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Sail With us to the Greek Isles
My wife Danielle and I love to cruise. It’s a fantastic way to explore multiple destinations without the intensity of a road trip, all while enjoying the onboard experience, great food, and a relaxed lifestyle. However, when some of those elements fall short, the experience isn’t quite the same. This was partly the case on our recent Greek Islands Cruise from Athens, Greece to Rome, one of the most popular Mediterranean cruise itinerary in Europe.
For this trip, we once again chose Princess Cruises . After nine sailings and 83 cruise days with Princess, we’ve reached Platinum status , which comes with perks like priority embarkation and disembarkation, better Wi-Fi, priority dining reservations, and discounts on spa treatments and onboard photography . These benefits make it harder to switch cruise lines, even when other options are tempting.
Table of Contents
- Sail With us to the Greek Isles
- Planning and Booking: Preparing for the Greek Islands Cruise
- What to Pack for an October Greek Islands Cruise
- Time Zone Adjustment & Jet Lag Tips
- Our Greek Islands Cruise Ship: The Island Princess
- Gluten-Free Dining Challenges
- Our Greek Isles Cruise Itinerary – Hitting All the Top Destinations
- Pre-Cruise Days in Athens
- Day 1 – Evening Departure from Athens and the Cruise Port of Piraeus
- Day 2 – Mykonos and the Cyclades: A Key Highlight of Our Greek Islands Cruise
- Day 3 – Sea Day
- Day 4 – Limassol, Cyprus
- Day 5 – Rhodes, Home of the Colossus
- Day 6 – Santorini, Greece, the Most Anticipated Stop on Our Greek Islands Cruise .
- Day 7 – Kusadasi, Turkey
- Kusadasi’s Grand Bazaar – A Shopper’s Paradise
- Day 8 – Crete (Heraklion), Greece
- Day 9 – At Sea and Leaving the Greek Islands
- Day 10 – Naples, Italy
- Day 11 – Disembarkation in Rome
- FAQ: Greek Islands Cruise Travel Tips
Planning and Booking: Preparing for the Greek Islands Cruise
We booked our cruise six months in advance , giving us plenty of time to research the ports of call , compare shore excursion options, and secure the best deals. Early booking allowed us to:
- Purchase travel guides to get a deeper understanding of the destinations. I like Lonely Planet but there are plenty of others.
- Consult with your cruise line, Airbnb hosts and previous travelers for local recommendations.
- Research the destinations on the web and check event calendars for what’s happening while you’re there
- Book tours well in advance —not only to secure our spots but also to take advantage of early-bird discounts. Also, the best departure times get booked fast so don’t wait until the last minute.
Popular excursions tend to fill up fast, especially in high season. Booking early can help you avoid disappointment while also saving money! Unlike many Caribbean cruises, you’ll want to spend as much time as possible ashore.
Happy Travel Tip: Planning
Popular excursions tend to fill up fast, especially in high season. Booking early can help you avoid disappointment while also saving money! Some recommend that you directly with the tour operators or resellers like Trip Advisor, Viator, Get Your Guide, etc. rather than with the cruise line. We feel that a back on board on time guarantee is worth a premium. But do your research and shop around.
Finding the Top Cruise Deals
Looking for the best cruise deals? The best time of the year to book a cruise is between Black Friday/Cyber Monday and between January and the end of March, know as Wave Season. The rest of the year offers Last Minute cruise deals if you’re not picky about cabin location.
Also keep an eye out for transatlantic cruises, often referred to as “crossings”. These include a large number of sea days and are great for rest and relaxation. If you want to head in the other direction, there are transpacific cruises as well.
What to Pack for an October Greek Islands Cruise
Packing for this trip required careful consideration of the October weather and planned activities. While summer crowds had thinned, the weather remained pleasant , with mild temperatures inland and cooler conditions at sea due to wind and humidity. In some ways, the list resemble what is needed for Alaska cruises: plenty of variety.
Clothing Essentials:
- Layered outfits—mornings and evenings can be chilly, but afternoons are warm.
- Comfortable walking shoes—many sites have uneven terrain and stairs.
- A light rain jacket or windbreaker, just in case.
- A bathing suit—even in cooler months, pools and hot tubs are heated.
- Chic attire for gala evenings, if your cruise includes formal nights.
Practical Travel Gear:
- Binoculars—great for spotting landmarks from the ship’s deck.
- A theft-proof bag or cross-body purse—to deter pickpockets in crowded areas.
- A refillable water bottle—essential for staying hydrated on shore excursions.
