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Discover the charm of Kotor with this private 4-hour tour exploring its ancient streets, Perast's scenic beauty, and the iconic Our Lady of the Rocks island.
If you’re visiting Montenegro and want a taste of its stunning coastal beauty, history, and authentic local charm, the Old Captain’s Smile Tour offers an engaging way to experience some of the best sights in the Bay of Kotor. This private 4-hour excursion takes you through the medieval streets of Kotor, the picturesque town of Perast, and the remarkable man-made island of Our Lady of the Rocks. It’s designed to be intimate, personalized, and packed with stories, making it an excellent choice for travelers seeking a meaningful glimpse into Montenegro’s rich maritime heritage.
One of the highlights we love about this tour is the knowledgeable guides who enrich the experience with their stories, local insights, and genuine enthusiasm. Plus, the flexibility of a private tour means you can enjoy a relaxed pace and personalized attention. However, because it’s a fairly packed itinerary, travelers should be prepared for a fair amount of walking and boat rides—nothing overly strenuous, but worth noting. This tour suits those who appreciate history, scenic views, and cultural authenticity, especially if you prefer an intimate experience over big group excursions.

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The tour kicks off in Kotor, a UNESCO-listed medieval fortress town that’s practically an open-air museum. As you stroll along its narrow, cobblestone streets, you’ll find yourself surrounded by centuries-old architecture, church spires, and lively squares. Your guide—who has earned high praise for their knowledge and personable style—will point out notable spots like the Square of Milk, Square of Salad, and Square of Timber. These names might seem quirky, but they’re packed with stories about local families, trades, and customs that give life to the stones beneath your feet.
Travelers frequently comment on how the guides make history come alive. One reviewer recalls, “Ana was a fabulous guide and showed us all the beautiful places to see in this gem of a country. Her knowledge about the history was amazing and truly opened our eyes to Montenegro’s soul.” This kind of insight adds depth that you won’t find in a guidebook.
With around 90 minutes allocated, you’ll have enough time to soak in the atmosphere, snap photos of the medieval walls, and ask your guide about local legends. The walk is relaxed, with plenty of stops for stories and photos, making it ideal for history buffs and casual travelers alike.
Next, the tour leads you to Perast, a charming coastal town that seems to have paused in time. The moment you step into its streets, you’re greeted by stone houses, seagulls perched on rooftops, and the gentle lapping of water against old quays. The scenery here is unforgettable—crystal blue waters reflecting steep, rugged mountains, and a peaceful atmosphere that feels worlds away from bustling city life.
Many reviewers mention how quickly they felt drawn into the town’s storybook setting. One noted, “Images of fishermen pulling in mussels, seagulls resting on rooftops, and the quiet streets will stay with us forever.” The town’s relaxed vibe and scenic beauty make this stop a favorite for photographers and romantics alike.
You’re given about one hour here to explore on your own, which is enough to stroll to the waterfront, admire the historic architecture, or simply sit and absorb the view.
The tour’s highlight is the visit to Our Lady of the Rocks, a man-made island that’s more than just a picturesque stop. Built on a tradition that dates back centuries, this island was created by local fishermen who laid stones into the water after each successful voyage. Today, it features a church filled with artworks, relics, and a revered icon.
The journey to the island includes a boat transfer, which adds a delightful element of adventure. The boat ride itself is smooth, and the guides typically share interesting tidbits about the island’s history. Once ashore, you’ll step into the church, where the detailed interior and stories told by the guide deepen your connection to the local maritime life.
Reviews emphasize how personal and authentic this experience feels. One reviewer said, “This church isn’t just another European church; it tells the stories of the local people, woven into every detail.” The entry fee to the island is included, so all you need is your curiosity.
Spending around 45 minutes here allows enough time to visit the church, explore the surroundings, and take in the views of the bay.

The tour provides private transportation, which is a real perk—no waiting around for buses or large groups. Pickups are offered, making it convenient to start your day without fuss. At $323.91 for up to two people, it’s a good investment for those wanting an intimate, attentive experience, especially considering that all ferry and entry fees are included. The tour lasts about 4 hours, which offers a well-paced journey without feeling rushed.
Timing-wise, most travelers book this tour around 92 days in advance, indicating its popularity. The small group size, essentially just your party, ensures personalized interactions, and the guides are often praised for their passion and local knowledge.
While the tour is designed for most travelers, be prepared for some walking and boat transfers. Also, do keep in mind that food and drinks are not included, so consider bringing water or planning to grab a snack after the tour.
When we consider the price, it’s clear that the tour aims for a well-rounded experience—covering key sights, providing insights from passionate guides, and including all necessary fees. It’s a comprehensive way to get a snapshot of Kotor’s history, scenery, and local life in just a few hours.

This tour is perfect for travelers who want a deep, personalized exploration of Kotor and its surroundings without the fatigue of a large group. It’s ideal if you appreciate storytelling, scenic beauty, and authentic cultural experiences. The private aspect means you can tailor the pace slightly, and the knowledgeable guides ensure you leave with a richer understanding of Montenegro’s maritime roots.
If you’re short on time but want to maximize your experience in Kotor, this tour’s combination of history, scenery, and personal attention offers exceptional value. It suits families, couples, or solo travelers who prefer an intimate adventure led by passionate locals.
Is transportation included in the tour?
Yes, private transportation is provided for the entire duration, including pickup and drop-off, which adds convenience and comfort.
How long is the tour?
The total experience lasts around 4 hours, giving you enough time to see the main sights without feeling rushed.
Are boat transfers included?
Yes, boat transfer to and from Our Lady of the Rocks island is part of the tour price, making it seamless and easy.
What are the main stops during the tour?
You’ll visit Kotor’s old town, the picturesque town of Perast, and the island of Our Lady of the Rocks, each offering unique sights and stories.
Is this tour suitable for children or older adults?
Most travelers can participate, but be aware of some walking and boat transfers. It’s best suited for those comfortable with light walking and small boat rides.
How far in advance should I book?
It’s recommended to book around 92 days ahead, especially during peak seasons, to secure your spot.
Are all fees included in the price?
Yes, all taxes, site entry fees, and ferry costs are covered. The only extras are personal purchases, food, and drinks.
Can I cancel the tour if my plans change?
Yes, free cancellation is available up to 24 hours before the tour, providing flexibility if needed.
To sum it up, the Old Captain’s Smile Tour blends scenic beauty, cultural storytelling, and personalized service into a memorable four-hour journey. It’s perfect for those who want to explore Kotor’s ancient streets, enjoy stunning views, and learn about local life in an intimate setting. Whether you’re a history enthusiast, a lover of scenic landscapes, or simply seeking a relaxed, authentic experience, this tour offers real value and memorable moments in Montenegro.