Blue Water sweeps up from the depths of the caldera. White washed buildings capped by bright blue domes glisten in the sun. Lovelies in bikinis or billowy dresses pose against the sunset. Grilled sardines, sizzling souvlaki, and honey sweet baklava beckon. Greek melodies waft through the byways and dancers sway barefoot on cool marble. Seductive Santorini is ready for you.

This ancient island in the Grecian Cyclades is a stunner from almost any angle. We were lucky to snag a vacation abode halfway between Oia (the main cliffside town you see in most of the Santorini photos) and Fira (the bustling capital just above the ferry and cruise ship port).

Traveling around Santorini can be challenging, however. You can go by taxi/uber, boat, bus, motorbike, dune buggy, or simply on foot. But we found it efficient to have a rental car despite the narrow roads and tourists wandering along them. Tip: Parking is TOUGH so find your favorite spots just out of the main locations if you can, and walk into town for the sights and eateries. Tip: For a real taste of ancient Greek lifestyle, try a donkey!

Oia is the “glamour locale” of Santorini. (Oia is pronounced EEE-AH by the way.) Everyone wants a once-in-a-lifetime photo here. Unfortunately the old, narrow lanes and uneven steps can make it especially difficult to navigate at peak crowd time.

We saw dozens of couples and instagrammers lugging their glamour-photo dresses (and photography staff!) to the top spots here during daylight hours. Between 10 am and 5 pm is particularly challenging because this is when the cruise ships offload passengers and everyone wants an Oia sunset shot.

In early morning and after sunset, traffic will be thinner. We arrived early for breakfast in Oia to beat the crowds one morning and also wandered around after sunset and found it charming—if a bit commercialized. (I recommend you stay in Oia if you really want to have the best of all worlds on Santorini. This will also give you walking access to Ammoudi Bay for its magnificent sunset views and lively waterside taverns.)

A few kilometers away is Fira (pronounced FEAR-A), the busy Santorini capital perched on top of the caldera. (Fira is also an excellent spot for accommodations since it’s more the center of commerce in Santorini and you can easily travel out around the island from here.) It’s filled with shops, eateries, and chic galleries. The views are wonderful and the food is delicious IF you find the right restaurants or bars. (Avoid the one that claims: “We Show Mama Mia Every Day Starting at 3 pm.”

We arrived in Fira early in the day to enjoy the narrow byways by ourselves. However, around 8 am when the (many) cruise ships bobbing in the Aegean began ferrying their passengers to the port, the byways became clogged with groups, large and small, soon after. As in Oia, come early, go late, or stay in town. Here’s a smattering of shots of our time in Fira.

More to my liking was one of the lesser known towns called Pyrgos (pronounced PER-GOES). This quiet village sits on the slopes of Mount Profitis Ilias just a short drive from Fira. We visited one morning and enjoyed the serene charm of its medieval structures, labyrinthine streets, fortified walls, and hidden passages. It is one of the villages of Santorini least spoiled by tourism. Here you’ll find relatively uncrowded bars, tavernas, galleries and boutiques along the pretty pathways.

At the top of the village, you’ll discover sparkling views of the surrounding vineyards, which produce the island’s renowned Assyrtiko white wines. You’ll also see the Museum of Icons and Ecclesiastical Artefacts set in the former Agia Triada chapel.

Pyrgos is notably home to the Kasteli, one of the best-preserved Venetian castles on the island. But by the time you reach it, you may be ready for a cool-down drink and a plate of pita and tzatziki. Be aware that workers haul the fresh ingredients and drinks BY HAND (or donkey) up the ancient steps—so tip well!

Worker hauls perishables up the ancient steps

Crowds are thinner here. And there’s less commercialism than in Oia or Fira, but you can still find some pretty souvenirs and snaps to take back home with you.

By far the best part of Santorini is the Aegean in my opinion. The azure seas are mesmerizingly beautiful, but hard to describe. A swim in these ultramarine waters is lovely. But a boat ride is an absolute must. And so we did!

We chose (from many options) a lunch-to-sunset catamaran cruise that took us from the tip of Santorini up to Ammoudi Bay just below Oia. It took about 5 hours. (Yes it sounds long, but it was well worth the price and time.)

From Oia, we were first bussed about 45 minutes south to Vlychada Port where the boats are anchored. There, we jumped onto a very modern, small-group Catamaran (20 people max). Interestingly, the Catamaran company has smartly deduced that more is more in the hyper tourism economy of Santorini. Thus, an entire FLEET of catamarans was sailing along with us—I counted at least 20 ships. (Apparently, they have more than 30 available our captain told us.)

