Espresso Boarding: Greek Isles
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Greek Isles:
Hiking, Swimming, Yachts, and Wine
The Greek Isles are one of the top playgrounds for Europeans. The shorter distance compared to the Caribbean and the relatively low prices make Greece the perfect place to vacation.
You can choose your ideal itinerary based on your desire for Adventure, Culture, or Relaxation. These itineraries are handy to bookmark - a blister or torn muscle may convert your Adventure plans into Relaxation plans. Let’s have fun.
- Cris
ADVENTURE!
| Day 1 | Day 2 | Day 3 | Day 4 |
|---|---|---|---|
| Climb a fortress then head down to the beach | Hike the Samaria Gorge | Pink beaches | Leave the tourists behind |
Day 1 Crete: Climb a Fortress Then Head Down to the Beach
Venetian Fortress
Ready to climb steep steps? Perfect! Head to Koules Fortress (Crete) and explore this Venetian fortress at the old harbor. Climb those steps to see stunning views in every direction. Wait — why is a Venetian fortress in Greece? Venice built it to defend their territory when they had possession of the island. You gotta love the ancient Venetians - they installed cannons for defense and marble wall art for beauty.
Run On The Beach
Go for a run on one of the beaches of Crete and then cool down while looking for seashells. I can’t imagine a more perfect setting - clear water, sand, and perfect weather. It can get crowded on these perfect beaches so use it as a chance to make friends from other countries. People are in a really good mood here.
Day 2 Crete: Hike the Samaria Gorge
Samaria Gorge
As the second-largest gorge in Europe, the Samaria Gorge is part of Crete’s White Mountains and was a critical source of drinking water in ancient times. The point-to-point hike starts at a 1200m (3937ft) altitude in the mountain town of Omalos, continuing right down to sea level at the black-sand beach of Agia Roumeli on Crete’s southern shore. In the summer, the Mediterranean beckons for a celebratory splash in the ocean when you make it to the end. The complete hike takes roughly 6-7 hours and hiking boots are strongly recommended. Keep your eyes open for the kri-kri (Cretan wild goat) because they are very cute but also blend in with their surroundings.
Day 3 Crete: Pink Beaches
Elafonisi Beach
Travel to Elafonisi Beach on southwest Crete, one of the most beautiful beaches in the world with pink sand and crystal-clear waters. This beach is where we worship nature on kayaks, paddleboards, or with snorkels. Pack tissues because you may cry when it’s time to leave.
Please, I beg you, don’t take the sand with you. Tourists began to bottle the sand to take home (“look - it’s pink!”) in the 90’s and have now taken so much that the beach is losing its pink hue and depth. That pink color comes from tiny fragments of shattered seashells. It regenerates but needs a little time. Are you looking for a similar beach with fewer crowds? This beach can get insanely crowded in the summer so head to South Crete for a little open space.
Day 4 Crete: Leave the Tourists Behind
Visit Remote Villages
Head to the center of Crete for a 4x4 Off-Road Tour of remote villages, hidden gorges, and beautiful views that are inaccessible by regular vehicles. Have a little patience because it’s unfair to expect the local villagers to speak your particular language. Use that translation app. Pause during the trip to park the ATV and swim in a cove to wash off the dirt. Look around - you are not surrounded by lots of people!
CULTURE!
| Day 1 | Day 2 | Day 3 | Day 4 |
|---|---|---|---|
| Architecture and Art | Uncover Depths and Perch On High | Religious Treasure and Personal Treasure | Traditional Wine and Food |
Day 1 Santorini: Architecture and Art
Walking Tour of Santorini
Get oriented by walking through the narrow streets of Fira, admiring the white-washed buildings, blue-domed churches, and boutique shops. The whitewashed walls and the blue domes represent the colors of the Greek flag. But Santorini buildings weren't always colored like that. During the Greek junta from 1967 to 1974, the right-wing military regime imposed that all buildings be painted white and blue to inspire patriotism and attract more tourists. Ha! That backfired. When the blue roofs returned, so did the tourists.
Cathedral of St John the Baptist
Originally built in the 17th century, along the path of the Crusades by the Jesuits, it was destroyed by an earthquake in 1956. Reconstruction finished in 1975 and it has been open to the public since then. Go inside and see the sheer magnitude of opulence with gold, marble, and art.
Archaeological Museum of Thera
Admire artifacts at the Archaeological Museum of Thera from the prehistoric to the Hellenistic periods, including sculptures, pottery, and frescoes unearthed from ancient Akrotiri. Look for the red and black checkered vases from the 15th century that have impressive geometric patterns. Someone had a sense of humor when they encountered a 480 kg volcanic boulder and carved “Eumastas, son of Kritobolos, raised me from the ground.” I like to imagine that Eumastas got such a scolding that the boulder was granted a place in the museum.
