A detailed look at the Old Captain’s Smile Tour in Kotor offers a charming blend of history, architecture, and stunning scenery. This private experience, rated a perfect 5.0 by six travelers, promises an intimate exploration of Montenegro’s most beloved spots. For around $324 per group (up to two people), you get a thoughtfully curated journey that combines walking, boat rides, and storytelling, all led by knowledgeable guides who clearly care about sharing their homeland.
What I particularly appreciate about this tour is how it balances culture with breathtaking views. The guides, such as Ana and Sanja, have rave reviews praising their local knowledge and engaging personalities. Another highlight is the inclusion of the Our Lady of the Rocks island, which isn’t just another church but a site filled with stories woven into its fabric—something that makes this experience stand out. A possible consideration is the price point, but given the private nature, personalized attention, and inclusive fees, many will find it offers good value.
One small note: while the tour covers major sights in about four hours, the pace is relaxed, and you’ll want to keep your camera handy for the incredible vistas. Plus, since transportation, boat transfers, and entry fees are included, there’s no need to worry about extra costs sneaking in. It’s a well-rounded package for those seeking authentic insights and memorable scenery.
Key points / Takeaways

- Exclusive Private Tour: Only your group participates, ensuring personalized attention and flexibility.
- Comprehensive Itinerary: Covers Kotor’s old town, Perast, and the captivating Our Lady of the Rocks island—each offering unique stories.
- Expert Guides: Guides like Ana and Sanja receive glowing reviews for their local knowledge and engaging personalities.
- Includes All Fees: Boat transfers, entry fees, and city taxes are covered, making planning easier.
- Stunning Scenery: Expect breathtaking views of the bay, ancient architecture, and the beautifully crafted man-made island.
- Ideal for Authentic Experience: The tour offers a deep dive into local life, customs, and history, perfect for curious travelers.
Exploring Kotor’s Old Town

Kotor’s medieval charm begins as soon as you step into its cobblestone streets. Walking through the Old Town feels like entering a living museum, with twisting alleys and squares that tell stories of centuries past. Your guide will point out spots like Square of Milk, Square of Salad, and Square of Timber, each with its own character. The reviews praise guides like Sanja for their ability to entertain and educate, making time fly.
Expect to learn about local families, old churches, and long-standing traditions that still influence life in Kotor today. The 1.5-hour walk offers enough time to soak in the sights without feeling rushed, and since admission is free, you can focus on the stories and scenery. Many visitors mention how guides make history come alive, turning what could be just old stones into stories of people and customs.
You can also read our reviews of more tours and experiences in Kotor.
The Charm of Perast

A short drive or boat ride takes you to Perast, a quaint fishing town that feels like a step back in time. Here, you’ll be greeted by stone houses, seagulls resting on rooftops, and boats bobbing in the bay. The atmosphere is relaxed, with imagery of fishermen pulling fresh mussels and locals living close to the water.
Travelers often mention how Perast’s architecture and peaceful vibe make it a favorite stop. As one reviewer put it, the town “will enchant you with its atmosphere and story,” which is exactly what you’ll experience. You’ll have about an hour here to wander, take photos, and simply enjoy the slow pace of life along this scenic bay.
The Unique Experience of Our Lady of the Rocks
The highlight for many is the visit to Our Lady of the Rocks, a man-made island with a church that tells a story of devotion and community effort. Built on a tradition dating back to the 15th century, it’s a site where the local population has repeatedly added stones and built the church over centuries.
The entry fee is included in the tour price, and the 45-minute visit allows plenty of time to marvel at the art, relics, and architecture. Guests often remark on the emotional stories woven into the church’s fabric—it’s more than just a tourist stop; it’s a symbol of local resilience and faith. The guides are praised for sharing these stories with warmth and depth.
Transportation and Logistics
One of the tour’s biggest advantages is that private transportation is included, removing the hassle of navigating unfamiliar public transit. The boat transfer to the island is also covered, giving you a smooth journey across the bay. The entire experience is designed for comfort and convenience, with most travelers finding it well-paced and stress-free.
The tour lasts about four hours, making it a perfect half-day trip. It’s scheduled to start early enough to avoid crowds but late enough to enjoy the sunlight hitting the bay’s waters beautifully. Since the experience is private, your group can customize the pace slightly or swap some stops if desired, adding a layer of flexibility.
Who This Tour Suits Best
This experience is ideal for couples, small families, or friends who want an intimate, engaging look at Montenegro’s coast. It’s especially suited for those who appreciate history, architecture, and spectacular views without the rush of larger group tours.
Travelers who value local stories and authentic cultural insights will find guides like Ana and Sanja a highlight of the trip. It’s also a good choice if you want to avoid public crowds and enjoy a tailored experience.
However, keep in mind the cost—though it covers many logistics and entry fees, it may seem high for solo travelers or those on a tighter budget. Still, for the private, all-inclusive nature, many find it offers excellent value.
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Final Thoughts on the Old Captain’s Smile Tour

This tour manages to combine stunning scenery, engaging storytelling, and a personal touch in a way that makes it memorable. The fact that all logistics—boat rides, entry fees, and transportation—are handled for you means you can focus solely on enjoying the sights and the stories.
The guides clearly love their region, and that passion translates into a richer experience. Whether you’re wandering the ancient streets of Kotor, soaking in the peaceful vibe of Perast, or marveling at the craftsmanship of Our Lady of the Rocks, you’ll leave with a deeper appreciation for Montenegro’s coastal treasures.
While it’s priced higher than some group options, the private nature and detailed attention make this a worthwhile choice for those seeking a more personal and immersive experience. It’s perfect if you want a mix of culture, history, and scenery, served with a friendly guide who genuinely cares about sharing their homeland.
FAQ

Is this tour suitable for all ages?
Yes, most travelers can participate, and the tour’s relaxed pace makes it accessible for families, couples, or small groups of friends.
What’s included in the price?
The tour covers private transportation, all fees and taxes, a boat transfer to Our Lady of the Rocks, and entry to the church. Food and drinks are not included.
Can I cancel if my plans change?
Yes, cancellations are free up to 24 hours before the tour, allowing flexibility if your schedule shifts.
How long is the tour?
The experience lasts approximately four hours, making it a perfect half-day outing.
Is this a group or a private experience?
It’s a private tour, so only your group will participate, providing a more tailored and relaxed experience.
Do I need to book in advance?
Yes, most bookings are made around 92 days in advance, especially during peak season, to ensure availability.
Who are the guides?
Guides like Ana and Sanja receive high praise for their knowledge and warm personalities, making the experience engaging and personal.
Are there any extra costs I should be aware of?
Everything essential—boat transfers, entry fees, taxes—is included. Additional purchases, like souvenirs or food, are at your discretion.
The Old Captain’s Smile Tour offers a well-rounded, authentic taste of Montenegro’s coast, perfect for curious travelers wanting more than just pretty scenery. With knowledgeable guides, stunning views, and a carefully curated itinerary, it’s a memorable way to experience Kotor’s historic charm and natural beauty.
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