These posts are placeholders for an upcoming European adventure that’s currently in the works. Beginning June 3rd, we will be backpacking across 33 cities in Europe over the course of three months, an experience we’re incredibly excited to share.
Along the way, we will be reviewing AI-generated itineraries in real time—putting them to the test and sharing what works, what doesn’t, and how they stack up against the reality on the ground. You can expect regular updates as the journey unfolds, with insights, tips, and firsthand experiences from each stop.
Once we’re back home, we’ll expand the blog with a wider range of content, including in-depth guides, recommendations, and reflections from the full trip. Be sure to check back often because we will be updating along the way and bringing you along for every step of the adventure!
explore it yourself:
The journey and accommodations:
We arrived by train from Luxembourg on the afternoon of June 11th and stayed until the morning of June 13th. We arrived and departed out of Brugge Train Station.
Below is what AI recommended for accommodations:
1. St. Christopher’s Inn – The Bauhaus
2. Ibis Budget Brugge Centrum Station
3. Hotel Notre Dame
4. Airbnb Studios or Private Rooms
We ended up selecting an St. Christopher’s Inn, because of the price and location.
Note: * our additions to ai itinerary
Day 1: Windmills & Local Corners
afternoon windmills
- Walk or rent a bike to the following:
- Jerusalem Chapel – Gothic private church from the 1400s
- Sint-Janshuismolen & Koeleweimolen (windmills)
- Minnewaterpark (Lake of Love) – Romantic, swan-filled park
- Begijnhof (Beguinage) – Peaceful monastery complex with white cottages
Dinner and nightcap
- Réliva – Farm-to-table with local ingredients
- Drink at Le Trappiste – an underground beer bar in a 13th-century cellar with 100+ Belgian beers
- Grauwwerkersstraat*
Day 2: Classic Bruges - The Medieval Heart
Coffee and Markt Square
- That’s Toast – Popular brunch cafe (get there early)
- Li O Lait – Trendy spot with good espresso and local vibes
- Markt (Main Square) – Colorful guild houses, central location
- Belfry of Bruges – Climb 366 steps for a panoramic view
Historium Bruges – Multimedia history museum (optional)
Tip: Arrive early (before 10:30 AM) to beat the tour groups at the Belfry.
Burg Square & Canals
- Burg Square – Home to:
- Basilica of the Holy Blood (free, ornate chapel)
- City Hall (Stadhuis) with Gothic architecture
- Walk toward the canals via Blinde-Ezelstraat, a charming narrow alley
Lunch & Hidden Gems:
- De Gastro – Modern Belgian food with a cozy feel
- OR Soup – A budget-friendly local favorite
- Tanner’s Square (Huidenvettersplein) – Quaint hidden square with cafes
- Rozenhoedkaai – Iconic photo spot by the canal
Gruuthusemuseum– Museum of Bruges life, art, and culture $18 each- Church of Our Lady Bruges – Michelangelo’s Madonna and Child
Hidden Gems:
- Stoofstraat – A tiny alley with medieval vibes for photos
- Luc Vanlaere Harp Concerts* – Free, intimate performances (check schedule- no reservation needed)
- Mariastraat* (street)
shopping & Exploring
- Browse chocolate shops: Try Dumon or The Chocolate Line
- Explore Bourgogne des Flandres Brewery – Hidden canal-side brewery with great beer and views
dinner
- Den Dyver – Upscale local cuisine with beer pairings
- OR Breydel-De Coninc – Known for excellent mussels and seafood
- OR Guest House La Civiere d’or (restaurant)
final thoughts:
Overall Rating:
Would I go again?
Favorite moment:
Bailey’s favorite:
Parker’s favorite:
Any surprises?
Anything we missed?
How did ai do?
Nailed it: We’ll add our thoughts here after our trip!
Needs work: