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Custom Designed Travel Experiences
that balance adventure, connection and relaxation for busy families of all sizes.
At Jenny Jay’s Journeys I bring together my love of adventure, creativity and years of project management to create custom travel experiences for busy families that balance adventure, connection and relaxation.
Jenny Jay’s Journeys was born from a moment of reflection during a much-needed getaway with my sister in Death Valley in 2023. Travel provides us with the opportunity to step out of our hectic routines to reconnect with ourselves and each other, experience new things, reflect and recharge.
It also takes a lot of research and coordination that can be stressful on top of our already busy lives.
Jenny Jay’s Journeys takes care of all the research and planning, carefully crafting an adventure specific to your interests and needs. This allows you to focus on what’s most important: making memories, connecting with loved ones, enjoying new experiences while also resting and recharging.
From Dream to Destination: I Plan, You Enjoy!
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Family Travel - I love planning activities that match the interests and needs of all family members.
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Multigenerational Trips - With many of us living far from extended family, multigenerational trips create unique opportunities to build memories with our loved ones.
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Families with Special Needs - Having lived with a special education teacher most of my life (my mom and husband are Sp. Ed. Teachers), I am sensitive to the additional considerations required for families with special needs when traveling.
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Couples Getaways - Sometimes parents and caregivers need a trip just for them! I love planning Honeymoons and Anniversary trips.
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Friends Trips - Embark on the ultimate friends' getaway, where adventure, laughter, and unforgettable moments come together.
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Solo Trips- Whether you’re seeking time for yourself or craving the excitement of meeting new people, exploring something new isn’t just about the destination; it’s about the personal journey you embark on along the way.
The journey is just as important as the destinations themselves. Whether it's a cross-country road trip or hopping between European cities, every leg of your adventure can be packed with excitement. I have a passion for finding hidden gems and fun activities between destinations and crafting itineraries that turn those in-between moments into highlights, helping you experience the full adventure along the way.
The awe-inspiring beauty of our National Parks, where breathtaking landscapes and unforgettable adventures await—perfect for nature lovers, thrill-seekers, and those looking to reconnect with the wild. My passion for these natural wonders began in childhood, when I traveled to many of them with my family, sparking a lifelong love for exploring nature and our country’s diverse landscapes.
The vibrant cultures and stunning landscapes of Latin America provide adventures filled with color, flavor, and endless discovery. I love planning unforgettable journeys through Guatemala’s ancient ruins and Mexico’s rich history and vibrant beaches and beyond. With 20 years of experience planning and leading group trips to Guatemala, I have developed a deep passion for sharing these diverse and fascinating places with others.
LATIN AMERICAN
DESTINATIONS
Hi! I'm Jennifer behind
Jenny Jay's Journeys.
Theatre Artist, Arts Administrator, Mother, Nature Enthusiast,
Roller Coaster Lover, and above all, An Adventurer at Heart!
Adventure has always been a part of my life. Growing up in a military family, we made the most of every new place we lived, often embarking on road trips to national parks. These parks became a haven for me, blending adventure, learning, and serenity. My husband and I have continued that tradition with our own family, setting out to visit every national park in the U.S.
In college, I studied abroad in Mexico, spending a semester learning Spanish and exploring the rich landscapes of central Mexico. After graduation, I moved to New York City, where between graduate school and freelance theatre work, I embraced solo travel, exploring Europe, studying in Ireland, and road-tripping through the Northeast with friends.
My passion for cultural immersion led me to pursue a long-held dream of living in Central or South America. In 2003, I moved to Guatemala through the Young Adult Volunteer program with Presbyterian Church USA. There, I worked in a rural village on a literacy program for girls and led leadership workshops for community leaders. That experience deepened my love for travel that is not only adventurous but also sustainable and respectful of local cultures.
After returning from Guatemala, I reconnected with my high school sweetheart, and we got married. We celebrated our honeymoon with a road trip through Hawaii and California, and ever since, travel has remained central to our lives. Thanks to his teaching schedule and my flexible work, we’ve spent summers exploring Guatemala, Spain, France, and many parts of the U.S. Now, as parents, we’ve continued our travels with our two girls, who’ve been adventuring with us for over a decade.
HOW IT WORKS
1
Interview
I gather info from you about what would make the best trip for you & your crew.
2
Research
I put together a custom travel plan keeping everyone in mind.
3
Book
This is where you give a thumbs up &
get excited!
4
Enjoy
You & your crew head out on your adventure
with your personalized itinerary on your phone.
Seeking adventure, relaxation, or a perfect blend of both?
—let us craft your dream getaway.
it’s a chance to step away from the everyday hustle, reconnect with ourselves and each other, and embrace new experiences. It’s how we reflect, recharge, and create lifelong memories together.
Laura Morton, KY
I've traveled quite a bit and know the ins and outs of finding interesting places to eat wherever I go, but this last trip was a bit different. I took my parents on a road trip through Ontario, Canada. I'm gluten free, my mother has health concerns and prefers local and organic food, and my father refuses to eat at a chain restaurant. I went to Jenny Jay's Journeys for a list of restaurant options.
