2 1/2 Week Greek Islands ItineraryI dreamt of going to Greece since, I kid you not, Sisterhood of the Traveling Pants came on the movie scene back in ’05. It sounds so corny, I know, but there was just something so captivating about the Grecian blue waters surrounded by white homes built along the coastline that was mesmerizing. I think I started telling Sterling about this dream honeymoon dream of mine from the second marriage came up for discussion. Haha, he didn’t stand a chance.

I received a ton of questions about planning, booking, etc. in regards to our Greek ‘island hoping’ honeymoon. We did everything on our own {all the research, plotting + booking}, so this post is meant to break down the itinerary itself at a basic level. I’ll of courseeee be breaking out each island into a blog post all its’ own + write a more in-depth travel guide for each. But I hope this gives those of you looking into a trip to Greece a little more guidance on how it can be done on your own {sans travel agent}, and the amount of time you may want to dedicate to each island!

What was supposed to be a 13 day trip, quickly turned into 17 days for us {no complaints here}, due to a Ferry Union Strike – this happens quite often in Greece. So here goes,  2 1/2 Week Greek Islands Itinerary

Day 1TRAVEL DAY; departed from Charleston the morning after our wedding, connected in Philly –> London –> Athens

Day 2Travel day; we dedicated to begin our trip in Santorini since it was the furthest from Athens, and work our way back up the islands. A late afternoon connection to Santorini put us there by nightfall. Just enough time to get checked-in, unpacked + watch our first sunset over the Aegean.

2 1/2 Week Greek Islands Itinerary

Day 3SANTORINI, we have arrived. Spent the entire day exploring Oia.

Day 4SANTORINI; poolside + relaxing.

Poolside in Oia4

Day 5SANTORINI; rented a car to explore the island for the day! We also witnessed the Easter lighting of Pyrgos, Santorini – such a magical experience.

Day 6SANTORINI; poolside morning + took the car out for a long drive around the island.

Hotel shot

Day 7Ferry to NAXOS, except we missed our ferry stop {rookies} and traveled to PAROS for the night instead. It ended up being the Greek Orthodox Easter and there were no other ferries back out for the day. Haha, just our luck.

Nauossa Paros Port

Day 8Morning ferry to NAXOS, at last! Haha. Spent the rest of the day getting settled at the hotel + took it easy that night since it was a bit rainy.

2 1/2 Week Greek Islands Itinerary

Day 9Late afternoon ferry to MYKONOS. Got a little dolled up in blue that first night at our hotel {Vencia Boutique Hotel} + took in the gorgeous views of Mykonos Town at sunset.

First night in Mykonos2

Day 10MYKONOS; rented ATV’s to explore the island – saw a few of the popular beaches.


Day 11Night ferry to SYROS; our favorite island {aside from Santorini of course}.

View of Ano Syros
Day 12SYROS; Our first full day in Syros was glorious. The island is not as much of a tourist destination {in comparison to other cyclade islands}, but that’s one of the main reasons we chose it!

2 1/2 Week Greek Islands Itinerary
Day 13SYROS; explore, explore, explore! Reviews said the architecture was modeled after Italy {which we found to be very true}, so the homes + businesses were a bit different from the other islands. More colonial-esk. This street in particular along the water was just spectacular. Just look at the detail of the buildings and vibrant colors! I swear I could have photographed this street for hours…if only Sterling would have let me. We took a LONG walk up to Ano Syros, the oldest part of the city. Unfortunately most of the shops and restaurants were closed due to low-season, but the small pathways and decorated doorways were worth the trek.

Syros street

Day 14SYROS; rented a car to explore the outskirts of the island a bit more. We visited a couple secluded beaches, made a friend at dinner {whom continued to give us a tour around the entire island}, and witnessed perhaps the most amazing sunset I’ve ever seen {yet of course my camera died earlier that evening, so no capture other then my iPhone}.

2 1/2 Week Greek Islands Itinerary
Day 15SYROS; the island had so much natural beauty surrounding us, it was incredible.

Cliff of Syros

Day 16Late night ferry to ATHENS; we basically only had time to grab dinner and take a stroll around the base of Acropolis {I had to at least SEE it}!

2 1/2 Week Greek Islands Itinerary

Day 17Travel day home. Earlyyyyy morning flight out of Athens, landed back state-side the same day, later that evening.

Itinerary in Review3PROS

2 1/2 weeks was the perfect amount of time for us. I felt like the 17 days allowed us to really explore several islands {especially Santorini + Syros}. We were able to get a feel for the people, the incredible food, the culture + customs – it was amazing. Greece would be tough to see everything in under 2 weeks {especially on your honeymoon}. So so so happy we chose Syros as our ‘out-lying’ island. It was breathtaking {staying at Hotel Ploes for 6 nights definitely helped out a bit}, and a perfect mix of history/exploring and relaxation.

I also loved that we were able to really have a different experience on each island {in part due to hotel choices}. For example, Santorini was the WOW honeymoon time, Mykonos was more lively and party-esk, Paros was practically untouched by tourists during our visit, Syros was low-key romantic, and Naxos was amazing for history.

We didn’t book our ferry tickets until we arrived in Santorini – I’d recommend doing it that way, as it’s much easier then navigating online.


Looking back, Sterling + I both agreed it would have been nice to stick to 3 islands max {we ended up doing 5 total with our mishap Paros pitstop}. That way you really have several solid days on each island to DO things. I don’t know about y’all, but if a hotel manager recommends 5 amazing  restaurants to visit, but you only have time for 2, I get major FOMO. Haha. Traveling to/from + in/around the Greek islands take time, so definitely make sure you plan for that and build in extra time for travel. Between all the flights + ferries, I don’t think we realized how much time we’d be spending just getting places.

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So would you suggest booking the hotels beforehand and leaving the ferries for when you get to Greece?

This looks like the perfect honeymoon spot! I definitely want to take a trip to Greece in the next few years! The scenery is stunning!


Such a beautiful trip…LOVE all the photos!

Cathy, your Poor Little It Girl

I’m ready to go!!!

xo Jessica
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