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Greek Island Hopping Itinerary: Athens to the Cyclades
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Your tailor-made itinerary – No cost, no commitment
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Trip curated by Roman Karin
ExpertThe cruise around Antiparos and Despotiko is the excursion most clients question before the trip and nearly all of them single out afterward. The partially excavated sanctuary at Despotiko is accessible only by boat, sees almost no independent visitors, and operates at a register the main island sites simply don't share; it's the kind of experience that makes a Cyclades itinerary feel genuinely distinctive rather than interchangeable. The Naxos food tour earns more when you carry its momentum directly into lunch at one of the market tavernas the guide introduces. For Santorini, keep the candlelight dinner and the sunset cruise on separate evenings; the caldera at dusk from the water and from a clifftop table are each complete experiences, and running both on the same day shortchanges the first.
The cruise around Antiparos and Despotiko is the excursion most clients question before the trip and nearly all of them single out afterward. The partially excavated sanctuary at Despotiko is accessible only by boat, sees almost no independent visitors, and operates at a register the main island sites simply don't share; it's the kind of experience that makes a Cyclades itinerary feel genuinely distinctive rather than interchangeable. The Naxos food tour earns more when you carry its momentum directly into lunch at one of the market tavernas the guide introduces. For Santorini, keep the candlelight dinner and the sunset cruise on separate evenings; the caldera at dusk from the water and from a clifftop table are each complete experiences, and running both on the same day shortchanges the first.
Recommended route
Customize at any time with an expert
Athens
Day 1 - 4
Dominating the Attica region of Greece, the country’s capital, Athens, is one of the oldest cities in the world. For over two and a half centuries, the astonishing Greek temples and monuments of Athens have continued to intrigue and amaze visitors from around the world. This icon of western civilization seamlessly combines ancient history with modern architecture and a surprisingly lively atmosphere. This is particularly apparent in areas at the foot of the Acropolis, Anafiotika, Plaka, Monastiraki, and Thissio where visitors will find numerous extraordinary Neoclassical buildings, trendy and traditional cafes, and shops, and narrow winding streets with historical treasures at every turn. Once you have enjoyed a history and art fix, try some mouth-watering Greek cuisine at one of the city’s fine local restaurants before indulging in the insatiable nightlife at the chic cocktail bars and waterfront dance clubs.
Your accommodation
Acropolian Spirit Boutique Hotel
Located in Athens (Athens City Centre), Acropolian Spirit Boutique Hotel is a 3-minute walk from Acropolis Museum and 5 minutes by foot from Athens National Garden. This luxury hotel is 0.1 mi (0.2 km) from Temple of Olympian Zeus and 0.3 mi (0.5 km) from Zappeion Hall.
Take in the views from a garden and make use of amenities such as complimentary wireless internet access and concierge services. Additional amenities at this hotel include a television in a common area and a reception hall.
Make yourself at home in one of the 40 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature rainfall showerheads and complimentary toiletries. Conveniences include phones, as well as safes and desks.
Your activity
Acropolis & the Acropolis Museum
This tour gives you an opportunity to observe the striking contraststhat make Athens such a fascinating city. Our expert guides will take you to see the Panathenaic Stadium where the first Olympic Gamesof modern times were held in 1896 (short stop). Continue and pass by the Prime Minister's residence (ex-Royal Palace) guarded by the Evzones in their colorful uniform, the Templeof Olympian Zeus, the Hadrian's Arch, the Parliament and thememorial to the Unknown Soldier, the Academy, the University, the National Library, the Constitution Square (Syntagma). On the Acropolis visit the Architectural Masterpieces of the GoldenAge of Athens: The Propylaea, the Temple of Athena Nike, the Erechtheion, and finally "the harmony between material and spirit", the monument that "puts order in the mind", the Parthenon. Continue and visit the place where at last the statues found their home and admire the wonders of the classical era: The new Acropolis Museum.
Guests spend approximately 1 hour and 50 minutes at the Acropolis and about 1 hour at the Acropolis Museum.
Start time: 08.45 and ends 13.30.
