Dreaming of sun-drenched beaches, ancient ruins whispering tales of gods and heroes, and vibrant island life? A Greece Travel Itinerary promises an unforgettable escape, and after crafting the perfect two-week journey through the Greek Islands and mainland, I can confidently say it’s a destination that exceeds all expectations. From the bustling historical heart of Athens to the iconic sunsets of Santorini, the charming villages of Paros, and the hidden gems of Milos, this itinerary is designed to immerse you in the best of Greece. Whether you’re planning a romantic getaway, an adventurous honeymoon, or simply seeking a rejuvenating vacation, this meticulously planned Greece travel itinerary offers a blueprint for an incredible experience.
The ideal time to embark on this Greek adventure is early September. Picture this: balmy 80°F days bathed in sunshine, the Aegean Sea warmed to perfection for swimming, and clear blue skies stretching endlessly above. Traveling just after the peak summer season offers a sweet spot – fewer crowds than July and August, yet still buzzing with life and blessed with phenomenal weather. In fact, this time of year has become our go-to for travel, ensuring pleasant experiences and avoiding the intense summer throngs.
To truly capture the magic of our trip, be sure to check out my Instagram Highlights titled ‘Greece’ – a visual diary filled with photos and videos that bring our adventures to life.
Planning this two-week Greece travel itinerary was a labor of love, fueled by recommendations from friends, family, and my online community. While we opted for a DIY approach, eschewing travel agents to fully customize our experience, the process itself became part of the adventure. The reward? A perfectly tailored trip that hit all the right notes, leaving us with memories to last a lifetime. Let’s dive into the details of how to plan your own unforgettable Greece travel itinerary, inspired by our journey.
Crafting Your Perfect Two-Week Greece Travel Itinerary: Key Planning Steps
Creating a seamless and enriching travel experience requires thoughtful planning. Here’s a breakdown of the key steps I follow when designing itineraries for new destinations, ensuring a balance of exploration, relaxation, and authentic experiences:
- Harness the Power of Recommendations: Begin by tapping into your network. Ask friends, family, and online communities for their must-see recommendations in each destination. Compile a comprehensive list, forming the foundation of your research.
- Strategic Accommodation Research: Go beyond typical tourist hotspots. Seek out accommodations in areas favored by locals, close to culinary hubs, and popular among travelers with similar interests. This often leads to more authentic and enriching stays.
- Embrace the Value of Airbnb: For budget-conscious yet discerning travelers, Airbnb can be a game-changer. Often significantly more affordable than hotels, Airbnb offers the opportunity to be selective, securing prime locations, spacious apartments, and benefiting from a wealth of honest reviews. The savings can be substantial, without compromising on quality or comfort.
- Activity-Driven Days: Resist the urge to simply “wander and explore” without structure. While spontaneity has its charm, pre-planning at least one or two key activities per day adds focus and depth to your itinerary. Consider historical tours, guided walks, food explorations, cooking classes, or cultural experiences.
- Prioritize Downtime and Recharge: Avoid the pitfall of over-scheduling. Factor in 2-3 hours of rest or downtime each day. Travel fatigue is real, and moments to relax and recharge are essential for enjoying your trip to the fullest. Balance activity with tranquility.
- Culinary Pre-Planning: For food enthusiasts, meal planning is paramount. Tourist traps abound in major cities, often clustered around popular attractions. Steer clear of these and delve into research. Explore food blogs by local residents, consult reputable culinary websites like Bon Appetit or Conde Nast Traveler, and make reservations in advance at restaurants that resonate with your palate.
- Logistics Management: Once the core elements are in place, turn your attention to logistics. This includes flights, ferries, trains, and local transportation. Booking in advance, with an eye towards flexibility, is crucial for smooth transitions between destinations.
Authentic Greek cuisine: A vibrant spread of traditional dishes enjoyed during our Athens stopover, showcasing the fresh flavors of Greece.
Day 1: Arrival in Athens – A Taste of Ancient History and Modern Buzz
Our journey began with a flight from Newark to Athens, capitalizing on more favorable fares compared to flying from Philadelphia. Opting for a Sunday of Labor Day weekend departure, we landed in Athens on Monday afternoon. Athens served as an initial immersion point, a prelude to the island adventures that awaited. Based on recommendations suggesting one full day is sufficient to grasp Athens’ essence, we allocated a half-day upon arrival and another half-day at the trip’s end. This proved to be perfectly balanced.
