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

Exploring Greece’s most famous islands can feel overwhelming—especially when trying to coordinate transport, accommodation, and activities. This 5-day private tour promises a hassle-free way to enjoy Mykonos, Santorini, Delos, and a Caldera cruise, all bundled into one well-organized adventure.

What we love about this experience is how it combines the freedom of independent exploration with the comfort and convenience of private transfers and pre-arranged ferries. The choice of 3-star or 4-star hotels means you can tailor your stay to your style and budget. Plus, the inclusion of guided tours at some sites, like Delos, provides rich context without the price of an all-in package.

On the flip side, a potential drawback might be the time spent traveling between islands—reviewers note that the ferry routes stop at other islands, which can extend your transfer times and reduce your overall sightseeing hours. But if you’re looking for a comprehensive, stress-free way to see the highlights, this tour hits the spot.

This trip will suit travelers who want an authentic, flexible experience with the comfort of pre-arranged logistics. It’s perfect for first-timers eager to tick off major sights or those who prefer a guided handle on island hopping without the hassle of booking every component themselves.

Key Points

• All-inclusive convenience: Transfers, ferries, and accommodation are organized, saving you time and stress.
• Flexible exploration: You get two nights on each island, allowing for personalized sightseeing and relaxation.
• Quality accommodation options: Choose between 3-star and 4-star hotels, tailored to your preferences.
• In-depth site visits: Explore highlights like Little Venice, Oia’s sunset, and Delos’ ruins, with optional excursions.
• Authentic experiences: Authentic local flavors and scenic views enhance the trip’s value.
• Ideal for comfort-focused travelers: The private nature and included transport make this a seamless way to enjoy the islands.

Detailed Review of the 5-Day Private Greek Islands Tour

Seamless Transportation and Accommodation

One of the biggest advantages of this tour is the organized transfer system. From the moment you’re picked up at your Athens hotel, everything is handled—from the ferry tickets to port transfers—so you don’t have to worry about navigating busy ports or figuring out schedules. This makes the trip much more accessible, especially if you’re unfamiliar with Greek island hopping logistics.

Depending on your choice, you’ll stay in either a 3-star or 4-star hotel. Reviewers mention that the hotels are well-chosen, providing comfort and a good base for exploring. The inclusion of breakfast each morning adds value, helping you start your days with energy before heading out into the sun.

Day 1: From Athens to Mykonos

Your journey kicks off early with a pickup from your hotel, followed by transfer to Piraeus port—an experience that often takes around 4 to 5 hours, including the ferry ride. The ferry itself is a highlight, offering sweeping views of the Aegean Sea. Many travelers have noted that the ferry stops at other islands along the route, which extends travel time but also offers glimpses of other charming spots.

In Mykonos, the buzz begins immediately. You’re dropped at your hotel, with plenty of time to explore the iconic Little Venice and stroll through the narrow alleys of Matogiania. Shoppers will appreciate the local boutiques and souvenir stalls.

Reviewers like Shabnam_K mentioned that the Blue domes and sunset in Oia are worth seeing, referring to later days, but the vibrant nightlife of Mykonos is also a big draw. You’ll have the evening free to enjoy lively tavernas, bars, or simply relax at your hotel.

Day 2: Excursion to Delos (Optional)

Many travelers opt to include the Delos tour, which is a real highlight. The UNESCO World Heritage site offers a peek into ancient Greek mythology and history—think temple ruins, mosaics, and relics that tell stories of gods and historical legends. The guided exploration lasts about 1.5 hours, and reviews indicate guides are knowledgeable, bringing history alive.

The boat trip to Delos includes a BBQ lunch onboard, which is a delightful way to enjoy authentic Greek flavors while taking in the sea views. After Delos, the boat sails to Rhenia, known for its pristine beaches perfect for swimming, snorkelling, or simply soaking up the sun. Reviewers appreciated the chance to unwind in Rhenia’s untouched natural setting, with one noting it was “the perfect escape from the crowds.”

Day 3: Transition to Santorini

After a relaxed breakfast, you’re transferred back to the port for a ferry journey to Santorini—another scenic crossing that may stop at a few other islands. Once in Santorini, the iconic views of Oia’s sunset await. The tour includes a stop in the island’s picturesque capital, where you can wander among whitewashed buildings, snap photos of blue-domed churches, and buy souvenirs.

