With so many Greek islands to choose from, planning your first trip to Greece can be difficult. But for first-time visitors that love wine, sunsets and beach visits, it may be best to combine a popular island with a lesser-known island to get the best of both worlds. So, Winetraveler’s top itinerary includes Santorini, followed by a stop in Paros — including a day trip to hidden gem Antiparos and ending in Athens.
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The best way to get to Greece is to first fly to a European hub such as London or Paris, and then fly nonstop directly to Santorini to start your trip. It’s best to consider a multi-city itinerary, flying out of Athens to head home. You can search for flight deals here.
Greece uses the Euro, so make sure to have some of this local currency on hand before arrival. Many smaller or family-owned bars and restaurants may accept cash only.
Car rental is possible — just note that the Greek drivers often make up their own rules of the road — beware of passers on both sides! Although you can visit Greece at any time of year, we suggest a September or October trip. The tourist crowds of summer will be thinning out, but seasonal spots remain open and you’ll see plenty of sunshine. And, a fall visit means you’ll be right in the middle of wine harvest season!
Note that Santorini is a pricier island, so plan accordingly. Travelers on a budget could spend fewer days there and more in Paros or Athens. We also provide other Greek island travel options on the free Winetraveler App.
Day 1: Land in Santorini and head to your hotel to settle in. There are endless hotel options to choose from in many different areas. Those wanting that traditional Santorini cliffside hotel experience should stay in Oia, famous for its sunsets. But Megalochori is where the real wine-lovers will want to lodge — this village has a history of wine-making and many places to sample Greek varieties.
Today, settle in and watch the sunset. If you can’t spot the rays going down from your hotel, then head up to the Oia Castle to see the sun dive behind the whitewashed, blue-domed buildings and shimmering sea.
Day 2: Santorini is one of the world’s oldest wine regions. Start with a trip to Venetsanos near Megalochori to wine taste, built into a cliff. Enjoy the gorgeous views as you sample Assyrtiko-based wines (this grape thrives in Santorini’s volcanic soil) from this unique and inviting space. We also highly recommend booking a private sunset wine tasting and tour. You can spend the day winery-hopping in the area, stopping at spots like Boutari. This stunning white-domed building is an Instagram vision in itself. But make sure to end the afternoon at Santo, the largest wine cooperative on the island. While everyone else is admiring the sunset in Oia, you can see it from this clifftop winery, organic Assyrtiko wine in hand.
Day 3: You can’t leave Santorini without visiting the gorgeous Red Beach, named for its pebbly red sand and stone mix. Swimmers may prefer Amoudi Bay, where you can dive from the rocks into the incredibly clear sea. Those wanting to hike should head up to the Santorini Volcano, if you prefer a journey by quad, ride up to the Akrotiri Lighthouse for magnificent views. Or, hire a private boat for the day and cruise around the island.
Day 4: Hop a ferry to Paros, which can take anywhere from two to almost four hours depending on which boat you take. It’s best to book your tickets in advance using a website like Ferry Hopper or Direct Ferries. Keep in mind that the faster boats are typically more expensive.
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Day 1: Arrive in Paros via ferry from Santorini. Parikia has a harbor and plenty of budget and mid-range hotel options. Naousa has a larger variety of luxury hotels and villas for rent. Take the afternoon to explore your immediate surroundings and relax by the pool. Or, enjoy an afternoon at Golden Beach, relaxing on the warm sands and dipping in the turquoise waters.
Day 2: Start by discovering the beautiful hidden village of Lefkes. Then, head over to the white village of Naousa, known as the Little Venice of Greece. Check out the old Venetian Harbor and castle, and make sure to catch the sunset.
While in Naousa, tour and taste at the Moraitis Winery. Paros is one of the few islands with its own PDO wine, making it an excellent island for wine fans. The island’s wine is made from grapes like Monemvasia and Mandilaria. The grapevines have deep roots in the soil that grow parallel along the ground. This protects the leaves and grapes from the elements like wind, rain and sun. Naousa is one of the best areas on the island for dining too. Make sure to sample delicious Mizithra Greek cheese soaked in honey, fresh seafood like gouna (roasted mackerel) and other Greek delights.
Day 3: A 10-minute ferry ride will take you to the quiet island of Antiparos. While a day trip gives you ample time to explore the island’s quiet beaches (like Soros and Livadia) and quaint villages (Kambos), an option is to spend a night here — you can even camp if you are feeling adventurous. Kids will love exploring the stalagmites of the Antiparos Cave.
Day 4: Catch a ferry (about three-and-a-half hours) to Athens or a quick flight from Paros Airport.
Day 1: Arrive in Athens. Your first stop should be the city’s most famous attraction: the Acropolis, including the popular Parthenon Temple. Get there as early as possible to avoid long lines, and make sure to bring sunblock and water. You can also skip the lines and schedule a private, customizable tour. There are a number of hotels not far from the Acropolis area. Sneakers with good traction are also a must (the area is hilly). After a long day in the hot sun, check out the Plaka neighborhood’s bustling shops and restaurants.
Day 2: If you have time before catching your flight, pay a visit to the National Garden, a large public park in the city center. Then, wave goodbye to Greece and head to the airport to catch your flight home.
