5 Day Private Tour, Santorini, Mykonos, Delos & Cruise to Caldera

Greece’s Islands in Style: A 5-Day Private Tour of Mykonos, Santorini, and Delos

Imagine strolling through the picturesque streets of Mykonos or watching the sun paint the sky in hues of orange and pink over Santorini—without the fuss of planning or worrying about transportation. This 5-day private tour covers the most famous Greek islands, offering a perfect blend of relaxation, sightseeing, and authentic experiences. For around $1,624 per person, you get four nights’ accommodation (either 3- or 4-star), all transfers, and ferry tickets, making this a solid choice for travelers craving a hassle-free escape.

What we really love about this tour is how much of the logistics are taken care of—no long waits at ports or stressful bookings. Instead, you’ll focus on soaking up the island vibes, taking in stunning views, and discovering hidden corners at your own pace. The included breakfasts start your days right, and the option to explore optional extra activities like the Delos archaeological site or Palea Kameni hot springs adds a touch of adventure.

One thing to keep in mind is that ferry routes sometimes stop at other islands en route, which can extend travel times—something to consider if you’re eager to maximize sightseeing. This experience is best suited for those who want a curated, comfortable trip that balances structured tours with free time, and who value the convenience of private transfers and pre-arranged accommodations.

Key Points

• All-Inclusive Comfort: Private transfers, ferry tickets, and hotel stays make for a seamless experience.
• Flexible Itinerary: Plenty of free time to explore each island at your own pace.
• Authentic Experiences: Visit iconic spots like Oia’s sunset and the ancient ruins of Delos.
• Good Value: Combines transportation, accommodation, and guided elements for a competitive price.
• Options for Comfort: Choice of 3- or 4-star hotels to match your style and budget.
• Ideal for Relaxed Travelers: Those who want to enjoy the islands without the stress of planning every detail.

In-Depth Look at the 5-Day Itinerary

Day 1: From Athens to Mykonos

Your adventure begins with a pickup from your hotel in Athens, followed by a transfer to Piraeus port. Once there, you’ll hop on a ferry to Mykonos, often called the “Island of Winds” for its steady breezes and lively atmosphere.

What makes Mykonos special? Besides its world-famous beaches, it’s the place to experience lively nightlife, stylish boutiques, and the iconic whitewashed buildings with blue accents. You’ll enjoy a ride to your hotel, with the evening free to explore Little Venice or wander the narrow streets of “Matogiania.” As one reviewer noted, a stroll through this area is “memorable,” offering plenty of shopping and photo ops.

Day 2: Delos – A Glimpse into Ancient Greece

Optional but highly recommended, this day involves a boat trip to Delos, a UNESCO World Heritage site and the mythological birthplace of Apollo and Artemis. The journey, lasting about 1.5 hours, takes you through the stunning Aegean waters.

Expect to see ancient ruins like temples, mosaics, and statues that tell stories of Greece’s earliest civilization. We loved that the tour includes a BBQ lunch on the boat—something simple but satisfying after exploring the ruins. Then, sail to Rhenia Island for a few hours of swimming, snorkeling, or just soaking up the sun in tranquil surroundings.

Although this activity incurs an extra fee, many travelers find the mix of history and relaxation well worth it. One guest said, “Mykonos and Santorini were beautiful, but the boat trip to Delos and Rhenia really added a memorable layer to our trip.”

Day 3: From Mykonos to Santorini

After breakfast, you transfer back to the port for a ferry ride to Santorini, the island famous for its breathtaking sunsets and dramatic volcanic landscapes. The ferry ride offers beautiful views of the Aegean and nearby islands, making the journey part of the experience.

Arriving in Santorini, you’ll check into your hotel, with plenty of free time to explore. Watching the sunset from Oia is an absolute must—crowds gather nightly to witness this natural spectacle. We loved how one reviewer said the sunset was “worth seeing,” and the town’s narrow streets, lined with boutiques and cafés, invite wandering and spontaneous shopping.

Day 4: The Volcano and White Beach

Another optional activity involves a cruise to visit Palea Kameni Hot Springs, where you can swim in therapeutic waters—though this costs extra. The cruise also provides views of the Indian Rock, the Ancient Lighthouse, and Akrotiri ruins, which you might find fascinating if you’re into archaeology or landscape photography.

