It’s Real Sailor Vibes with Sea Cloud on a Cruise in the Greek Islands 

Sea Cloud Cruises in the Greek Islands on sailing ship Sea Cloud II.

Our hike to the top of the hill in Astypalaia brought us to the castle ruins and these incredible views. That's Sea Cloud II down there at anchor. (Photo by Colleen McDaniel)

It was mid-morning, and we had been cruising through the Aegean Sea for about 16 hours since we departed the port of Piraeus, Greece, the previous evening. 

I was up early to head outside to watch the sun rise and wander the teak decking of our sailing ship. The Aegean Sea's refreshing breezes washed over me. 

Temps would reach the mid-90s every day during our week in the Greek Islands, but while we were out to sea, conditions were perfect, especially when I was the only person up and strolling around Sea Cloud Cruises’ Sea Cloud II. 

A sun rises in the Aegean Sea on our Greek Islands cruise with Sea Cloud Cruises

I was up early every day to watch the beautiful sunrises and wander the empty teak decks. (Photo by John Roberts)

By 9 a.m., most of my fellow cruisers had arisen and joined me outside after having breakfast. The ship carries up to 94 people. We had 79 cruisers on during our voyage, and most of us gathered on deck to see the sailors set the sails for the first time. 

Sea Cloud II sailors set the ships sails on a cruise in the Greek Islands

Sailors climb the masts and set the sails during our trip. (Photo by John Roberts)

Sea Cloud II features three tall masts and 23 sails, which are set by about a dozen sailors who nimbly scamper along the decks, climb rope ladders and shuffle along the arms to unfurl the sheets.  

Sailors on Sea Cloud Cruises' Sea Cloud II work the ropes on deck

The decks are filled with ropes and buzzing with activity when the sailors get to work. (Photo by John Roberts)

It’s a fun spectacle to witness. Our traditional clipper ship features countless lengths of rope that are expertly coiled, wrapped and stored on pegs when not being used to set up to 3,000 square meters of sails. 

When the sails come down and catch the strong winds of the Aegean Sea, you feel like a true sailor, even if you’re just a passenger along for the ride. This is a big part of the attraction for cruisers who choose a voyage with Sea Cloud.  

Colleen and I had a blast during our time onboard the ship, meeting new friends, eating delicious regional cuisine and visiting beautiful remote islands that are especially attractive in summertime. 

Here are the five best things about a Greek cruise with Sea Cloud Cruises on Sea Cloud II. 

1. Being Under Sail 

Watching the sunrise in the morning on deck on Sea Cloud II

Cruisers love to be outside to view all the beautiful scenery on these summer cruises in the Greek Islands. (Photo by John Roberts)

This is a cruise ship for people who want to experience a proper sailing experience. When the white sails go up and catch the famous Meltemi winds of the Aegean Sea, you can feel the ship heel to either the port or starboard side. This means you’re being powered by nature, and I think it’s a blast to be out on deck leaning into it and witnessing the whoosh of the waves and feeling the winds across your face. 

The sails on Sea Cloud II cruise ship

Sea Cloud II features three tall masts and 23 white sails. (Photo by John Roberts)

It’s a brilliantly romantic nautical experience. Sea Cloud says that passengers can ask to help set the sails and haul the lines during their voyages. This was never offered to us on our trip formally with any announcements, but I guessed that maybe you just have to ask whether you can join in when the sailors are in action.  

Your ship really is one of the main attractions for this type of vacation. Sea Cloud II is one of three windjammer ships in the Sea Cloud Cruises’ fleet, joining the flagship Sea Cloud (64 passengers) and Sea Cloud Spirit (136 passengers). 

The Lido Deck and bar on Sea Cloud II

The Lido Deck has the lido bar, and cruisers enjoy meals, music and dancing out here. (Photo by John Roberts)

We had most of our lunches and dinners outside on the Lido Deck. There was always a wide variety of food at the buffet and plenty of grilled meats and fish offered by the chefs. Passengers spend most of their time onboard soaking up the sun, scenery and fresh air.  

There are loungers and day beds scattered around the outer decks, and the Lido Deck bar is open from 9 a.m. on for drinks. You can sit back and relax and have a front-row seat for when the sailors spring into action to work the ropes and sails. 

Photo Gallery: More Spaces on Sea Cloud II

I’m now going to mention a couple things that you might get to see and do on your cruise depending on the weather and wind conditions in the seas when you are sailing — whether on itineraries for the Mediterranean, Aegean Sea or the Caribbean.  

However, we were disappointed not to be able to do any of these during our cruise because they add can so much more fun to the overall trip experience. 

Photo Safari: The captain will position the ship in a scenic location, and cruisers hop into a tender to take a ride around the ship to see Sea Cloud II in all its glory with all 23 sheets fully unfurled and the sailors attending to their duties. This makes for an incredible photo opportunity, as you circle your majestic clipper ship and get snaps from all the angles.  

Swimming in the Sea: Sea Cloud II doesn’t have a swimming pool. I have also sailed on another clipper ship, Star Clipper, which has a small pool. But on Sea Cloud Cruises, the sea is your swimming pool.  

