theMilesWeKeep

Cruising the Mediterranean: Greece, Turkey, and What I’d Do Again (and Differently)

January 14, 2026

Cruising the Mediterranean—especially through the Greek Isles and Turkey—is one of the best ways to sample a lot in a short amount of time. If you’re someone who loves to explore but also wants to be intentional about where you return for a longer stay later, this kind of itinerary is incredibly valuable.

This trip confirmed something I already suspected: cruising isn’t about deep immersion—it’s about discovery. Seeing multiple islands back-to-back helped me quickly identify which places I’d love to revisit and which were perfect just as a taste.

Here’s what stood out most—highlights, tradeoffs, and the recommendations I’d absolutely make if you’re considering a similar route.

Why a Mediterranean Cruise Works So Well

A Smart Way to “Scout” Destinations

Greece and Turkey are rich, layered, and wildly different from island to island. Cruising allowed us to experience:

Bustling ports and quiet beach towns
Iconic views and everyday local life
History-heavy stops and purely restorative ones

Instead of guessing where to spend a full week later, this trip gave clarity. Some places immediately landed on my “come back and linger” list—others felt complete as day-long experiences. That insight alone made the cruise worth it.

Excursions Worth Every Penny

We chose to do two excursions through the cruise line, and both were absolutely worth it—but only because we researched them carefully ahead of time.

Santorini Wine Tasting

Santorini is stunning on its own, but pairing the views with a curated wine experience elevated the day entirely. The logistics were seamless, the pacing was right, and it felt like a meaningful way to experience the island without rushing through crowded viewpoints.

Bodrum Gullet Sailing

Sailing the coast of Bodrum on a traditional gulet was one of the most memorable experiences of the entire trip. Calm water, incredible scenery, and the kind of relaxed rhythm you want when you’re at sea anyway.

Important note: Not all cruise excursions are created equal. Some are overpriced or overly rushed. If you’re booking through the cruise line, research reviews carefully and compare alternatives when possible.

The Drink Package: Worth It (If You’ll Use It)

If you plan to enjoy cocktails, wine with dinner, or drinks by the pool, the drink package is absolutely worth it.

It removed the mental math entirely—no tracking tabs, no second-guessing whether something was “worth ordering.” It made the trip feel more relaxed and indulgent in the best way. If you’re not much of a drinker, skip it—but if you are, it pays for itself quickly.

The Cons (Because There Always Are Some)

Bundling Flights with the Cruise

This is the one thing I would not do again.

While bundling flights with the cruise initially felt convenient, it became frustrating the moment anything needed to change. When schedules went awry or adjustments were necessary, we had far less control than if we’d booked independently.

Takeaway: Flexibility matters—especially with international travel.

Kids + Pool Areas

There were a lot of kids onboard, particularly around the pools. If you’re traveling without children and envision relaxed pool days, this may be something to factor in when choosing a cruise line or ship.

Port Transfers

Port logistics weren’t always intuitive. Some transfers were smooth; others required patience and extra time. It wasn’t a dealbreaker, but it did require flexibility and realistic expectations.

Unexpected Wins & Practical Recommendations

The Gym Was a Game-Changer

If you work out regularly, check out the ship’s gym early—and often.

It was state-of-the-art, rarely crowded, and became part of my daily routine. Keeping that rhythm made me feel better physically and mentally throughout the trip, especially with indulgent meals and long days exploring.

Book Specialty Dining—But Not Every Night

The ship had multiple excellent restaurants, and I highly recommend booking a few specialty dinners early.

That said, don’t overbook. Leave space for spontaneity—some nights you’ll want something casual, or you’ll linger longer in port, or you’ll just want flexibility. A mix is ideal.

Always Arrive at Least a Day Early

This is non-negotiable.

Whether you’re flying domestically or internationally, arrive in the port city at least one day before embarkation. Travel delays happen, and cruises wait for no one. That buffer removes stress and often adds a bonus city experience.

Final Thoughts

Cruising the Mediterranean isn’t about doing everything—it’s about learning where your heart wants to return.

This trip gave us incredible views, unforgettable moments, and clarity about future travels. With a little planning, realistic expectations, and intentional choices, it can be an incredible way to experience Greece and Turkey—especially if you see it as a starting point, not the finish line.