The highlight is probably the visit to Red Beach—a striking volcanic beach with red sands, and White Beach accessible only by boat, offering seclusion and pristine scenery. The onboard BBQ buffet, featuring fresh seafood and local delicacies, rounds out the day.

Finishing the day in Oia for sunset viewing is a quintessential Santorini experience, leaving plenty of room for personal exploration or quiet reflection.

Day 5: Return to Athens

Your last morning involves a transfer to the port for the ferry back to Piraeus, then a private transfer to your hotel or onward journey. The entire process is smooth, with most of the stress handled for you, saving precious vacation time and energy.

Authentic Experiences and Practical Details

This tour is designed for travelers who want to focus on enjoying the islands’ beauty rather than stressing over logistics. The included ferry tickets are a significant advantage, as booking ferries independently can be time-consuming and confusing, especially during high season.

The private transfers from hotel to port, and the choice of quality accommodation, are also notable. According to reviews, the hotels chosen are “very good,” providing comfort after busy days sightseeing. Breakfast is included, providing a good start to each day without extra planning.

Timing is well-managed, with start times early enough to maximize days, and the itinerary balances sightseeing with downtime. Some travelers noted that ferry routes sometimes stop at other islands, which can extend travel times—but that adds a bit of variety, and most agree the overall value outweighs this minor inconvenience.

Price and Value

For $1,624, you receive not only the ferries and hotel stays but also the convenience of private transfers and the flexibility to explore independently. While optional tours like Delos or hot springs cost extra, most reviews find the included activities and accommodations deliver good value, especially considering how much easier your trip becomes with pre-arranged logistics.

Who Is This Tour Best For?

This experience suits travelers who prefer a comfortable, well-organized trip without the hassle of coordinating every detail. It’s great for those who love a mix of cultural sights and leisure, and who appreciate a private setting over large group tours. If you’re eager to experience Santorini’s sunsets or explore Delos’ ruins without the stress of planning, this tour offers a balanced, enjoyable package.

The Sum Up

Choosing a 5-day private Greek Islands tour like this offers a wonderful way to see Mykonos, Santorini, and Delos with minimal fuss. It’s perfect for travelers who value ease, comfort, and flexibility, combined with authentic sights and stunning scenery. You’ll enjoy the freedom to explore at your own pace, backed by the assurance that your transportation, accommodations, and key activities are handled.

The tour’s highlights—beautiful sunsets, archaeological sites, and relaxing beaches—are well complemented by the convenience of private transfers and included ferry tickets. While some optional activities cost extra, most travelers find the core experience provides excellent value for money.

This trip is ideal if you want a thoughtfully curated Greek island experience that blends the best of history, scenery, and leisure, all wrapped up in a comfortable package. It’s especially suited for those who prefer to avoid the complexities of independent planning but still crave personal freedom and authentic moments amid Greece’s legendary islands.

FAQ

How are the transfers arranged?
You’ll be picked up from your hotel in Athens and from your hotels on Mykonos and Santorini, with private transfers to ports and ferries included, making the journey smooth and stress-free.

Are the hotel choices comfortable?
Yes, the package offers a choice between 3-star and 4-star hotels, both selected for comfort and convenience, providing a good base after busy days exploring.

Is breakfast included?
Breakfast is included each morning, ensuring you start your day energized before heading out to explore.

Can I customize the itinerary?
While the core itinerary is set, you can opt for additional activities like the Delos tour or the volcano cruise—though these cost extra.

What about the ferry schedule?
Ferry tickets are included, and the schedule is arranged to maximize your time on each island. Be aware that routes might stop at other islands, which can extend travel times.

Will I have free time?
Absolutely. The itinerary combines guided activities with ample free periods to wander, shop, or relax at your own pace.

Is this tour suitable for all ages?
Most travelers can participate, but those with mobility issues might want to verify specific activity details, especially for boat trips or walking around towns.

How far in advance should I book?
Most bookings are made around 59 days in advance, but early planning ensures better hotel choices and availability.

What’s the overall value?
Considering transportation, accommodations, and included activities, most guests agree it’s a good deal for a stress-free, memorable Greek island holiday.