Our Perfect Greek Island Hopping Itinerary

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Last summer we embarked on the best of Greek Island hopping holidays. With the help of some experienced collaborators, we assembled a perfect getaway to Greece. Since then, we have been asked about our Greek island hopping itinerary many times. We are always happy to share it with friends and family, but wanted readers to have it too! Read more to see how we blended the best of everything. We really had it all on this vacation! There was relaxation, partying, history and amazing Greek food during our Greek island hopping tour.

How to pick the best Greek Islands

One reason we think we have the best Greek island hopping route is that we carefully picked the best Greek islands. The travel between then was simple and the mix of destinations gave us a taste of everything we wanted in a Greek island vacation.

Tips for picking your Greek Island Hopping Routes

  • Most importantly, when planning your island-hopping itinerary, consider the ferry schedule. greeka.com is a good resource.
  • Schedule your trip so that you can easily move from one island to the next.
  • You may pay more to use a high-speed ferry, but you’ll gain time on the islands and it’s usually less money and time than flying.
  • Consider the reputation of the island. Some draw a party crowd and others draw a more mature crowd seeking relaxation.
  • Plan your activities in advance based on what each island offers.
  • Make sure you are covered with flights, lodging, and travel insurance. Before you continue, check out our Travel Resources page to make sure.

Our Greek Island Hopping Route

We flew in and out of Athens which made the transportation a bit easier than flying into the islands. We saved money by taking the high-speed ferry to each island instead of a flight. Time was saved as well because we didn’t sit in airports. This was also a beautiful way to enjoy the waters and passing islands.

You can read our itinerary for a day in Athens HERE. It’s a great way to make the most of a limited time in Athens.

From Athens, we moved on to Sifnos. There we had some relaxation on the beaches. Sifnos boasts fantastic shores, some mild nightlife and restaurants. Next, we moved on to Santorini. We could have easily spent a week in Santorini. There’s a lot of nightlife, layers of history, world-famous beaches, great sunsets, a gorgeous natural landscape and fantastic foods. Our last island was Mykonos. This island also had incredible beaches, a vibrant party scene, LGBT nightlife and some excellent restaurants.

Here is our itinerary:

  • Fly into Athens (spend 1 night)
  • Hellenic high-speed ferry to the island of Sifnos (2-3 nights)
  • Hellenic Seaways high-speed ferry to the island of Santorini (3 nights)
  • Minoan Lines Ferry to the island of Mykonos (2-3 nights)
  • Fly from Mykonos into Athens (spend 1 night)

You can stretch or shorten any of these destinations by a night or two. It all depends on your personal preference, but for us, this was just about right.

Flying into Athens

We flew into Athens from Copenhagen on Norwegian Airways. Flights on SkyScanner are showing roundtrip airfare from New York City to Athens under $500 USD in July. From within Europe you’ll much cheaper fares – we paid $230 USD. As always. If you’re flexible with your travel dates and times, you’ll have the best fare.

We spent most of our touring in Athens on the back-end of our trip. Our first night in Athens we spent settling in, organizing for the trip ahead and meeting some relatives of our travel partners. We spent this night in Athens and our time in Sifnos with our close friend and his Greek-American parents.

They showed us around some of their favorite places in Athens that they have visited over the years. It was cool to see how locals are out eating dinner late at night. The Southern European meal schedule meant the streets were bustling well past 10pm. We had our first real Greek salad and souvlaki of the week. Then we got to bed for our early ferry.

Greek Island Hopping Stop 1: Sifnos

Why go to Sifnos?

We took an early ferry out of Athens with our friend Yianni and his parents. We reached our destination after 2 hours and 40 minutes on the high-speed ferry. Our first island stop in this Greek island vacation was Sifnos.

This was our quiet relaxation portion of the island itinerary. It was a perfect Greek island to gear up for the busy touring in Santorini and the partying of Mykonos.

