WINDSTAR CRUISES: TREASURES OF THE GREEK ISLES review
If you follow me on Instagram you know that Payton and I had a trip of a lifetime this summer. We went on a 7-day cruise around the Greek Islands in June 2025 with Windstar Cruises, and I have so much I want to share with you. This was our first cruise ever and the experience was above and beyond any of my expectations (This cruise was hosted by Windstar Cruises, as always, all opinions are my own).
Sailing through the Greek Islands with Windstar Cruises was truly a trip of a lifetime. Over seven days, we explored postcard-perfect islands like Santorini, Mykonos, and Milos. All while enjoying the luxury and intimacy of a small ship. From ancient ruins to sun-drenched beaches, each port offered something unique, and the service onboard made it even more memorable. If you’re considering a Greek Isles cruise, here’s everything you need to know before you book. It could possibly be one of the best trips I’ve ever taken.
OUR ITINERARY
We were on the Treasures of the Greek Isles seven-day cruise. The cruise began and ended in Athens with stops in:
Mykonos
Kusadasi, Turkey
Milos
Santorini
Patmos
Monemvasia
Overview of the Windstar Cruise Experience
Small-ship luxury. Windstar ships carry 150-340 passengers. Our ship, the Wind Spirit only had 148 passengers
Yacht-style ambiance: no crowds, no lines
Exceptional crew-to-guest ratio. Almost 1 crew per passenger.
Casual but elegant vibe (no formalwear required!)
Sails at night, so you wake up in a new island each morning (no travel time wasted on ferries carrying your luggage)
Sailing with Windstar felt more like being on a private yacht than a traditional cruise. I kept telling Payton “I feel like we’re in our own “Below Deck” episode.” We could feel the difference of small yacht sailing the minute we got on board. No long lines, no large crowds. Staff that knew our names by the second day and could remember if you were at breakfast or not. The ship itself is beautiful, with its tall white sails and teak decks, it never felt crowded on the pool deck. We totally fell in love with Windstar and our crew.
EMBARKATION DAY
Since I had never been on a cruise before, I wasn’t sure how embarkation worked. Boarding began at 1pm with the ship departing at 5pm. We had spent the previous three nights in Athens, so we planned to arrive around 2pm. This worked out well for us however, if you want to arrive at 1pm, you can have a wonderful meal in the Veranda, then head to the pool deck - that would have been wonderful too!
I pre-booked a private transfer from our hotel in Athens to the Piraeus Cruise Terminal with Welcome Pickups. This was so smooth. We provided our ship information ahead of time, so they knew exactly where to take us. He dropped us directly at the Windstar gate where a WS attendant got our luggage out of the car, took our information and whisked us to the waiting area. The waiting area was staffed, and Windstar had a table with cold drinks and snacks you could enjoy until it was time to board.
After checking in, you’ll pass through security before boarding the ship
We were in the terminal waiting area less than five minutes before we were taken through security and checked in - this is where we got our room keys (this is what you need to swipe in and out when you get on/off the ship and to get into your room), cruise itinerary, on-board amenity information (spa services, boutique, restaurants, etc.). You will hand in your passport here and you will get it back on the last day of your cruise. By the way, the staff that checks you on-land are the same staff on-board providing great service so this is a good time to start getting to know your crew.
The main salon
Once on board, you are greeted by the staff, offered a cool towel and drink. We were lucky that our room was ready, and we headed straight there. Guess what? Our bags were already in our rooms which I’ll never know how they got them up there so fast. One tip is to carry on what you’ll think you’ll need for the first few hours. We had our bathing suits in our backpacks just in case it took our luggage a while to arrive.
We changed into our bathing suits and headed straight for the pool deck. The bar staff was so friendly and from the first interaction made an effort to get to know you. I think they knew our names by the second day which is beyond impressive.
With only 148 passengers on board, the pool deck never felt crowded
We enjoyed drinks, sun, chatting with guests and staff until the Signature Sail Away which is pretty cool when they lift the sails and play dramatic music and then attended the safety meeting. Windstar knows how to create special moments.
Need a reason to embark early? Hanging out on the pool deck and meeting new friends was so fun!
