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

Planning a trip to Greece often means balancing the desire to see multiple islands with the practicality of transport, accommodations, and timing. This 5-day private tour offers a well-structured way to experience Mykonos and Santorini without the stress of booking ferries or finding hotels on the fly. With private transfers, included ferry tickets, and the flexibility of choosing your hotel level, it promises a blend of scenic beauty, lively nightlife, and cultural highlights.

One of the standout features is the chance to explore Delos, the UNESCO World Heritage site, along with a cruise around Santorini’s famous caldera. We particularly appreciate that the package includes breakfast daily and offers a choice of 3-star or 4-star accommodations, catering to different budgets. That said, the trip’s pace, especially the ferry crossings, might be a consideration if you prefer ultra-relaxed or slow-paced travel.

This experience is ideal for travelers who want a blend of guided convenience and freedom to explore. It suits those looking for a balanced mix of sightseeing, relaxation, and vibrant nightlife—perfect for first-timers or anyone wanting to tick off major Greek island highlights in just a few days.

Key Points

• All-inclusive transport and ferry tickets mean you won’t need to worry about booking or navigating complex schedules.
• Private transfers enhance comfort and streamline your arrivals and departures.
• Flexible hotel options allow you to choose between 3-star or 4-star accommodations, aligning with your preferences.
• The itinerary includes iconic sights like Oia’s sunset and Delos ruins, offering authentic experiences with minimal hassle.
• Guided excursions and free time balance structured exploration with personal freedom.
• Reviews highlight knowledgeable guides, stunning views, and good value, making this a popular choice for many travelers.

An In-Depth Look at the 5-Day Itinerary

Day 1: Arrival and Mykonos

Starting with a hotel pickup in Athens, your first journey takes you from the bustling city to the port of Piraeus, where you’ll board a ferry to Mykonos, the “Island of Winds.” Known worldwide for its beach parties, picturesque Cycladic architecture, and luxurious hotels, Mykonos offers a lively introduction to the Greek islands.

Once you arrive, your driver will transfer you to your hotel—either a 3-star or 4-star depending on your choice. The hotel location is typically near the action, making it easy to explore Little Venice or stroll through the charming alleyways of “Matogiania.” Reviewers mention that the walk through these narrow streets, shopping for local crafts and clothes, remains a highlight—something to do while soaking in the local vibe.

You’ll likely want to relax and soak in the lively atmosphere, especially as the Mykonos nightlife is renowned. Guests have noted the vibrant bar scene and sunset views that make evenings here truly magic. The hotel stay at this stage offers a good base, and having breakfast included helps start the day right.

Day 2: Delos and Rhenia Islands

A highlight for many is the optional excursion to Delos, the mythological birthplace of Apollo and Artemis. For an extra fee, you’ll be picked up from your hotel and transferred to the port for a boat trip. The 1.5-hour guided exploration reveals ruins of temples, mosaics, and ancient structures, with insightful commentary on the island’s significance.

Reviewers like Shabnam_K appreciated the knowledgeable guides, mentioning that the Ruins of Delos are astonishing, especially when learned about through a local guide. The visit includes free time to wander and absorb the history.

After exploring Delos, the boat continues to Rhenia, an uninhabited island with pristine beaches. Here, you’ll have the chance to swim, snorkel, or sunbathe—a peaceful contrast to the lively streets of Mykonos. Many guests find this part of the trip particularly relaxing, with some quoting that the swimming and snorkeling on Rhenia was a highlight.

The entire trip lasts about 6 hours, and while the admission is free, the BBQ lunch prepared onboard is a popular feature, allowing you to enjoy fresh grilled seafood while soaking in the sea views.

Day 3: Transfer to Santorini

Your journey continues with a private transfer to the ferry port, followed by a scenic crossing to Santorini—the island famed for its spectacular sunsets and cliffside villages. The ferry ride offers stunning views of the Aegean, with many noting how smooth and efficient the transfer is, which makes the whole experience stress-free.

Once in Santorini, you’ll be transferred to your hotel. Reviewers consistently mention that arriving in Santorini feels like stepping into a postcard—the dramatic caldera views, whitewashed buildings, and blue-domed churches are truly breathtaking. You’ll have free time to explore the charming streets of the capital, Fira, or to relax and enjoy the sunset from Oia, where crowds gather to witness one of the most famous sunsets in the world.

Guests like Zoila_M noted that the hotels were “very good,” though she also pointed out that the ferry trips between islands take a full day, which can eat into your time. Still, the overall pace is generally appreciated for giving enough time to enjoy each place without feeling rushed.

Day 4: Santorini Cruise & Sunset in Oia

This day involves a Santorini cruise (optional with extra cost), which many travelers find to be the highlight of their trip. The cruise includes stops at Palea Kameni Hot Springs,** the Red Beach**, and White Beach—each offering unique volcanic landscapes and swimming opportunities.

Guests have praised the cruise for its delicious onboard BBQ buffet, complete with fresh seafood and salads, and the opportunity to capture stunning photos of the caldera, Indian Rock, and the lighthouse. The hot springs are often a hit, with many mentioning that the thermal waters are surprisingly warm and provide some fun for swimmers.

