The reason for the dates

The hours the day visitors never see

Join Majestic Dream Vacations in Greece for eight nights in mid-September, when the sea is at its warmest, the summer crowds have thinned, and the light over the Aegean turns gold in the early evening.

We begin on Santorini with three nights above the caldera, take the ferry north to Mykonos for three more, then cross the Aegean by sea to Athens for the last two, so you fly home from the capital. The point of staying is the hours the day visitors never see: the caldera from the water with the whole day to enjoy it, Oia and Fira after the cruise ships have left, dinner in Little Venice after the last tender has gone back out, and an evening in Plaka below the Acropolis.

See how the days are arranged

Who this is designed for

This journey suits you if

The sea is the draw

A sailing day on the Santorini caldera, beaches on both islands, and every move between stops made by ferry across the Aegean.

You want to stay, not visit

Three nights on each island and two in Athens, with free days and free evenings built in. Evenings are the reason the trip is built this way.

You are traveling solo, or as a couple, or with friends

A small group with a set plan and room to go your own way. The prices for a shared double, a triple and your own room are all stated below.

Day by day

Itinerary

Three nights on Santorini, three on Mykonos and two in Athens. You fly into Santorini, every move after that is by ferry, and you fly home from Athens.

8 Sep

Arrive on Santorini

Fly into Santorini, where a transfer takes you from the airport to your hotel. Check in, rest after the journey, and find a place on the caldera rim for the first sunset of the trip. The day boats and the cruise passengers are gone by then, and the island is quieter than anyone who only visited for the afternoon would guess. Meals: none included today.

9 Sep

A day on the caldera

A semi-private sailing day cruise out onto the caldera, the flooded volcanic crater that gives Santorini its cliffs and its views. You see the island the way it was formed, from the water looking up. The cruise runs through the day, so the evening is still yours. Meals: breakfast.

10 Sep

A free day on Santorini

A slow day. Swim, walk to the village, or sit with a coffee and the view. Santorini’s beaches are volcanic, black and red sand. If you want more, two optional add-ons fit here: the Santorini Wine Roads, a winery tour on a volcano where the vines are trained low into baskets against the wind, or a sunset sailing cruise, the caldera from the water as the light goes. We are happy to arrange either. Meals: breakfast.

11 Sep

By ferry to Mykonos

Breakfast, then a transfer to the port and the ferry north through the Cyclades to Mykonos, a crossing of a little over two hours. A transfer meets you at the port on Mykonos. In the early evening walk into Mykonos Town: the windmills on the ridge, the houses of Little Venice built right out over the water, and dinner in the lanes of Chora once the day visitors have gone back to their ships. Meals: breakfast.

12 Sep

Essential Mykonos

A guided tour of the island beyond the harbor: Chora, the lighthouse, the beach at Kalafatis, and Ano Mera, the village in the island’s interior. The rest of the day is yours. Meals: breakfast.

13 Sep

A free day on Mykonos

A full free day. Beach, spa, or simply the pool. We are happy to arrange anything you want to add. In the evening, Little Venice again for the sunset, or back into Chora, which is at its best after dark. Meals: breakfast.

14 Sep

By ferry to Athens

Breakfast, then a transfer to the port and the ferry across the Aegean to the mainland. On arrival a transfer takes you from the port to your hotel in Athens. In the evening, walk the streets around Plaka, with the Acropolis lit up above the city. Meals: breakfast.

15 Sep

Athens on foot

A shared half day walking tour of Athens, with transfers from and back to your hotel. The rest of the day is yours. If you want to spend it eating, the Athens food lovers walk is an optional add-on we are happy to arrange. Meals: breakfast.

16 Sep

Departure from Athens

Breakfast, and a transfer to Athens International Airport for your flight home. Meals: breakfast.

Ferries and tour days

Ferry times are set by the operators and are confirmed closer to travel, as is the day each tour runs. The Aegean has a summer wind, the meltemi, which can make a crossing lively and can occasionally move a boat trip to another day. We build the schedule with room for that.

Book a Consultation

Arriving by sea

Sailing with us from Athens to Rome?

Our Virgin Voyages Athens to Rome sailing reaches Civitavecchia, the port for Rome, at 6:30 AM on 7 September. From there you fly Rome to Santorini on the 7th or the 8th and join the group on Santorini on 8 September. That flight is not included, and we are happy to quote it, along with an extra night on Santorini if you arrive on the 7th. The islands you glimpsed for a day become the islands you actually stay on.