I was looking forward to jumping into the Aegean Sea just off the side of our vessel — from a marina platform — to swim and relax on the floating mats. I hear that the ship also has snorkel equipment and paddleboards, but we never were offered any of these activities during our week in the Greek Islands. 

The cruise director warned us at the start of the trip that the photo safari and marina activities are subject to weather conditions and the captain’s permission. It seemed like we had plenty of chances to take an afternoon to set up somewhere to do these things, but it never transpired on our cruise. 

2. Visiting Idyllic Islands 

Swimming at Sarakiniko Beach on the island of Milos in Greece

We made a stop after our coastal hike in Milos to swim at Sarakiniko Beach. (Photo by John Roberts)

Our weeklong cruise began and ended in Piraeus. Our itinerary was called “Hidden Pearls of the Aegean Sea,” which had a starting price around $7,000 per cruiser. 

After the first day at sea, we then visited Astypalaia, Milos, Amorgos, Naxos and Syros before returning to Piraeus.  

We were off the ship in the morning and had to be back onboard around 1 or 1:30 each day before we would sail during the afternoons to our next destination. We wish there had been more time in these beautiful towns, but we tried to make the most of it while we were there — with a mix of hikes, beach time with swimming and a little shopping in most spots. 

Colleen and I had a fun hike in Astypalaia, and we finished with a swim and time at a beachside tavern. (Photo by John Roberts)

Astypalaia is an island of about 1,200 people, with many fishing villages. The island is in the Dodecanese archipelago in the southeastern Aegean Sea. We tendered ashore, and Colleen and I hiked up to Chora Town that looms in the hillside overlooking the beaches and marina below.  

The hike up to the castle ruins yields incredible views, and you’ll wander up steep stairways and through narrow streets and alleys lined by cute whitewashed homes and shops. There also is a series of windmills up there.  

We explored the area at the top first before the temperatures started to spike. Then, we settled in at a beachside taverna to have a couple cold drinks. I also jumped in for a swim to cool off before we headed back to the ship.  

Coastal hike shore excursion in Milos with Sea Cloud Cruises

We joined an active group of travelers for our six-mile-long coastal hike in Milos. (Photo by John Roberts)

At Milos, we signed up for a shore excursion. The coastal hike sounded like a fun option, and I wasn’t expecting it to be too challenging. However, our group of 12 hikers covered about six miles of rugged coastline on the island.  

Milos is the southwestern-most island in the Aegean and is known for its beautiful beaches (especially Sarakiniko and its moonscape appearance) and a history of mining and pirate activity. 

We started at caves along the rocky coastline that were used as pirate caches. Then, we made our way along the shore and up and down jagged lava rock until we reached the uber-popular Sarakiniko Beach for a little swim stop to refresh. After our dips, Colleen and I grabbed a cold craft beer from a roadside vendor. 

Swimming in Amorgos, Greece

We found a pretty and serene spot to swim after our hike at Amorgos. (Photo by Colleen McDaniel)

In Amorgos, many people made their way up to the famous hillside monastery, an 11th-century structure that is dramatically perched on a hillside, unmistakable with its bright white color in contrast to the brown cliffs. 

Colleen and I opted to use our few hours in port to take a hike out to a church on the coast and into a stunning olive tree grove. Then, we wandered down to the coast to enjoy some swimming in the perfectly clear waters. We left some time to check out the shops and eateries near the marina and found an incredible sweets shop where we shared huge slices of honey-sweet baklava and apple tart. 

Swimming in Naxos, Greece

Yes, swimming again! This time at a beautiful beach in Naxos, with Sea Cloud II keeping us company. (Photo by Colleen McDaniel)

That afternoon, we sailed on toward Naxos, which we reached the next morning. We joined friends Stefan and Eva for a relaxing day on Naxos, which is filled with beautiful resorts and sandy beaches. Visitors with families filled up the beachfront by late morning, proving that Naxos is quite popular for tourists in summertime.  

We spent our morning swimming, drinking cold beers and Naxos spritzes and snacking on Greek food. 

Sea Cloud II at Syros, Greece

Sea Cloud II sits in the harbor at Syros as we enjoyed an overnight stay on the island. (Photo by John Roberts)

In the afternoon, Sea Cloud II cruised to Syros, where we would have an overnight stay. We had been looking forward to this destination, which allowed us to enjoy an evening in town shopping, checking out a few bars for cocktails and then a late dinner outside at the marina.  

It was a wonderful evening spent with our friends. Colleen picked up some hand-crafted jewelry, and we had a huge delicious meal of traditional Greek specialties, including mezzes like taramasalata (creamy salted cod roe), saganaki, feta cheese, grilled octopus and hummus. 

Vlog: Cruising in the Greek Isles and a Full Tour of Sea Cloud II

We had the next morning in Syros, too, and Colleen and I hiked through town and all the way up to the church in the hillside that overlooks the entire town all the way to the marina. It’s a challenging walk straight up into the hills climbing hundreds of steps. You can’t help but wonder how people live in these homes.  