Group Size: Max pax 48
Mykonos
Day 5 - 6
Out of all of the Cyclades - the group of islands that surround the sacred Greek island of Delos - Mykonos is perhaps the most famous. It is known for its gorgeous green rolling hills, exquisite beaches and the glamorous, cosmopolitan crowd that typically vacations here. While Mykonos makes for an ideal base for archaeological day trips to the nearby islands, the island itself has plenty to offer. Spend your days exploring the quaint winding alleyways strewn with iconic whitewashed houses; sailing around the picturesque harbour and out into the glistening Aegean Sea; unwinding on the idyllic beaches, and dining in the numerous fine restaurants. If it’s unforgettable nightlife, a bit of luxury, and plenty of natural beauty you are after, Mykonos is undoubtedly the destination for you.
Your accommodation
Vencia Boutique Hotel
When you stay at Vencia Boutique Hotel in Mykonos, you'll be near the beach, within a 5-minute drive of Mykonos Old Port and Mykonos New Port. This spa hotel is 0.6 mi (0.9 km) from Windmills of Mykonos and 2.4 mi (3.9 km) from Ornos Beach.
Pamper yourself with a visit to the spa, which offers massages, body treatments, and facials. You're sure to appreciate the recreational amenities, including a seasonal outdoor pool and bicycles to rent. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and babysitting (surcharge).
Stay in one of 34 guestrooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Bathrooms feature showers with rainfall showerheads and complimentary toiletries. Conveniences include phones, as well as safes and complimentary bottled water.
Your activity
Traditional Dinner at Mykonian Farm
Mykonians love to eat and cook, and that’s why our island is a place where you’ll never feel hungry. Known for rich aromas and authentic flavors, our cuisine is rooted in traditional Greek heritage—and there’s no better place to experience it than at a traditional Mykonian farm. During your visit, you’ll learn the art of Greek cooking, enjoy warm hospitality, and take in the natural beauty of the farm surroundings.
Traditional Lunch Menu
• Spinach pie
• Traditional Gemista (stuffed tomatoes, peppers, zucchini)
• Tzatziki
• Seasonal salad
• Giouvetsi with veal (orzo) – Main dish
• Fresh fruit
• Sweet preserves
• Yogurt with honey
Upon request:
Menu adjustments can be made to accommodate allergies or special dietary needs.
Start time: 19:00
Group size: Max 20 pax
Naxos
Day 7 - 8
Situated in the Aegean Sea, the Greek island of Naxos is the largest of the Cyclades Archipelago. Its fertile landscape features ancient ruins, quaint mountain villages with sheep-dotted slopes, and vast stretches of magnificent beaches. With their crystal-clear waters, soft white sands and watersports such as swimming, windsurfing, kitesurfing and surfing on offer, the beaches here provide the ultimate holiday experience, while the island’s lush interior makes it an ideal destination for hiking and mountain biking enthusiasts. Make sure to visit the mysterious Cave of Zas, filled with incredible stalactite formations and dedicated to Zeus in ancient times. The wide variety of historic attractions includes breathtaking Venetian mansions, Byzantine country churches, and the medieval old quarter of Kastro, with its centuries-old stone paving, arches and buildings.
Your accommodation
Nissaki Beach Hotel
With a stay at Nissaki Beach Hotel in Naxos, you'll be on the beach, a 5-minute walk from Agios Georgios Beach and 11 minutes by foot from Port of Naxos. This beach hotel is 3.6 mi (5.9 km) from Agia Anna Beach and 26.3 mi (42.4 km) from Piperi Beach.
Take advantage of recreational opportunities offered, including an outdoor pool, a hot tub, and bicycles to rent. This hotel also features complimentary wireless internet access, babysitting (surcharge), and wedding services.
Make yourself at home in one of the 26 air-conditioned rooms featuring refrigerators and DVD players. Wired and wireless internet access is complimentary, while 32-inch LED televisions with satellite programming provide entertainment. Bathrooms have complimentary toiletries and hair dryers. Conveniences include phones, as well as safes and coffee/tea makers.
