A sailing day on the water makes Dubrovnik feel different. You get Dubrovnik’s old city walls in view from a distance, plus a calm, wind-driven day run by a licensed skipper with serious local know-how.

I also really like the human side: Mato (often written as Matthew) is chatty, comfortable with the story of the region, and skilled at reading the sea so your ride stays smooth.

The big highlight for me is the Lopud stop. You’re scheduled to swim on Sunj Beach, the only sandy beach in the wider Dubrovnik area, and snorkeling gear plus water are part of the deal.

One consideration: food is not included. Lunch is possible at a nearby restaurant on Lopud, but you’ll want to budget for it—and the Blue Cave moment near Kolocep is a possibility, not a guarantee.

Key Points at a Glance

• Dubrovnik city walls seen from the sea on the way to the Elaphiti Islands
• Sunj Beach on Lopud for a swim break at the area’s only sandy beach
• Blue Cave chance near Kolocep on the return route (weather and conditions matter)
• Snorkeling equipment and water included so you can actually use the clear water
• Mato/Matthew’s 20+ years seamanship and local stories make the day feel personal
• Private group format (up to 8) keeps the experience flexible and unrushed

A Private Boat Day That Makes Dubrovnik Feel Less Crowded

There are plenty of Dubrovnik days that start with a checklist. This one starts with the water. You leave Cavtat by boat, slide toward the Elaphiti Islands, and spend the day seeing the coast from a side most people don’t get. It’s a practical way to enjoy the big sights without being stuck in the thick of them.

I like that the plan includes both classic views and real downtime. You’re not just cruising for photos; you’re built around time to swim and (if you feel like it) snorkel. And because it’s private for a small group of up to eight, the skipper can work with your pace instead of herding anyone.

Still, the day is weather-dependent in the way sailing always is. If you’re hoping for one specific moment—like that Blue Cave stop—you’ll want to keep expectations flexible.

Meeting in Cavtat: Where to Find the Boat Start

Your tour begins in Cavtat, starting from the Old City port area, and you’ll meet next to the waterpolo training field. That’s a useful detail because Cavtat’s center is compact but easy to misread if you arrive without a clear landmark.

Plan to arrive a few minutes early. Even on a private tour, you want time for basics: getting oriented, meeting your skipper, and sorting out swim gear and snorkeling equipment before you head out. Once you’re underway, the day moves fast in a good way.

For context, the return is also part of the fun: you’ll finish back at Cavtat’s harbour, where you can see lots of luxurious super yachts docked inside. It’s a neat contrast to the quiet water time you just had.

Dubrovnik City Walls From Distance: The Best Kind of First Look

On the sail toward the Elaphiti Islands, you’ll see the ancient Dubrovnik city walls from the water. Not up close like the walking routes, but from a perspective that’s actually easier to take in. From the sea, the walls and the cliffs make more sense as a defensive system, not just a photo background.

This is one of those “smart planning” moments I appreciate. You get the big visual cue of Dubrovnik without spending your day fighting crowds or rushing between viewpoints. And because you’re on open water, you also get a sense of how the coastline folds around the islands—exactly the kind of thing that helps you understand what you’re seeing later.

If you care about history, this ride has a bonus. Mato is comfortable talking about Croatian history and everyday life in the region, and that makes the wall views feel less like a spectacle and more like context.

Sailing to the Elaphiti Islands: Why This Route Feels Worth It

The Elaphiti group sits just off the Dubrovnik coast, and sailing there gives you that “coastline by boat” feeling. You’re surrounded by the kinds of turquoise-blue sea views people spend hours trying to find from land.

A practical upside: you’re moving. That means you’re not repeating the same street scene all day. You get a changing perspective every time the coastline turns.

Also, the private format matters here. In a small group, the skipper can time the day based on wind, water conditions, and crowd levels. One of the most positive themes from past groups is that Mato knows when to hit places for the best atmosphere—especially in the moments before crowds build.

Lopud and Sunj Beach: The Swim Break That Actually Delivers

Lopud is where the tour turns into a vacation. The main stop is planned on Lopud Island, with a scheduled swimming break at Sunj Beach—described as the only sandy beach in the Dubrovnik area. That detail matters. Many island beaches nearby are rocky or pebbly. A sandy spot is easier on bare feet and feels more “beach day” than “jump off a boat day.”

This is also where your included gear pays off. You’ll have water and snorkeling equipment on board, so you can choose your rhythm:

• swim and relax on the sandy beach
• snorkel if the water’s clear and you feel like it
• do a quick mix of both

The timing is built into the flow of the day, so you don’t feel like you’re rushing the island. You get a real break, not just a stop for five photos.

Lunch on Lopud (Not Included, But Manageable)

Lunch is not included in the tour price. That said, there’s a chance to organize lunch at a nearby restaurant on the island. In at least one experience, the skipper also helped with lunch planning for the group. So if you want a sit-down meal, you should be able to make it happen on the spot—just expect it to be paid directly.

If you’re the kind of person who likes to eat “on island time,” this is a good match. If you prefer to budget tightly, you’ll want to decide in advance what you want for lunch so you’re not making choices while hungry and sun-warmed.