- Travel guides & maps—helpful when wandering ports on your own.
Accessibility & Comfort:
- A walking stick or cane—if steep hills and cobbled streets are a concern.
Happy Travel Tip: When to go
October is an ideal time to visit —tourist numbers drop, and the extreme summer heat fades, but it’s still warm enough to enjoy outdoor activities. However, pack a few warm layers for cooler evenings at sea!
Time Zone Adjustment & Jet Lag Tips
Athens operates on GMT+3 , meaning it’s 7 hours ahead of Eastern Time (ET) . Adjusting to the new time zone can take one day per hour of difference , meaning you may feel jet-lagged for the first few days of the cruise.
To ease the transition:
- Gradually shift your sleep schedule before departure—going to bed and waking up earlier in the weeks leading up to the trip.
- Stay hydrated and limit alcohol during your flight, as dehydration worsens jet lag.
- Sleep on the plane if possible—consider using a melatonin supplement for a natural sleep aid.
- Resist the urge to nap on arrival —stay awake all day and go to bed at a local time to adjust faster.
If you’re sensitive to jet lag, arriving in Athens a day or two early not only helps with adjustment but also allows extra time to explore before embarkation. We had low expectations for Athens but were pleasantly surprised.
Happy Travel Tip: Jet Lag
If you’re sensitive to jet lag, arriving in Athens a day or two early not only helps with adjustment but also allows extra time to explore before embarkation. We had low expectations for Athens but were pleasantly surprised. The Plaka neighborhood where we stayed is clean and safe. The archeological sites were interesting and well maintained. And the food was exceptional. We promised ourselves to return there someday.
Our Greek Islands Cruise Ship: The Island Princess
Our ship, the Island Princess , felt well-named for this itinerary. At 92,882 tons, carrying 2,200 passengers and 900 crew , it was among the smallest ships in the Princess fleet—cozier than some of the massive ships we’ve been on.
The smaller size had its benefits, but also some trade-offs. Fewer dining options, no International Café (which disrupted my usual morning coffee routine), and a smaller Horizon Court buffet made the ship feel less accommodating than we’d hoped. Also, The Horizon Court’s location at the front of the ship meant more noticeable movement while sailing—something to keep in mind if you’re sensitive to motion.
Gluten-Free Dining Challenges
One of the biggest disappointments was the lack of gluten-free options .
- The Horizon Court buffet staff was inconsistent —one person would say an item was gluten-free, while another would contradict them. Worse, they didn’t seem particularly concerned.
- Thankfully, the buffet still had a dedicated clean toaster for gluten-free bread and some gluten-free baked goods (mostly muffins) . But if you want them, get up early —the gluten-free section closes by 9 AM .
- In the main dining room , gluten-free meals were available but often uninspired—usually made by simply removing ingredients rather than providing thoughtful alternatives.
- Despite the chef’s reassurances about plenty of options, his crew clearly didn’t get the memo.
Our Greek Isles Cruise Itinerary – Hitting All the Top Destinations
Pre-Cruise Days in Athens
Arriving at least a day before embarkation is highly recommended, especially in winter when flight delays and cancellations due to weather are common. This buffer can help avoid the stress of missing your sailing.
We arrived in Athens two days before embarkation—a must for adjusting to time zones and avoiding travel delays. Athens turned out to be one of the best parts of our trip, with phenomenal food, incredible culture, and breathtaking archaeological sites like the Parthenon.
Of course the main reason for choosing this cruise itinerary was the stops in Sanorini and Mykonos, two of the most celebrated Greek Isles.
Read about our 2 days in Athens (coming soon)
Day 1 – Evening Departure from Athens and the Cruise Port of Piraeus
Embarkation day was a little different from usual. We boarded around noon, as expected, but the ship didn’t depart until after nightfall.
This meant we had a unique chance to see the cruise port of Piraeus illuminated at night, with ferries and cargo ships moving in and out. The number of massive ferries in the harbor was staggering—these vessels are the lifeline for Greece’s 6,000+ islands.
At the time, Greece was experiencing maritime worker strikes, causing ferry service disruptions. Thankfully, our cruise ship set sail without issue, gliding into the calm waters of the Saronic Gulf under the glow of city lights.
Day 2 – Mykonos and the Cyclades: A Key Highlight of Our Greek Islands Cruise
We were eager to reach our first island after leaving Piraeus— Mykonos , one of the most iconic Greek islands. It’s part of the Cyclades , named for their circular layout in the Aegean. I was particularly eager to capture images of the iconic windmills that stand proudly in the heart of Mykonos Town.
