

    Booking Management
    Corporate Meetings & Events
    Complimentary VIP Perks with Preferred Partners
    Pre-Planning & Consulting
    Transportation Management
    Travel VISAs
    24/7 Support


    South America

Travel Styles

    Escorted Tours
    Event Travel
    Food and Wine
    Honeymoons & Anniversaries
    Luxury Hotels & Resorts
    Ocean & River Cruising
    Private Villas
    Solo Travel
    Spa & Wellness Travel

The Process


Dream Trip Planning

Together, we'll discuss your vision for this trip. Tell me everything you'd love to have happen.


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.


Seamless Booking and Logistics

Sit back and relax. My global team and I will handle every detail of getting you where you need to go. You just need to figure out what drink you should order next.



It's here. Enjoy the trip of a lifetime. You deserve it.

Why Travelers Choose Me

100% Done For You


Tell me what you want, and you're done. I'll handle literally everything else.

1 Call Away Support


Whether you're on a glacier in the Alps or an island in the Indian Ocean, I'm only 1 call away.

VIP Treatment

VIP Treatment Wherever You Go

My global network of partners are on call to give you the VIP treatment you deserve, every leg of your journey.

My Global Travel Network at Your Service

I have relationships with top luxury travel brands worldwide to benefit you. If you need anything while traveling, my network and I are there 24/7 to make sure that your trip goes off without a hitch!

Expedited Airport Security

The Ritz-Carlton Yacht Collection
Virgin Voyages
Classic Vacations
The Haven Collection

Getting Started is So, So Easy


Pick a Date

I set time aside to have uninterrupted Discovery Calls. Find a date convenient for you.


Pick a Time

Do you prefer morning, afternoon, or evening? I have several options available.


We'll Chat!

Our discovery call is the first step to your luxury dream trip, I can't wait to explore your ideas with you!

What My Travelers Are Saying


Fun Trip! Excellent, professional, committed to your trip. Very responsive and knowledgeable. Lolita really put a great together. She researched hotels, booked the right airlines, provided all-around support, and checked in on me, even when I was overseas. I felt confident that she was looking out for me!

--Ms. Travelbug--Bali & Signgapore

Aruba Vacation

We stayed at a timeshare and she was very helpful in supplying us with the information we needed to enjoy our first time in Aruba! Great options for dining, activities, spas, and getting around the island.


Jamaica Vacation

She booked our trip to Jamaica and every detail was smooth sailing thanks to Lolita! 


Free Travel Trends Guide

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 our monthly newsletter for travel inspiration delivered right to your inbox!

Never Settle.Get the Travel Expertise you Deserve.

Schedule your free initial Discovery Call to begin the trip of a lifetime today.





Owings Mills, Maryland


Travelpreneur Podcast

The Art of Crafting Iconic Travel Experiences For Your Customers, with Lolita

In this episode of Travel-Preneur, we embark on an inspiring journey with Lolita Jackmon, the visionary Founder of Global Gypsy Travel. Dive into the world of crafting iconic travel experiences and exceptional customer service in the luxury travel industry. Hop on as we explore Lolita’s insights, journey, and vision for the future of Global Gypsy Travel.