White cylindrical windmills topped with thatched roofs stand against a brilliant blue sky above Mykonos. The windmills, whitewashed lanes and blue water gave us the classic Greek-island scenery I had been waiting for.
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When I started planning our Bucket List trip to Greece, I briefly considered putting together an independent island hopping trip. I figured we’d start in Athens, but then I had no idea which other islands we should visit. Or how we would get from one place to the other.

Instead, Bill & I chose to do an 8-night cruise with extra time in Athens before and after the cruise. The cruise gave us an easy way to sample 6 destinations while letting someone else handle all the transportation logistics between them.

My friend Melanie and her daughter did it differently. They did two weeks of island hopping in Greece and spent several days in each place.

Looking at our two trips side by side makes it pretty easy to see the tradeoffs—and show you which type of Greece trip might be right for you.

Greece Cruise vs. Island Hopping: Quick Verdict

  • Choose a Greece cruise if you want an easy introduction to multiple destinations with your transportation between ports already handled. You can see a surprising amount of Greece without planning every logistical detail yourself.
  • Choose island hopping in Greece if you want several days in each destination and more control over how you spend your time. You’ll have more hotel changes and transfers, but you won’t have to watch the clock, worrying your ship is about to leave without you.

Kari’s Travel Tip: I don’t think either approach is better. The real question is whether you want to sample a cross-section of Greece or explore fewer places more deeply.

The Two Greece Trips We’re Comparing

Our Greece Cruise

Bill & I spent two weeks in Greece, including an 8-night cruise aboard Celebrity Infinity, plus a few days in Piraeus before the cruise and several days exploring Athens afterward. Our cruise took us to:

  • Athens
  • Rhodes
  • Mykonos
  • Thessaloniki
  • Santorini
  • Ephesus in Turkey
An image of a map with a red and white sailboat on it and the word Rhodes. Readers who click the image can watch the ship sail the route of our cruise.
Click to watch our Cruise Route. Video made with the TravelBoast app

The biggest convenience was obvious: our cabin was both our hotel and our transportation between destinations. We’d spend the day exploring an island, come back to the ship, have dinner and go to bed—and then wake up somewhere new.

We covered a lot of ground without doing much work to get from one place to another.

Celebrity Infinity stretches across the blue water beneath a clear sky, its white hull and rows of decks visible from shore. The ship served as both Kari and Bill’s hotel and transportation while they sampled several destinations around Greece.

Curious about the ship itself? My Celebrity Infinity Review: Should You Book This Greece Cruise? covers our cabin, food, entertainment and the places we visited. The Infinity offers 7-8-9-10-14 day itineraries visiting different ports in Greece between March and October.

Melanie’s Island Hopping Trip in Greece

My friend Melanie and her daughter spent the same amount of time in Greece, but they concentrated on fewer destinations.

Their itinerary was:

  • 2 nights in Athens
  • 3 nights in Mykonos
  • 3 nights in Santorini
  • 5 nights in Crete
  • 1 final night in Athens

That meant three full nights in two places where we only had a cruise port day. They also took ferries between each island except for Crete to Athens when they flew instead.

Melanie said the towns and islands got way less crowded once the cruise ship tourists left in the evening (oops – that would be us!). And they were able to enjoy beautiful sunset dinners while we were getting back on the ship.

And that is really the fundamental difference between our trips. We saw more destinations. They had more time to fully explore the destinations they chose.

Melanie and her daughter smile together over dinner on a Santorini terrace as the orange sun sinks toward the Aegean Sea behind them. Staying overnight gave them time to enjoy Santorini at sunset and experience the island after many cruise passengers had returned to their ships.
Melanie and her daughter on Santorini

Greece Cruise vs. Island Hopping: The Differences That Matter

You can make either type of Greece trip as simple or complicated as you want, but there are some fundamental differences worth considering.

Planning & Logistics

This was one of the biggest reasons the cruise appealed to me.

Once I had booked our cruise, I didn’t have to figure out how we were getting from Rhodes to Mykonos or Mykonos to Santorini. Celebrity handled that part. We went to sleep and the ship did the traveling.

If I were planning my own island hopping in Greece itinerary, I would be researching hotels, ferry schedules, port locations and transportation on each island. I enjoy independent travel planning, but sometimes I just don’t want to spend that much time figuring everything out.

Of course, you don’t have to do it yourself. A good travel agent can arrange an island hopping trip for you, or you can choose an organized Greece island hopping tour where many of those details are handled.

But even when someone else makes the arrangements, you still have to physically move from one hotel and island to the next.

With our cruise, we unpacked once. That was pretty nice.

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How Much Time Do You Want in Each Place?

This is where island hopping wins.

Our cruise gave us a taste of Mykonos and Santorini. Melanie had three nights in each. That’s a completely different experience.

A cruise port day of 10-11 hours gives you enough time to explore, take a tour, eat some Greek food and decide whether you like a place. But eventually, you have to head back to the ship.

With several nights on an island, you can have dinner without watching the clock. You can spend a morning wandering around without an itinerary. If you find somewhere you love, you can go back the next day.

Our cruise helped me discover which parts of Greece I’d like to return to. An island hopping trip would give me the time to experience those places more deeply.

Kari and Bill stand above Santorini beside a blue-domed church, with whitewashed buildings, volcanic islands and deep-blue water stretching behind them. Their port day gave them a memorable taste of Santorini while also leaving Kari wishing she had more time to explore.
Bill and I on Santorini

How Much Freedom Do You Want?

Cruises are easy, but you trade some freedom for that convenience.

The ship determines when you arrive and when you leave. If you’re having the greatest day of your entire trip in Mykonos, too bad. When the ship sails, you’re going with it.

Island hopping gives you much more control over your days.