Upon arrival at Athens International Airport, taxis offered seamless door-to-door service, a convenient and only slightly more expensive alternative to the train. Our accommodation, A for Athens Hotel, located in the vibrant Monastiraki Square, proved to be an ideal choice for a short stay. Its central location provides easy access to key attractions, and the rooftop bar boasts breathtaking Acropolis views.
The hotel’s complimentary drink voucher was immediately put to good use at the rooftop bar. A crisp glass of white wine marked the official beginning of our Greek adventure – the first of many. Intrigued by further recommendations, we ventured across the street to 360 Cocktail Bar. While famed for its Acropolis vista, cloudy skies led us indoors to the bar. Here, I savored an exceptional (albeit pricey) spicy margarita, a house specialty worth indulging in.
For our first authentic Greek culinary experience, we chose Efcharis. This proved to be a culinary gem – genuinely authentic, affordably priced, and utterly delicious Greek fare. The bustling atmosphere, filled with locals, was a testament to its quality. A generous platter of grilled meats and flavorful dips, accompanied by appetizers, dessert, and a bottle of wine, all for an incredible $42, solidified Efcharis as a must-visit for anyone seeking a quick, delicious, and authentic Athenian meal.
Energized and excited, we concluded our first night with a final drink at the A for Athens rooftop bar. The illuminated Acropolis against the night sky was a spectacular sight, amplifying our anticipation for the Greek adventure ahead.
Day 2: Santorini Beckons – Iconic Views and Caldera Charm
An early morning flight facilitated a swift transition from Athens to Santorini. A pre-arranged hotel transfer from Charisma Suites from Santorini Airport proved invaluable. Navigating Santorini without pre-booked private transfers can be challenging, a lesson quickly learned. Arranging transportation through our hotel for all local journeys became seamless.
Having typically favored Airbnbs in past travels, research indicated boutique hotels are the preferred accommodation style in Santorini. Utilizing Chase Sapphire points, we secured a “free” stay at the exquisite Charisma Suites in Oia. Oia, in my opinion, reigns supreme as the best location on Santorini. While Oia hotels tend to be pricier than those in Fira, Oia exudes a refined ambiance compared to the slightly more touristy and bustling Fira.
Charisma Suites, nestled into the Oia cliffs, is a haven of luxury. Each room, resembling a private cave, offers breathtaking caldera views. The staff’s attentiveness, the welcome fruits and wine upon arrival, and the daily gourmet breakfast served on our private balcony elevated the experience. The hotel’s two pools, including Oia’s largest, and poolside bars serving Aperol spritzes, offered perfect relaxation amidst stunning scenery.
Transportation within Santorini is best coordinated through your hotel. With only 50 taxis on the entire island, relying on spontaneous taxi pick-ups is impractical. Hotel assistance is key. Our stay at Charisma Suites was exceptional, and I wholeheartedly recommend it.
A word of caution about Santorini: prepare for steps. Reminiscent of Positano, the island is characterized by numerous steep staircases – a leg workout in itself!
Santorini’s Cliffside Beauty: The mesmerizing caldera view from our hotel in Oia, capturing the iconic white-washed architecture and azure waters of Santorini.
Our first Santorini day involved leisurely exploration and lunch. Getting acquainted with a new locale through walking is our preferred method. A quick, delicious lunch stop at the famed Pitagyros, followed by further exploration, led us back to the hotel for afternoon relaxation by the pool. Tom, a devoted pool enthusiast, immediately took a dip, while I indulged in reading and wine – pure bliss.
Dinner reservations at Sunset Ammoudi were secured a month in advance – essential for coveted Santorini dining spots. Located at the base of a steep hill, Sunset Ammoudi is accessible by car or via a challenging walk. Opting for the active route, we walked down (and back up!) – a strenuous but rewarding choice, albeit with the unavoidable presence of donkey droppings along the path.
