Sailing the Greek Isles always sounded dreamy, but after spending two weeks hopping around the Cyclades by ferry, I’m convinced: ferries are the way to go! This trip was the perfect mix of relaxation and adventure, and since we were celebrating my sister’s 60th birthday, you’re getting the perspective of a slightly older (and hopefully wiser!) traveler.
Athens: The Perfect Kickoff
Like most Greek adventures, we started in Athens. We had two days to soak up the history at the Acropolis—the iconic hilltop “city” with the Parthenon and other ancient temples. We stayed at the Astor Hotel, right in the heart of the city. It was clean, walkable to everything, and the rooftop views of the Acropolis at breakfast (or with an evening drink) were unbeatable. I highly recommend!
Stress-Free Travel with Fantasy Travel
We booked our hotels and transfers through Fantasy Travel (feel free to PM me for details). We wanted flexibility, not rigid tours, and they delivered—plus, they saved us big time when we missed a ferry in Santorini! They also arranged a half-day catamaran outing on Santorini, which was a highlight. If you want to travel at your own pace but with a safety net, they’re a great choice.
Mykonos: Fun in the Sun
Our first island stop was Mykonos, about a three-hour ferry ride from Athens. We stayed at the lovely Adonis Hotel, just a short walk from town. My sister and I loved wandering the charming streets, shopping, and sampling drinks and meals. Mykonos is famous for its beach parties, so we checked out Paradise Beach—though honestly, I think I’d have enjoyed it more in my 20s! The party really starts after 4pm, but we went earlier in the day and just took the local bus (super easy). Unless you’re a party animal or on your honeymoon, two or three days here is probably plenty.
Paros: Laid-Back Charm
Next up was Paros, just a two-hour ferry ride away. Many say Paros is what Mykonos was 15-20 years ago—less crowded, more authentic, and still developing its beach scene. We stayed at the Agnanti Resort & Spa, which was beautiful but the rooms were a bit basic and the beds not super comfy. Our balcony had a nice view, though it did overlook some construction (we traveled in May, just before peak season). May is a great time to visit—the locals are happy to see you and the crowds haven’t arrived yet!
If I went back, I’d stay in Naoussa, an adorable, less touristy town. We also loved exploring Lefkes, a charming medieval mountain village. Renting a car was the best way to see the island. Paros was wonderful—three nights and four days felt just right.
Santorini: A Dream Come True
Santorini was hands-down our favorite. The ferry ride was under an hour, and we stayed at the Secret Spa in Oia (pronounced “ee-ya”). Three nights here was perfect. Yes, it gets crowded at sunset, but during the day it’s a joy to explore and shop. We rented a car to see the island, visited ancient ruins, and relaxed on Kamari’s black sand beach. The roads are narrow and sometimes bumpy, but the adventure is worth it (though my sister wasn’t a fan of the mountain switchbacks—no guardrails!).
The absolute highlight? A catamaran cruise around the caldera. If you do one thing in Santorini, make it this!
Milos: A Happy Accident
Mother’s Day brought a little hiccup—we missed our ferry to Milos! Oops. Thankfully, Fantasy Travel swooped in and found us a last-minute hotel in Fira (another Santorini town), and even arranged our transfers. As luck would have it, it rained in Milos that day but stayed sunny in Santorini. Sometimes, things just work out!
When we finally made it to Milos (a couple hours by ferry), things felt a bit more rustic and less organized. The port is a little tricky—your ferry might not be visible from the main restaurants, so keep an eye out! Milos is quieter than the other islands. We loved the stunning white sand beach and the cute fishing village of Klima, but otherwise, there wasn’t as much to do. The roads are very narrow and often unpaved, so we skipped driving here. Two days is probably enough, though another catamaran trip could have been fun.
Heading Home
The ferry back to Athens took about four hours—the longest ride of the trip. By then, we were ready to head home, but we felt refreshed and relaxed (no need for a vacation after our vacation!).
Final Thoughts
If you’re dreaming of the Greek Isles, I can’t recommend this style of island-hopping enough. Ferries are fun, the islands are gorgeous, and you get the perfect balance of adventure and downtime. This trip was pure heaven—and I’d do it all over again in a heartbeat!