Your activity
Naxos Castle & Portara Sunset Walk
Discover the rich history, myths and beauty of Naxos Town on a captivating walking tour guided by a professional licensed expert. This small-group experience takes place every Monday, Wednesday and Friday in the evening from 1st of May to 31st of August at 18:00 and from 1st of September to 20th of October at 17:00, offering the perfect setting to explore the town as the sun sets over the Aegean.
The tour begins with a pleasant stroll along the coastal path and into the narrow, winding alleys of the Old Town and Venetian Castle. As you walk through the medieval quarters, your guide will share stories of ancient gods, legendary heroes, and the island’s noble past, bringing the stone walls and historic buildings to life through engaging storytelling.
You’ll marvel at the coats of arms carved into marble doorways, pass by 13th-century Catholic cathedrals, and enjoy scenic viewpoints perfect for photos. The walk ends at Naxos’ most iconic landmark, the Portara, the massive marble gate of Apollo’s unfinished temple, where you’ll take in a breathtaking sunset over the Aegean Sea.
This tour is ideal for those who want to blend culture, mythology and stunning scenery in just two unforgettable hours. The small group setting ensures a relaxed pace and personal interaction with your expert guide.
Start time: 17:00/ 19:00
Group pax: Max 15 pax
Naousa
Day 9 - 10
Naoussa is a beautiful, authentic-feeling fishing village set on the north side of Paros, Greece, 10 kilometres east of Parikia (the capital city). A 15th-century Venetian Fortress watches over the port, where it once defended the city against pirate invasions. The Piperi town beach provides the perfect place to take a dip in the crystal clear waters, for which the town is famous, along with its true-to-culture atmosphere and brightly coloured sea-facing bars and restaurants. Take a full-day sailing cruise, enjoy the freshest, most traditional seafood dishes, and explore the winding cobbled alleyways up the hill.
Your accommodation
Sandaya Luxury Suites
A stay at Sandaya Luxury Suites places you in the heart of Paros, within a 15-minute walk of Naousa Harbour and Piperi Beach. This beach hotel is 6.5 mi (10.5 km) from Port of Parikia and 26.6 mi (42.9 km) from Port of Naxos.
Relax at the full-service spa, where you can enjoy massages, body treatments, and facials. You're sure to appreciate the recreational amenities, including an outdoor pool and bicycles to rent. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and a hair salon.
Make yourself at home in one of the 19 individually decorated guestrooms, featuring minibars and espresso makers. Rooms have private furnished balconies or patios. LED televisions with satellite programming provide entertainment, while complimentary wireless internet access keeps you connected. Private bathrooms have designer toiletries and hair dryers.
Your activity
Cruise Around Antiparos & Despotiko
Embark on unforgettable new adventures aboard our traditional Kaiki, a wooden motorboat typically used by fishermen, as we explore the stunning islands of Antiparos and Despotiko. We'll arrange a convenient transfer from your hotel (or a nearby stop) to the port of Pounta.
Get ready to uncover the hidden gems of the Aegean Sea that are only accessible by boat. With crystal-clear waters, you'll truly feel like you've stepped into paradise! Our journey begins at 10:00 am from the Pounta port, where we will guide you to breathtaking beaches, sea caves, and small islands, leaving you in awe of the exotic destinations around you. This cruise offers a unique opportunity to reconnect with the untamed beauty and natural wonders of the area.
While the following itinerary is indicative, our captain will select the best locations for each cruise based on the weather conditions, ensuring you have an extraordinary experience around Antiparos and Despotiko islands. Discover the enchanting Panteronissi, where the turquoise waters will make you feel as if you're swimming in a vast pool crafted by nature herself. The wild landscapes of the southeast coast feature cliffs that dive into the sea, creating a chain of caves, including the captivating cave of Mastichari. Enjoy several stops for swimming in these crystal blue waters!
During the trip, we'll provide morning coffee, a snack, and a BBQ lunch featuring either chicken or pork skewers, paired with two types of salads, tzatziki, pita bread, and of course, local beverages such as white house wine, soft drinks, and mineral water. For dessert, indulge in delicious fresh fruits. We'll return to the port of Pounta at 4:30 pm, followed by a transfer back to your hotel or a nearby stop.