OUR STATEROOM
All state rooms on the Wind Spirit have ocean views. There are no interior rooms. We were booked in a two-twin deluxe stateroom. Our room was located on Deck 2 midship, and our room number was 217. The room was intimate with a small dining area, seating for two, mini fridge, dresser and closet with plenty of room for our clothes. There is a safe inside the closet and more shelving for clothes or shoes.
The bed was very comfortable. Payton and I both slept great every night. There is an outlet only one side of the bed, so consider bringing an extension cord if the person in the other bed needs to charge their phone, have a fan, etc.
The bathroom was small but had everything we needed. Plenty of counter space and storage for all of our toiletries. The shower had fantastic water pressure which surprised me. Toiletries included shampoo, body wash, conditioner and lotion by L’Occitane. A hair dryer was provided in the top drawer of the dresser. There are several hooks in the bathroom to put towels and wet bathing suits to dry.
We had a Room Attendant assigned to us for our seven-day cruise and he took such good care of us. Our room was always clean, fresh towels, trash was emptied, and the bed turned down each night with a special treat. We were definitely spoiled!
Coming back to the room in the evening to a turned down bed with a little treat on the pillow was such a special touch
Some features of the room include:
Big screen TV. We used the TV primarily to access Wayfinder - which is where you’ll get all your information for the cruise (more on this below), but there are also hundreds of on-demand movies (we didn’t know they were free, so we never clicked on them) and TV shows.
American outlets in the room. We weren’t prepared for this and only packed our euro USB chargers.
Mini fridge which was stocked with various soft drinks and alcohol
Glass water bottles were refilled daily
Fruit basket
the ship lounge and bar
The ship lounge is where everything happens. Port talks, trivia games, crew talent shows and nightly musical performances. With plenty of seating for everyone, games and puzzles (which I loved that the teens were doing). There is a gorgeous bar in the corner, and the stairs in the back take you right up to the pool deck.
POOL DECK AND BAR/LOUNGE AREA
The pool deck was our favorite place to hang out while we were on the ship. There are a lot of seating options, from table top seating, loungers to comfy sofas and chairs on the top deck. There are two gorgeous bathrooms off the pool deck, so you don’t have to go back to your room to use the bathroom. On the top deck you’ll find more seating options and it’s such a great place to watch the sun set.
DAILY PROGRAM AND WINDSTAR WAYFINDER
Wayfinder is like your personal concierge. You can access Wayfinder from the TV in your room or on your phone while on board
Windstar’s complimentary Wayfinder is where you will find everything related to the ship and your cruise. You can access this on the TV in your room or scan the QR code (there will be a flyer in your room on the dresser) and have it right on your phone. Information in Wayfinder includes:
The Daily Program
Deck Maps
Port information
Restaurant hours and menu
Safety information
I recommend scanning the QR code when you get to the room and take a look at what’s on the schedule for that evening and the following day. Try to attend each evening event. The Crew Welcome, the Crew Talent Show, The Crew Farewell, this is all part of the experience, and the staff work so hard to make it special for you.
DINING ON BOARD
All meals and non-alcoholic beverages are included on all Windstar Cruises. You can upgrade to the All-In Package for just $99 per person which includes all meals, all wine, beer and cocktails, gratuities and Wi-Fi up to five days before departure.
Cruises aren’t particularly known for having great food so one unexpected highlight of our cruise was the food. Windstar partners with the James Beard Foundation, which means the onboard menus are curated by some of the most talented chefs out there. I suggest letting the dining staff share the evening's menu and ask for their recommendations. We did this and the staff was always spot on with what they chose for us (thank you to Ridwan for pushing us out of our comfort zone on this and getting us to try new food).
I never received an email about our cruise before departure, so I wasn’t quite sure what to expect as far as dining goes and required dress. There are two main dining rooms. The Veranda is open for breakfast and lunch. It’s casual buffet and full-service dining. They have an omelet station, and I think Payton ordered everything off the menu at least once. In the evening, Veranda becomes Candles, which is upscale dining. Dining at Candles is complimentary however, to ensure everyone gets an opportunity to eat there, passengers are limited to one visit per cruise -so make your reservations once you board.
