Small Group Trips, the Traveling Tessie Way
Why I Host Group Trips
Travel should feel connected, intentional, and a little magical — not rushed, overwhelming, or transactional.
My goal is to host small group trips for travelers who want to explore thoughtfully, stay somewhere with character, and experience a destination with people who feel more like travel friends than strangers.
If you’ve ever wanted to join a group trip but hesitated because it felt too big, too rigid, or not your style — you’re in the right place!
Group travel gets a bad reputation — and honestly, I get why.
Too many trips feel like being herded from place to place, ticking boxes without actually connecting to where you are or who you’re with. Needless to say, that’s not how I travel.
I believe the best experiences happen when:
The group is small enough to actually know each other
The pace allows for curiosity, rest, and spontaneity
The details are handled, but you still have freedom
You don’t have to choose between comfort and adventure
My goal is to create trips that feel warm, human, and well thought out — the kind you look back on and think, “I’m so glad I said yes to that.”
Be the First to Know
If group travel with Traveling Tessie sounds like something you’d love to do someday, this is your place to raise your hand!
You’ll be the first to hear about:
New trip ideas before anything is announced publicly
Early access when future trips open
Occasional behind-the-scenes planning updates
What Makes My Group Trips Different
This is not mass tourism, and it’s not luxury-for-luxury’s-sake either.
Small groups - Intimate by design. Fewer people, more connections.
Thoughtful pacing - Enough structure to feel supported, enough flexibility to explore on your own.
Comfort-forward travel - Boutique-style accommodations, good locations, and spaces you actually want to spend time in.
Soft adventure - Think culture, food, scenery, light activity — not extreme, not exhausting.
Solo-traveler friendly - Many people come alone. No one feels alone.
The Types of Trips I Want to Offer
I want these trips to grow organically — inspired by my own travels and by what you’re excited about. Future group trips may include:
Destinations I’ve personally explored and shared extensively
European trips, especially places rich in culture, food, and walkable charm
Italy-inspired experiences, from food-focused regions to slower-paced stays
Seasonal trips designed around weather, festivals, or shoulder-season magic
Trips shaped by reader interest, not trends
Help Shape Future Trips
I don’t want to guess what kind of trips you want — I want to build them with you! If you’re open to it, I’d love your input. Fill out the form below to help influence what I plan next!
Some past trip concepts explored destinations like Croatia and Costa Rica.
While those specific trips aren’t currently open, they helped clarify something important: my audience values trips rooted in destinations I know deeply and share often.
That insight is shaping everything that comes next!