Over the next several hours we sailed up the coast with swim stops at Red Beach, White Beach, Indian Rocks and Venetian Lighthouse, then lingered at the Volcano Hot Springs (in the middle of the caldera). We later sailed into the sunset at Oia docking at colorful Ammoudi Bay. Along the way, we had a tasty barbecue at sea with stellar cuts of beef and chicken, plus the best of Greek cuisine AND all the champagne, wine, beer, and soft drinks one could imbibe.

Once we disembarked and only glimmers of the sunset remained, we enjoyed a sumptuous dinner at Ammoudi Fish Tavern. They sell the lobster by the kilo there, by the way! As the moon rose, we finished our warm baklava and steeping-hot Greek coffee and savored our sailing adventure. It was the end of another picturesque day on Santorini.

In retrospect, here are some tips and observations from our Santorini visit:

Tourist Overload. Santorini’s local population is around 20,000. During peak tourist season, the island swells with millions of visitors however. (The locals told me they are exhausted by season’s end; still they were friendly and welcoming.) Fortunately, Santorini has begun limiting the number of cruise ships that can dock at any one time to reduce the thick crowds. So plan your time here wisely.
Fira to Oia walk. This hike is much lauded by the travel pros and bloggers. Be aware that it is about 10.5 km or 6.5 miles long! It will take from 2 hours to a whole day to complete. Part of the walk is a dusty trail. Part of it is along the two line highway that you will share with cars, buses, motorbikes, and animals. If you try it, wear walking or hiking shoes not flip flops. Bring water. Have a map or clear directions. And prepare for the heat and humidity (which is considerable).
Cruise ships. Many, many cruise ships stop here. If you are on one, it is beautiful way to see the Greek Islands. But you will be in the company of thousands and it will be challenge to see and do everything you’d like on Santorini.
Avoiding Crowds. We were lucky enough to stay on Santorini for nearly a week. We did what the locals do (and talked with them in depth about what to do and where to go.) We shopped and toured early. We scoped out the best parts and waited until the crowds were gone. It worked.
Tour Guides. A packaged tour or tour guide will provide interesting details and history to the sights. More importantly, they will know how to get around Santorini AND the best places to dine (and get you into the most popular places). Above all, they are a wealth of information and tips—and the Greeks are some of the most charming, helpful people on the planet. Get Your Guide is a great source.
Reservations. On Santorini, it’s wise to research the eateries, wineries, and activities you want to enjoy. Then make reservations weeks or even months in advance.
Climate and Peak Seasons. March to October is peak season, with some tours continuing in November and starting up again in February. We were there in late September, early October. The crowds were still large. And the humidity was palpable, with some days being very windy. Pack layers, a bathing suit, good shoes, and above all a hat and sunglasses for sun glare.
Wine. Santorini has a deep-rooted and historical wine history and produces some wonderful vintages. There are currently 21 operating wineries on Santorini. Our favorites for tastings were Domaine Siglas and Santo Wines. (Yes we brought back wine AND signature glasses.)
Toilet Issues. Greece has an entire infrastructure of narrow plumbing pipes that clog easily. Thus you must dispose of toilet paper (and what’s in them) in handy trash bins near your feet. Yes, it caused me to have a gag reflex when I first discovered this. After a few days or so of living with it, however, it became second nature. You will cope.
Language. I talked with quite a few Greeks about language. I assumed they were poly-lingual like most of Europe. They told me adamantently, however: “We speak two languages: Greek and English. End of Story.” And their English was impeccable.
Getting There. We flew into Santorini’s surprisingly modern airport from Athens, then retrieved our rental car and went on from there. However, the fast ferries called Sea Jets are a better way to go. Next time, we will probably fly into Mykonos from Athens. Then we will travel around the islands via Sea Jet. (You can buy your tickets in advance and they are very comfortable with assigned seats and plenty of snack areas.)
Fun Fact: They serve ice cream/gelato WITH alcohol and WITHOUT. I tried both. Superb.
Next Time: Despite the challenges, we are already planning a return to Greece and Santorini (as well as other islands). Our plans include: visiting Akrotiri (the prehistoric Bronze Age ruins), staying in town in either Santorini or Fira or both, seeing more of the local villages, and doing another boat trip around the island (superb photography opps).