Dining in Amphora
Amphora offers course by course dining and is open every night (except for the evening of the Ephesus and Deck BBQ events). While the menu changes every evening (it’s posted right outside the restaurant entry) they do offer the same menu items each night if you have a picky eater like I do (grilled chicken, steak, mashed potatoes, etc.). Dress is country club type clothing for Amphora and Candles. No shorts for men. Candles is upscale dining and is a fabulous dinner to take advantage of. Dress is elevated. We saw fancier dresses and suit jackets. You can choose to dine on the veranda at Candles and watch the sunset which is what I would recommend.
The Veranda set up for breakfast
In the morning, you can head to the Yacht Club Cafe right off of the lounge (opens at 0600) and get coffee made to order, sandwiches, muffins, etc. before Veranda opens at 0700. They also have a self-serve coffee station. I always asked for my coffee in a to-go cup so I could drink it up on the pool deck to watch the ship pulling into each port in the morning.
If you’re an early riser, the Yacht Club Cafe opens at 0600 for coffee and light breakfast
Room Service: Tired after a long day? Room service is available 24 hours a day. One night we ordered hamburgers and fries to the room and it was wonderful!
Food allergies/gluten: Notify the staff of any food allergies. We did notice that there were food allergy/gluten tags on all the food in the Verandah and on the menu. We met a friend who has gluten allergies on board and said he had no issues finding food and even the dinner at Ephesus was accommodating.
ON-BOARD SERVICES AND AMENITIES
Daily Program: Every day in Wayfinder (on your TV or on your phone) you can see the schedule for the day. There are presentations, classes and tours for those that choose to stay on board. This includes Port Talks every evening (where you get information about the Port and excursions for the next day), nightly entertainment, etc.
Medical -There is a doctor and nurse onboard and available for anything you need. The clinic is located on Deck 2.
Fitness Center - There is a large fitness center on Deck 2 across from the medical clinic with just about every piece of equipment you can think of.
World Spa: Services included everything from a massage, hair services (a friend we met got a blow out and loved it) manicures, teeth whitening, etc. Plus - you can use your on-board ship credits in the spa!
Star Boutique: Beautiful little shop just off the lounge with clothing, jewelry, gifts and essentials. This is duty-free shopping and you can apply your on-board ship credit towards any purchase.
Marina - We had two days that the water sports platforms were out on the Marina. This was one our absolute favorite things to do on board so please make sure you take advantage of it. It’s so fun to dive off the back of a sailing yacht and meet so many cool people. This is an experience you just don’t get on bigger ships. Water toys included swim mats, trampoline, kayaks, pool noodles, etc. All complimentary.
Jumping off the back of a yacht in the Mediterranean? Yes, please!
Open Bridge: On Windstar Cruises there is an open bridge policy when weather allows. This means you can go into the bridge, talk to the captain and ask questions. It’s pretty cool!
DISCOVERY EVENTS/ENTERTAINMENT
You know the magic I keep talking about that Windstar creates? The magic comes from the Windstar staff and crew. Hands down. I don’t know what their training model is, but it is the most exceptional service I have ever experienced.
On every Windstar cruise, there is a Discovery Event. On the Treasures of the Greek Isles Cruise, our signature event was the Kusadasi: Evening in Ephesus. We were bussed to Ephesus at sunset and had the most amazing white glove, 4 course meal sitting in front of the Celsus Library while the sun went down. There is no other way to see the library at night, this event is exclusive to Windstar Cruise passengers. There was a string trio from the Aegean Chamber Orchestra playing, and the monuments were lit up. Just a once in a lifetime experience that we will never forget.
Windstar had a professional photographer there and he took photos of everyone. The next morning all the photos were printed to pick up - we got over 10 photos he took of us, and they were all free. Pretty amazing. This event alone is worth the price of the cruise in my opinion. Just magical. I don’t know what else will ever compare to it.
Almost every night, there is music and dancing in the lounge by talented musicians. The crew also provides entertainment in the lounge (like the crew talent show - don't miss it!) or the Deck BBQ dinner on the pool deck overlooking Santorini at sunset (another magical night) and the Crew Farewell Show. I really encourage you to check Wayfinder every day and try to make these special events. They are what sets Windstar apart from other cruises.
