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

Winter Weekend Wonders in Fira: Explore Santorini’s Scenic Beauty and Wine Heritage

Embrace the mild winter weather in Fira, where the scenic beauty of Santorini unfolds in a weekend of exploration and indulgence. Discover the island’s rich history, savor its renowned wines, and uncover hidden gems that promise an unforgettable experience.

A Stroll Through Fira’s Enchanting Streets

As the sun rises over the caldera, casting a golden hue across the whitewashed buildings of Fira, the city awakens to a day of exploration and indulgence. The mild weather, with temperatures hovering around 56°F, invites you to wander through the narrow cobblestone streets, where every corner reveals a new delight. The gentle breeze carries the scent of the sea, mingling with the aroma of freshly baked pastries from local bakeries.

Begin your day with a leisurely walk along the cliffside path, offering breathtaking views of the Aegean Sea. The iconic Three Bells of Fira, with its blue dome and stunning vistas, is a must-see landmark that captures the essence of Santorini’s charm. As you meander through the town, take a moment to explore the quaint shops and art galleries, where local artisans showcase their crafts.

For those seeking a deeper connection with the island’s history, the Akrotiri Archaeological Site offers a fascinating glimpse into Santorini’s ancient past. This well-preserved Minoan settlement, buried by volcanic ash, reveals intricate frescoes and advanced architecture that speak to a sophisticated civilization. The site is open in the morning, allowing you to immerse yourself in history before the afternoon sun sets in.

Savoring Santorini’s Wine Heritage

No visit to Fira would be complete without indulging in the island’s renowned wines. The volcanic soil and unique microclimate create the perfect conditions for producing exceptional wines, and a wine tour is the ideal way to experience this viticultural paradise. Available from 10:00 AM to 3:00 PM, this five-hour tour takes you to three of Santorini’s top wineries, where you can savor over 12 different wines paired with local Cycladic cheeses.

The tour begins at the Venetsanos Winery, perched above the caldera with panoramic views that are as intoxicating as the wines themselves. As you sip on the island’s signature Assyrtiko, the sommelier guides you through the nuances of each varietal, explaining how the volcanic terroir influences the flavor profile. The journey continues with visits to two more esteemed wineries, each offering a unique perspective on Santorini’s winemaking traditions.

“An unforgettable Tour into the World of Santorini Wines - My experience was amazing! Yiannis introduced me to the world of wine and made my experience unique. Highly recommended.” - Reviewed on 2024-08-04

Discovering Hidden Gems and Scenic Views

As the afternoon unfolds, the private highlights tour offers an exclusive opportunity to explore Santorini’s most picturesque locations. From 7:00 AM to 12:00 PM, this private tour takes you on a journey through the island’s diverse landscapes, blending history, culture, and breathtaking views.

The tour includes a visit to the Red Beach, where the striking contrast of red volcanic sand against the azure sea creates a mesmerizing scene. At the Prophet Elias Monastery, perched atop the island’s highest point, you’ll be rewarded with panoramic views that stretch across the Aegean. The charming village of Pyrgos, with its medieval architecture and labyrinthine streets, offers a glimpse into a bygone era.

Conclude your day with a visit to the Art Space Winery, where contemporary Greek art meets traditional winemaking. Here, you can taste four local wines while admiring the works of talented artisans, creating a sensory experience that captures the essence of Santorini’s creative spirit.

“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.” - Reviewed on 2024-12-21

As the sun sets over the caldera, painting the sky in hues of pink and orange, Fira’s enchanting beauty leaves an indelible mark on your soul. This winter weekend exploration, with its perfect blend of mild weather, scenic beauty, and cultural richness, promises an unforgettable journey through the heart of Santorini.

Popular in Fira
JOURNAL

Exploring Santorini’s Volcanic Wonders: A Lava Islands Adventure

Drawn by the allure of Santorini’s volcanic wonders, I embarked on the Lava Islands Adventure, eager to explore the warm, sultry waters of Nea and Palea Kammeni. With the ocean as my playground, this journey promised a unique blend of exploration and relaxation.

Dante Escobar
Sep 27, 2025
Beach Adventures in the Caribbean
JOURNAL

Unveiling Santorini’s Soul: A Journey Through Timeless Beauty

Drawn by the allure of Santorini’s iconic landscapes and hidden gems, I embarked on a personalized tour that promised to reveal the island’s soul. With a warm welcome and a journey through breathtaking vistas, this experience was a perfect blend of romance and discovery.

Adrian Dupont
Aug 5, 2025
Romantic Getaways for Couples in Europe
JOURNAL

Discovering Santorini’s Soul: A Personalized Island Journey

In search of a deeper connection to Santorini’s rich culture and history, I embarked on a personalized island tour that promised more than just sightseeing. Join me as I explore the soul of this iconic island, guided by a local expert who crafted a journey filled with breathtaking views, authentic flavors, and timeless beauty.

Yuto Saito
Aug 2, 2025
Cultural Experiences Worldwide
JOURNAL

Santorini’s Timeless Allure: A Journey Through Iconic Blue Domes

Drawn by the allure of Santorini’s iconic blue domes and rich history, I embarked on a journey to explore the island’s most picturesque locations. Join me as I recount my experience of cultural immersion and breathtaking beauty.

Yuto Saito
Jul 26, 2025
Cultural Experiences Worldwide
JOURNAL

Santorini’s Hidden Gems: A Romantic Journey of Discovery and Connection

Seeking a romantic escape, my husband and I embarked on a journey to Santorini, where the island’s hidden gems and breathtaking landscapes awaited. Our private tour, guided by the ever-gracious Dimitris, was a perfect blend of adventure and intimacy, leaving us with cherished memories and a deeper connection.

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

Exploring Santorini’s Hidden Gems: A Cultural Odyssey

Drawn by the allure of Santorini’s rich history and breathtaking landscapes, I embarked on a private tour to uncover the island’s hidden gems. Join me as I explore the caldera, UNESCO sites, and volcanic wonders that define this enchanting destination.

Yuto Saito
Jul 11, 2025
Cultural Experiences Worldwide
SEASONAL

Santorini’s June Breeze: A Weekend of Windy Adventures and Scenic Views

Experience the magic of Santorini this June with clear skies and a refreshing breeze perfect for exploring. Dive into personalized tours and luxurious yacht cruises, capturing the island’s breathtaking beauty and rich culture.

Yuto Saito
Jun 9, 2025
Cultural Experiences Worldwide
JOURNAL

Unveiling Santorini’s Secrets: A Family Adventure with Iconic Blue Domes

When I heard about the Santorini Highlights Tour, I knew it was a must-experience for my family. Join me as I share our unforgettable journey through the island’s iconic blue domes, charming villages, and hidden gems.

Olivia Barnes
Jun 8, 2025
Family-Friendly Travel Worldwide
SEASONAL

Santorini’s Sunlit Escapes: A June Weekend of Sailing and Serenity

Experience the magic of Santorini this June weekend with clear skies and warm breezes, perfect for sailing adventures. Dive into the island’s hidden gems and savor traditional Greek cuisine as you explore the stunning coastline.

Layla Hart
Jun 2, 2025
Water Activities Worldwide
SEASONAL

Santorini’s Early Summer Weekend: Wine, Dine, and Divine Views in Fira

Experience the allure of Santorini this early summer weekend with mild weather perfect for scenic tours and wine tasting. Discover the island’s rich viticulture and culinary delights as you explore Fira’s enchanting streets and indulge in exquisite wines and dining under the stars.

Henry St. James
May 26, 2025
Wine and Culinary Journeys in France and Italy
Activities in Fira