Sunset Ammoudi’s setting is unparalleled. Perched directly on the crystal-clear caldera waters, the views are breathtaking. As dusk descends, lights illuminate the water and surroundings, creating a magical atmosphere. Dinner highlights included a shared bottle of wine, the obligatory (and delicious) nightly Greek salad, and the renowned Lobster pasta – a splurge-worthy dish featured prominently on their Instagram. Rich, flavorful, and incredibly filling, it lived up to the hype. Post-dinner, the walk back up the hill led to panoramic island views from a lookout point – a must-do at night.
Concluding the day in quintessential Erin and Tom fashion, gelato from Solo Gelato provided the perfect sweet ending. A chance encounter with an ELW follower added a delightful personal touch to a perfect Santorini debut.
Day 3: Santorini Hike and Sunset Cocktails – Adventure and Views
Santorini Hiking Trails: Breathtaking vistas along the Fira to Oia hiking trail, showcasing the rugged beauty and dramatic cliffs of Santorini’s landscape.
Day three was dedicated to adventure: the famed Fira to Oia hike. Following a fortifying breakfast on our patio, we prepared for what we knew would be a challenging day. The Fira to Oia trail is lauded for its unparalleled views.
Our hotel driver dropped us in Fira, and from there, navigating north towards Oia is the general direction. While some trail signs exist, pre-planning and a map are advisable to avoid confusion. The hike is commonly estimated at 4 hours. We commenced at 10 am, aiming for afternoon downtime before dinner.
The hike’s beauty is undeniable. While largely a walking trail, sections are steep, demanding legwork. We impulsively added a detour to Skaros Rock – a further 30-minute steep ascent. Think stair-master for half an hour – intensely challenging and sweat-inducing, but the panoramic views from Skaros Rock are arguably the island’s best and worth the exertion for those in good physical condition. It felt like a serendipitous discovery. The overall hike included other steep stretches, resulting in over 20,000 steps by 2 pm.
Arriving back in Oia around 3 pm, exhilarated but exhausted after 7.5 miles, we were ready for pool time. Our calves, already sore from Santorini’s steps, were definitely feeling the hike! An afternoon of poolside relaxation, swimming, and drinks was the perfect reward.
Evening drinks were planned at PK’s Cocktail Bar in Fira, highly recommended for sunset views. Our hotel provided transport, and PK’s lived up to its reputation. The sunset was spectacular, complemented by expertly crafted cocktails – an ideal start to a memorable evening.
Dinner followed at Metaxi Mas, another highly praised recommendation, accessible by taxi from Fira. Metaxi Mas is celebrated for its authentic, delicious cuisine favored by locals, tucked away from main tourist routes. The food quality rivaled top restaurants in Philadelphia – truly exceptional. The charming setting, dining outdoors amongst locals and travelers alike, enhanced the experience. Metaxi Mas is an absolute must-visit for food lovers in Santorini. The restaurant efficiently arranged a taxi for our return, concluding another perfect Santorini day.
Day 4: Santorini Catamaran Cruise – Sun, Sea, and New Friendships
Santorini Catamaran Adventure: Sailing through the crystal-clear waters of Santorini, enjoying swimming stops and stunning views of the caldera from the sea.
Day four was all about the Aegean Sea. A Catamaran Sailing Cruise was booked through Viator a couple of months prior, following extensive research to find the best option. A 6-hour cruise with lunch and drinks included seemed ideal for experiencing Santorini’s coastal beauty.
The tour included convenient pick-up and drop-off. Sharing the catamaran with six other couples, many our age, fostered a convivial atmosphere. The cruise included three swim stops, one with a lunch break. Snorkeling, swimming, and enjoying inflatable floats were encouraged. Even jumping from the catamaran’s top deck added an adventurous thrill. The day flew by, filled with sun, sea, and camaraderie.
Post-cruise, a nap, shower, and then drinks with our newly made catamaran friends were in order. Pre-dinner drinks at Strogili (Aperol Spritz count increasing!) led to dinner at Elinikon. Both venues perfectly suited the casual, celebratory mood. Elinikon’s food was superb, particularly the Baklava (the trip’s best) and the unexpectedly delicious honey sesame feta donuts – a must-try! Another Santorini day, perfectly executed.
