Cycladic Bliss: Sifnos, Milos & Santorini in 9 days

When staying in Sifnos, and the surrounding islands, it’s important to note that the nightlife isn’t as vibrant. However, one area I absolutely love is Platis Gialos. It’s centrally located, offers great beaches, and has some fantastic beach bars. The bus routes are straightforward and affordable, making it easy to get from point A to point B. Start your day by relaxing at one of the organized beaches near the beach bars. For lunch, head to NUS — they serve farm-to-table dishes, and trust me, you’ll want to avoid feeding the cats (it’s an inside joke you’ll get when you visit!). Sifnos is famous for its beans, so make sure to try some when you can. After a relaxing nap, you absolutely must enjoy cocktails in Apollonia. Check out Argo Bar, where you can sip great drinks on their rooftop. Spend some time wandering through the charming whitewashed alleys and do a little shopping. For dinner (or lunch), Drakakis is a must-visit — it’s an iconic spot you shouldn’t miss!

I highly recommend taking a day trip to either Kimolos or Serifos — both islands are just 30 minutes away by ferry, with regular services running during the summer. Be sure to pack your swimsuit, sunscreen, towels, snacks and goggles for a day of relaxation. Both islands are ideal for a slow-paced, peaceful day. You can enjoy their beautiful beaches and indulge in a leisurely lunch or dinner at a local taverna, depending on how long you stay.

Explore Kamares, the main port town of Sifnos, renowned for its pottery. The town is lined with charming restaurants and shops, and I love getting lost in the pottery stores while soaking in the local craftsmanship. Spend a relaxing day on its beautiful beaches. If you’re into history and culture, I highly recommend visiting two unique churches: Chrisopigi, known for being a miracle site, and the Church of the Seven Martyrs, which is truly special. For dinner, Fasolou is a must-visit. The owner, Michalis, is a local and serves up some of the island's best traditional recipes. If you’ve got a sweet tooth, make sure to stop by Gerontopoulos — it's the place to go for breakfast, coffee, Greek pastries and delicious ice cream, and it’s open all day long.

Milos is a larger island that’s easily accessible by boat. The island is home to charming fishing villages and, thanks to its volcanic origins, boasts some of the most stunning landscapes in the Aegean. Milos is a true photographer’s paradise, with its dramatic rock formations, the surreal white limestone cliffs of Sarakiniko and impressive sea caves and coastal grottoes. Celebrities like Justin Bieber and Gwyneth Paltrow have visited this enchanting island, adding to its allure. If you're an outdoor enthusiast, Milos is an absolute must-visit, offering endless opportunities for adventure, exploration and taking in breathtaking natural beauty.

Most tours depart around 10:00 am and include light bites during the trip. Be sure to bring some cash for tipping your crew at the end. Not all boats provide goggles, so if you're into snorkeling or exploring underwater caves, I recommend bringing your own — along with sunscreen and a hat to protect you from the strong sun.

After a full day out on the water, wind down with some local Greek comfort food. I’d go for souvlaki — it’s a classic, originally known as the “working man’s meal” after WWII. Here’s how to order it like a local: choose beef or chicken, ask for it “with everything” (which means tomato, thick-cut onions, tzatziki sauce and fries all wrapped in a warm pita). Pro tip: ask them to add feta inside the pita — it takes it to the next level.

Take the day to unwind — whether that means lounging at the beach or simply relaxing by your hotel’s pool. For lunch, head over to Mandrakia, a postcard-perfect fishing village. I’d definitely recommend booking a table at Medusa in advance — it’s a popular spot for a reason. After lunch, take some time to stroll through the village and soak in the charming seaside vibe.

Klima is, in my opinion, one of the most underrated fishing villages in Milos. We had the best octopus at Astakas Restaurant — absolutely worth the stop. I recommend going for a late lunch so you can enjoy the golden light and relaxed vibe. After your meal, take some time to wander through the colorful little alleyways and soak in the charm of the seaside homes. Just next to the restaurant, there’s a beautiful little church that’s worth a visit — quiet, peaceful, and perfect for a few photos or a moment of calm.

In the late afternoon, grab your swimsuit and make your way to Sarakiniko Beach. Known for its moon-like white rock formations, it’s one of the most unique beaches on the island. Try to go a few hours before sunset or time your visit to catch the sunset there — it’s a surreal experience, and it tends to be less crowded later in the day.

From Milos, I’d recommend flying to Santorini — the seas can get rough, and a quick flight saves you the hassle. Once you arrive and check in to your hotel, the biggest thing to consider is where you want to stay. Most people choose Oia, since it's the iconic spot you picture when you think of Santorini — with its whitewashed buildings and famous sunsets. If it’s your first time visiting, I’d suggest staying in Oia to get the full experience. That said, catching the sunset in Fira is also a must — it offers a totally different but equally stunning perspective. Just keep in mind, Santorini isn’t really known for its beaches, so focus more on the views, wine and charming towns. Amoudi beach is the best spot for lunch — it's a quick walk down the caldera — there will be people offering to take you down with donkeys (politely decline). For sunset make your way to Fira where you can enjoy plenty of dining options and a beautiful sunset. In Oia, a notable place with authentic cuisine is Roka, and for a view, Ambrosia.

If you're looking for a day trip from Santorini, there are several options that go to Crete or Mykonos. Keep in mind that Mykonos offers a less authentic experience, and if you're traveling with young children, it may not be the most family-friendly destination.

If island-hopping isn't your thing but you still love a bit of adventure, consider doing the hike from Oia to Fira. It’s about 6 miles (roughly 3 hours) and offers breathtaking views the entire way. It’s a great way to see the island from a different perspective and take in the dramatic landscapes at your own pace.

For your final day in Santorini, I recommend ending on a memorable note with either a wine tour or a cooking class. One of my favorite experiences was a cooking class we did in Imerovigli — it’s conveniently close to the airport, making it a great option if you're flying out later. The class was small and intimate, and we learned how to cook traditional moussaka using Santorini’s unique white eggplant, which you can’t find anywhere else. It was the perfect way to connect with local flavors and culture before heading home.