Our Story
Tom Leveroni founded Sentiero Custom Travel to design journeys that feed both body and mind. His enthusiasm for travel stems from lifelong interests in literature, language, history, and culture, sparked by a classical education at The Roxbury Latin School and Harvard College and sealed by a post-college backpack-and-rail adventure through Europe. Years of further exploration deepened his appreciation for the ways travel inspires energy, curiosity, and lasting memories. After two decades building and leading a successful financial advisory business, Tom combined his professional strengths in client consulting, research, and strategic planning with his love of travel to launch his own luxury travel advisory business.
Tom specializes in designing active luxury journeys throughout Italy and Europe, with golf journeys through Ireland and Scotland. An avid cyclist, golfer, and long-distance runner, Tom is drawn to adventures that unite physical activity with cultural immersion in the spirit of mens sana in corpore sano— a healthy mind in a healthy body. Through his affiliation with Huffman Travel and Virtuoso's global network, he curates itineraries built on real access — the private guide, the table that isn't on any list, the vineyard you can't just walk into — that invite travelers to move, explore, and connect with each destination. Just as he once helped clients navigate complex financial decisions, Tom now guides clients each step of the way to meaningful journeys — carefully listening, researching, and tailoring each itinerary to reflect their interests, pace, and style.
Tom lives in Boston and, when not traveling or planning trips for his clients, enjoys exploring local trails with fellow running club members and discovering the next great pizzeria with his wife and son.
Why Us?
Working with a travel advisor like Sentiero Custom Travel provides personalized informed guidance, saves you significant time, spares you the stress of handling complex logistics, and offers timely support during disruptions. Most importantly, through our affiliation with Huffman Travel, an award-winning agency with three decades of experience and an elite network of global luxury travel brand partners, we extend to you value-add amenities not available to the general public and provide exclusive access to properties and insider experiences.
Consulting Process
We get to know you and work in close collaboration to get every detail right to customize and shape your trip around your interests and travel style.
- Discovery —we schedule a free 30 minute call to discuss your ideas, interests, motivations, preferences, style and pace.
- Design — after completing our client onboarding forms and approving our design fee (if applicable), we start research on your trip.
- Review — we share a draft itinerary for your review and we refine based on your feedback until the trip is the perfect fit for you.
- Confirm — after finalizing all details, we start making hotel, transportation, and guided tour bookings on your behalf.
- Insurance — once reservations and deposits are made, we can quote trip insurance to protect your investment.
- Concierge — with the itinerary framework set, we move on to the fine tuning with spa & dining reservations and suggested activities options.
- Travel — during your trip we arrange an on-the-ground point of contact should you need any assistance.
- Feedback — after your trip, we'd love to hear all about it, learn more about the destination and your preferences, and start thinking about your next adventure.
How We Work
There are three ways to work with us, and the right one depends on how much planning you actually need. If you already know where you're going, we handle the booking at no charge. If you want a fully designed trip, we charge a planning fee that reflects the work involved.
Preferred Hotel & Resort Booking
For travelers who already know where they want to stay and want an advisor working the details in the background.
- No planning fee — this service costs you nothing
- Preferred relationships with brands like Four Seasons, Aman, Rosewood, Rocco Forte, Belmond, and more, giving you access most travelers don't have on their own
- Rates that match or beat what you'd find booking direct, plus perks reserved for Virtuoso clients: room upgrades, resort credits, complimentary breakfast, and priority check-in/checkout
- A point of contact if anything goes sideways during your stay, not just at the moment of booking
- Recommendations shaped by how you actually like to travel, not a generic star rating
Small Group Active Luxury Tours
For travelers who want the energy of a group without giving up comfort, pace, or quality.
- No planning fee — same price as booking directly with the tour operator
- Set-departure cycling, hiking, and walking trips through Italy and Europe with partners like Backroads and Abercrombie & Kent
- A direct line to our contacts inside each operator, so your questions get real answers before you commit
- Guidance on choosing the right departure — pace, group size, and route — for how you like to travel
- Full support arranging your pre- and post-tour hotels and travel, so the whole trip flows together, not just the tour itself
Fully Custom Trip Design
For travelers who want an itinerary built from a blank page, shaped entirely around them.
- Planning fee starting at $750, reflecting the depth of research and coordination custom trips require
- Multi-destination itineraries shaped around what you care about, how fast or slow you want to move, and what each day should feel like, always with a foundation of food, wine, and movement
- Private guides, drivers, and once-in-a-lifetime access that no booking engine can hand you
- A trip mapped out so travel days, activity days, and rest days flow into each other, instead of feeling stitched together
- Every detail connected — hotels, transportation, private touring, dining, and spa — so nothing is left to chance
Additional Services
Most clients book flights independently, but we're glad to help when needed. Air ticketing starts at $100 per ticket/transaction. At this time, we don't manage points or mileage programs on clients' behalf.
Travel Insurance
We help you find, select, and purchase comprehensive travel insurance to protect your trip investment and give you peace of mind, covering trip cancellation, delays and disruptions, and sickness or injury while traveling.
Preferred Partners
Let us extend to you the exclusive amenities and VIP perks from our preferred partner network of the world's leading luxury hotels.
Start Planning Your Journey
We personally design every itinerary to match your interests, pace, and style.
Let's begin the conversation.
