Amazing 10-night Greek island hop itinerary

My husband I went on an incredible 10 night trip through Greece. Now, you could say that we are pros at seeing the most in the shortest amount of time so you could also say that this is too fast paced of an itinerary. Not everyone loves to travel like this so this kind of island hop itinerary may not be your cup of tea but if it is, hopefully, you will get some inspiration. This 10-night Greek island hop itinerary outlines our stops and accounts for travel to and from the United States.

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10-night itinerary

• 1 night – overnight travel

• 1 night – Athens

• 2 nights – Mykonos

• 1 night – Paros

• 2 nights – Milos

• 2 nights – Santorini

• 1 night – London

A few facts

• We traveled in the “shoulder season” for Greece (May)
• We booked this trip with a mixture of credit card points and cash
• We used our Memorial Day holiday – which means we had 10 nights of travel and only had to take 5 days off work

When to go

Greece was everything we dreamed of but one of the things we were most concerned about is the crazy crowds. We were thrilled to find out that the end of May quite possible may be the best time to travel to Greece. Why?

• It is before their summer rush
• It is warm and pleasant but not extremely hot
• The Greeks who are there working for the season are still fresh and extremely excited to be there  
• And did I mention: no crowds!

Getting there

Its no easy feat to get from Dallas to Athens solely on points and miles (unless you are in the off-season or want to burn through all of your travel points). We ended up utilizing a 2 stop route.

• DFW to AUS. American Airlines.
• AUS to LHR. We wanted to be comfortable on our long haul flight and it was worth throwing in one extra stop (AUS) to purchase affordable Premium Economy seats on Virgin Atlantic to be comfortable while “crossing the pond”. We are both 6’+ and it was well worth it to get Premium Economy for the extra leg room. We loved flying on Virgin Atlantic – they had a fantastic crew and great service, plus, Virgin Atlantic offers great deals for points purchases making getting round trip to London in a premium class affordable.
• LHR to ATH. British Airways flight down to Athens (which we scored with points).

How to island hop

The best way to hop between islands is by using the ferry system. Make sure you check out Ferryhopper to check schedule times and book your tickets in advance.

Fair warning for the mega ferries: you are funneled in where the cars are loaded and then sent up a narrow hallway to the seating area. The seating area is very nice but I wasn’t a fan of being stuck in a closed space while the boat was cruises out of the port.

There are also smaller ferries that go in between the smaller islands. I found these much easier to get on and off but they did ride a bit rougher.

While the system seems chaotic, the ferries stuck to their schedule very well during our trip.

What to pack

When it comes to packing, I would say to pack the usual for a beach / warm weather vacation.

• A few nicer pieces: flowy dresses and skirts for the ladies / linen button ups for the guys
• Swimsuits and cover ups
• Athletic clothes for hiking
• Comfortable shoes – you will be walking a lot
• Jean jacket or other light jacket option (if you are traveling in shoulder season, it can get cool in the evening)
• Sunscreen

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Athens

To start off our 10-night Greek island hop itinerary we spent one night in Athens – this was the perfect amount of time for us as we are not history buffs or city vacationers. 

• How many nights: one
• Where to stay: AVA Hotel – walking distance to the Acropolis
• What to do: tour of the Acropolis and shopping in the Plaka area
• Where to eat: Makrigianni Street on the south side of the Acropolis
• Tips: I would highly recommend visiting the Acropolis early in the morning when it opens as the crowds are minimal. As the day goes on, the cruise ship tours start arriving and there are swarms of people. After having some rooftop coffee and doing a little shopping we were already off to our next stop.
• Check out our Athens blog post for more details.

Mykonos

Mykonos is a great first island to start to the island hop through the Greek islands! In Mykonos, you have the freedom to party it up or relax and get adjusted to the time change (if you’re coming from the USA). We chose the relaxing option.

• How many nights: two
• Where to stay: Mykonos Ammos Hotel
• What to do: explore and enjoy seaside drinks in Little Venice; see the windmills; relax on the beach
• Where to eat and drink: nice n easy, Negrita
• Tips: The picturesque white washed streets of Mykonos are best enjoyed during off season. Crowds will make these street uncomfortable as they are pretty narrow.
• Read more about Mykonos!

Paros

Paros was described as “what Mykonos would be without the crowds” and I would agree with this. We stayed in the Naoussa area for the first day and the second day we checked out of our hotel and went to Parikia.

• How many nights: one
• Where to stay: Adonis Hotel in Naoussa
• What to do: explore Naoussa, Parikia, and Piso Livadi; enjoy some local wine; visit a beach
• Where to eat: main square in Naoussa
• Tips: rent an ATV – it is truly the best way to see the island
• Read more about our Paros here.

Milos

If you are looking for crystal clear waters and volcanic cliff formations, Milos is the place for you! Don’t skip it on your Greek Island Hop – it is truly one of a kind.

• How many nights: two
• Where to stay: Santa Maria Village in Adamantas
• What to do: boat trip to Kleftiko; Sarakiniko Beach
• Where to eat: Mikros Apoplous – seaside strip in Adamantas
• Tips: make sure you cliff jump at Sarakiniko Beach
• Read our Milos blog post for full details!

Santorini

Why not end your Greek island hop on the most iconic island of them all. With beautiful sunsets, volcanic beaches, blue domed churches, and ocean view plunge pools galore, Santorini cannot be missed if you are making your way through the Greek isles.

• How many nights: two
• Where to stay: Cave Suite Oia (in the postcard)
• What to do: dinner in Ammoudi Bay; catamaran cruise; take in all the views
• Where to eat: Sunset Taverna – have the Lobster Linguini
• Tips: Book your table in Ammoudi Bay ahead of time and set up a photoshoot – you wont regret it!
• See our Santorini blog post for more.

Getting home

To maximize our time in Greece, we took an evening flight from Santorini to LHR on BA with points where we stayed one night at the Hyatt near the airport. This made the next morning’s 11am flight extremely easy. Then (insanely) we were home by about 4pm to get ready for work the next day

Hope you got some inspiration from our Greek island hop itinerary and dang, talk about maximizing that PTO!

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