The crew set up a full-service BBQ on the pool deck. There was so much great food. We got a fabulous sunset over Santorini and then we got to dance and were entertained by the crew
This was an amazing experience. So much work went into this. Two hours before the BBQ, Payton and I were laying out on the pool deck. They really transformed the space.
CRUISE ITINERARY AND WHAT WE DID
ATHENS - Our cruise started and ended in Athens. We arrived three days before embarkation. I'll share the Athens portion of our trip in a separate post.
I love seeing our little ship when we jet off on the tender
STOP ONE: MYKONOS - We chose not to purchase an excursion for Mykonos. Our ship was one of the first ships to arrive. The tender took us straight to the nearest port - which was just a five minute walk to Mykonos town (vs the port that is over a 30 minute walk or Sea Bus ride that the larger ships go to). Payton and I spent the first couple of hours just exploring the white washed cobblestone streets, shopping and taking photos. If you want to visit a beach club, do your research before you arrive (or book an excursion there). They are not created equal. Friends from the ship said they went to one and were charged $50 for two drinks. There is a bus station by the windmills by Little Venice or download Imove (like an Uber app, cheaper than taxi) to get you to the beach clubs.
The Windmills are up the hill from Little Venice. Head here first before the large cruise ship crowds arrive
Must do/see:
Stroll the cobblestone paths
Try to find all the windmills
Explore Little Venice
Count the number of cats your come across
Try to find a pelican by the Little Venice
Hike to the top of Old Town for sweeping views of Mykonos
We had drinks at Breeze Bar for the great views
KUSADASI, TURKEY - We booked Ephesus: Mary’s House Tour with ticket + lunch (for cruisers) tour through Get Your Guide and ended up being the only ones on the tour. After our tour we explored the Old Port town and had lunch before getting ready for the Evening in Ephesus event.
Our tour included a visit to the:
Virgin Mary House (knees/shoulders must be covered. Scarves are provided)
Ephesus
Artemis Temple
Carpet making demonstration and lunch
In the evening, we headed out for our Discovery Destination Event at Ephesus where we had a wonderful 4-course, white glove service dinner at the Celsus Library which was accompanied by members of the Aegean Chamber Orchestra.
STOP TWO: PATMOS
Patmos, Greece is a UNESCO World Heritage Site known as the sacred island where St. John wrote the Book of Revelation. We chose not to do an excursion here but in hindsight it may have saved us a lot of time and even money.
We thought we could walk to a nice beach, and really, it was too far away. The closest beach, on the backside of town, was way too rocky (very large boulders). We ended up paying for a taxi to take us up the village of Chora where we explored the winding alleyways. This is where you can visit the Monastery of St. John which was built in 1088. The Grotto of St. John is where he heard the voice of God, wrote his revelations and spent 16 months in exile. Before you head back down to Patmos, make sure to check out the windmills on top with amazing views of the port.
Since taxis are hard to find in Chora, I recommend paying for a roundtrip fare from the port so you don’t get stuck up there. You can tell the taxi driver when to return. Also, while you’re on the tender to Patmos, talk to your fellow passengers and see if anyone wants to split the cost of taxi to Chora - this could be a money saver.
After exploring Chora we had the taxi take us to a local beach club on the other side of Patmos. We booked him to pick us up at 3pm and it worked perfectly.
At every port, Windstar provides shade, cold drinks and snacks to have while you’re waiting for the tender to return. Such a nice touch.
STOP THREE: SANTORINI
Pulling into Santorini - I love early mornings on the pool deck
This was the stop we looked forward to the most, but it was so crowded, it ended up being our least favorite. This was the only port on our cruise where there were 7 other large cruise ships in port when we arrived.
We booked the Scenic Drive to Oia and Free Time excursion through Windstar ($129 per person), primarily because I was concerned about getting up the hill. We took the tender to the ferry port where we all loaded up on a bus. I will say the first part of the tour was a little interesting. We stopped at the top of a big mountain above the airport where there were really no views. By the time we got to Oia, it was late morning hot and super packed. We spent some time exploring Oia (it’s really hot with zero shade). We had almost 2 hours in Oia before going back to the bus for the 30 minute drive to Fira.