Hiking to the top of the hill in Syros, Greece

Our morning hike into the hills over Syros gave us this stunning views. (Photo by John Roberts)

How difficult is it to get furniture all the way up here? Groceries? It’s just an incredible way of life to comprehend, but the homes are so picturesque and the views are incredible.  

Plus, you might enjoy spotting the dozens of pretty cats that reside on the steps and alleyways. 

Sea Cloud II departed Syros in early afternoon, and we sailed for one more day before returning to the mainland for the end of the voyage. 

3. Dining on Fantastic Food 

Surf and turf dinner on Sea Cloud II

We were treated to a variety of cuisine, including this surf and turf dinner. (Photo by John Roberts)

The ship has a main restaurant inside with open seating. There is a set time for dinners with a four- or five-course menu in the restaurant. However, we also had a few nights with a dinner buffet on the Lido Deck. Most of us preferred dining outside. We could enjoy the beautiful sunsets and the warm breezes. Plus, there was a beautiful Greek dinner buffet one evening.  

Breakfasts were buffets in the restaurant, and lunches took place as a buffet, too. Lunch was served a couple times in the restaurant but usually on the Lido Deck. 

Fresh seafood on Sea Cloud II

Seafood was always a fresh and delicious option on the menus. (Photo by John Roberts)

Early risers can find a beautiful array of pastries, fruits and coffee and tea set out each day at 6 a.m. on the Lido Deck. 

The food was a nice mix of fresh regional cuisine and international dishes. There also were cakes and three flavors of ice cream always available for dessert. Additionally, there was a big selection of cheeses, breads and jams. 

Menu items included rack of lamb, sea bass, wild boar, three kinds of pasta, turkey, grilled steaks and crab legs. 

4. Cruising with International Flare 

Cruisers enjoy the sunset in Greece on Sea Cloud II

We made great new friends with some of our 77 other travelers, a mix of American and European cruisers. (Photo by John Roberts)

We travel so that we can meet people from different backgrounds and learn about various cultures. This means trying to learn new languages, discovering little tidbits about the history or trying regional foods. 

Greece is a favorite spot for all of this — especially for the history, culture and food.   

Our Sea Cloud II itinerary gave us the chance for plenty of this, visiting charming Greek villages and coastal towns. Instead of seeing hordes of foreign tourists, these places were mostly occupied by island residents and Greece mainlanders enjoying their holidays.  

Milos and Syros certainly were bustling with tourists from all over, but these spots had a pleasant rhythm to them as opposed to other spots that get overwhelmed in high season, such as Santorini, Rhodes and Mykonos.  

The international mix we experienced offered a certain vibrancy to our strolls through the narrow cobbled streets while shopping or hunting for a place to enjoy a cocktail or bite to eat. 

Also, our crew was mostly from the Philippines, and this included the sailors, stewards and waitstaff.  

Other crew members were from places like Montenegro, Serbia, Romania, and Germany, of course. 

Speaking of Germany, most of our fellow cruisers hailed from Deutschland or other German-speaking nations such as Switzerland or Austria. 

Colleen and I found that we were two of just eight Americans onboard — and we loved it.  

We learned a bunch of new German-language music hits while dancing the night away with new friends. It was fun to sit down to a meal with a fellow cruiser and learn about where they came from and how much they also love to travel.  

In fact, we made great friends with a couple from Basel, Switzerland.  

Our greatest memory of the trip probably is sharing time at the beach, playing cards each afternoon on the lido deck and dancing late into the warm evenings with Eva and Stefan.  

5. Staying in Elegant Accommodations 

Cabin 319, a suite on Sea Cloud II from Sea Cloud Cruises

This is our spacious suite, Cabin 319, that we made our home on Sea Cloud II. (Photo by John Roberts)

None of the staterooms have balconies on Sea Cloud II. The top cabins are the two Owners’ Suites, which measure 335 square feet.  

The other 45 cabins range in size from 150 square feet to 231 square feet, which is what we had.  

Our suite on the B Deck (No. 319) was spacious with vintage stylings and lavish marble and gold decor in the bathroom, which has a bath tub and shower combo. 

We had a living room, decorative fireplace, TV, comfortable bed and walk-in closet. (Check out my cabin tours below.) 

A mini fridge can be stocked with included sodas and waters. Laundry service is available. Bring an adapter if your devices have North American-style power plugs. The cabins feature European outlets. 

Your cruise fare includes welcome Champagne and daily fresh fruit basket in your cabin, all meals, fine wines, coffee, teas and soft drinks, open bar (except premium brands), bottled water on excursions, gratuities and port fees. 

Colleen and I enjoyed our vacation cruise on Sea Cloud II. Small ships, especially traditional sailing ships, are a fantastic way to travel. The time on the open waters is more adventurous, and you get to visit tiny villages that are special places, made even more so because they are crowd-free.  

This trip could have been better if we had more time in our ports and had been able to enjoy some of the activities like the photo safari and swimming in the sea along with having water sports.  

But we can’t complain at all about the wonderful mix of active hikes, beautiful scenery, beach time, dancing at night with new friends and delicious food and drinks.  

The Greek Islands always deliver.  

Photo Gallery: Scenes from Our Sea Cloud Cruises Voyage in Greece

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