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!
Comprehensive Travel Planning
When you hire me as your travel advisor, you’re not just booking a hotel or a flight—you’re partnering with me to thoughtfully plan your entire vacation, from start to finish. My comprehensive planning approach brings all the pieces together: flights, hotels, transfers, tours and experiences, restaurant recommendations, and those special hidden gems that can turn a good trip into a fabulous one.
I research the details, coordinate the moving parts, and help you make confident decisions along the way—so your trip feels seamless, personalized, and truly yours.
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
Thoughtful travel planning takes time, research, and expertise. My planning fee allows me to dedicate that time to creating a trip that is genuinely tailored to you—not simply pulling together a booking.
To ensure I can dedicate the time and resources necessary to craft the perfect trip, I charge the following planning fees:
$75 for 1 traveler
$150 for a couple
$200 for families of 3-6
$400 for groups of 6-10
$500 for groups of 10+
Your planning fee isn't a booking fee. It's an investment in the expertise, research, and personalized design that happens before you ever make a reservation.
Planning Fee FAQs
Why is there a planning fee?
Your fee covers the time and expertise that go into researching, designing, and refining your trip—from destination research and personalized recommendations to creating your initial proposal and final itinerary.
When do I pay the fee?
The planning fee is paid before I begin research or itinerary design. Your complimentary Discovery Call comes first, so we can make sure we're a good fit before you commit to planning.
What does the fee include?
Your planning fee includes destination research, a personalized initial proposal, itinerary design, and up to three rounds of reasonable revisions based on your original trip goals.
What if I decide not to book?
The planning fee is non-refundable because it pays for the time and research already invested in your trip. Whether you ultimately book the trip, make other arrangements, or decide not to travel, the fee remains earned.
Can I make changes to my trip?
Absolutely! Travel planning is collaborative. Your fee includes up to three rounds of reasonable revisions. Significant changes—such as changing destinations, dates, trip length, or adding substantial new components—may require an additional planning fee.
What happens if I decide to book part of my trip myself?
You're always welcome to make your own travel arrangements. However, your planning fee covers my professional expertise, research, and time spent designing your trip—not an unlimited research service.
If you decide to independently book a substantial portion of the trip, the scope of our planning may change. At that point, I may close the planning project and remove access to the proposal in Travefy. If you'd like me to continue planning the remaining arrangements, we can discuss a revised scope and any additional planning fee that may apply.
Are there additional fees?
Sometimes. Rush requests, holiday or peak-season travel, extensive re-planning, additional destinations, or services outside the original planning scope may require an additional fee. I'll always discuss that with you before moving forward.
Does the planning fee cover my travel costs?
No. The planning fee is separate from the cost of your trip and does not cover supplier deposits, airfare, hotels, tours, cruise fares, cancellation or change penalties, or other third-party charges.
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.