top of page
  • Writer's pictureParadoxTravel

Best of the Greek Islands - a hybrid travel itinerary for Mykonos, Santorini and Naxos

Updated: Jan 24

Luxury Travel in Oia, Santorini Photo: Jen Stover - Paradox Travel     See complete itinerary at

Traveling to the Greek islands – my mind always conjures up romantic, sun-soaked, luxury travel images of this beautiful archipelago. I’ve experienced them twice. Once years ago, I backpacked with a girlfriend, with no advance accommodation planning, a limited budget and adventures that included late night scooter rides and an introduction to nude beaches. Hey, I was thirty. But the second time I went, I was married and had a little larger budget. This time I wanted to experience two of my favorite islands with my husband and I was hoping he would love them as much as I did.

So this travel itinerary includes Mykonos, Santorini and I added in Naxos. It was an island I had yet to visit and was on the return ferry route back to Athens. Each of these three islands have a completely different personality: Mykonos is all about sexy affluence, fine dining, beach parties and shopping. Santorini oozes quiet romance, serenity and style. Naxos, with it's rich history, is casual, laid-back, unpretentious. This is the beauty of these islands - they each are so very different.

In contrast to our Dolomites Trekking trip, which was all about Active Travel, this trip was primarily about romantic Luxury Travel. We did manage to walk a lot and did a few runs and hikes to counterbalance our food and wine indulgences. But hopefully, this simple, straight-forward itinerary encourages you to plan that surprise romantic birthday or anniversary trip for that special someone. I’m not knocking the trip with my girlfriend – I can count numerous tales with fond memory. But nothing beats watching the sun set with your spouse or a romantic partner. So with that in mind, let's go to the islands.

The Active

On the islands, you can walk almost everywhere or rent a scooter to get around. Do it! Ride double, if one of you doesn’t know how to drive. Or rent a 4-wheeler if that set up makes you more comfortable. On Santorini, there is a long walk path that connects Oia to Fira. It will take a few hours to walk its full length but the views are beautiful and there are plenty of sidewalk cafes en route.

The Leisure

Mykonos and Santorini are both chock full of gorgeous hotels and upscale dining. So you won’t have a problem finding one that fulfills your need for luxury or comfort. See links within the itinerary below for some of our favorites.

TIP: I use this site to book hotels frequently, as very often they don't need a deposit and have very lenient cancellation policies.

How to Connect

On Santorini, Tours by Locals can help you see the island in unique ways and keep your tourism money on the islands. On Mykonos, you can help local guides like Antonis make a living by enlisting their local services to learn more about the island.

Trip Rating – L1 English spoken, European and Mediterranean food, very international destination.

Month of travel – End of September/October; Gorgeous weather, we got really good flight prices this time of year.

Length of trip - 10 or 12 days

If you want to see three islands and spend a day in Athens to see the Acropolis as we did, plan on 12 days in total. If you simply want to go to Mykonos and Santorini, you can save a few days. You can fly into Mykonos from Athens, ferry to Santorini, then fly directly back to Athens from Santorini. This is a fairly cost, and time, effective option.

Mykonos Island, Greece Photo: Jen Stover - Paradox Travel     See complete itinerary at

The Details

Day 1 – Getting to Mykonos

Flight - 6:30a San Francisco > JFK > Athens, arrives 3p (Delta)

Flight - 4:45p Athens > Mykonos, arrives 5:20p (Aegean Airlines)

NOTE - I bought these two tickets separately for better overall price

Accommodation suggestion - Bluetopia Suites – Sea View Suite – 3 nights

This place was a find! Great location – walking distances to old town Mykonos, restaurants, shopping and bars, yet still a very quiet location. Modern rooms, breakfast served on your balcony with views of the windmills. No pool. But when on Mykonos, go to the beaches! This was perfect for our three night stay. Next visit, we may stay a week and would consider another area of the island.

Activity suggestion - Mykonos nightlife does not get going until well after 11pm. And most locals don't eat dinner until 9 or 10pm. So once you settle in, go walk around and have a cocktail at Belvedere’s lounge before dinner.

Dinner suggestions - Some of the best restaurants in old town are deep within the streets of Mykonos, so wander in. It is very well lit, surrounded by great shopping. For casual restaurants, you can typically get in without a reservation of you dine before 9pm. Simply wander around and see what entices you. For more upscale establishments, make reservations before you arrive on the island.

Grilled octopus at Nikolas Taverna, Mykonos  Photo: Jen Stover - Paradox Travel

Day 2 – Mykonos

Activity suggestion - rent a scooter or a 4-wheeler and explore the island! We spent a day at Elia Beach and loved it. Bring your own towel or rent one there. They have chairs for rent and a modern style bar and restaurant.

Happy Hour suggestion - 180 Sunset bar – about a 20 minute walk from downtown, up a hill to the terrace of Mykonos Castle. Open air, best view of sunset and the downtown area. Reserve in advance! This place fills up fast.

Accommodation suggestion - Bluetopia Suites

Dinner suggestions - as above

Luxury Travel -180 Sunset lounge, Mykonos Photo: Jen Stover - Paradox Travel  See complete itinerary at

Day 3Mykonos/ Delos Island Day trip

Activity suggestion - go on your own or hire a guide and check out the ruins on Delos Island. Or if you feel like sleeping in, go shopping!

Happy Hour suggestion - Semeli bar

Dinner suggestions - as listed above

Delos Island, Greece Photo: Jen Stover - Paradox Travel    See our complete itinerary at

Day 4 Santorini

Ferry – 10am: SeaJets Champion 2 – high speed (2 hours)

Activity suggestion: check into hotel in Oia – preferably on the caldera. Go to local store and buy a bottle of wine or champagne. Not much is going to beat your own view at sunset if you have a caldera room with at least a small deck.

