Kirsten Sheppard is the founder of Travel Well Collective, a boutique travel advisory service born from a simple belief: how we travel matters just as much as where we go. With more than 20 years in international education and a Master’s in International Education, Kirsten has spent her career creating meaningful global experiences. Her work has always centered on connection—between people, cultures, and purpose. Today, she brings that same heart to her clients, collaborating to design intentional journeys that reflect who they are and what they need—whether it’s adventure, rest, fun, or something deeper. Every trip is rooted in the philosophy of what it means to truly travel well.
The value of working with me at Travel Well Collective, goes far beyond booking. We design experiences with thoughtful planning, reliable support and intention.
Whether you’re interested in river or ocean cruises, group getaways, or independent journeys, I curate experiences for families, multi-generational, adventure, expedition, and solo travelers. I work closely with you to provide the antidote to the time-consuming and often stressful process of travel planning, to ensure your next adventure is seamless and memorable!
From the first consultation to your safe return home, every detail is handled with care so you can travel well, live fully, and connect deeply.
When You Travel with Us, You Receive:
- Travel Support, so you’re never navigating alone
- Customized Itinerary Design, tailored to your interests, pace and preferences
- Real-Time Travel App Access, centralizing all trip details and updates
- Complete Booking Management, including flights, accommodations, & activities
- Deep Destination Knowledge, informed by ongoing education and trusted partnerships
- Documentation Guidance, including passport, visa and health entry requirements
- Ongoing Consultation & Support, before, during, and after your journey
If the idea of working with a travel advisor feels unfamiliar - you're not alone. Many of my clients come to me planning their first intentionally designed journey, unsure of what to expect. Think of this not as handing off your trip, but as inviting in a partner to help you travel more deeply, more meaningfully, and with far less stress.
1. Book a Discovery Call
Start by scheduling a complimentary 30-minute call through my [Calendly link]. This is our chance to connect, explore your travel goals, and see if we’re a good fit.
2. Let’s Talk Travel
On the call, we’ll discuss what kind of experience you’re craving, whether that’s an immersive cultural trip, a river cruise, a rail adventure, or a thoughtfully curated group journey.
3. Planning Fee
If we decide to move forward, you’ll pay a one-time planning fee. This small investment covers the time, care, and expertise I put into researching and designing a meaningful travel experience tailored to you.
4. Receive Your Proposal
Next, I’ll craft a personalized proposal: this may include custom-designed travel, or connections to trusted travel partners offering immersive small-group experiences, cruises, or rail journeys that align with your vision.
5. Refine Together
You’ll have a chance to explore the proposal, ask questions, or refine the details. This is a collaborative process, shaped around your goals.
6. Confirm & Go
Once you’re ready to move forward, I’ll finalize the details and take care of the logistics. You get to enjoy the excitement—without the overwhelm.
At Travel Well Collective, it’s not just about booking a trip...it’s about co-creating an experience that’s intentional, culturally rich, and deeply fulfilling. Whether you’re new to this process or just looking for a different kind of travel partner, I’m here to help you travel well.
I work with a limited number of clients at a time to ensure each trip receives the attention it deserves
Thank you for considering my travel planning services! My goal is to create a seamless, personalized travel experience tailored to your unique preferences. To ensure I can dedicate the time and resources necessary to craft the perfect trip, I charge the following planning fees:
$75 for 1 travelers
$150 for a couple
$200 for families of 3-6
$350 for groups
What’s Included:
- Comprehensive Planning: I handle all aspects of your trip, including flights, hotel accommodations, and itinerary planning.
- Personalized Service: We’ll begin with an introductory form and either a phone call or in-person meeting to discuss your travel goals, preferences, and interests.
- Tailored Proposals: Based on my research, I’ll create customized proposals designed to match your vision. I’ll make as many edits as necessary to ensure your trip is exactly what you’re looking for.
- Final Itinerary: Once approved, I’ll provide a detailed itinerary, including booking confirmation numbers, so you have everything you need for a stress-free experience.
Additional Benefits:
- Expert Recommendations: I leverage my industry knowledge and connections to provide insider tips, exclusive options, and the best value for your trip.
- Ongoing Support: I’m here to assist you every step of the way, from the initial planning stages to your return home.
This planning fee is non-refundable and compensates me for the time, expertise, and care I dedicate to creating your perfect travel experience.
Itinerary planning begins with a quick introductory form and a personal call (free to inquire!) —designed to get to know you, understand what lights you up, and uncover the details that will transform your trip from great to unforgettable.
I look forward to working with you to make your travel dreams a reality!
At Travel Well Collective, the hummingbird is more than just a logo - it’s a symbol of how we believe travel should feel: purposeful, joyful, and transformative.
Tiny but powerful, the hummingbird travels thousands of miles on sheer instinct and heart. It moves with grace, can fly in any direction (even backward!) and always seeks out life’s sweetness. Across cultures, it represents resilience, adaptability, joy, and presence - all qualities we believe define what it means to travel well.
To travel well is to move with intention. To explore with curiosity. To connect deeply - with cultures, communities, and yourself.
We’re also inspired by a story often told by environmentalist Wangari Maathai:
When a forest fire breaks out, all the animals flee—except the hummingbird, who carries drops of water in its beak, trying to put out the flames. When the others say, “What are you doing? It’s not enough,” the hummingbird replies, “I’m doing what I can.”
That’s the heart of our mission:
Travel that’s intentional. Impact that’s meaningful. Joy in every drop.
And this is how we travel well.