Getting Around Mykonos
The Island Princess docked at the New Harbor , a facility designed for cruise ships. There’s a handy ferry service that shuttles passengers to Mykonos Town every 30 minutes for just €2 —highly recommended! If your main interest is seeing the windmills and Little Venice, there’s no need to book a tour as we did.
Exploring Mykonos Town
Our guided tour took us through the postcard-perfect whitewashed streets of Mykonos Town , accented with blue shutters, doors, and vibrant pink bougainvillea . The narrow, stone-paved streets were spotless , and unlike some tourist hubs, there were no aggressive street vendors .
Highlights of Mykonos:
- Little Venice – A row of 18th-century houses perched over the water , once home to wealthy sea captains.
- The Windmills – The most iconic landmark of Mykonos. Just be prepared to crop out souvenir stands and tourists when taking photos.
- Ano Mera – A charming inland village, home to the Panagia Tourliani Monastery and one of the least crowded spots on the island.
The roads on Mykonos are steep, twisting, and bumpy . If you’re prone to motion sickness , sit near the front of the bus to avoid getting green around the gills. If the front seats are taken, try to stay well ahead of the rear wheels.
Happy Travel Tip: Motion Sickness
The roads on Mykonos are steep, twisting, and bumpy. If you’re prone to motion sickness, sit near the front of the bus to avoid getting green around the gills. If the front seats are taken, try to stay well ahead of the rear wheels.
(A full Mykonos post is coming soon!)
Day 3 – Sea Day
A much-needed day of relaxation at sea. As we sailed south, temperatures climbed, making the pools even more inviting .
To make the Sea Days more interesting, on Princess cruises, these days are also Gala nights , with the usual Champagne waterfalls, formal portraits, live music and special dining options (Beef tenderloin is a staple for these nights!)joy a robust red while Danielle sipped a crisp Chablis—a perfect match for a leisurely evening at sea.
Day 4 – Limassol, Cyprus
We docked at Limassol’s industrial port , surrounded by rows of newly imported cars —not the most scenic arrival.
We hadn’t booked a tour, so we opted to stay on board and enjoy the ship’s amenities . And what pairs best with a warm, sunny day? Ice cream. The Premier package includes unlimited specialty desserts , and while these sundaes were sugar bombs, they were worth every bite!
Day 5 – Rhodes, Home of the Colossus
Rhodes was one of the highlights of our cruise, a place steeped in history and legend. Known as the Island of the Sun, it was once home to one of the Seven Wonders of the Ancient World—the Colossus of Rhodes, a massive statue of the sun god Helios that stood at the entrance of the harbor. Though it was destroyed by an earthquake in 226 BC, the island’s historical significance remains undeniable.
We booked a guided tour that covered Rhodes Town and its medieval Old Town, a UNESCO World Heritage site as well as the Filerimos Monstery. Our guide, Maria, was incredibly knowledgeable, bringing the island’s rich history to life as we explored.
Filerimos Monastery – A Tranquil Retreat
Our tour started by taking us to Filerimos Monastery , located on a hilltop overlooking Rhodes. This peaceful site, once a Byzantine fortress, was later fortified by the Knights of Saint John and restored by the Italians.
As we walked along the Path of Golgotha , lined with stone shrines, we were met by a surprising sight— peacocks roaming freely ! Their iridescent feathers glistened in the sunlight as they strutted across the grounds, adding an unexpected charm to the visit.
If you visit Rhodes, take time to explore beyond the main tourist areas. Hidden gems like Filerimos offer a more authentic and peaceful experience of the island.
At the top of the hill stood the Filerimos Cross , a towering structure that offered breathtaking panoramic views of the island. It was a perfect moment of serenity away from the bustling crowds of Old Town, our next stop on the tour.
The Medieval Old Town
Walking through the stone-paved streets of Old Town felt like stepping back in time. The towering walls, originally built by the Knights of Saint John , still stand strong today, surrounding a labyrinth of narrow alleys, arches, and hidden courtyards.
Some key highlights included:
- Palace of the Grand Master – A stunning medieval castle originally built by the Knights, later restored by the Italians in the 20th century.
- Street of the Knights – One of the best-preserved medieval streets in Europe, lined with inns that once housed the knights of different European nations. Today, many of these house foreign consulates.
- Socrates Street – A bustling area filled with shops, cafés, and market stalls selling local goods, including handmade ceramics and olive oil.
Though the Old Town is undeniably beautiful, we did notice obvious signs of over-tourism. Many of the historic streets were saturated with souvenir shops selling all kinds of trash made in China, and at times, the crowds made it difficult to fully appreciate the surroundings.