Going from town to town, I thought it would be a little luxury for us to have a list of restaurants that fit the strange venn diagram we required. Once we were on the road, Jen's list of restaurants and health food stores went from being a luxury to a necessity. I definitely recommend using Jenny Jay's Journeys for any travel support or needs - it allows you to spend the time on what matters most.
Mike and Jill Guelda, IN
Jenny Jay's Journeys made planning our honeymoon to Grand Haven, MI an absolute breeze! From the start, Jenny was incredibly attentive to our needs, ensuring that every detail fit within our budget without sacrificing quality or experience. She curated a perfect itinerary, complete with affordable yet charming accommodations and a mix of romantic and fun activities, like The Historic Music Fountain Show and exploring the local downtown.
Jenny’s recommendations for hidden gems, from The Unicorn Tavern to beautiful nature spots, made our trip feel truly special and personalized. Her attention to detail and constant communication gave us peace of mind throughout the planning process, and we never felt overwhelmed. We couldn’t have asked for a better way to celebrate our honeymoon, and we’ll definitely be using Jenny Jay's Journeys for future trips! Highly recommend for anyone seeking expert travel planning on a budget.
The Hainer Merwarth family, KY
Jennifer helped me plan a trip with my family out to the Grand Canyon. It was a long road trip and it had a lot of interesting challenges. We were driving through five states. We wanted to camp most of the way and we were driving a fully electric vehicle. She planned an amazing trip for us! One we’ll remember for the rest of our lives. I am so grateful for her expertise and insights. I would highly recommend her for your next family adventure. - Mom
I had so much fun on our trip! We got to see so many amazing things, the Painted Desert, the Grand Canyon and Mesa Verde! Definitely the highlight of my year!
- 15 yr old daughter
At Your Service
Choose Jenny Jay’s Journey to elevate specific aspects of your trip and enhance your travel experience with personalized assistance.
Navigator's Insight Package
$50 One-Time Fee
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Personalized Travel Coaching: Begin your journey with a one-hour coaching session, where I provide insights, answer questions, and guide you through the initial steps of planning your trip.
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Trip Planning Templates: Access a suite of invaluable trip planning templates, including a trip budget, planning checklist, and links to helpful apps, streamlining your planning process.
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Discount on Planning Packages: Enjoy a special discount should you decide to upgrade your planning experience to another package.
Wanderer’s Canvas Package
$150 One-Time Fee
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Thorough Introduction: Begin with an in-depth survey and an initial consultation to understand your travel aspirations and preferences.
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Detailed Recommendations: Receive a meticulously curated list of options based on your research needs.
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Trip Planning Templates: Access a suite of invaluable trip planning templates, including a trip budget, planning checklist, and links to helpful apps, streamlining your planning process.
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Discount on Planning Packages: Enjoy a special discount should you decide to upgrade your planning experience to another package.
Explorer’s Signposts Package
$40 per Planned Travel Day
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Initial Consultation: Begin your journey with a detailed survey and initial consultation, allowing me to grasp travel preferences and interests.
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Accommodations Booked: All lodging booked according to your preferences including hotels, resorts, campgrounds, AirBnB, and Vrbo.
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Destination Travel Arrangements: We will book any rental cars, airport transfers, trains, buses or boats needed to get you around at your destination (note: booking of flights not included).
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Itinerary Outline with Recommendations: Receive a itinerary outline with suggestions of things to do and restaurants based on your individual interests and needs.
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Mobile Accessibility: easy access to your itinerary and recommendations on your mobile device.
Voyager’s Atlas Package
$55 per Planned Travel Day
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Initial Consultation: Begin your journey with a detailed survey and initial consultation, allowing me to grasp travel preferences and interests.
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Accommodations Booked: All lodging booked according to your preferences including hotels, resorts, campgrounds, AirB&B, and Vrbo
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Destination Travel Arrangements: We will book any rental cars, airport transfers, trains, buses or boats needed to get you around at your destination. (note: flights not included).
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Unique Experiences: Tours, attractions, and activities booked to enhance your travel experience.
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Dining Perfection: Enjoy restaurant reservations and curated dining suggestions based on your preferences.
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Detailed Daily Itinerary: Receive a detailed daily itinerary accessible on your mobile device, guiding you effortlessly through each day's activities.
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Mobile Accessibility: Easy access to your itinerary and recommendations on your mobile device.
Optional services available with all packages for additional fee:
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Optional Travel Insurance: Secure your peace of mind with the option to add travel insurance for added protection.
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Photo Book Creation ADD-ON: Capture and cherish your memories with an optional photo book add-on, priced at $15 per day of the trip, plus the cost of the photo book.
A La Carte Services
Prices Vary Per Service
For those seeking tailored support for specific aspects of their journey, I offer à la carte services to complement your existing plans or address specific travel needs.
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Accommodation Sourcing - $50 (up to 3 stops):
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Restaurant or Things to Do Recommendations - $50 per list:
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Airline Reservations - $65 per person:
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Changes to Booked Itinerary - $99/request:
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Additional Services and Travel Consultation - $50/hr
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Photo Book Creation - $15 per day of the trip plus photo book cost
Custom Packages also available upon request
Get in Touch
For personalized travel planning and expert guidance on your next adventure, get in touch with us today!
We’re here to help you create unforgettable journeys, tailored to your preferences and interests.