Snorkeling Equipment and Water: Small Inclusions That Change the Day

The tour includes snorkeling equipment and water. That may sound minor, but it’s the difference between doing an activity versus thinking about it. If you arrive without gear, renting or buying it wastes time and momentum. Here, you can just go.

One thing I’d keep in mind: snorkeling is only as good as the water conditions. The region’s sea is clear often, but sailing also means you’ll feel the day shift with wind and swell. If the water is calm, you’ll love having gear ready. If it’s rougher, you can still enjoy the swim break and skip snorkeling without feeling like you “missed” something.

Kolocep and the Blue Cave Chance: The Fun Uncertainty Part

On the return trip, the boat sails close to Kolocep Island. You may get a short break next to the famous Blue Cave. The key word is possibility. Sailing conditions and timing decide what you can do.

I like that the plan doesn’t overpromise. It gives you a chance at one of the area’s signature sights without setting you up for disappointment if it’s not practical that day.

Even if the Blue Cave moment doesn’t happen, the Kolocep sailing portion still keeps your route varied. You’re not just retracing the same line back to Cavtat—you’re still in motion, still seeing the coastline with a different angle.

The Skipper Factor: Mato/Matthew Makes It Feel Like a Local Day

This is a private tour, and the skipper is a big part of the value. You’re with a professional licensed guide who has more than 20 years of experience, and you can feel it in the way the day flows.

From real accounts of past groups, the strongest praise is about the human side:

• friendly company and easy conversation
• comfort sharing Croatian history and day-to-day life
• skilled sailing that keeps things feeling relaxed

There’s also a detail worth mentioning: in one group’s experience, Mato organized lunch at a restaurant and had soft drinks available for guests. That’s not listed as a guaranteed inclusion, but it’s a good sign of how the skipper thinks about small comforts.

In short, you’re not just paying for boat time. You’re paying for someone who knows how to run the day well.

Price and Value: $706 for Up to 8 on One Boat

At $706 per group up to 8, the pricing works best when you split it sensibly. If you’re traveling as a couple, it can feel “premium” compared with a shared group cruise. But private sailing isn’t meant to be cheap—it’s meant to be frictionless: your own pace, your own small group, and a skipper who can shape the timing to your day.

Where it becomes good value is when you compare what’s included:

• the boat experience for a full 8 hours
• water and snorkeling equipment
• professional licensed guidance
• multiple sea-view moments plus a structured swim break

Food isn’t included, so you should budget lunch or drinks separately. But you’re also not paying for a big meal inside the boat price, so the core sailing portion stays the focus.

My practical rule: if your group can fill the boat enough to spread the cost—and you want swim time plus curated route moments—this is a strong deal.

Who This Tour Fits Best (And Who Might Want Something Else)

This sailing day is a great fit if you want:

• a private experience with a small group
• real water time, including a swim at a sandy beach (Sunj)
• a chance to see Dubrovnik’s walls without committing to a full day on foot
• a skipper who explains what you’re seeing

It’s also ideal for families, as long as everyone is comfortable being on the water for part of the day. The tour is long enough for adults to feel like it’s a proper excursion, and structured enough that kids (or anyone who gets restless) still has a clear swim moment to look forward to.

If you want a day packed with walking stops and multiple shore excursions, this isn’t that style. This is water-first. You’re buying time at sea, plus a couple of island beats.

Quick Tips to Make the Day Easier

I’ll keep this simple because you don’t need a checklist to enjoy sailing:

• Bring swimwear and something easy to wear after you get out of the water.
• Pack sunscreen and a hat if you’re sensitive to sun.
• If you care about snorkeling, go when the water looks calm and clear.

And emotionally: expect a relaxed schedule. The best sailing days don’t feel rushed.

Should You Book This Private Cavtat and Dubrovnik Sailing Tour?

Yes—if you want a private boat day that mixes iconic coastline views with a real swim stop, this is a smart choice. You’re getting Dubrovnik’s walls from the water, a Lopud break at Sunj Beach, and a return route that can include the Blue Cave area if conditions allow. Add in included water and snorkeling gear, and the day holds together well.

Book it especially if your group wants something more comfortable than a busy sightseeing day. Cavtat is a great base, and this is one of the best ways to let the sea do the sightseeing work for you.

If you’re strict about food costs, plan for lunch separately on Lopud. And if the Blue Cave is your top must-see, keep your expectations flexible, since it’s treated as a possible add-on.

FAQ

How long is the private sailing tour?

The tour lasts 8 hours.

Where does the tour start and where do we meet?

It starts from the Old City port of Cavtat, and the meeting point is next to the waterpolo training field.

Is food included in the price?

No. Food is not included. Lunch can potentially be organized at a nearby restaurant on Lopud, but it’s paid separately.

What’s included on board?

The tour includes a professional licensed guide, water and snorkeling equipment, and the sailing boat experience.

Is this tour private?

Yes. It’s a private group, with capacity up to 8 people.

Does the guide speak English and is free cancellation available?

Yes, the guide/instructor is English-speaking, and there is free cancellation up to 24 hours in advance for a full refund.