NOTE: off all the small caldera towns, Oia the quietest, most romantic and has many terrific restaurants. Fira is a tourist trap. TIP: Tourists from cruise ships come to Santorini between noon - 4pm. If you want to avoid this, get up early, then either take a nap or spend time by the pool, then go out again after 4pm.

Accommodation suggestion: Katikies (Junior Suite) – 4 nights

NOTE - when we arrived, the concierge wanted to give us an ‘upgrade’ room, which was larger but did not have the same view and felt very dark. We actually declined and stayed with the Queen bed Junior Suite and loved it.

Accommodation alternatives

Dinner suggestion - Catch bar, Black Rock, Karma

Luxury Travel at Katikies Hotel, Oia Santorini  Photo: Jen Stover - Paradox Travel   See our complete itinerary at

Day 5Santorini

Activity suggestion - sleep in, eat breakfast on your balcony, lounge by the pool, drink midday champagne and enjoy the incredible caldera view!

Dinner suggestion - hike down the many stairs to Amoudi Bay and Ammoudi Fish Tavern. Get a donkey ride back up the stairs, or cab back.

Oia, Santorini - Paradox Travel  See our complete itinerary at

Day 6 – Santorini

Activity suggestion - after having breakfast outside somewhere, walk the Oia to Fira path and have lunch with a view en route at Onar. Cab back to Oia. If you are hungry once in Fira, have a gyro and a beer at Lucky’s – fantastic!

NOTE - if you stay at Katakies, they will give you a private cell phone to call the resort’s driver to come pick you up from wherever you are. Nice perk.

Dinner suggestion – Ambrosia

(Imerovigli is the picturesque luxury, caldera-edge village between Oia and Fira)

Day 7 – Santorini

Activity suggestion - Wine tasting day! Venetsanos winery and Santos winery have terrific views (try the Assyrtiko – unique island grape)

Happy hour suggestion - a Sunset Cruise

Dinner suggestion - wander around Oia and pick one that calls to you! For more a more casual night out, grab beer and sit outside at Pitagyros

Oia, Santorini Photo: Jen Stover - Paradox Travel   See our complete itinerary at

Day 8 – Naxos

Ferry – 10:45 a Seajets Champion Jet 1 (1 hour) Santorini to Naxos

Activity suggestions - Explore the castle area (Kastros) in downtown Naxos, walk to the ruins of the temple of Apollo (Portara) for sunset, wander down into the streets around the castle area for cocktails at 520 Bar and then dinner at La Vigne wine bar

Accommodation suggestion - Boutique Hotel Glaros

Naxos Island, Greece - view from Portara Photo: Jen Stover - Paradox Travel   See our complete Greek Island itinerary at

Day 9 - Naxos

Activity suggestion - rent a car for the day or take the bus to Plaka Beach. Or drive the island and explore the ruins of Temple of Demeter or check out some of the other villages.

Dinner suggestion - Typografio

Accommodation suggestions - Boutique Hotel Glaros

Temple of Demeter, Naxos Photo: Jen Stover - Paradox Travel   See our complete Greek Island itinerary at

Day 10 – Back to Athens

Ferry - 9:30 a Blue Star from Naxos to Pireus (Athens) - arrives Athens 3pm

NOTE – You could easily end your journey here if you are short on time, simply head to the Sofitel Athens airport hotel and fly home the next morning (10 day total). If you decide to stay and see the Acropolis, you can either stay downtown Athens or close to the airport. It depends on how much time you want to spend in downtown Athens. We only wanted to have one day to see the Acropolis. So for us, we opted to stay at the airport hotel, so we could leave our bags there and easily catch our international flight our early the next day. The Metro train runs every 30 minutes directly to and from the airport and downtown Athens/Acropolis. Below is our schedule:

Metro - ferry to hotel > Line 1 (green) to (change at Monastiraki) Line 3 (blue) to get from ferry dock to Sofitel Athens Airport Hotel.

Athens metro map

Accommodation suggestion - Sofitel Athens airport hotel (directly across from and walking distance from terminal)

Dinner suggestion - The hotel has a really nice lobby bar, with a good food menu. We opted for this due to simplicity and easy access.

Day 11 - Acropolis

Metro - Line 3 (blue) to Syntagna stop and walk, OR switch to Line 2 (red) and go 1 stop to Akropoli.

See Metro map here.

Activity suggestions - stroll the Acropolis and the visit Ancient Agora on the NE side. Check out the Temple of Hephaetus and then exit the property on the back side. Stroll back to the Metro station through the Plaka neighborhood with all its coffee shops and quaint restaurants.

Dinner suggestion - any one of the restaurants that call to you in the Plaka area.

Metro - back to Airport.

Accommodation suggestion - Sofitel Athens airport

Athena's temple at the Acropolis - Photo: Jen Stover - Paradox Travel   See our complete itinerary at

Day 12 – Home

Flight - 6am Athens > Paris > SFO

Have fun!


Feel free to check out some of our other travel itineraries 

from all other world! (as well as another area where I love to give a lot of free stuff away!)


If you like van-camping, check out some of the cool road trips we've done in our Sprinter van !


 Are you a photographer looking to hone your skills? My husband's a pro and hosts affordable online classes as well as a terrific speaker series with tips from other world-class professionals that will enhance you skill and creativity.

Check it out!

303 views0 comments


bottom of page