Day 6 – Santorini, Greece, the Most Anticipated Stop on Our Greek Islands Cruise.
Santorini was one of the most anticipated stops on our itinerary, and for good reason. Known for its whitewashed buildings, blue-domed churches, and stunning caldera views , this island is the quintessential Greek postcard.
We arrived on the last official day of the tourist season , which meant fewer crowds than in peak summer months. Still, Santorini remains one of the most visited Greek islands, and even in late October, it was bustling.
We reached the island by shuttle craft , which was a much more comfortable experience compared to the lifeboat tender crafts often used for shuttling passengers.
Our first stop was the ancient ruins at the Akrotiri Archaeological Site , a fascinating ancient city buried by a volcanic eruption around 1600 BCE.
Often referred to as the “Pompeii of the Aegean,” Akrotiri showcases remarkably well-preserved buildings, streets, and even remnants of advanced Minoan plumbing systems.
Next, we visited Pyrgos, a charming village known for its church bell tower and panoramic views of the island. As we wandered through the town, we noticed an abundance of cats lounging on doorsteps, sunbathing in courtyards, and playfully darting across narrow alleyways —a true staple of Santorini and many other Greek Islands we visited.
Winery Visit – A Taste of Santorini
Our tour included a stop at Artemis Karamolegos Winery , one of the most respected wineries on the island. Here, we sampled a variety of white wines , including the distinctive Pyritis , made from 100% Assyrtiko grapes, as well as Vinsanto , a rich, sweet dessert wine with deep historical roots. We were also served a meal of various Greek and island specialties. Delicious!
Oia’s Blue Domes
No visit to the island would be complete without a stop in Oia to observe the postcard perfect view of the iconic blue church domes set against the backdrop of the caldera and Aegean below.
Exploring Fira & The Gondola Ride
Happy Travel Tip: Mobility
If you’re visiting Santorini, plan ahead for the cable car ride—lines can get long when multiple cruise ships are in port. Alternatively, you can walk the 588 steps up from the old port, but it’s quite a workout!
Day 7 – Kusadasi, Turkey
Arriving in Kusadasi, Turkey, we were immediately struck by how different it felt from our previous stops. The call to prayer echoed through the air as we disembarked, setting the tone for a destination rich in cultural contrasts.
Kusadasi’s Grand Bazaar – A Shopper’s Paradise
We wandered through the bustling Grand Bazaar , filled with stalls selling everything from spices and textiles to “genuine fake” designer goods. The vendors were friendly but persistent, making bargaining an essential skill!
Happy Travel Tip: Shopping
If you’re shopping in Kusadasi’s Grand Bazaar, be prepared to negotiate! Vendors expect haggling, and you can often get a better deal by walking away and letting them call you back with a lower price.
Day 8 – Crete (Heraklion), Greece
Our arrival in Heraklion, Crete, was similar to Limassol in that we docked in an industrial port rather than a picturesque harbor. However, the port authorities have organized a shuttle service to take cruise passengers from the dock to a designated area where tour buses and taxis await. This made for an easy transition into the day’s explorations.
Exploring Knossos – The Heart of Minoan Civilization
The highlight of our time in Crete was a visit to the Palace of Knossos, one of the most importantarchaeological sites in Greece. This ancient Minoan palace, dating back over 3,500 years, is said to be the legendary home of King Minos and the mythological Labyrinth of the Minotaur.
We spent several hours exploring Knossos, taking in the intricate frescoes, grand staircases, and complex architectural design that hinted at the sophistication of the Minoan civilization. While some of the reconstructions by Sir Arthur Evans are controversial, they do help visitors visualize what this vast palace may have looked like in its prime.
Happy Travel Tip: If you’re visiting Knossos, arrive early to avoid the crowds and consider hiring a guide for deeper historical insights. The site can be overwhelming without context
Heraklion’s Old Town & Venetian Harbor
After Knossos, we returned to Heraklion’s Old Town, a lively area filled with cafés, shops, and historic landmarks. Some key sites worth visiting:
- The Venetian Fortress (Koules Castle) – A sturdy fortress guarding the harbor, offering great views of the coastline.
- The Morosini Fountain – A charming landmark at the heart of the town square, surrounded by inviting outdoor cafés.
- Heraklion Archaeological Museum – One of the most significant museums in Greece, showcasing an incredible collection of Minoan artifacts.