At Fira we had the option of getting off or continuing back to the port. Getting off meant you were on your own to get back to the boat via cable cars (with possibly very long lines) or walking down the zig zag path with the donkeys. We chose to take the bus back and skip Fira because of the heat and the crowds. We ended up spending the afternoon on the pool deck. It was very nice.
My recommendation in Santorini is to try to be on the first tender of the day to try to beat the crowds. Take the cable car up and head straight to Oia via taxi (pre-pay your return to Fira).
Deck BBQ - this evening we were treated to a Deck BBQ on the pool deck overlooking Santorini. The crew prepared huge spreads of food, desserts and capped the night off with dancing and entertainment. The captain turned the boat around so we could all see the sunset. Another night made special by the crew and meeting new friends.
STOP FIVE: MILOS, GREECE
Milos is known for its moon like rock formations and clear blue water. We booked the Amazing Beach excursion through Windstar but it’s not one I would recommend to my readers.
Our tour was $109 per person for transfer to a beach. The description said it’s one of the nicest beaches on the island and the transfer was $109 pp when the bus we were on said it costs $2 per person. A lot of people were not happy with this. There was no attendant, no service, the beach was in a port pretty much. Not what any of us were expecting.
We made lemons out of lemonade and spent some time in the water and got to meet some new people from the ship which was nice. Other passengers booked the Milos Highlights tour through Windstar and said it was really good.
We had a quick lunch in Milos before heading back to the ship and spent the afternoon off the marina playing with the water toys.
STOP SIX: MONEMVASIA, GREECE
Known as the Gibraltar of the East, Monemvasia is tied to mainland Greece by a single causeway. The town walls and several churches date back to the 12th Century. Payton and I did not book an excursion, but we heard great things about the Castle and Olive Oil Factory tour offered by Windstar.
Payton and I got on the tender after breakfast wanting to beat the heat. Right when you get off the tender, cross the street and you’ll see the bus stop. We had to go inside the bus station/office and buy roundtrip tickets. You can walk to the walled city, it’s about 30-40 minutes and there is no shade. The bus was super easy although we did have to wait a little bit on the return.
After spending a couple of hours in Monemvasia, we took the tender back to the yacht where we ate lunch, changed into our swimsuits and spent about 4-5 hours swimming off the back of the ship. This was the absolute best day.The water was perfectly clear, the weather was perfect, everyone was in good spirits. We just had a blast. It was the perfect last day!
Tonight, we were treated to the Crew Farewell event in the lounge. This was a fun evening where we got to say goodbye to the special staff that took such good care of us all week.
DISEMBARKATION
Two days before disembarkation, we received a flyer in our room with all the details we needed to know about disembarkation. We were provided with a form to turn in with our flight information and if we were taking any shore excursions in Athens.
Priority for disembarkation was for those with early flights and those who booked the Windstar shore excursions. On the morning of disembarkation, everyone has to put their suitcases out in the hallway at 0630 so we had everything packed up the night before. We went up and had breakfast and coffee, said goodbye to new friends and crew members before our disembarkation time.
We were so sad to leave. Once we were in the cruise terminal, we quickly found our luggage and just waited for our ride to the airport. I had prebooked our airport transfer through Welcome Pickups. He was waiting outside the terminal holding a sign with our name on it.
WHAT TO PACK AND BRING ON BOARD
We traveled with a carry-on only suitcase and still managed to overpack. If you’re traveling in the summertime on this cruise, I recommend bringing dresses (I brought a long skirt and it was very hot) that you can wear sightseeing and dressy enough for dinner at night. We saw lots of cute athleisure wear that worked for both sightseeing and dinner. All you really need is two pair of shoes. A pair of tennis shoes and a pair of sandals you can wear on the pool deck and to dinner.
The bathroom had shampoo, conditioner, body gel and lotion so you don’t need to bring any of that with you. You can find almost everything we travel with in my Amazon Storefront.
Between the dresser and the closet, we had plenty of room to unpack for the time ever on a trip to Europe!
Here’s what was “in my bag” for our cruise.
