© TravelWithTim 

TravelWithTim offers boutique two‑week tours in small groups led by Tim himself. Discover iconic sights and off-the-beaten-path gems with warmth, trust and family care. Explore confidently, connect deeply, escape overtourism, and create lasting memories.

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TravelWithTim 

Fill out the form and we’ll be in touch with information about upcoming opportunities on our personally designed tours. Whether you want to explore hidden gems or deepen your experience of iconic sights, we’ve got you covered.

Welcome to TravelWithTim; we design intimate small‑group tours for 10–15 curious travellers, each personally led by our passionate founder, Tim. With us, you won’t just tick off tourist boxes; instead, you’ll enjoy meaningful experiences that blend iconic highlights with off-the-beaten-path gems, escaping overtourism at a pace that lets you truly savour every moment with ease and connection.

Skip the Hassle, Enjoy Boutique Travel

Small Groups

Founder-Led Tours

Relaxed & Enjoyable

Tailored & Memorable

TravelWithTim is a boutique travel company led by Tim, a lifelong explorer and storyteller. Each small-group tour of 10–15 guests is personally guided by Tim, blending iconic highlights with hidden gems. More than holidays, these journeys feel like travelling with family, built on authenticity, warmth, and trust. With TravelWithTim, you can explore confidently and comfortably, create lasting memories, and enjoy travel that goes beyond tourism, boutique in spirit yet refreshingly down‑to‑earth.

Boutique Tours, Like Family

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Small Groups, Big Adventures, Lifelong Memories

At TravelWithTim, travel is about connection, discovery, and belonging. With small groups personally led by our founder, Tim, we offer warmth and attention rarely found in larger companies. We guide you beyond landmarks to explore with intention, creating curated experiences and lifelong memories, always focused on escaping overtourism and finding beauty in overlooked places.

Stress-Free Travel

We handle logistics and accommodations so you can enjoy every moment.

Authentic Local Experiences

We connect you with local culture, cuisine, and communities for a richer travel experience.

Personal Care, Always

From planning to the journey itself, we handle every detail with care.

TravelWithTim offers small-group, founder-led tours designed to create meaningful and memorable experiences. Explore iconic sights, hidden gems, and off-the-beaten-path adventures in Romania, the Benelux, and beyond, painted churches, canals, centre squares, and landscapes that surprise and delight at a relaxed pace, while enjoying the personal touch and care that only a boutique tour can provide.

Small, Intimate Groups

Only 10–15 travelers, so you feel like part of the family.

Founder-Led Journeys

Every tour is personally guided by Tim, sharing his passion and insider knowledge.

Curated & Flexible

Itineraries blend landmarks with unique discoveries for you.

Explore Iconic Destinations and Hidden Gems Around the World 

Save $200 on your dream getaway with TravelWithTim. Join 10–15 guests on boutique tours led by Tim himself, blending comfort with authentic, off‑the‑beaten‑path experiences. Travel at your own pace and feel like family on every journey.

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TravelWithTim 

Sighisoara was definitely one of my favorite highlights. The atmosphere was so immersive; it felt like stepping back in time. We stayed for just the right amount of time, too. Sibiu was also fantastic—I could easily see myself living there! I love how locals seamlessly blend the historic parts of the town into their daily lives while preserving their culture and Sibiu truly stands out in that regard.

Ricardo

★★★★★

I found the people of Romania, in the shops, restaurants and hotels, friendly and genuinely wanting and willing to help. I really liked the Romanian village houses; how people lived and their cultures were of great interest. I also thought that the local guides were a home run. The lunch at the farm was a real pleasure, super fresh and well prepared. I loved the salt mine and rowing around in the water at the bottom of the mine.

John

★★★★★

I liked learning about the history of Romania and its transition to a western society; I liked seeing the different areas of the country, including Budapest, the beautiful Transfagarasan Road, the medieval walled cities in Transylvania, the outdoor museum, the rustic inn and painted monasteries in Bucovina and the salt mine; I enjoyed the excellent food throughout the trip; I enjoyed the very small group, which made it easy to get to know everyone; and I enjoyed the guide, who made the trip fun and interesting. Overall, a great trip.

Kirk

★★★★★

I loved the salt mines, but also the lunch we had on the road with delightful hosts in the farm-to-table restaurant. The painted monasteries were also beautiful. The differences in the Orthodox churches compared with so many European churches are quite striking. So many highlights—I also loved the Transylvanian castle.

Althea

★★★★★

The contrast and yet the individual beauty of all the Benelux towns and cities visited. The opportunity to see the SAIL festival was memorable for a lifetime. Maastricht and the WWII cemetery were surprisingly good. Having the dynamic of an expert guide dedicated to a small group of travelers made it feel like traveling with friends and learning together.

Kevin

★★★★★

We loved our tour with Tim and highly recommend it! Go before it's discovered, as we didn't encounter other Americans, which was a plus! It's a fascinating country, so rich with history and culture and beautiful sights.

Jalyn

★★★★★

The three hotels were very comfortable and I enjoyed being in each one. It was great to be in each hotel for several nights.

Lisa

★★★★★

Tim is great. They went out of their way for each of us. It was more like traveling with a group of friends than a tour. (Tim) is sooo good. Romania was fantastic!!!

Liz

★★★★★

I just loved this tour. Our stay in Bucovina was so memorable. It was just beautiful and I really enjoyed the "eccentricity" of our host and the food there was extraordinary.

Scottie

★★★★★

Stories from Our Travel Family