Day 2 Santorini: Uncover Depths and Perch on High
Guided Tour of Ancient Akrotiri and Santorini Wineries
Many people speculate that Akrotiri was the origin for the story of Atlantis. Similar to Pompeii, Akrotiri was frozen in time by ash falling from a Minoan volcano 3,600 years ago. It’s fascinating to peek at an ancient civilization that was destroyed and yet preserved. Take a private tour from a local Guide who will also take you to three Santorini wineries where you can (taste) see traditional wine making of 15 different styles.
The Monastery of Profitis Ilias
Enjoy a light lunch (especially if you are afraid of heights) and head to The Monastery of Profitis Ilias. Nearly everyone believes they will die while driving up a tiny road, with cars going in both directions, on the edge of a cliff. While official statistics are (intentionally) not kept regarding how many people actually die, there are documented instances of tourists falling off the cliff. No joke. Hire a guide/driver. The Monastery is located on the highest point of the island. Once you make it to the top, you can turn in a full circle and admire the island without anything blocking your view.
Day 3 Santorini: Religious Treasure and Personal Treasure
The Church of Panagia Platsani
Remember those blue-domed churches? Head to Oia to see them. Visit the Greek Orthodox church of Panagia Platsani to appreciate its architectural beauty and spiritual significance. Wander through the Oia Treasures Art Gallery as you walk among the churches taking selfies. A quick view at their website and I knew that I would need to invest in packing crates to get my treasures home.
Day 4 Santorini: Traditional Wine and Food
Wine Tour of Santorini
Wine is historically and culturally important to Santorini. It remains a critical part of the identity of Santorini today. Explore some of Santorini’s renowned wineries such as Venetsanos Winery and Gaia Wines. Learn about the island’s unique grape varieties like Assyrtiko and the wineries that were built to use gravity to move the wine around (they pre-date electricity).
Take A Cooking Class
The mere mention of Greek food is enough to make me hungry but I didn’t know how to master those sauces. The perfect solution is to take a cooking class in a traditional cave house in Santorini! Are you intimidated because you don’t know how to cook? Perfect - it’s a class. You will be comfortable making this food when you return home with your new skills. You will also know how to make those yummy desserts because Greeks consider dessert to be a main course.
Relaxation
| Day 1 | Day 2 | Day 3 | Day 4 |
|---|---|---|---|
| Walk The Streets of Naoussa | Lounge On The Beach | Sailing and Gratitude | Spa Day |
Day 1 Paros: Walk The Streets of Naoussa
Wander The Streets of Naoussa
Drop your luggage off and head out to soak up that Mediterranean sunshine. Stroll through the narrow streets of Naoussa and get hopelessly lost. Feeling panicked? You are on a small island and so you can’t truly get lost. Just keep walking in the same direction until you reach the ocean. Then turn around, peek at the GPS on your phone, and head back to your original destination. Getting lost in this city is part of the charm because you discover fantastic shops, sample lots of ice cream or gelato, and meet very friendly people. Enjoy the lack of deadlines and just immerse yourself in the local vibe.
Venetian Port
Go yacht shopping! It’s fun to walk through the Harbor and admire the yachts docked everywhere. You may be forgiven for thinking you walked into a yacht store but these are all privately owned and are never truly empty and unattended. That’s great news for you because it’s surprisingly easy to make friends with the guy left behind to watch the boat….and get a tour 😉 Feeling hungry? Look around you. While half of the boats are yachts, the other half are fishing ships. All of the restaurants serve fish that was caught earlier that morning. I’m not a fan of fish unless it is freshly caught and this is heaven (for me).
Day 2 Paros: Lounge On The Beach
Kolymbithres Beach
Naoussa has four different beaches and so today we will lounge at Kolymbithres Beach. Kolympithres is one of the most famous beaches in Paros, and in Greece as well, due to the sleek rocks which give you the impression of being on the moon. Some inlets have been formed among the rocks with small beaches. If you get here early, you can use them as your private beach. The water at Kolympithres is clear, shallow and warm. You can rent an umbrella and sunbed but most people use the rocks as shade. Put your phone away and enjoy the shallow water and beautiful sunshine.
Day 3 Paros: Sailing and Gratitude
Go Sailing
Take a private boat tour around Paros. Visit secluded beaches, swim in hidden coves, and perhaps even enjoy a picnic on a remote island. You control how quiet or crowded you want the swimming area to be because you control where you go. Tell the Captain “I don’t want to see people” and be taken to luxurious private coves for a swim.
