If you’re planning a trip to Montenegro, especially to the beautiful coast of Kotor, you might have come across the Old Captain’s Smile Tour. While I haven’t personally taken this exact tour, I’ve gathered enough insights from reviews and descriptions to give you a thorough idea of what you can expect. This private experience promises a blend of history, stunning scenery, and a touch of local storytelling—all in about four hours.
Two things that really stand out about this tour are the personalized attention from the guide and the chance to see some of the most picturesque spots in the Bay of Kotor, like the legendary Our Lady of the Rocks. Plus, the detailed storytelling about local families and the architecture makes the experience richer than just ticking off tourist sights. On the flip side, a key consideration is the time constraint—four hours isn’t long, so you’ll want to be ready for a fairly packed schedule.
This tour seems well-suited for travelers who want a well-rounded, intimate look at Kotor and its surroundings—perfect if you prefer private tours over large groups and crave authentic stories rather than just photos. It’s especially great for those interested in history, scenic beauty, and local culture. If you’re after a slow, relaxed day, this might feel a bit brisk, but for most, it hits the right balance.
- Key Points
- What the Tour Covers and Why It Matters
- The Itinerary Breakdown
- What’s Included and Why It Matters
- The Experience: What Travelers Say
- The Practical Side
- Who Will Love This Tour?
- The Sum Up
- The Old Captain’s Smile Tour in Kotor
- FAQ
- More Tours in Kotor
- More Tour Reviews in Kotor
- More Kotor experiences we've covered
Key Points

- Private experience means personalized attention and flexibility
- Stunning views of the Bay of Kotor, Perast, and the island of Our Lady of the Rocks
- Knowledgeable guides who share captivating stories about local families and history
- Efficient four-hour itinerary perfect for travelers with limited time
- Cost reflects private transport and entry fees; overall good value for a curated experience
- Ideal for those seeking culture, scenery, and storytelling in a compact tour
What the Tour Covers and Why It Matters
Planning more time in Kotor? We've covered other experiences worth considering.
The Itinerary Breakdown
Kotor Old Town – 1 Hour 30 Minutes
Your journey begins in Kotor’s UNESCO-protected medieval streets. This is where you’ll really get a feel for the city’s layered past. The cobblestone alleys and squares like the Square of Milk, Square of Salad, and Square of Timber each have stories to tell, from old churches to local families. The guides here are usually eager to share tales that bring the city’s 2000-year history to life.
Based on reviews, visitors love the stories about local families and old customs, which add a personal touch to the sights. One reviewer said, “What a wonderful day…Her knowledge of all the interesting history was amazing,” highlighting the value of a passionate guide. You’ll see old churches and meet some of the city’s hidden corners, all while getting insider tips that you wouldn’t find in a guidebook.
Perast – 1 Hour
Next, we move to Perast, a tiny town that feels like stepping into a painting. It’s renowned for its architecture, peaceful atmosphere, and remarkable setting. The images of crystal-clear water reflecting steep rocky mountains are unforgettable. Here, you can imagine the lives of fishermen and captain families who once thrived in this quiet town.
Travelers rave about how Perast’s atmosphere makes you forget the world outside. One reviewer mentioned, “Images of crystal blue water reflecting the steep rocky mountains…will be deeply imprinted in your hearts.” It’s the kind of place that stays with you, especially as seagulls rest on stone roofs or fishermen continue their routines.
Our Lady of the Rocks – 45 Minutes
Arguably the highlight for most—the man-made island of Our Lady of the Rocks with its church. This is no ordinary church; it’s steeped in local stories, woven into every detail. The entry fee is included in the tour, which makes this stop not just scenic but also culturally enriching.
Visitors describe this as a church that tells of the lives of local people, emphasizing how much the community has invested into this site. The boat transfer to the island adds an extra element of fun, giving you a taste of local transport while enjoying the bay views.
What’s Included and Why It Matters
The tour covers all fees and taxes, including the boat transfer and entry fees, which means no surprises on site. The private transportation ensures a comfortable and intimate experience, avoiding the hassle of large groups or crowded buses.
One standout feature is the personalized service—only your group participates, so you can ask questions and get stories tailored to your interests. The tour is perfect for travelers who want an efficient but meaningful day. The price, around $324 for up to two people, reflects the private nature and all-inclusive approach.
The Experience: What Travelers Say
Reviews consistently praise the guides—calling them knowledgeable, passionate, and capable of entertaining all ages. One reviewer exclaimed, “Sanja was an amazing tour guide and we loved her personality,” showing how a good guide can turn a sightseeing trip into a memorable experience.
Others appreciated the attention to detail and the way the guides shared not just facts but stories that made the sights come alive. The feedback highlights the authentic storytelling about local families and the history of the region, which adds depth to the experience.
The Practical Side
Timing-wise, the tour fits well into a morning or early afternoon slot, leaving you with time afterward to explore further or relax. The pick-up service adds convenience, especially if you’re staying nearby.
In terms of value, the cost includes entrance fees, boat transfer, and private transport, making it competitive when considering the personalized experience and expert guides. Food and drinks aren’t included, so plan for a lunch break afterward if you want to continue your day with local cuisine.
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Who Will Love This Tour?

