Our Story
Tom Leveroni founded Sentiero Custom Travel with the goal 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 of building and leading a successful financial advisory business, Tom chose to combine 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 Europe and North America with deep destination expertise in Italy and New England. An avid cyclist 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 of exceptional properties and exclusive experiences, he curates itineraries 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
Hotel-only Booking [No Charge]
We do not charge you to use us for simple and straightforward requests when you already know exactly where you want to go and stay, We can make those hotel reservations for you at the same (or better) rate you'd pay online. Thanks to our preferred relationships with the world's top luxury brands including Four Seasons, Aman, Rosewood, Rocco Forte, Belmond, The Oetker Collection, Peninsula, The Dorchester Collection, Relais & Châteaux, Hyatt Privé, Marriott luxury brands, Jumeirah, and more —we are able to additionally extend exclusive amenities such as room upgrades, resort credits, free breakfast and early/late check in/out.
Small Group Tour Booking [No Charge]
We do not charge you to use us to book set-departure small group tours offered by any of our Virtuoso tour operator partners such as Backroads or Abercrombie & Kent for cycling, hiking, walking, trekking, safaris, cruises, festivals and culture. You will pay the same price as booking directly yourself. We can help you select the best tour option and can reach out to our personal contacts at each tour operator to get your questions answered. We can also handle arrangements for any of your pre and post tour travel.
Custom Itineraries [Planning Fee]
Air Booking Services
While many clients choose to book flights independently, we are happy to assist with air arrangements when needed. Our air ticketing service starts at $100 per ticket/transaction. At this time, we do not manage points or mileage programs on behalf of clients.
Travel Insurance
Helping you find, select and purchase comprehensive travel insurance protects your investment and aids your peace of mind. Insurance reimburses you for trip cancellations, trip delays/disruptions, and sickness/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 dreams, interests and style.
Let's begin the conversation.