Panagia Ekatodapiliani
Τhe sacred temple of Panagia Ekatodapiliani, The Church of Our Lady of One Hundred Gates, celebrates the Assumption of the Virgin with traditional religious ceremonies but also fireworks, red smoke signal flares and a large celebration. At other times of the year, it is a place of quiet contemplation to feel gratitude that you can get away on such a wonderful trip.
Day 4 Paros: Spa Day
Avant Mar
The spa at Avant Mar is a temple to healing and rejuvenation. The treatments are private and semi-outdoors, allowing you to breathe ocean air while you have the stress rubbed out of your muscles. After enjoying a massage and facial, spend the remainder of the day enjoying the pool and hydrotherapy.
Crete
$: Taverna To Thalassino (Rethymno): Even at the most affordable price point, this restaurant gets rave reviews for their fresh fish and vegan meals.Located in the Old Town of Rethymno, it offers great views and fantastic food. Try the Souvlaki: Grilled meat skewers served with pita and tzatziki.
$$: To Pigadi (Rethymno): Sample traditional Cretan dishes made from fresh, local ingredients. Try the Dakos: A traditional Cretan salad with barley rusks, tomatoes, feta cheese, and olives.
$$$: La Vigne (Naxos Town): Located inside of a Venetian castle, it is run by two French friends who fell in love with the island after visiting it and decided to settle there permanently. It is a small, homey establishment that showcases the traditional Cycladic architecture combined with bold strokes of color and pretty flowers. Because of its size, tables are limited, so booking one beforehand is highly recommended. Try the Cretan Lamb with Herbs: Tender lamb infused with local herbs, served with seasonal vegetables.
Santorini
$: Mama’s House (Kamari): Located near Kamari Beach, it’s an ideal spot for a casual and satisfying home-cooked meal after a day by the sea. It gets mixed reviews and people either love it or hate it. Try the Spanakopita: Spinach and feta cheese in flaky phyllo pastry.
$$: Metaxi Mas (Exo Gonia): Offering a blend of Cretan and Santorinian cuisine, people love this place for the fresh ingredients that are grown in their kitchen garden and raki (the grape-based brandy of Crete). Try the Keftedes: Greek meatballs served with tzatziki.
$$$: Selene (Pyrgos): Located in what used to be an 18th century Catholic Monastery, their Wine Master is one of only 400 in Europe and they take food and wine very seriously. Book the Mnēmes Experience, a unique experience exclusively for one party of 2-4 guests per evening. This unrivaled experience begins to unfold within the captivating tunnel of the 18th century monastery with a brief guided exploration of the restaurant’s intriguing history accompanied by small bites, indicative of Santorini’s culinary tradition. The storytelling tour is followed by dinner at the Atrium, Selene’s most privileged spot with a majestic ambience right next to our fountain. The dinner presented is a special variation of Selene’s Full Moon menu, matched with a premium wine pairing experience. You only live once and can eat cheap for the next few weeks to pay for this. It’s worth it.
$: Hellas Restaurant (Parikia): Many visitors come back here several times on their vacation because the food is good, the atmosphere is casual, and the prices are modest. Try the Saganaki (Fried Cheese): a crispy on the outside, gooey on the inside cheese dish.
$$: Taverna Glafkos (Naoussa): Located right next to the sea, this is a wonderful place to watch the sunset as you sip local wine and enjoy fantastic food. They do not accept reservations and so some strategy will be required to get into line and get a coveted table. Try the Seafood Risotto.
$$$: Yemeni Wine Restaurant (Naoussa): Their specialty is rustic food and the ambience is cheerful, friendly and unpretentious. You sit in a busy alley, which makes it great for people watching. There is no way you will get a table prior to 10pm without a reservation - this place is in high demand. Try the Lamb Moussaka: A refined take on the classic Greek dish, featuring layers of tender lamb, eggplant, and béchamel sauce, baked to perfection.
Paros
Hungry?
One of the ways that I afford to see everything I want - including shopping - is by eating out of local grocery stores for 80% of my meals. The remaining 20% are typically from $$$ restaurants because, for me, that is part of the experience of travel. This is particularly true in Greece because fresh produce, cheeses, and bread are abundant in shops between the hours of 10-12am and 2-4pm. Personally, I don’t like to wait in line or curb my hunger until dinner is served at 9pm and so picnicking works great for me.
Crete
$$$: The Blue Palace is synonymous with luxury in Crete, offering an opulent retreat with stunning views of the Aegean Sea and the historic island of Spinalonga. The resort boasts elegantly designed suites and villas, many featuring private pools, spacious terraces, and direct beach access.