You still have reservations and transportation schedules to work around, but once you’re staying somewhere for several nights, you can decide how you want to spend that time.

You can sleep late. Find a beach. Spend three hours over dinner watching the sunset. Go back to somewhere you loved yesterday. Or decide you don’t feel like doing much of anything.

For some travelers, that freedom will matter far more than the convenience of a cruise.

Kari stands above Mykonos harbor wearing a sunhat and holding an open hand fan, with white buildings, boats and blue water behind her. Exploring Mykonos independently during their cruise port day gave Kari a taste of the freedom she would have with several days on the island.
Me on Mykonos

How Many Places Do You Want to See?

This may be the easiest way to make the decision. Do you want to see more places—or know fewer places more deeply?

Our cruise was a sampler platter of Greece. In eight nights, we experienced 6 very different destinations. Melanie’s trip concentrated her time in Athens, Mykonos, Santorini and Crete.

Neither approach is wrong.

For a first trip, I loved sampling several parts of Greece because I didn’t know which places I would love until I actually saw them.

Massive gray-stone fortress walls and rounded defensive towers rise above the entrance to medieval Rhodes Old Town. Rhodes was one of several very different destinations Kari and Bill were able to experience during their eight-night Greece cruise.
Old Towne Rhodes

What About Cost?

I wouldn’t choose between a Greece cruise and island hopping based on the assumption that one is automatically cheaper.

You can book an inexpensive cruise cabin or a luxury suite. You can stay in modest apartments while island hopping or beautiful hotels overlooking the caldera in Santorini.

Food, tours, transportation and the time of year you travel can change the numbers even more.

For us, the Celebrity Infinity cruise was a surprisingly affordable way to see several destinations because we booked a last-minute deal. We also chose to skip the ship’s drink and Internet packages, which kept our onboard spending considerably lower.

You need to price out the complete trip you actually want rather than assuming either cruising or island hopping will automatically save you money.

Who Should Choose a Greece Cruise?

A Greece cruise may be the better choice if:

  • You want an easy introduction to Greece.
  • You want someone else handling most of the transportation between destinations.
  • You want to experience several places during one vacation.
  • You don’t want to change hotels every few days.
  • You already enjoy cruising.
  • You’re comfortable having a limited amount of time in each port.
  • Planning all the details of a multi-destination trip gives you analysis paralysis.

For me, that last one was important.

I do a tremendous amount of travel planning, and sometimes it’s really nice to let someone else do part of the work. Our cruise gave us a simple way to sample Greece and figure out which destinations we might want to return to someday.

Kari sits on the private veranda of her Celebrity Infinity cabin with the blue sea stretching behind her. Having one comfortable home base while the ship carried them between destinations was a major reason the cruise worked so well for their first Greece trip.
Me on the balcony of our cabin

Who Should Choose Island Hopping in Greece?

Island hopping may be the better choice if:

  • You want several days in each destination rather than several hours.
  • You want more control over your daily schedule.
  • You enjoy choosing your own hotels and restaurants.
  • You like independent travel.
  • You don’t mind transferring between destinations during your trip.
  • You already know which Greek islands you most want to experience.
  • You want time for slower mornings, evenings and unplanned exploring.

And remember, enjoying the freedom of island hopping doesn’t mean you have to enjoy planning it.

If researching ferry schedules, hotels and transfers sounds miserable, you can always use a travel agent or look at Greece island hopping tours that handle more of the logistics for you.

A small white Greek Orthodox church with a vivid blue dome stands beside the rocky Mykonos waterfront under a clear sky. Spending several nights on islands like Mykonos gives travelers more time for slower mornings, evenings and independent exploring.

What Would I Choose If I Went Back to Greece?

For our first trip, I would choose the cruise again.

It gave us exactly what I wanted: a simple, easy and affordable way to experience several parts of Greece.

But here’s the interesting part.

Now that I’ve sampled Greece, I think I’d make a different choice for our next trip.

I’d seriously consider an independent trip with time in Athens, Mykonos and Santorini. Those were the places that most closely matched what I had imagined Greece would feel like before we went—the ancient history of Athens and those beautiful whitewashed island towns surrounded by incredibly blue water.

Instead of another quick taste, next time I’d want more time.

Whitewashed buildings cascade down Santorini’s steep cliffs with the deep-blue Aegean Sea stretching toward the horizon. Seeing Santorini during the cruise helped convince Kari that she would want more time to explore the island on a return trip.

If Athens is part of your plans, our Athens Itinerary 2 Days: Before or After a Greece Cruise shows exactly how we made the most of our time there.

And if this will be your first trip to Greece, my Greece Travel Guide: What First-Time Visitors Need to Know covers all those little practical questions about Euros, Schengen rules, transportation, phone service, electrical outlets and more.

A glowing red-orange sun touches the horizon above calm water as the sky fades from gold to dusky pink. The peaceful view at sea captures the easy cruise experience that made sampling several parts of Greece work so well for Kari and Bill’s first visit.

Island Hopping in Greece vs. a Cruise: My Bottom Line

Our Greece cruise gave us exactly what we wanted from a first trip: an easy way to sample several destinations without having to plan every logistical detail ourselves.

Island hopping gives up some of that built-in convenience, but you get something valuable in return—time.

If your Bucket List goal is to experience several different parts of Greece and discover what you love, I’d seriously consider a cruise. It worked beautifully for us.

If you already know you want to explore Mykonos, Santorini, Crete or another Greek island for several days, island hopping in Greece may be worth the additional logistics.

Neither way is better.

The real question is whether you want to sample Greece or explore it more deeply.

More Greece Guides

Here are some more guides about Greece. If you’d like to receive emails when I’ve posted new content to the website, please complete the short form above.

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