Day 5: Ferry to Paros – Island Charm and Naoussa’s Beauty
Day five marked our departure from Santorini and arrival in Paros. Following our now-routine delicious breakfast spread, we packed, checked out, and left our bags at hotel reception for a final morning stroll in Santorini before our 2 pm ferry to Paros. A hotel-arranged driver ensured a timely transfer to the port by noon.
Allow ample time for ferry port transfers. The 30-minute drive from our hotel to the port was compounded by traffic congestion on the single access road – an extra hour of buffer is wise. A pre-ferry Aperol Spritz at a portside cafe helped pass the time.
Ferries in Greece have gained notoriety on social media for rough crossings and seasickness. Having personal susceptibility to motion sickness, I came prepared. Nausea wristbands, behind-the-ear patches, and Bonine were my preemptive measures. Fortunately, our ferry day was blessed with calm seas. The two-hour journey was smooth and uneventful – a far cry from the turbulent tales online.
Paros Port Arrival: Stepping off the ferry in Paros, ready to explore the island’s charming villages and beautiful beaches.
Upon arriving in Paros, we headed directly to our Airbnb in Naoussa. This Airbnb proved to be the most exceptional we’ve ever experienced. Located a mere two-minute walk from Naoussa’s downtown, it offered both proximity and tranquility. Extensive research had led me to this incredible Airbnb with outstanding reviews and a prime location. Naoussa is undeniably the best base in Paros – vibrant, accessible, and well-connected for island exploration by car or ATV.
The host, Christos, was exceptional. From pre-trip transport arrangements from the ferry port to dinner reservations and constant communication, his service was top-tier. The Airbnb itself was stunning – waterfront location with sunset views from the patio, impeccably clean, and exuding five-star hotel quality. Unreservedly recommended.
After settling in, we explored Naoussa on foot. Paros immediately felt calmer and less tourist-saturated than Santorini, a welcome change. Its charm was undeniable – quaint, windy alleyways adorned with pink bougainvillea against whitewashed buildings. While Santorini’s cliffside grandeur is unique, Paros resonated more with my personal preference for relaxed island vibes.
Naoussa Charm: Exploring the picturesque harbor of Naoussa in Paros, with its colorful fishing boats and waterfront tavernas.
Sunset Aperol Spritzes on our patio preceded dinner at the popular Sigi Ikthios. A 7:30 pm reservation felt early – we soon learned Paros dining typically begins closer to 9 or 9:30 pm. A quick reservation time adjustment for future meals was made. Sigi Ikthios, surrounded by other popular restaurants, offered delicious fresh food (Greek salad still a nightly staple), fresh fish, tzatziki, risotto, and crusty bread. While all Paros meals were exceptional, Sigi Ikthios, while very good, ranked slightly lower simply due to the consistently high culinary bar set on Paros.
Post-dinner drinks at Sante Cocktail bar, another recommendation, were a delight. Charming outdoor seating and a vast cocktail menu made it a winner. Dessert followed – mini donut holes called Loukoumades from Loukoumades to Paradosiako. These Greek honey-soaked donut holes, topped with melted white and milk chocolate, were addictive. A must-try, even for a dedicated gelato fan.
Day 6: Paros Beach Hopping and Winery Delights
Day six began with breakfast at Almond, a health-focused cafe with rave reviews. Smoothie bowls, yogurt and granola, and avocado toast with eggs provided a healthy and delicious start.
Paros ATV Adventure: Exploring Paros island on an ATV, ready for a day of beach hopping and discovering hidden gems.
An ATV, rented from Motorland ATV (pre-booked by Tom), became our mode of transport for a beach-hopping day. While pre-booking is advisable, walk-ins seemed readily accommodated.
Kalogeros Beach was our first stop. Unique for its natural clay deposits at the far right, we indulged in DIY clay masks, coating ourselves and rinsing off in the sea. Skin-smoothing and fun!
Golden Beach followed, a windsurfing hotspot with exceptionally clear water. Swimming, lounging, and soaking up the sun were the activities. Reminiscent of Jersey beaches, but warmer and clearer.
Kolimbithres Beach was the final beach stop – characterized by unique rock formations perfect for sunbathing. Exploring the rocks and cliffs was Tom’s highlight. It was notably busier than the previous beaches.