Location: Elounda
Pro: Private Pools and Panoramic Views.
Con: You may not want to leave and go see things outside of the hotel. It’s perfect here.
$$: The Casa Delfino Hotel & Spa is a charming boutique hotel housed in a restored 17th-century Venetian mansion.
Location: Chania
Pro: Great location near major attractions, shops, and restaurants in Chania Old Town.
Con: Some rooms may be on the smaller side.
$: The Yannis Apartments are perfect for budget-conscious travelers who prefer the flexibility of preparing their own meals.
Location: Heraklion
Pro: Great value for the money.
Con: The apartments are more basic compared to higher-priced accommodations.
Santorini
$$$: Canaves Oia Hotel is a pinnacle of luxury in Santorini, renowned for its stunning cliffside location overlooking the Caldera. The hotel features elegantly designed suites and villas, many with private plunge pools and expansive terraces offering unparalleled views.
Location: Oia
Pro: Private plunge pools and breathtaking views.
Con: You get what you pay for but this is a surprisingly affordable $$$ hotel.
$$: The Hotel Thira & Villas is a comfortable and stylish stay in the heart of Fira.
Location: Fira
Pro: Rooftop terrace with panoramic views offers stunning views of the Caldera, perfect for enjoying sunsets and relaxing evenings.
Con: Not all rooms offer Caldera views, so it's advisable to request a room with a view during booking.
$: The Caveland Hostel is known for its unique cave-style rooms and vibrant social atmosphere. It attracts solo travelers and backpackers seeking affordable accommodations without sacrificing character.
Location: Fira
Pro: The hostel offers both dormitory-style rooms and private accommodations, along with communal areas for socializing and activities.
Con: Some areas such as bathrooms and kitchens are shared, which may not appeal to travelers seeking more privacy.
Paros
$$$: The Parilio Hotel is set amidst olive groves and offers elegant suites and rooms with private terraces, some featuring plunge pools.
Location: Naoussa
Pro: Do you like beaches that aren’t crowded? Your stay includes a day of relaxation at the Cosme private beach club with complimentary transfer service. This is exclusively available for Parilio’s guests.
Con: Due to its popularity and exclusive nature, rooms can book up quickly, especially during peak seasons.
$$: The Archipelagos Studios feature amenities such as a swimming pool, free Wi-Fi, and complimentary breakfast, enhancing the overall stay experience.
Location: Naoussa
Pro: Modern design and friendly staff.
Con: No on-site restaurant.
$: The Hotel Galini features basic amenities, including air conditioning and free Wi-Fi, ensuring a pleasant and affordable stay.
Location: Parikia
Pro: Situated close to the beach, shops, and restaurants, making it easy to explore Parikia.
Con: The rooms are more basic and may lack some of the comforts found in higher-priced accommodations.
Crete
Elafonisi is not only famous for its stunning beaches but also for its artisan shops that offer a variety of handmade crafts and local products. These shops are perfect for finding unique souvenirs while enjoying the natural beauty of Crete. Shop for:
Handcrafted Jewelry: Unique pieces featuring local gemstones and designs.
Cretan Textiles: Traditional woven fabrics and embroidered items.
Natural Cosmetics: Locally made beauty products using Cretan herbs and oils.
Santorini
Santo Wines (Megalochori) is not just a winery but also a premier destination for unique local products. Visitors can explore a wide range of Santorini's famed wines, olive oils, and gourmet products. The stunning views from the winery's terrace add to the shopping experience, making it a perfect spot to purchase authentic Santorini goods. Shop for:
Local Wines: Including Assyrtiko, Vinsanto, and other varietals unique to Santorini’s volcanic soil.
Olive Oil and Honey: High-quality, locally produced olive oils and honey are perfect gifts for people who are impossible to please.
Gourmet Products: Tomato preserves, capers, and traditional Greek spreads are ideal for bringing a taste of Santorini home.
Paros
The Lefkes Village Shops are located in a traditional inland village that offers a serene shopping experience away from the tourist crowds. The village's narrow, winding streets are home to charming shops and boutiques that sell a variety of handmade goods and local products. The picturesque setting enhances the shopping experience, making it a delightful stop for those seeking authentic and artisanal items. Shop for:
Handmade Textiles: Traditional Greek fabrics, scarves, and embroidered garments.
Ceramics and Pottery: Beautifully crafted ceramics, including plates, bowls, and decorative pieces.
Local Wines and Spirits: Paros is known for its excellent wines; purchase a bottle or two to enjoy later.
Traditional Greek Sandals: Handcrafted sandals made from high-quality materials, perfect for both style and comfort.
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