Sunscreen (we bought some in Athens)
Sun hat (bought one in Athens)
Shoes: sneakers for sightseeing; a nice pair of sandals that can double as beach wear but nice enough to wear to dinner
Dresses - wish I brought more sundresses - better in the heat and could have been dressier than shorts for dinners
We bought a small tote in Mykonos that we carried to the pool deck and on sightseeing days we put our portable fan, charger and camera in there
No shorts for men at dinner so remember to pack 1-2 pair of nice pants they can rewear
Medications: I’m a nurse and always travel with a little pharmacy every time we go to Europe This is what was in our med bag for the cruise:
Dramamine (never needed it, luckily)
GI meds: Tums, omeprazole, Imodium
Pain reliever, Dayquil/Nyquil
Band aids for blisters (sweaty feet plus walking 10 miles - it will happen)
Portable Mini fan - for noise and air - this fit perfectly beside my bed and made a huge difference. The room felt a little warm, so it was nice to have.
My portable fan fit perfectly here! You can find it in my Amazon store - I’ve had it over 7 years.
Euros: While gratuities are included, we liked to tip our bar staff and those that made our cruise extra special. We tipped our Room Attendant at the end of the cruise as well. Of course this is not mandatory, but we like to tip for excellent service.
Laundry service is provided on board for an additional fee and many people think its worth the cost.
Travel Insurance: We never travel anywhere without travel insurance and I highly recommend you don’t either. On our cruise alone we saw two people get injured. One so severely after a fall that they had to leave the cruise after the 2nd night. We have the Allianz Premium Annual Plan. While I have credit cards that come with trip delay/cancellation insurance, they don’t have emergency evacuation insurance so that was something I was specifically looking for.
FAQ AND TIPS
I got so many questions from my Instagram readers about our cruise that I thought I would answer them here in case you were wondering the same thing.
Is Windstar kid friendly? The youngest age allowed on Windstar is 8 years old. The youngest person on our cruise was 10 years old and he was a little celebrity on board. His mom said they had done Disney Cruises before and he thought this was more fun. From what I understand, you can fit 3 people in a room. The dining area can be turned into a twin bed for a third passenger.
Is Windstar just for older people? You guys, this is what I thought too. Were there older people on board? Yes! But there were also teenagers, college kids, and multi generational families traveling together. I really thought it was going to be all over 70 and that is just not the case. We met people from all walks of life and getting to meet so many people was one of the best parts of the cruise. If my 17-year-old said this is the best trip she’s ever taken, you better believe her!
Did we get seasick? This was my biggest fear since I had never cruised before. We never needed the Dramamine I brought. There was one night, sailing from Mykonos (which is always windy) to Kusadasi, where the boat was really rocking. Payton and I actually liked it, but heard from others that they got sick. Our room was midship which I hear is best for sea sickness. The captain did a great job of announcing when he expected things to get rocky. I recommend taking a non-drowsy Dramamine when you hear that announcement just in case.
How was it without a balcony/outdoor access? I have never cruised before, so I have nothing to compare it to. I loved waking up and looking out the port window and I loved having breakfast on the Veranda each morning. I never felt closed in or claustrophobic. The ship is so small that it’s not a chore to go get coffee or breakfast. I actually loved eating on the Veranda and seeing the reflection of a new place in the windows.
Is smoking allowed on board? Yes, on the pool deck. I never smelled cigarette smoke and only saw one person smoking a cigar and he asked if we were ok if he smoked his cigar near us. It wasn’t an issue at all.
Is tipping required? Gratuities are included in your cruise rate, however, we brought euros on board so that we could tip our bar staff (these guys knew our first names by day 2, knew our drink orders, went above and beyond for us day and night) and anyone else we felt provided exceptional service. We tipped our room attendant at the end of the cruise as well.
Cruisemapper is an app that shows you every ship in a certain port. We had fun looking at cruisemapper every day to see what ship and who’s yacht was next to us.
Have more questions about cruising on Windstar? Here is a link to all of their general information.
The top deck is the perfect spot to watch the sun set.
FINAL THOUGHTS ABOUT OUR FIRST WINDSTAR CRUISE
We had the absolute best time on our Windstar Cruise. Every misconception I had about cruising, they blew it out of the water. If you are a never-cruiser like I was, I highly encourage you to take a look at small ship sailing. This may be the best trip I’ve ever been on. For more information on Windstar Cruises, click here to get more information.
Happy Cruising!
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