Santorini Solo: A Digital Nomad's Guide to Shoulder Season Bliss
Santorini. The name alone conjures images of dazzling white villages clinging to volcanic cliffs, the impossibly blue Aegean Sea stretching to the horizon, and sunsets that paint the sky in fiery hues. But what if I told you there's a way to experience this iconic Greek island without the hordes of summer tourists? As a solo female traveler and digital nomad with a passion for photography and sustainable travel, I recently discovered the magic of Santorini in the shoulder season – late September to early October. The sunsets were just as breathtaking, the views just as stunning, but the pace was slower, more relaxed, and infinitely more authentic. And let's be honest, finding reliable Wi-Fi while sipping a glass of Vinsanto wasn't too shabby either! Let me share my guide to experiencing Santorini solo during this blissful time.
Why September/October is Perfect for visiting Santorini
Santorini in September and October is a completely different world compared to the summer months. The intense heat has subsided, leaving behind pleasantly warm days and cool evenings, ideal for exploring. The crowds have thinned considerably, meaning you can actually wander the narrow streets of Oia without battling through a sea of selfie sticks. You'll also find accommodation prices are significantly lower, and you're more likely to snag a table at that restaurant with the caldera view. But beyond the practical advantages, there's a certain magic to Santorini in the shoulder season. It feels more authentic, more connected to the local culture, and simply more peaceful. This allows for amazing photo taking opportunities in a less crowded area.
Sunset Wine Tasting: A Must-Do Experience
One of my most cherished memories from my Santorini trip is the sunset wine tasting tour I took at a family-owned vineyard in Megalochori. Far from the bustling tourist spots, this hidden gem offered an intimate and authentic experience. Nestled amidst rolling vineyards, the estate exuded a rustic charm, with its traditional stone buildings and fragrant herb gardens. The family, who has been producing wine for generations, greeted us with warm smiles and stories about their craft. We sampled a variety of their local wines, including the renowned Vinsanto, a sweet dessert wine made from sun-dried grapes.
But the real magic happened as the sun began to dip below the horizon. The sky exploded in a kaleidoscope of colors, casting a golden glow over the vineyards and the Aegean Sea. Sipping on the rich, honeyed Vinsanto, with its notes of dried apricot and caramel, while listening to the family share their passion for their land and their wine, was an experience I'll never forget. I highly recommend booking a tour directly with a smaller, family-run vineyard to support local businesses and enjoy a more personal experience. Santo Wines and Boutari Winery are other great options but can be a bit more touristy.
Sailing the Caldera: A Unique Perspective

While Santorini is stunning from land, seeing it from the water is an entirely different experience. I opted for a private catamaran cruise around the caldera, and it was worth every penny. Leaving from the port of Vlychada, we set sail towards the iconic caldera, the submerged volcanic crater that defines Santorini's unique landscape. As we glided across the turquoise waters, the views were simply breathtaking. The sheer scale of the cliffs, the whitewashed villages perched precariously on the edge, and the volcanic islands rising from the sea created a panorama of unparalleled beauty.
The cruise included stops at various points of interest, including the volcanic hot springs, where we had the chance to swim in the therapeutic waters, rich in minerals. We also snorkeled in secluded coves, exploring the vibrant marine life. But the highlight of the cruise was undoubtedly the sunset. Watching the sun sink below the horizon, painting the caldera in shades of orange, pink, and purple, while enjoying a delicious onboard dinner, was pure magic. Opting for a smaller catamaran tour contributes to sustainable tourism by supporting smaller, local boat operators and minimizing environmental impact compared to larger cruise ships. Consider Sunset Oia Sailing or Spiridakos Sailing Cruises for an amazing tour around the caldera.
A Taste of Tradition: Santorinian Cooking Class
To truly immerse myself in the local culture, I decided to take a hands-on Santorinian cooking class. It was an experience that not only tantalized my taste buds but also provided a deeper understanding of the island's culinary heritage. The class was held at a charming farmhouse, surrounded by vegetable gardens and olive groves. We learned to prepare traditional dishes using fresh, local ingredients, many of which were grown right there on the farm.
Under the guidance of our enthusiastic instructor, we chopped, stirred, and kneaded our way through a menu that included tomatokeftedes (tomato fritters), fava me koukia (yellow split pea puree), and chlorotyri (fresh goat cheese). We learned about the unique characteristics of Santorini's produce, like the intensely sweet Santorini tomatoes, grown in the volcanic soil. The experience was incredibly interactive, and we all had the chance to get our hands dirty and learn the secrets of Santorinian cuisine. At the end of the class, we sat down to enjoy the fruits of our labor, savoring the delicious flavors of Santorini, paired with local wine. Consider Selene Restaurant or Petra Kouzina for an excellent cooking class.
Foodie Adventures: Savoring Santorinian Flavors
Santorini's cuisine is a delightful blend of fresh, local ingredients and traditional Greek flavors. Here are a few dishes you absolutely must try:
- Fava me koukia: This creamy, yellow split pea puree is a Santorini staple. Made with locally grown fava beans, it has a smooth, velvety texture and an earthy, slightly sweet flavor. Often served with chopped onions, capers, and a drizzle of olive oil, it's a simple yet incredibly satisfying dish.