Post-beach, Moraitis Winery, Paros’s most renowned, beckoned. Wine flights, glasses of local wine, and card games in the outdoor setting made for a perfect late afternoon. Greek wines, particularly whites, impressed.
Pre-dinner drinks were enjoyed at Stilvi, a cool cocktail bar (opens at 7 pm) we loved so much we returned another night.
Dinner was at Gemeni, another highly recommended spot. Handwritten menus and a packed house are hallmarks of quality. Reservations are essential. Tzatziki, Greek salad, Mousakka, and fresh fish were all exceptional.
Gelato at S. Cream and then home concluded a day of Paros exploration and culinary delights.
Day 7: Lefkes Village, Cooking Class, and Ferry Drama
Day seven started with breakfast at Ragoussis Bakery, quickly becoming our favorite breakfast spot on Paros. A vast array of baked goods, freshly squeezed OJ, and regular breakfast options made it a paradise for food lovers. The orange cake, a Ragoussis specialty, was heavenly.
Post-breakfast, we ATV-ed to Lefkes, a charming village in Paros. Picturesque, small, with white houses adorned with pink flowers, Lefkes was perfect for exploring and souvenir shopping. Afternoon coffee in Lefkes was a must.
A cooking class at 3 pm was the afternoon’s highlight. Recommended by TikTok and online reviews, the class led by Maria, a lifelong Paros resident, promised authenticity. Maria’s family recipes and hands-on approach made it an incredible experience.
The class was interactive, with each participant involved in preparing dishes. Free-flowing wine and Greek music added to the festive atmosphere. We learned to make spanakopita, Greek quinoa salad, seabream with lemon, stuffed grape leaves, mousakka, and baklava – a feast of Greek flavors. The class culminated in a traditional Greek dance – a truly immersive and fun experience.
Paros Cooking Class Fun: Immersed in a Greek cooking class, learning to prepare traditional dishes and enjoying the convivial atmosphere.
The day’s lightheartedness took a turn when another couple in our class received news of their next-day ferry cancellation due to high winds. Checking our own ferry to Milos for the following night revealed a similar cancellation – only one ferry per day from Paros to Milos meant a potential disruption to our itinerary. Uncertainty about continuing to Milos with reduced time loomed.
Our Airbnb host reassured us ferry cancellations were rare, even in windy conditions, but these were near-hurricane force winds at sea. Fortunately, the incoming Airbnb guests were also ferry-stranded, allowing us to extend our stay in our exceptional Airbnb – a huge relief, avoiding a hotel scramble. After navigating the ferry uncertainty, a relaxing drink downtown concluded a day of varied experiences.
Day 8: Monastiri Beach Club and Siparos Dinner – Paros Perfection
Day eight dawned with improved spirits, hopeful for calmer winds and our rescheduled noon ferry to Milos. Breakfast at Ragoussis (again!) and then an ATV ride to Monastiri Beach Club for a full day of relaxation. Beach club days are a European travel indulgence, reminiscent of a South of France beach club experience last year. Pre-booked chairs, Aperol spritzes, beachside menu orders – a day of pure leisure.
Monastiri Beach Club was chosen partly for its facilities – bathrooms and showers, useful for a pre-ferry freshen-up (though ferry plans shifted). The day unfolded as a dream – crystal-clear, calm water, perfect temperature, and seamless water access. Burgers, fries, chicken club sandwiches, and Aperol spritzes flowed throughout the day. We lingered until 5 pm before heading back to prepare for dinner.
The ferry cancellation turned out to be a blessing in disguise, allowing us to dine at Siparos, a restaurant initially deemed out of reach due to time constraints. Siparos became our favorite Paros restaurant. Off the beaten path, taxi transport is recommended (especially for enjoying beverages). Our Airbnb host assisted with taxi arrangements.
Siparos was exceptional. Choosing our own fresh fish, the best tzatziki yet, Greek salad (of course!), fresh octopus, and tableside fish filleting highlighted the meal. Phyllo-wrapped ice cream for dessert was a perfect finish. Another drink at Stilvi (Tom’s repeat request) and Loukoumades donuts concluded our extended, and ultimately enhanced, Paros stay.