This experience is ideal for those who want a comprehensive, personalized exploration of Kotor’s highlights without the hassle of navigating alone. It’s perfect if you love storytelling, scenic views, and cultural insights. The private aspect makes it especially appealing to couples, friends, or small families wanting an intimate experience.
If you’re someone who appreciates guided tours with knowledgeable guides and doesn’t mind a bit of walking, you’ll find this tour offers a lot of value. It’s less suited for travelers who prefer a relaxed, unstructured day, as the schedule is quite packed, but for most, it balances sightseeing with storytelling beautifully.
The Sum Up

All in all, the Old Captain’s Smile Tour offers an engaging, well-paced look at some of Montenegro’s most charming sights. The knowledgeable guides and the stunning views are the highlights, ensuring that your four hours will be both enriching and visually memorable. The inclusion of private transport and all fees means you’re paying for a seamless, curated experience that takes the stress out of sightseeing.
This tour is especially suited for travelers who want to dive deeper into local stories and enjoy a personalized approach. If you’re after a day filled with scenic beauty, history, and authentic local flavor, this could be a perfect choice. It’s an experience that balances the must-see sights with storytelling, making your visit to Kotor and its surroundings genuinely special.
The Old Captain’s Smile Tour in Kotor
“What a wonderful day in Montenegro with Ana! She was a fabulous guide and showed us all the beautiful places to see in this gem of a country. Her …”
FAQ

How long is the tour?
It lasts approximately 4 hours, making it a good option if you’re short on time but still want to see key sights.
Is the tour private?
Yes, only your group will participate, providing a more personalized experience and flexibility.
What’s included in the price?
All fees and taxes, boat transfer to Our Lady of the Rocks and back to Perast, entry to the church, and private transportation.
Can I cancel if my plans change?
Yes, free cancellation is offered up to 24 hours before the tour, with a full refund.
Is transportation provided?
Yes, private transportation is included, making the day more comfortable.
What are the main stops?
Kotor’s old town, Perast, and the island of Our Lady of the Rocks.
Are meals included?
No, food and drinks are not included, so plan to eat before or after the tour.
Is this suitable for families?
While not specifically marketed for children, the tour’s pace and outdoor elements can be enjoyable for families, especially those interested in culture and scenery.
How do I meet the guide?
The tour offers pickup, so your guide will come to your location, or you can coordinate a meeting spot if preferred.
If you’re looking to experience the magic of Kotor with an expert guide, enjoying scenic views and stories, this tour offers a well-balanced, memorable day. Just come prepared for a bit of walking and an hour or so of storytelling, and you’ll leave with plenty of beautiful memories.
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More Kotor experiences we've covered
- Njegusi Smokehouse, Farm to fork experience & Kotor walking tour
- The Old Captain’s Smile Tour in Kotor
- Special Montenegro: Lipa cave Njego’s Mausoleum – Njegui village Cetinje
- Private North Montenegro, Durmitor, Tara and Ostrog Tour
- Blue Cave Guided Tour in Kotor Bay
- Kotor walking tour and Jaz beach – private tour
- Kotor Bay Sailing Tour from Kotor
- Cycle & SUP: A Complete Circumnavigation of Kotor Bay (new tour)
- Cable car ride, food tasting in Njegusi and Kotor Old Town
- Private Perast and Kotor Speed Boat Tour – Rick Steves Recommended
- Farm Oysters and Mussels( Perast and Lady of the rocks )
- Private Blue Cave Speedboat Tour In Bay Of Kotor