Oia
Day 11 - 13
Known as one of the most picturesque villages on the spectacular Greek island of Santorini, Oia, also known as Megalohori, is a quiet village scattered over a hillside on the island’s westernmost point. It features traditional white-washed Greek buildings and a labyrinth of steep alleys and narrow streets and is encircled by countless vineyards, providing it with its fame for top-quality wines. Visitors can sample an array of delicious varietals from the famous Boutari Winery, enjoy a mouth-watering traditional meal at one of the many village square tavernas, and immerse themselves in the local culture in a variety of ways. The town provides the opportunity to take cooking classes, learn the language, and participate in a Greek singing lesson. Don’t miss the local Greek music evenings at the Geromanolis tavern every Saturday night.
Your accommodation
Villaki Oia
When you stay at Villaki Oia in Santorini, you'll be in the historical district, just steps from Oia Blue Dome Church Viewpoint and 4 minutes by foot from Santorini Caldera. This luxury hotel is 0.3 mi (0.4 km) from Castle of Oia and 12.7 mi (20.4 km) from Kamari Beach.
Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. Additional features at this hotel include complimentary wireless internet access, concierge services, and discounted use of a nearby fitness facility.
Make yourself at home in one of the 7 air-conditioned rooms featuring minibars and espresso makers. Rooms have private furnished balconies. LCD televisions with satellite programming provide entertainment, while complimentary wireless internet access keeps you connected. Private bathrooms have jetted bathtubs and complimentary toiletries.
Your activity
Cruise with lunch, winery & Oia sunset
Get picked up from your hotel and embark on a catamaran cruise around the amazing Caldera of Santorini. Relax on a 5-hour morning tour sailing to the volcanic islands and get the chance to swim and snorkel in its crystal deep-blue waters. Visit the impressive Red Beach and White Beach, and stop at the Hot Springs for a mud bath. Enjoy a delicious barbecue prepared on board, paired with unlimited Santorinian white wine and soft drinks. Return to the port, meet your guide and start the second part of your tour. Your first stop is Santo Wines Winery, where you will taste 3 distinctive wines of the island while gazing at the volcano. Continue with the Wine Museum, a family-owned winery with a long tradition in winemaking. The last stop will be Oia and the Sun Spirit Cocktail Bar, one of the best places to watch the sunset. Relax and enjoy your wine in this idyllic setting while watching the sun fall into the sea.
Group Size: Max 20 pax
Athens
Day 14 - 15
Dominating the Attica region of Greece, the country’s capital, Athens, is one of the oldest cities in the world. For over two and a half centuries, the astonishing Greek temples and monuments of Athens have continued to intrigue and amaze visitors from around the world. This icon of western civilization seamlessly combines ancient history with modern architecture and a surprisingly lively atmosphere. This is particularly apparent in areas at the foot of the Acropolis, Anafiotika, Plaka, Monastiraki, and Thissio where visitors will find numerous extraordinary Neoclassical buildings, trendy and traditional cafes, and shops, and narrow winding streets with historical treasures at every turn. Once you have enjoyed a history and art fix, try some mouth-watering Greek cuisine at one of the city’s fine local restaurants before indulging in the insatiable nightlife at the chic cocktail bars and waterfront dance clubs.
Your accommodation
Athenian Callirhoe Hotel
With a stay at Athenian Callirhoe Hotel, you'll be centrally located in Athens, just a 5-minute walk from Acropolis Museum and 9 minutes by foot from Temple of Olympian Zeus. This hotel is 1 mi (1.7 km) from Acropolis and 1 mi (1.7 km) from Parthenon.
Enjoy recreational amenities such as a sauna and a fitness center. This hotel also features complimentary wireless internet access, concierge services, and wedding services.
Stay in one of 84 guestrooms featuring LCD televisions. Your bed comes with down comforters and premium bedding. 20-inch Smart televisions with satellite programming provide entertainment, while complimentary wireless internet access keeps you connected. Private bathrooms have complimentary toiletries and hair dryers.