Sifnos is a small island in the Cyclades Island group with soft sand beaches and famous pottery. There’s just the right amount of excitement in Sifnos and it’s one of the best Greek islands for couples.

Sifnos Island Greek Ferry Greek Island Hopping
Arrival on Sifnos Island, Greece

Where to stay in Sifnos

We stayed in Kamares, the town where the ferry drops off visitors. It was a short trek to our hotel and we rented a car in Kamares to explore the island.

The hotel, Sifnaika Konakia, is air-conditioned and has great views of the beach and surrounding mountains. It also boasted 3-stars for around $125 USD per night. In this area you have a lot of restaurants, shops, cafes and a few beach bars. There’s no shortage of things to do in Kamares.

What to do in Sifnos

Spend a night in Apollonia. This is the main village of Sifnos and the best bars and nightlife. The city has the winding, white-walled structures that you picture when you dream of the Greek islands. There’s a lot of great shops, so it’s also perfect for an after-dinner stroll.

Visit Sifnos Castle. This is hardly the most impressive castle in the world, Europe or even Greece, but it’s a cool afternoon activity. This is a fortified city, or citadel, from the 14th century. It’s mostly in ruins, but a great historical stop to easy your restlessness on this relaxing island.

Chrisopigi Monastery is worth a visit for the picture alone. The beautiful surroundings of this structure make it an incredible photograph. Inside you’ll find artwork and it sits right on the water.

chrisopigi sifnos island
Beautiful Chrysopigi Monestary in Sifnos, Greece

Sailing is great in Sifnos. There are many sailing tours offered from the shops in Kamares. We did not go sailing, we spent most of our time on the beach, but the sailing winds were present. Another option is speedboating. This is more affordable as a group, and will cost $159 USD for 4 people to do a 4-hour boat trip to Poliegos Island. You can click HERE for those details.

Beaches in Sifnos

Vathi Beach was my favorite beach on Sifnos. Parking was tough so go there, but get there early. There are some great restaurants on your way in or off of the beach too. Along the coast there are a couple of nice beach bars where you can rent chairs for 5€. It’s a beautiful sandy beach and very comfortable if you just bring a towel.

Vathy Beach Sifnos Greek Island Hopping
Mike snap chatting the shoreline in Vathy Beach – lucky umbrella number 13

Kamares Beach was the closest to our hotel, so we spent a lot of time there. The water was super warm since it’s along a protected harbor and in the direct sun all day. The shore is lined with beach bars. This means you can eat and drink between swimming or have service to your beach lounger.

Apokofto Beach is another fantastic beach option in Sifnos. You will have to drive from Kamares but it’s worth it. They have shower and changing rooms available. The beach also host some nice tavernas and gorgeous views. Like the rest of Sifnos, it’s a soft, fine-sand beach with crystal-clear water.

Greek Island Hopping Stop 2: Santorini

Why go to Santorini?

After 3 days and two nights in Sifnos, Mike and I took the ferry to Santorini with our friend Yianni. We booked our ferry for tickets on Hellenic Seaways for 51€ each. This once again placed us on the high-speed ferry and we reached Santorini in 2.5 hours.

On Sifnos we relaxed, on Santorini we were go, go, go. Santorini is the best Greek island for travelers who want a lot to do. It’s a tourist’s heaven with stunning natural features, some very unique beaches, great food and ancient ruins. There are a ton of activities in Santorini and we got through most of them in two nights and three days.

Where to stay in Santorini

Like most of our Greek island hopping, we rented a car. There are bus options on Santorini, but renting a car was best. It was cheap to do and made the most sense for our plans. It was easy to find a rental once we arrived in Santorini. We used Kronos rental agency and they were great. you can also look into a private transfer for about 15€ per person HERE.

With the car rented, we drove to our hotel, Hotel Thirasia. We had a pool-view apartment that had two rooms and air-conditioning. It was 126€ per night, which was a low-cost option for 3 of us to share. They had parking for our rental car, a very helpful front desk and a pool.