Although we didn’t have time to sample them ourselves, Cretan cuisine is highly regarded, with specialties like bougatsa (a custard-filled pastry), kalitsounia (cheese pies), and honey-drizzled loukoumades being local favorites. If you have time, stopping at a local bakery for these treats would be a great addition to your visit.
Happy Travel Tip: Local Cuisine
If you’re planning a longer stay in Crete, be sure to seek out some of the island’s renowned traditional dishes—it’s a food lover’s paradise!
Day 9 – At Sea and Leaving the Greek Islands
After several busy days of exploring, a sea day was the perfect way to relax and catch some extra Zs. After all, this is supposed to be a vacation, right? Most of the Tours start out early. As early as 7:30 am, which because of the time zone difference feels like the middle of the night.
Happy Travel Tip: Time Zones
On this cruise, the time zone keeps changing from day to day and your devices may find it hard to keep track, particularly if you turn off data roaming. Go to your date and time settings to sync the timez zone manually
The ship continued westward toward Italy, and we took advantage of the day to enjoy some onboard amenities.
- Poolside relaxation – With the warming Mediterranean sun, we spent time by the pool, reading and enjoying frozen cocktails.
- Afternoon trivia & games – A fun way to engage with fellow passengers and test our knowledge.
- Specialty dining experience – We used our last specialty dining credit to book a dinner at Crown Grill, indulging in a perfectly cooked steak and excellent wine.
Happy Travel Tip: Shipboard Activities
Sea days are great for taking advantage of ship activities you may have missed earlier—whether it’s a cooking demo, a spa treatment, or simply finding a quiet spot to enjoy the ocean views.
Day 10 – Naples, Italy
Our final port of call before Rome was Naples, a city bursting with energy, history, and, of course, pizza! The ship docked right in the heart of the city, making it easy to explore.
Pompeii – A Step Back in Time
For our shore excursion, we opted for a tour of Pompeii, the ancient Roman city buried by the eruption of Mount Vesuvius in AD 79. Walking through the well-preserved ruins, we marveled at the still-visible frescoes, mosaics, and even the eerie plaster casts of victims caught in the disaster.
It was humbling to walk the same streets that Roman citizens once did, imagining life before the catastrophic eruption.
Happy Travel Tip: Footware
Pompeii is vast, and the terrain can be uneven—wear comfortable shoes and bring water, especially in warmer months.
Neapolitan Pizza – A Must-Try Experience
No trip to Naples is complete without indulging in authentic Neapolitan pizza. After returning from Pompeii, we stopped at a local pizzeria for a classic Margherita pizza, made with San Marzano tomatoes, buffalo mozzarella, and fresh basil. The thin, soft crust with its slight char from the wood-fired oven was absolute perfection.
Happy Travel Tip: Pizza!
The best pizzerias in Naples can have long waits, but it’s worth it! Arrive early or be prepared to queue—it’s part of the experience.
Day 11 – Disembarkation in Rome
Our cruise ended in Civitavecchia, the port of Rome, which is about an hour’s drive from the city. Rather than dealing with the standard €150 taxi fare, we pre-arranged a private transfer to Rome for just €10 more. The extra comfort of a luxury sedan made the journey into the Eternal City much more enjoyable.
With a few extra days planned in Rome, we were excited to continue our adventure in one of the most historic cities in the world.
Happy Travel Tip: Transfers
If disembarking in Civitavecchia, consider pre-booking a transfer—public transport can be unreliable, and taxis fill up fast.
Conclusion: A Journey Through Time and Beauty
Sailing through the Greek Islands was a truly unforgettable experience—each destination offering something unique, from the medieval history of Rhodes to the breathtaking caldera views of Santorini. Whether exploring ancient ruins, tasting local wines, or simply soaking in the stunning landscapes, every day brought new discoveries.
That said, the journey wasn’t without its challenges. Overtourism in some areas, occasional accessibility concerns, and logistical quirks of cruise travel all played a role in shaping our experience. But as with any adventure, the magic is in embracing both the highs and the unexpected surprises.
For anyone considering a Greek Islands cruise, my biggest takeaways are:
Book shore excursions early, especially for popular stops like Santorini. Plan for varied weather, especially if traveling in the fall. Be prepared for crowds, particularly in hotspots like Fira and Rhodes Town. Take time to explore beyond the tourist hubs—hidden gems often offer the most authentic experiences.
Would I do it again? Absolutely. The Greek Islands are a blend of history, culture, and natural beauty that make them a must-visit for any traveler. And next time, I’d love to spend more time on each island, exploring at a slower pace. For insights into other cruise destinations, check our cruise destination guides.