ITINERARY FOR THE WEEKEND OF JANUARY 18 - JANUARY 19, 2025

Winter Wonders in Oia: A Weekend of Scenic Beauty and Hidden Gems

Experience the enchanting allure of Oia this winter weekend, where partly cloudy skies and moderate temperatures set the stage for exploring Santorini’s scenic beauty and hidden gems. Discover ancient ruins, savor local wines, and capture unforgettable moments against the backdrop of the caldera’s breathtaking views.

Morning Magic in Oia

As the sun rises over the Aegean Sea, Oia awakens with a gentle embrace of light and shadow, painting the whitewashed buildings in hues of gold. Begin your winter weekend exploration with a Santorini Highlights Tour that starts early in the morning. This private tour, available from 7:00 AM to 12:00 PM, offers an intimate glimpse into the island’s rich history and breathtaking landscapes.

The tour takes you to the Akrotiri Archaeological Site, where the echoes of ancient civilizations whisper through the well-preserved ruins. As you wander through the site, imagine the lives of those who once thrived here, their stories etched into the frescoes and pottery. The journey continues to the Red Beach, a striking contrast of red-hued sand against the azure sea, a testament to Santorini’s volcanic origins.

Conclude your morning with a visit to the Art Space Winery, where the fusion of art and wine creates a sensory delight. Here, you can savor four local wines, each sip a reflection of Santorini’s unique terroir. As one recent visitor reviewed on December 21, 2024:

Amazing Experience! - Where can I even begin? Theodore, our guide, was the history right up to current times. Even an idea about buried treasure from the pirate Barbarossa on an island across the water. So exciting! I feel like I need to come back and look for a treasure map. The wine tasting was amazing and we are taking a little bit of Santorini home with us. We have memorable photos of the caldera and the sunset at the lighthouse. I would do it all over again in a heartbeat!

Afternoon Adventures and Hidden Gems

As the day unfolds, the winds may pick up, but the allure of Oia remains undiminished. For those seeking a deeper connection with the island, the Hidden Gems Tour offers an afternoon of discovery from 9:00 AM to 3:00 PM. This private tour is a journey through Santorini’s lesser-known treasures, guided by a knowledgeable local who doubles as your personal photographer.

Stroll through the charming streets of Oia, where every corner reveals a new perspective of the caldera’s majestic beauty. The tour includes a visit to a traditional wine museum, where the history of winemaking on the island is brought to life. As you taste the local wines, paired with cheese and olives, you’ll find yourself immersed in the flavors and stories of Santorini.

A recent review from September 30, 2024, captures the essence of this experience:

Here’s a tour that is customized for you! - We had a 5 hr tour with Nikos as our guide. We traveled all over the island and Nikos really gave us a total perspective of the islands history and culture. So glad we did this tour. If you have the time, it’s a “must”.

Evening Elegance and Sunset Splendor

As the sun begins its descent, casting a warm glow over the island, Oia transforms into a realm of romance and tranquility. The evening is a perfect time to reflect on the day’s adventures and indulge in the simple pleasures of life.

Consider a leisurely stroll through the village, where the narrow alleys and blue-domed churches create a picturesque setting. As you wander, the scent of Mediterranean cuisine wafts through the air, inviting you to dine at one of Oia’s charming tavernas. Here, the flavors of Greece come alive, each dish a celebration of the island’s culinary heritage.

As the day draws to a close, find a spot to watch the sunset, a spectacle that has captivated travelers for centuries. The sky transforms into a canvas of vibrant colors, a fitting end to a day of exploration and discovery. Whether you’re sipping wine on a terrace or simply enjoying the view, the magic of Oia is sure to leave a lasting impression.

Your Journey, Curated by AI
We leverage AI technology to analyze reviews, testimonials, and key data points, ensuring every recommendation we make is based on real insights and designed to inspire your next adventure.
About the Author
Author Image
Adrian Dupont
Adrian pulls data on boutique hotels, local dining, and seasonal events to create romantic trips for couples. His data-backed suggestions inspire enchanting escapes, whether it's a gondola ride in Venice or a Parisian stroll.
Popular in Oia
SEASONAL

Santorini’s May Magic: Family Adventures in Oia’s Breezy Beauty

Experience the magic of Santorini this May with perfect weather for exploring Oia’s stunning landscapes and cultural treasures. Discover hidden gems and breathtaking sunsets that promise an unforgettable family adventure.