- Tomatokeftedes: These crispy tomato fritters are a true taste of Santorini. Made with the island's famous sweet tomatoes, herbs, and spices, they are deep-fried to golden perfection. The sweetness of the tomatoes combined with the crispy texture makes them utterly addictive.
- Chlorotyri: This fresh, tangy goat cheese is another Santorini specialty. With its light and creamy texture and slightly sour flavor, it's incredibly versatile. It can be enjoyed on its own, sprinkled on salads, or used as a filling for pies and pastries.
- Vinsanto Wine: This is Santorini in a glass. Made from sun-dried white grapes, it boasts a deep amber color and a luscious aroma of honey, dried fruits, and spices. On the palate, it's rich and sweet, with a velvety texture and a long, lingering finish. It's the perfect accompaniment to dessert, especially chocolate or nuts. Pair it with baklava for a truly decadent experience. The color resembles amber, giving the wine a unique texture. The Vinsanto is Santorini's most popular dessert wine.
Exploring Santorini's Unique Beaches

Santorini's volcanic landscape extends to its beaches, creating a coastline unlike any other. The Red Beach, near Akrotiri, is a sight to behold, with its dramatic red cliffs and volcanic sand. Walking on the red sand, with the turquoise water lapping at your feet, feels almost surreal. The Black Beach of Perissa and Perivolos offers a different experience, with its long stretches of black volcanic sand and crystal-clear water. The feeling of the warm, dark sand between your toes is incredibly grounding. These beaches are popular, but in the shoulder season, you'll find plenty of space to relax and soak up the sun.
Whitewashed Wonders: Oia, Fira, and Imerovigli
No trip to Santorini is complete without exploring its iconic whitewashed villages. Oia, famous for its breathtaking sunsets, is a maze of narrow streets, blue-domed churches, and charming shops. Fira, the island's capital, is a bustling hub with stunning views of the caldera, while Imerovigli, known as the "balcony to the Aegean," offers a more tranquil escape. Wandering through these villages, admiring the unique architecture, and soaking up the panoramic views is an essential Santorini experience. Take your time, get lost in the labyrinthine streets, and discover hidden gems around every corner.
Santorini Arts Factory Film Festival
During my visit, I was fortunate enough to attend the Santorini Arts Factory Film Festival. It was a wonderful opportunity to immerse myself in the local arts scene and connect with talented filmmakers from around the world. The festival showcased a diverse selection of films, from documentaries to short films, offering a glimpse into different cultures and perspectives. The atmosphere was vibrant and engaging, with post-screening discussions and Q&A sessions with the filmmakers. It was a truly enriching experience that added another layer to my Santorini adventure. Check local listings for current schedules.
Staying Connected: Wi-Fi and Co-working
As a digital nomad, staying connected is crucial. I found that most cafes and restaurants in Santorini offer free Wi-Fi, although the speed and reliability can vary. I recommend checking reviews or asking the staff about the Wi-Fi before settling in to work. In terms of co-working spaces, options are somewhat limited in Santorini. However, some hotels and guesthouses offer dedicated workspaces for their guests. The best option is to find a cafe with a stunning view and strong Wi-Fi!
Vegan and Vegetarian Delights in Santorini
For vegan and vegetarian travelers, Santorini offers a surprising array of delicious options. Traditional Greek cuisine is naturally rich in plant-based dishes, and you'll find plenty of restaurants serving fava me koukia, tomatokeftedes, and other vegetarian delights. Many restaurants are also happy to adapt dishes to accommodate vegan requirements. Supermarkets also stock a variety of plant-based products, making it easy to prepare your own meals. Be sure to try the local Santorini tomatoes; they are amazing!
Sustainable Travel in Santorini
Santorini is a beautiful but fragile island, and it's important to travel responsibly and minimize your impact on the environment. Here are a few tips for sustainable travel in Santorini:
- Support local businesses: Choose family-run restaurants, guesthouses, and tour operators to ensure that your money stays in the local economy.
- Minimize waste: Avoid single-use plastics, bring your own reusable water bottle and shopping bag, and dispose of your waste responsibly.
- Respect the environment: Stay on marked trails, avoid disturbing wildlife, and be mindful of water usage.
- Choose eco-friendly accommodations: Look for hotels and guesthouses that have implemented sustainable practices, such as solar panels, water conservation measures, and waste reduction programs.
- Consider travel during the off-season: Travel during the shoulder season helps to reduce the pressure on the island's resources and infrastructure.
Santorini Solo: An Unforgettable Experience
Santorini in the shoulder season is a truly magical experience, especially for solo female travelers and digital nomads seeking a blend of beauty, culture, and productivity. The slower pace, the stunning landscapes, and the warm hospitality of the locals make it an ideal destination for those looking to escape the crowds and immerse themselves in the authentic spirit of the island. So, pack your bags, grab your camera, and get ready to discover the bliss of Santorini solo. Remember to travel responsibly, support local businesses, and respect the environment. Your unforgettable adventure awaits!