Hotel Thirasia Santorini Greek Island Hopping
The lovely pool at Hotel Thirasia

The hotel is located in Fira, which was a great location. It’s central to everything and basically the heart of Santorini. Fira is loaded with cafes, shops, restaurants and bars. I also suggest staying in Oia, which is on the northern tip of the Santorini caldera. Oia is known for its spectacular views, especially of sunset. It’s lined with cute pathways that are home to restaurants, shops and hotels. There are paths down the hillside of the caldera.

What to do in Santorini

Explore the Natural Landscapes of Santorini

Hike the caldera. There are hiking trails between Fira and Oia that are great. Walking along the streets of

Caldera drive Santorini Greek island hopping
Taken from a pull-off as we were driving the caldera – facing towards the volcano and North Santorini

Drive the caldera. We didn’t have time for a hike, but we were able to drive along much of the caldera on the southern part of the island. There are areas to pull off for pictures and to enjoy the panoramic views.

Take a boat to the volcano. We took a 3-4 hour tour from the Fira old port (there is a ski lift between Fira and the old port). This went to the Hot Springs and Nea Kameni, which is the volcano. You can swim in the hot springs and hike up the volcano (about a 20 minute hike) for spectacular views. Make sure to wear an older bathing suit – the minerals in the water of the hot springs may stain your swimwear. You can also save money by bringing your own refreshments including alcohol. If you are short on time you can purchase them on the boat.

Boat tour Santorini
This is the same boat we took, just one that was leaving as we were arriving

We took this boat tour through GetYourGuide and it was a highlight of the entire trip. Click HERE to book your own for 39€.

Visit the spectacular beaches

The Red beach is incredible. Reaching the Red Beach requires a bit of a hike from a parking lot (15 minutes, rugged terrain). We recommend you wear sturdy shoes to reach the red beach because of the terrain.

Red Beach Santorini Greek Island Hopping
The Red Beach – entirely worth the hike

The Black Beach is neat. To reach it, you drive down a steep stone road and park right near the beach. The sand is not very comfortable as it’s mostly volcanic rock. It’s almost mandatory that you rent a chair if you want to lay out. Also be sure to wear your footwear onto the beach because the sun’s heat is absorbed by the black beneath you.

Black Beach Santorini
Santorini’s Black Beach

There are other spectacular beaches on the southern coast, and some are more accessible by water taxi. Look into visiting these other beaches. The east coast of the island has more resort-type beaches – Kamari and Perissa are the most popular.

Visit some ancient ruins

Ancient Thera requires a drive up crazy switchbacks. It’s worth the intense drive. Once up the hill, you see that it is a neat town that was built over several times. There is still a bit of a hike up from the parking area, and the sun is intense. Make sure you wear sunscreen, I got a nice red burn due to the lack of cover on the top.

The excavation of ancient Akrotiri in Santorini - Greek Island Hopping
The excavation of ancient Akrotiri

Ancient Akrotiri is an active excavation site of an ancient town. Wandering through, it was amazing to see the excavation. Even more fascinating is that many of the ancient structures resemble the modern ones.

Ruins of Ancient Thira in Santorini
The ruins of Ancient Thira

This site is massive and overwhelming without a guide. There is a bus tour that includes stops at Prophet Elias’s Monastery, Megalochori village, the black beach and the red beach a winery and a tavern for a meal of fresh fish. The cost is 35€ and does not include the 12€ fee to enter Akrotiri. Click HERE to book.

Visit a winery or brewery

There are a couple wineries and wine tours you can do around the island. Each can coordinate wine tastings for you, or you can book a tour to several wineries around the island by clicking HERE.

There is also Santorini Brewing Company which has decent beers. We were not able to visit their brewery, but did make it to their restaurant in Fira. When we were there, we sampled many beers and would have planned a day with them if we had additional time.


Sunsets in Santorini are absolutely spectacular. People flock to Oia for the sunset. The best way to see a sunset there is to sit out on Oia Castle (an old Byzentine fort) and be amazed.