Olivia Barnes
May 19, 2025
Family-Friendly Travel Worldwide
SEASONAL

May in Oia: A Weekend of Sun, Sea, and Scenic Exploration

Experience the magic of Oia this May with perfect weather for exploring its stunning landscapes. From luxurious catamaran cruises to breathtaking sunsets, this weekend promises elegance and adventure in the heart of Santorini.

Nina Carmichael
May 12, 2025
Luxury Travel in Asia
SEASONAL

Aegean Adventures: Discover the Breezy Beauty of Santorini’s Oia

Experience the perfect blend of adventure and relaxation in Oia, Thira, with clear skies and mild temperatures. From luxurious catamaran cruises to private island tours, discover the breathtaking beauty of Santorini this weekend.

Layla Hart
May 5, 2025
Water Activities Worldwide
JOURNAL

Rediscovering Santorini: A Tailor-Made Adventure with Santorini Road Trips

Returning to Santorini felt like coming home. With a personalized itinerary crafted by Santorini Road Trips, I was eager to explore more of the island’s hidden gems. Join me as I share the unforgettable experiences and breathtaking landscapes that made this trip truly special.

Olivia Barnes
May 1, 2025
Family-Friendly Travel Worldwide
JOURNAL

Crafting Unforgettable Memories: A Tailor-Made Santorini Adventure

When I heard about the Private Santorini Tailor-Made experience, I was intrigued by the promise of a personalized adventure. As a family travel writer, I was eager to see if it could offer a stress-free and enriching experience for families.

Olivia Barnes
Apr 30, 2025
Family-Friendly Travel Worldwide
SEASONAL

May Day Magic in Oia: Celebrate Spring with Wine, Sun, and Scenic Views

Celebrate May Day in Oia with clear skies and mild temperatures, perfect for exploring the vibrant festivities and indulging in Santorini’s exquisite wines. Discover hidden gems and savor the flavors of the island, all while capturing the magic of Oia’s iconic sunset.

Henry St. James
Apr 28, 2025
Wine and Culinary Journeys in France and Italy
SEASONAL

Santorini Springtime Splendor: Embrace the Island’s Natural Beauty and Outdoor Adventures

Experience the enchanting beauty of Oia, Thira, this spring with clear skies and perfect temperatures for outdoor adventures. From a magical flying dress photoshoot to a luxurious yacht tour, discover the romance and splendor of Santorini’s natural wonders.

Elena Marquez
Apr 21, 2025
Romantic Getaways for Couples in the USA and Caribbean
SEASONAL

April Sunshine in Oia: Capture the Magic of Santorini’s Scenic Views

Experience the enchanting allure of Oia this April, where mild temperatures and clear skies create the perfect backdrop for romantic adventures. From stunning photoshoots to hidden gem explorations, discover the magic of Santorini’s iconic landscapes.

Elena Marquez
Apr 14, 2025
Romantic Getaways for Couples in the USA and Caribbean
JOURNAL

A Day with Aris: Discovering Santorini’s Hidden Charms

Drawn by tales of Santorini’s beauty, I embarked on a journey with Aris, a guide whose warmth and knowledge made the island’s history come alive. Join me as I recount a day filled with hidden gems, heartfelt moments, and the timeless charm of slow travel.

Lydia Beaumont
Apr 10, 2025
European Train Journeys
SEASONAL

April Adventures in Oia: Discover Santorini’s Hidden Gems and Breezy Beauty

Experience the enchanting allure of Oia, Thira, this April with a blend of cultural exploration and luxurious relaxation. With mild temperatures and a gentle breeze, it’s the perfect time to uncover Santorini’s hidden gems and breathtaking landscapes.

Adrian Dupont
Apr 7, 2025
Romantic Getaways for Couples in Europe
Activities in Oia