Travel More, Worry Less
Travel is transformative. We think exploring the world is one of the most worthwhile things you can do, and we’re passionate about helping you do it. We’ll design your perfect trip, no matter where in the world you want to go. Let us handle the details—all you need to do is pack!
No two trips are ever the same. We can arrange a family truffle hunt in Tuscany. Or a day of vineyard-hopping in Burgundy with a sommelier. Hard-to-get tickets to an animation museum in Tokyo. You can expect excellent hotels, behind-the-scenes tours, and authentic local experiences.
Planning your vacation shouldn’t feel like work. Let us take care of it.
Small Group Tours
Our small group tours aren’t for everyone. They’re designed for travelers who want authentic cultural experiences, not to check places off a list. And our tours are truly small—no more than 8 people—so it feels personal, more like traveling with a group of friends.
We limit the number of guests so we can stay in off-the-beaten-path hotels; visit family-owned wineries for private tastings; or learn to make pasta with an Italian nonna in her home kitchen. The itineraries are thoughtfully curated, based on over 30 years of international travel experience.
We think the greatest gift of travel is the joy of discovery, and we hope you’ll join us for an unforgettable journey!
Learn more about our small group tours.
“Janet did an excellent job planning our trip to Tuscany and making us feel more like locals than tourists. She took care of all of the logistics including finding the best hotels, restaurants, guides and drivers. We went to a gorgeous estate which was inhabited by the same family for 6 generations. They took us on a truffle hunt and then we had an amazing meal in their dining room. We had a pasta-making experience on another day and ate our pasta (with a sauce cooked by the instructor’s mama!) By the end of the evening, we felt as if we were part of their family!”
— Wendy A, CT, 2026 Women’s Tuscany Tour guest
Get to Know One Street Over
One Street Over Travel grew out of a passion for discovering new places, and the joy we get from sharing that passion with others – going beyond the usual tourist sites to meet local people, learn something new, eat unfamiliar foods, and be immersed in the culture.
The name One Street Over originated in a family conversation about our longstanding rule of never choosing a hotel or restaurant within sight of a major tourist attraction (think Eiffel Tower or Colosseum). We always go “one street over” in favor of somewhere that locals hang out and the food is authentic. And that’s the experience we want to share with you. Whether you’re interested in a custom vacation or a small group tour, we’re deeply invested in your good time.
Custom Travel Planning
We plan custom vacations tailored to your specific interests, travel style, and budget. Whether you’re traveling solo or vacationing with a group of friends or family, we go beyond generic guidebook recommendations to find authentic experiences and unique activities just for you. Our mission: Provide a one-of-a-kind travel experience that you’ll be talking about for the rest of your life.
Learn more about custom travel planning or check out our frequently asked questions.
Traveler Reviews
Janet from One Street Over Travel was an absolutely wonderful host during our time in Italy! She was warm, welcoming, knowledgeable, and went above and beyond to make our experience truly special. Her kindness, enthusiasm, attention to detail and great sense of humor made our trip even more memorable. We couldn’t have asked for a better host and would most definitely go with Janet for future travel!
— Laura P, NY
We had THE BEST time in Italy with Janet and our group! Everything went so smoothly, and we truly appreciated all the effort that went into planning our trip. From the itinerary to the little details, it was clear how much thought and care was put in. We were able to just relax, enjoy, and experience Italy without any stress. I would absolutely recommend One Street Over Travel to anyone looking for a fun, well organized, and unforgettable trip!
— Paige R, MA
I was extremely pleased with the travel planning services that One Street Over provided to me when scheduling a last minute international trip. I love to travel but HATE travel planning, and I was immediately assisted with a range of route, hotel, and tour options to fit not only my interests, but my budget. OSO Travel made the entire process easy, and importantly, quick — so I could book travel and not miss the window I had to take the trip. I strongly recommend OSO Travel for not only fabulous, carefree, pre-planned package trips but also for any range of travel planning services to make your life easier!
— Joanne D, MA
There are not enough stars for rating this amazing service. Janet at OSO made a dream come true vacation happen for me. She did everything from the suggestion of my destination, to helping me travel very light (only a small back pack). She helped me book outings including a swim with sea turtles and surfing everyday. Always going the extra mile for me, she found me an emergency room for a sudden eye injury, in the middle of the night. It was super valuable to me as I was traveling as a single women in an area where I didn’t understand the language completely. She took all the work and research over for me. Her fee was VERY reasonable. I could go on forever with all the reasons I will ALWAYS consult with her for my future travels. You would be wasting your time and money looking any further.
— Sandra B, MA
Read more traveler testimonials.