Santorini Greek Island Hopping Sunset
The sunset over Oia

We also saw one sunset right in Fira. There is a restaurant that has elevated seating so you can have drinks and dinner while watching the sunset.

Wherever you watch the sunset – get there early! Crowds take over for sunset, but if you arrive an hour or so early you’ll secure a spot. In the quieter season (September through May) you should be fine.

Crowds gathering to watch the sunset in Oia Greek Island hopping
Crowds gathering to watch the sunset in Oia

There are also sunset boat tours available. For 98€ you can do a 5-hour sunset cruise that includes dinner, drinks (including wine), snorkeling in front of the red and white beaches and a visit to the hot springs and volcano. To book or see more information click HERE. This includes a lot and is one I would recommending splurging on.

Greek Island Hopping Stop 3: Mykonos

After not enough time in Santorini, Mike and I headed solo to Mykonos. We took the early ferry on Minoan Lines for 52€. Paying extra for the high-speed ferry kept the travel time to 2.5 hours. The time went quick as we ate breakfast and had a few Mythos beers on the ferry.

Mykonos sea port Greek island hopping
Pulling into the sea port in Mykonos

Why go to Mykonos?

Mykonos is known the world over for its vibrant party atmosphere. There are wild beach parties with thumping electronic music and all-night parties in Mykonos Town. It’s a popular Greek island hopping stop for LGBT travelers. It’s also well-known by those who wish to follow the footsteps of Jackie Kennedy-Onasis. There’s even a pricey gay bar called Jackie O’s and a beach party by the same name.

Mykonos while greek island hopping
Mykonos is just perfect

Still, Mykonos offers so much more. Pristine beaches, an iconic row of 16th century windmills and a fabulous food scene attract all types of visitors. This is the reason why we have recommended our itinerary to friends and family of diverse ages and backgrounds and they all love Mykonos.

Where to stay in Mykonos?

The best area to stay is Mykonos Town, or Hora. This is the area of the old port, the nightlife, the iconic windmills and the streets of winding whitewashed buildings. All the action is in Mykonos City. There may be a little sticker shock in Mykonos, as this is the most popular and expensive destination for anyone doing some Greek island hopping. It’s worth the price you’ll pay though – Mykonos is easily one of the best Greek islands to visit.

Greek Island Hopping - Mykonos
Definitely stay in Mykonos Town – you won’t be disappointed

We can recommend a few options in this area. One is the luxurious Oniro Suites. The rooms at this boutique hotel are gorgeous and have unbelievable views of the sea. There is a free breakfast and WiFi as well as a 24-hour front desk and concierge. The hotel has a gorgeous pool that also has a fabulous view. Best of all, Oniro Suites is in the heart of Mykonos City. A room at this 4-star location will cost about 350€ per night and you can find out more HERE.

hotel pool mykonos
From the beach to the pool with a view

The Elena Hotel is a 3-star version of Oniro Suites with more availability. The rooms are well-appointed and it also includes breakfast BUT will bring the price down by about half – 173€ per night. There is no pool, but it’s also close to the beach and will give you a fabulous cost-friendly stay.

For LGBT travelers, The Elysium Hotel is the ultimate gay hotel in Mykonos. There is a gorgeous pool with a sprawling deck, immaculate landscaping and super fun pool bar. The nightly drag show is fantastic and draws huge crowds throughout the season. The sunsets on the deck here are reason enough to visit The Elysium Hotel. A nightly rate of 190€ makes it the best place for LGBT travelers to stay while in Mykonos.

What to do in Mykonos

Get lost in Mykonos Town. The place is a maze – just wander around the streets. It was one of our favorite things to do while we were in Mykonos and you won’t be let down. Worst case, you’ll stumble into a neat cafe or cool shop. We could not find a free walking tour, which we can usually get in European city break trip, but if you prefer a guided tour and are willing to pay 39€ – theres one you can book HERE.

