Travel More, Worry Less
Travel is transformative, full stop. 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 can design your perfect trip, no matter where you want to go. Let us handle the details so you can just enjoy your vacation.
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 the most authentic local cuisine.
Planning your vacation shouldn’t feel like work. Let us take care of it.
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.
We take care of the nuts and bolts as well, like booking flights and rental cars, and we’re available on-call while you’re away–just in case. From missed connections to natural disasters to a change of heart about your itinerary, you can count on us to help.
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.
Small Group Tours
Our small group tours are truly small–no more than 8 people–so it feels more like traveling with a group of friends. We keep our guest list limited so that we can stay in off-the-beaten-path hotels; dine in intimate restaurants; visit family-owned wineries for private tastings; or learn to make pasta with an Italian nonna in her home kitchen.
Our itineraries are thoughtfully planned, with a pace that never feels rushed and gives you time to explore on your own. Our group tours are designed with a particular kind of traveler in mind, someone who’s looking for authentic cultural experiences, not to check places off a list.
We think the greatest gift of travel is the joy of discovery, whether it’s a new food or a breathtaking landscape. We hope you’ll join us for an unforgettable journey!
Learn more about our small group tours.
Traveler Reviews
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, Massachusetts
“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
“It was an exceptional tour. I really appreciated the thoughtfulness and detail you put into all the choices and arrangements involved. You offered to us unique experiences. Thank you!! Great value for the overall tour with its truly exceptional activities. I liked the small group idea which made it easier to get to out-of-the-way places for quality experiences: wine tastings, pasta making class, truffle hunt and also the small hotels we could stay in.”
– Nancy S, Massachusetts
“Janet planned an incredible vacation for me and my two friends. Our AirBnb was stunning, clean, affordable and absolute paradise. She arranged great and reasonable flights and gave us a long list of wonderful eateries. She also recommended fun day trips close to our accommodations. She is very responsive to questions and reachable when needed. I would highly recommend One Street Over and will definitely be using their services again! Thanks Janet for a relaxing get away!”
– Laurie B, New Hampshire
“My family and I went to Paris for my parents 50th anniversary, and I am so happy we had One Street Over to help us with our trip! From finding us an amazing apartment overlooking the Seine on Ile Saint-Louis, to walking around Montmartre and stopping in to eat at the best off the beaten path cafes. One Street Over truly made our trip a one of a kind, personalized experience!”
– Patrick M, Florida
Read more traveler testimonials.
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. Our mission: to create a travel experience you’ll be talking about for the rest of your life.