617.752.2669 – Call or Text
Don’t allow the unknown stop you from exploring the world.
All you need to do is dream
— and we’ll take it from there.
Travel is personal — every journey a collection of moments that should feel seamless, effortless, and entirely your own. We craft each itinerary with precision, ensuring that every detail enhances your experience. Because the difference between a trip and an unforgettable journey is the care put into every step.
Private Travel
We help make dreams a reality. We provide professional travel planning – providing advice on how to make your journey unforgettable. We handle all the reservations and administration work, and organize everything in a beautiful mobile app so you can focus on your experience.
There's nothing cookie cutter about our tours.
Your itinerary is carefully curated to suite your travel preferences and desires.
Travel any time you want.
Aside from our set small group tours, your itinerary is designed specially for you.
You're never alone.
View your travel details, ask questions, or request changes right from our mobile app.
Group Travel & More Ways to Travel
Our team hosts a select few fully-guided small group tours throughout the year. With a maximum group size of 12, these experiences provide a convenient way for couples or solo travelers to explore the world, and make new friends along the way. These are not your cookie-cutter group tours - with such a small group, we have the ability to create personalized experiences.
Our professional travel planners make it easy for you to coordinate a group tour for your social club, business, or friends and family. We craft a custom itinerary, handle payments, and organize everything in a beautiful mobile app to give you the tools you need to lead your group.
Our travel concierges are available for traveling with you or your group, and can be as involved or in the background as you like. From reviewing the day's itinerary over breakfast, to guiding you through the airport - experience the epitome of personalized service.
Trip Details
Messaging
Local Info
FAQs
Flight Details
Detailed Guidance
Mobile App
Everything you need for your trip, in one place. With personalized guidance, confirmations, contact details, and more in an easy to use mobile app, you’ll feel more confident than ever during your travels.
“I’m not very tech-savvy, but this app was so easy and it made it
feel like our concierge was right there with us every step of the way!”
Linda B. – Massachusetts
Founder & Professional Travel Advisor
Peter Boll is the founder of Confident Travel and a lifelong planner who got his start organizing youth trips as a teen Eagle Scout. Since then, he’s helped travelers of all kinds explore the world with ease — from first-time flyers to frequent jetsetters.
He’s passionate about creating meaningful, memorable journeys and believes travel should feel empowering, not overwhelming. When he’s not crafting personalized itineraries or leading small-group tours abroad, you’ll find him catching up on his favorite shows, lifting weights (or trying to), or dreaming up his next great escape.
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