The iconic streets of Mykonos
The iconic streets of Mykonos

Grab a Drink in Town

Go to Jackie O’s and the gay bars in town. It’s an iconic bar in an iconic area of an iconic island named after an iconic woman of history. It’s a little pricier than Babylon Bar next door, but now you know where to have your second drink of the night. Start your night with a happy hour, sunset drink at Elysium Hotel and stay for the nightly drag show. It’s an excellent show, has great views and the crowd is fantastic. Everyone will be there, so should you.

Sunset Mykonos while Greek island hopping
Sunset from the deck of Elysium Hotel

Little Venice is right on the water and one of the most beautiful places I have ever sat for a drink. There is a waterfront sidewalk that you can watch the waves crash into. The bars lining Little Venice are more expensive but worth it for a drink or two. As mentioned, there is some sticker shock in Mykonos, but average these prices with Sifnos, and it comes out in the wash.            

Little Venice Mykonos greek island hopping
It’s worth the sticker shock for a drink or two along Little Venice

Dine out in Mykonos City

There are lots of small restaurants in Mykonos and they can be a bit touristy but nice.

We ate at Nice n Easy right on the waterfront between Little Venice and the Windmills. The restaurant was “Mykonos pricy” but had great views, a lovely deck and a great organic menu.

Little Venice in Mykonos
Another shot of Little Venice – a bit pricey to eat or drink but – location, location, location!

Another good dinner was at Niko’s Taverna (link for google maps only). This is a Mykonos staple and was crowded, but not for lack of service. We had a hearty meal and since we were going out the night we ate there, this was a good thing. The menu is Greek, with a heavy selection of fresh sea food.

Go to beaches

Beaches in Greece generally have beach chairs and umbrellas that you rent for the day. In Mykonos they were typically 20€ for two chairs and an umbrella. The cool thing was that if you spent 20€ in food or beverages, it was waived. Some chairs had a higher mandatory spend so note that your charge may vary.

Elia Beach one of the most popular beaches in Mykonos. The beach is a little more relaxed when compared to Paradise and Super Paradise beaches. The water is calm, clear and the sand is soft and white. When you arrive from the road, the beach area to your right is mostly occupied by straight or mixed crowds. Moving farther down the beach to the right you will find more gay beachgoers and some clothing optional area closest to the rocky outcrop.

elia beach mykonos greek island hopping itinerary
Gorgeous Elia Beach

Paradise Beach is a gorgeous beach. It’s more of a party beach than Elia and ranked #14 in the best beach club in the world. Read up on what beaches you want to visit for the right mix of relaxation and amenities.

Super Paradise Beach is the home of Jackie O’s Beach Bar. Mentioned above, this is a popular beach party with electronic music, world-famous DJs and a large gay crowd. It’s not as much a beach to relax on as one to party on, but highly worth the visit.

Our Greek Island Hopping ended: back to Athens

We finished our time in Greece the way we started – in Athens. This time we were alone and set out to explore. We flew back to Athens from Mykonos and had one full day.

Stoa of Eumenes
The stoa of Eumenes

Where to stay in Athens

Yes Athens is big, but most of the action is in the city center. Stay somewhere around the center of the city. We stayed near Omonia in the northern central area, and took the metro into the sights. There are plenty of western hotels around the city the most desirable location is walkable to Plaka, Syntagma or near a metro stop that will take you there. Everything to see is basically right around the Acropolis.

We stayed at The Best Western Candia Hotel. It’s 4-star quality and included free breakfast and WiFi. Best of all it was easy to get around from that location and only 85€ per night. You can book it HERE.

Taxis are everywhere and relatively cheap (except to/from the airport). The metro is clean and quick, and that is how we returned to the airport for our departure.

We give you a full itinerary for our 24 hours in Athens HERE in this post.

It was an amazing experience visiting Athens and getting to island hop around Greece. There are even more islands we want to return for and some time in the future we will.

Where else do we need to go? Comment below and let us know.

Try any of our suggestions? Give us your thoughts!