Many reviewers, like Zoila_M, highlight the transport delays due to stops at other islands, which can take nearly a full day from Mykonos to Santorini. While some see this as a bit of a time drain, others enjoy the scenic breaks and island views.

Day 4: The Caldera and Volcano Cruise (Optional)

The highlight of many travelers’ days is the cruise around the Santorini Caldera. This optional tour includes visits to Palea Kameni Hot Springs, where you can swim in therapeutic waters, and the volcanic islands of Aspronisi and Indian Rock. The cruise also features stops at Red Beach—famous for its volcanic, reddish sand—and the secluded White Beach, accessible only by boat.

The onboard BBQ buffet with fresh seafood and grilled meats is praised for its quality, and many mention this cruise as a memorable, picture-perfect experience. The sunset in Oia at the end of the day leaves a lasting impression.

Day 5: Return to Athens

The final day is all about returning to Piraeus via ferry, with a transfer to your Athens hotel. The 4-hour transfer generally allows travelers to reflect on their island adventures and plan their next Greek stop or return home.

Authentic Insights from Reviewers

Reviewers consistently praise the knowledgeable guides who enhance each experience—one highlighted how the guides provided interesting details without overwhelming. The hotels received good remarks for comfort and strategic locations, making it easy to explore on your own.

Many appreciated that ferry tickets and port transfers are included, removing the stress of last-minute bookings. The delicious food, especially the BBQ onboard and local eateries, added a layer of authenticity and enjoyment.

A key point from reviewers is that the tour offers good value—especially considering the convenience of private transfers, accommodations, and included ferries. The flexibility to explore independently in the evenings, combined with guided excursions, strikes a good balance.

Practical Tips for Future Travelers

• Be prepared for some travel time; ferry routes can be longer than anticipated due to stops at other islands.
• Choose your hotel based on your preferred level of comfort; the options cater to different budgets.
• If you’re a sunset lover, make sure to plan time in Oia—many reviewers mention how breathtaking the views are.
• Consider adding the optional excursions, like Delos or the Caldera cruise, for a richer experience.
• Download WhatsApp or have a communication plan ready to stay updated with the itinerary and any last-minute changes.
• The tour starts early at 6am, so plan accordingly and get a good night’s sleep before Day 1.

Who Is This Tour Best For?

This trip suits travelers seeking a structured yet flexible island-hopping experience without the hassle of planning every detail. It’s particularly good for those who appreciate comfortable accommodations, included transport, and the option to customize with guided excursions.

First-time visitors who want to hit the highlights of Mykonos and Santorini, while still leaving time for spontaneous exploration, will find this package ideal. It’s also a solid choice for those who value quality logistics and authentic local flavors without breaking the bank.

FAQ

Does this tour include hotel stays?
Yes, it includes 4 nights of accommodation, with options for 3-star or 4-star hotels.

Are ferry tickets included?
Yes, all fast ferry tickets between Piraeus, Mykonos, Santorini, and back are included.

Are transfers from and to the ports arranged?
Absolutely, private transfers are included for all ports and hotels in each location.

Can I explore the islands at my own pace?
Yes, you have two nights on each island to explore independently, with some guided activities and optional tours.

What’s the breakfast situation?
Breakfast is included in your hotel stay, helping you start each day ready for adventure.

Is the cruise around Santorini optional?
Yes, it’s an optional tour, but many find it well worth the extra cost for the stunning views and unique experiences.

How much time do we spend traveling between islands?
Most of day 3 and day 4 involve ferry rides, which can take a significant part of the day, especially with stops at other islands.

What kind of accommodations are available?
You can opt for either 3-star or 4-star hotels, depending on your preferences and budget.

Will I get a detailed itinerary?
Yes, after booking, you’ll receive a detailed itinerary with hotel details and pickup times.

Is this tour suitable for all ages?
Most travelers can participate, but consider the early start times and ferry travel if traveling with very young children or elderly guests.

This 5-day private tour offers a balanced mix of guided and independent exploration, comfort, and scenic beauty—making it a smart choice for travelers eager to see Greece’s iconic islands without the hassle. Whether you’re chasing sunsets, ancient ruins, or vibrant nightlife, this package delivers a comprehensive and memorable experience.