Day 9: Paros to Milos – Turbulent Seas and Lunar Landscapes
Day nine meant farewell to Paros and hello to Milos. One last breakfast at Ragoussis (predictable, but perfect) and then taxi to the port. Our ferry, thankfully, was not cancelled – but the ride was turbulent. The infamous “ferry sickness” TikToks became reality. Rough seas induced seasickness in a significant portion of passengers. Bathrooms were overwhelmed. My preemptive nausea対策 proved miraculous – I remained unaffected, while Tom felt unwell but avoided sickness. Preparation is key!
Arriving in Milos, we grabbed a quick lunch at Gyros of Milos (trip highlight gyro!), rented a car (ATV plans cancelled due to ferry delays), and headed to our Airbnb. Securing a rental car spontaneously proved lucky – advance booking is recommended. A car was needed both for transport and luggage storage the following day.
Milos Coastal Scenery: The dramatic coastline of Milos, showcasing the unique volcanic rock formations and crystal-clear waters.
Our Milos Airbnb in Mandrakia was stunning – peaceful, remote, near the popular Medusa restaurant. Spotlessly clean, high-tech, and with welcoming snacks, it was perfect, albeit too short a stay. Highly recommended.
After check-in, Sarakiniko beach, aka Moon Beach, was our destination. A lunar landscape of white volcanic rock formations – truly unique. While rough seas prevented swimming, exploring the otherworldly landscape was captivating. A quick stop in Plaka town on the way back revealed its small-town charm. Maximizing our limited 30 hours in Milos was the goal.
Sarakiniko Beach “Moon Beach”: The otherworldly landscape of Sarakiniko beach in Milos, with its white volcanic rock formations creating a lunar-like scenery.
Dinner at O! Hamos! in Milos was eagerly anticipated. A farm-to-table, family-owned restaurant, arguably Milos’s most popular. No reservations, expect a wait, but a nearby drinks spot helps. The meal was exceptional – farm-fresh ingredients, handwritten menu, incredibly affordable prices. Pitcher of wine, Greek salad, Tzatziki, Saganaki, fried meatballs, and pork shoulder – all outstanding. Two shared desserts – orange cake with chocolate and pudding – perfect finales.
Day 10: Milos Boat Tour – Aegean Paradise and Captain Elias
Day ten, the trip’s highlight, was dedicated to a 9-hour boat tour with Oneiro Boat Tours. Highly recommended, and now I understand why. This tour showcased Milos’s best beaches and waters. Crystal-clear, sparkling Aegean waters – Milos beaches are unparalleled.
Milos Boat Tour Paradise: Unveiling the hidden coves and turquoise waters of Milos during an unforgettable boat tour experience.
Captain Elias, the tour’s heart, is a native Milos resident, brimming with island knowledge and passion. The 9-hour cruise circumnavigated Milos, stopping at stunning swim spots and offering fascinating insights. Captain Elias personally guided us at each stop – secret caves, snorkeling hotspots, and captivating stories. A highlight was a guided swim into a hidden cave, accessible only by flashlight and a bit of adventurous spirit. The water clarity was unbelievable, amplified by the white seabed. Exiting the cave involved a tiny underwater passage – exhilarating!
Lunch onboard was a feast – octopus, pasta, Greek salad, endless wine, bread, and snacks. Nuts and ouzo flowed throughout the day. Pure magic – disembarking felt reluctant. Captain Elias and Oneiro Sailing are wholeheartedly recommended – the best part of our Greece trip.
Post-boat tour, a dash to Milos airport for a 7:10 pm flight to Athens. Tight connection, but made it. Athens arrival, hotel check-in, quick dinner at Ella, final gelato, and then sleep – exhausted but elated.
Day 11: Athens Shopping and Departure – Homeward Bound
Day eleven, our departure day. A 2 pm airport departure allowed for a final half-day in Athens. Instead of further sightseeing, we opted for shopping – a little retail therapy abroad. Athens shopping was enjoyable, and a few treasures were acquired.
Airport transfer, flight to Newark, and 10 hours later, we were home. A truly amazing Greece adventure, and I wholeheartedly encourage you to use this Greece travel itinerary as inspiration for your own unforgettable journey.
Happy Travels!
Note: This post may contain affiliate links. By purchasing through recommended links, I may receive a small compensation, which helps support this blog. I only recommend products and services I genuinely love and use. Thank you for your support.
