Cruise or Island-Hop the Greek Islands? A Travel Advisor's Honest Verdict
The question I get asked more than any other: should you cruise the Greek islands or hop them by land?
So I went and tested it.
Quick honesty first: this was an award trip from my host agency for being a top seller. Azamara didn't host me, and nobody told me what to say.
The cruise
I sailed Azamara Onward's Greece Intensive. Small ship makes a huge difference. Other than tendering at Santorini, I never waited in a single line to get off the ship, and historically, I have. Small ships also get into ports the 4,000-person ships can't, so you're not fighting a floating city for the same view.
Onward was the right size for me. Honestly, I'd go even smaller, because I don't care about onboard entertainment. If you do, this is about as small as you want to go.
But you're moving every single day. That's the point. I was up early, out late, and tired the whole time, and I never once got to sleep in. Do not underestimate the value of sleeping in.
The stops, fast and honest
At most ports, one day was plenty. Two of them, I wanted to stay longer.
Syros: We had a local driver take us around, and it was a great day. We saw every corner, took 100 pictures, and asked a million questions.
Patmos: We saw the site where John is said to have written the Book of Revelation in exile. This is a very religious port.
Rhodes: Very medieval, with lots of day trips and all-inclusive hotels. It felt touristy.
Marmaris: Turkey, but I'd rather see a different part of it for a different perspective. I did visit a mosque for the first time, which was really interesting.
Crete: A cooking class, a driver, and some gorgeous hotels I've already sent to my mom. This is my new bucket list.
Santorini: She's always gorgeous. This is where the small ship matters most.
The steps, though
Either way, Greece is stairs. I fell twice, twisted my ankle, and busted up my left knee, and I'm able-bodied and work out a lot. Very embarrassing, and very real.
My friend Charmaine came with me. She lost her husband two years ago, and what she kept coming back to was that by the end, with his mobility challenges, he couldn't have handled this trip. Even the "accessible" excursions are a lot of walking.
So go sooner than you think. Not in year eight of retirement. Go while your knees still say yes.
So here's my verdict
Planning you is not traveling you. You think you want to go, go, go and see as much as you can. Then you get there and realize you actually like sleep and some chill time. The lack of downtime was the killer.
And here's what nobody tells you: you cannot budget cruise the Greek islands.
If you want Greece on a budget, go by land. We piece together great four-star hotels and ferries, go a little slower, and still do it right. My perfect combo is Athens, Santorini, and Crete, built so every stop is better than the last. But that's my perfect trip, not necessarily yours, and not necessarily your kids'. That's why we talk it through.
If you want to cruise it, because you're short on time or mobility is a factor, it has to be a small ship, and that means premium. Fast and cheap don't go together here. What you get is that you unpack once, skip the ferries, never haul bags up hotel stairs, and you can skip any excursion and still wake up somewhere new.
My rule: land-hop within a cluster, cruise across clusters. Santorini, Paros, and Mykonos are easy by ferry. The Cyclades, Crete, and the Dodecanese in one trip is a pile of flights through Athens, and that's where a small ship earns its keep.
If you cruise, which line?
People always ask how this compared to Virgin Voyages. We actually pulled up next to a Virgin ship, and the size difference was obvious. They're not on the same playing field: different inclusions, ports, and size, and a totally different energy on board. I preferred Virgin's modern approach, the app, and the food. I preferred Azamara's size. Which one fits depends on you.
Azamara is the entry point to small-ship cruising. It's the most accessible price in the category and one of the few that still has interior and ocean-view rooms. It's great for the right client, and I'd sail it again.
The next level up is balconies and suites only, because at that price point, that's what people want. The small ships I'm watching are Explora, Emerald Yacht, and Silversea. I haven't sailed Explora myself, but I book it a lot, and my clients who've sailed it absolutely love it. It's the more modern take on what Azamara does.
If you cruise, do it right
Small ship only. If you're one of my people, we're not looking at Royal or Norwegian for Greece.
Choose the itinerary for the ports, not the price.
Schedule downtime on purpose, because the ship won't do it for you.
Spend your money on the experiences in port. A lot of people choose a cruise as the budget way to see Greece, then nickel-and-dime every excursion ("wait, how much was that?") and end up skipping the exact things they came for. A cruise lets you use every single day, so make those days count.
Is it cheaper to book it yourself?
Sometimes, on paper. You can book every hotel, ferry, and transfer yourself. What you can't tell from a screen is whether it'll be baloney or really, really good, and in Greece, that gap is enormous.
There's no skill in finding a great five-star property. Anyone willing to pay $4,000 a night can do that. The skill is finding the great property, in the great location, with real hospitality, that isn't $4,000 a night. That's what I do really well.
I go do this homework so you don't have to. That's the job.
And for the record, Charmaine loved this trip as much as I did. We both needed it. She's the perfect travel buddy: low-key, loves gelato, and always up for girl dinner. What more do you need?
Neither cruise nor land is the "right" answer. The right answer is the one that fits how you actually travel.