The package

What is and is not included

Included in your package

Eight nights in hand-picked hotels: three on Santorini, three on Mykonos, two in Athens, with breakfast daily
Semi-private Santorini sailing day cruise
Essential Mykonos tour
Shared half day Athens walking tour, with transfers
The ferry from Santorini to Mykonos and the ferry from Mykonos to Athens
All arrival, port and departure transfers
A Majestic Dream Vacations host with the group, once ten or more travellers have paid
A Majestic Dream Vacations T-shirt

Not included

International flights, into Santorini and home from Athens. We are happy to quote them
For Virgin Voyages guests: the flight from Rome to Santorini, and a night on Santorini if you arrive on 7 September
Travel insurance, which we strongly recommend
Meals not listed as included. Breakfast is included daily; lunches and dinners are not
Optional tours and add-ons, including the sunset sailing cruise, the Santorini Wine Roads tour and the Athens food lovers walk
Greece’s overnight stay tax, charged by each hotel per room per night and paid locally at checkout
Gratuities for guides, drivers and boat crews
Personal expenses and anything not listed as included

Investment

Pricing and payment

Per person in United States dollars. International flights are not included.

Double, two sharing, per person$3,740

Triple, three sharing, per person$3,380

Single, your own room, per person$5,370

Deposit to reserve, per person, non-refundable$500

Balance due9 July 2027

A $500 per person deposit, which is non-refundable, reserves your place. After you book, we send a monthly payment schedule to spread the rest, with the balance due 9 July 2027.

Book a Consultation Start Your Travel Inquiry

After you book a consultation

What happens next

1

We talk it through

Who is traveling, how you want to room, and whether you are arriving from home or from our Virgin Voyages sailing.

2

You get it in writing

Your price, the $500 non-refundable deposit and the 9 July 2027 balance date, set out in writing before you pay anything. Once you book, your monthly payment schedule follows.

3

Flights and insurance

International flights, into Santorini and home from Athens, are not in the price and we are happy to quote them. Both ferries inside Greece are included. We can arrange travel insurance too.

4

Everything you need before you fly

Once your final payment is in, your pre-departure information follows: documents, ferry times, and what to pack for islands of steps and a lively wind.

Questions

Important notes

Will a Majestic Dream Vacations host travel with the group?

When ten or more travellers have paid, a Majestic Dream Vacations host travels with the group. Below that number the trip runs without one, and you have a named contact at Majestic Dream Vacations who handles anything that comes up while you are away.

How do the payments work?

A $500 per person deposit, which is non-refundable, reserves your place. After you book, we send a monthly payment schedule to spread the rest, with the balance due 9 July 2027.

Are payments refundable?

The deposit is non-refundable and non-transferable. If you cancel before the final payment due date, 9 July 2027, payments made after the deposit can be applied as a travel credit toward a future booking with us. The credit is non-transferable and valid for one year from the date you cancel. After that date, all payments are non-refundable and non-transferable. Travel insurance is strongly recommended to help protect your vacation investment.

Where does the trip start and end?

It starts on Santorini on 8 September and ends in Athens on 16 September. You book your own flight into Santorini and your own flight home from Athens, and we are happy to quote both. If you are coming from our Virgin Voyages sailing, you fly Rome to Santorini on 7 or 8 September; that flight is not included.

How active is this trip?

Moderate. Santorini is a place of steps: its villages sit on cliffs, and paths are often stepped and uneven. Athens is a walking city with little shade. Comfortable shoes with grip matter more here than almost anywhere. There are two ferry crossings, Santorini to Mykonos and Mykonos to Athens, so pack to carry your own bag onto a ferry.

What is the weather like?

Mid-September is still warm, typically in the 70s and 80s F, with the sea at its warmest of the year.

Where do we stay?

Hand-picked hotels on Santorini, on Mykonos and in Athens, with breakfast daily. We will name the properties here once they are confirmed.

What documents do I need?

Tell us your citizenship when you book and we will confirm the travel documents that apply to you, well before you travel.

8 to 16 September 2027

Stay for the evening

$3,740 per person sharing a double, with a $500 deposit to reserve. Book a consultation and we will talk you through the trip, your room and your payment dates.