The cruise culminates with a sunset in Oia, which many reviewers describe as “magical,” “breathtaking,” or “worth every penny.” The views as the sky turns violet over the caldera are some of the most memorable images travelers take home.

Day 5: Return to Athens

On your final day, a private transfer will take you from your hotel to Santorini Port, followed by the ferry back to Piraeus. From there, you’ll be transported to your hotel in Athens, wrapping up this whirlwind of island hopping. The entire transfer takes about four hours, and guests appreciate how smoothly the logistics are handled.

Real Experiences from Travelers

Feedback from past travelers paints a vivid picture of what to expect. Shabnam_K praised the efficiency and professionalism of the private guides and transfers, highlighting how they helped streamline a sometimes complicated process of island-hopping. She also noted that the blue domes and sunset in Oia were worth seeing, capturing the classic Santorini vibe.

Zoila_M, while happy with the hotel choices, pointed out that ferry stops in other islands can extend travel time, so patience might be required if you want to maximize sightseeing. Still, she appreciated the good value for the experience, especially considering the private transfers, ferry tickets, and accommodation.

Several reviews highlight the knowledgeable guides and the quality of the included breakfast, which provides a great start before heading out for the day’s adventures. Many travelers also mentioned that the hotel options are well located, making it easy to explore on your own or relax after busy days.

Practical Considerations and What to Expect

• Transport: The private transfers between hotels, ports, and ferries are a big plus, removing the stress of navigating public transport or taxis. The ferry rides between Athens, Mykonos, and Santorini are included, making this a well-organized way to travel between islands.
• Hotel Options: You can select between 3-star or 4-star accommodations, which affect the overall budget but offer different levels of comfort and amenities. The hotels are generally well-rated, and some reviewers note they are conveniently located for exploring.
• Timing: The tour starts early (6:00 am pickup), which helps maximize your days, though the ferry schedules can mean full travel days—especially when crossing from Mykonos to Santorini.
• Extras: Optional excursions like Delos and the Santorini cruise are available at an extra cost, which many find well worth the investment. The cruise, in particular, receives praise for its scenic stops and onboard amenities.
• Reviews & Feedback: The tour maintains a solid 4.5/5 rating from travelers, citing excellent guides, stunning scenery, and good value. Some note that island travel time can eat into leisure time, but overall, most find the experience worthwhile.

Who Would Love This Tour?

This trip is perfect for those seeking a comprehensive yet manageable way to see Greece’s top islands. The inclusion of private transfers and ferry tickets offers peace of mind, especially for first-time visitors. If you love scenic views, historic sites, and vibrant nightlife, this tour hits all the right notes. It’s especially suitable for travelers who appreciate guided logistics with free time to explore independently.

Couples, small groups, or solo travelers who want a balanced mix of structured activities and personal discovery will find this trip rewarding. It’s a good fit for those who prefer organized logistics over DIY planning, but still want the freedom to explore at their own pace.

The Sum Up

This 5-day private Greek island tour strikes a nice balance between convenience, sightseeing, and authentic experiences. The inclusion of private transfers, ferry tickets, and flexible hotel options makes it an excellent choice for travelers who want to maximize their time without feeling overwhelmed by logistics. From the lively streets of Mykonos to the breathtaking sunsets in Oia, every moment is curated to deliver a memorable holiday.

The knowledgeable guides, stunning views, and good value for money truly shine through in reviews, making this an attractive option. It’s ideal for first-timers or anyone eager to see Greece’s most iconic islands with ease and comfort.

If you’re looking for a well-organized, scenic, and culturally rich island-hopping adventure, this tour offers a practical and enjoyable way to experience the Greek archipelago without sacrificing comfort or authenticity.

FAQ

What is included in the tour?
The tour includes 4 nights of accommodation (with your hotel choice), private transfers from/to ports and hotels, ferry tickets between Athens, Mykonos, and Santorini, and breakfast daily.

Are the ferries and transfers arranged for me?
Yes, all ferry tickets and private transfers are included, designed to make your journey smooth and stress-free.

Can I customize the hotel level?
Yes, you can choose between 3-star or 4-star hotels as part of the package, depending on your budget and comfort preferences.

What if I want to do optional excursions?
Optional activities like the Delos trip and the Santorini cruise are available at extra cost. Many travelers find these add significantly to their experience, especially the scenic cruise and visits to archaeological sites.

How long are the ferry crossings?
The ferry trips vary but generally take a few hours, with some days involving full travel days, especially between Mykonos and Santorini.

What’s the best time to book?
Most travelers book about 2 months in advance, with an average booking window of around 59 days, which helps secure the preferred hotel options and ferry schedules.

Is this tour suitable for solo travelers?
Absolutely. The private nature of the tour and flexible schedule make it ideal for solo travelers seeking comfort and convenience.

Can I participate if I have mobility issues?
While the tour involves ferry rides and some walking through narrow streets, private transfers help reduce walking distances. It’s best to check specific hotel accessibility if needed.

What’s the overall value of this tour?
Considering the included accommodations, private transfers, ferry tickets, and guided options, many guests feel it offers great value for a comprehensive Greek island experience.