To Cruise or Not to Cruise?
Disclaimer: I generally prefer not to book group tours or huge hotels. So with biases declared, here’s my most objective opinion of cruising. To cruise or not to cruise depends entirely on the operator and your style and expectations. Cruises can be great IF you pick the right boat and the right circumstances.
In addition to unobstructed sea views, the biggest reason to cruise is that you pack and unpack only once, while enjoying multiple destinations. No additional trains, planes and automobiles. If you’re someone who wants to see a handful of ports without a lot of organizing, a cruise is perfect! Expect to pay for that convenience though; cruises are NOT cheap, especially if you don’t want to be crammed into a tiny space.
Cruising is definitely more tourist than traveler. So if you’re heavy on the traveler side, you may be better skipping the cruise and hiring a boat and crew to sail you privately. Or pick two or three destinations and take the train or a couple short flights during your trip.
If you’re someone who can’t narrow down your destinations or you want a taste of a region (think Mediterranean or Caribbean highlights), a cruise is like a destination sampler. You can pick your favorite for a longer return trip another time.
Mykonos town 
And locals beach
With a cruise, you’re in and out of each place quickly so wont have as much opportunity to really get to know each destination. You and hundreds or thousands of others will all be trying to see the same sites in each port. To avoid the crowd, skip the prearranged ship tours and take the extra time to hire a local guide to meet you at the port and take you somewhere different. It’s a little more effort, but worth it to do your own thing at your own pace. In Santorini, this allowed us to explore Thira, Oia and lesser visited Pyrgos all in one day. Our guide also offered a local’s viewpoint on the Greek crisis, since we were there the week before the payment default deadline in 2015. It was a really interesting way to experience history in the moment, much better than the canned schpeel and jokes you often find in a group tour.
Restaurant to ourselves in Pyrgos 
And nearby church
If your ship drops you walking distance from the main site, like in Rhodes, explore it on your own and then taxi to a locals beach. Make sure to allow ample time to get back to your boat; if you miss the departure, you’re responsible to get yourself to the next port.
Rhodes old town and locals beach
In my opinion, a cruise is best if you’re starting and ending in two different cities that are of high interest to you; extend your stay a few days in each spot. Then the cruise serves as transport and lodging, with added perks.
We loved our Celebrity Cruise that embarked in Athens, stopped Rhodes, Mykonos, Santorini, Ephesus and then disembarked in Istanbul. With a few added days in Athens and Istanbul, it was a great way to get from country to country and see a few islands on the way. Another one I’ve been eyeing takes you through the Baltic countries and adds an overnight stop midway in St Petersburg, allowing multiple days to explore a spectacular city.
Cruise Tips
Plan ahead so you can arrange your vacation time around the destinations you want to see. If you don’t have to squeeze it into a week, build a day or two buffer before you embark, accommodating potential flight delays.
Splurge on a family room, multiple rooms if your kids are older (since cruise price is per person), or a suite. If booked, ask to be on the waitlist, or call the week before to see if they have any nicer rooms they’re willing to upgrade for less than usual. Standard rooms are easier to fill, so you can sometimes get a last minute deal. In addition to more space, most suites include access to different restaurants, special areas and priority embark/disembark. Celebrity also included a butler who delivered a full breakfast and a 4pm daily snack. Kids loved “steering” the ship at the special captain’s launch party one evening.
If you’re prone to seasickness, choose a bigger ship, since the stabilizers help the boat feel like a land-based hotel. We even survived a thunder and lightning storm without feeling any rocking on our giant ship! Make sure to get a room with balcony for fresh air. It may sound snotty, but a porthole would not be manageable for me for a week. BYOD (Dramamine), or get a patch from your doctor, and make sure to sufficiently hydrate.
On the other hand, if claustrophobic, a smaller ship or river cruise might be better. Try Viking or National Geographic river cruises, although with a large retiree crowd, these may not the best match with young kids. Silversea offers small luxury cruises and National Geographic offers small expedition style cruises as well. Whatever you choose, make sure to get a balcony and make frequent visits above deck. Stick to itineraries with few at sea days, and get off the boat at each port.
Splurging on Norwegian’s Haven or Celebrity Aqua or Concierge Class is another way to get added perks without the cost of a suite. There are budget lines, but I wouldn’t recommend them unless you really want to cruise and aren’t bothered by crowds and lesser facilities, food and service. If the special classes are too pricey, and you just need to make the standard room work, choose a mid-range line, and book a couple nights at a quiet boutique hotel when you disembark. That way you can fully unwind before heading home.
Look carefully at the drink plan. Sometimes the added suite cost is almost covered by extras like included spa, special meals and drinks. Those $10 sodas add up. If you’re not in a suite, consider pre-booking a beverage and tip package; it often pencils in the end.
Dine in the smaller paid restaurants (typically included in upgraded rooms or prebook for a better rate). They’re not as fast, nor all you can eat, but food quality, service and atmosphere are worth it. Most ships have at least one with spectacular views. Parent pro tip: bring the kids to the buffet early, and then drop them at kids club while you enjoy a dinner date night.
Fresh sea air 
King of the boat
If you have multiple kids, look into the age breakdown for kids club. Each line is different, and if your kids will go more easily if together, it may be worth selecting a ship where they’re in the same age bracket. We almost never used kids club because my 7-year-old wanted to be with her 9-year-old brother, and the ship wouldn’t allow her to go to the 8 to 10s room.
Consider how much time you’ll be on the boat and how much entertainment your kids need. We toured 6+ hours each day, so by the time we showered and ate dinner, we were ready for bed. If you have several days at sea, or kids under school age, you may want to try a Disney cruise offering characters and kid shows; for tweens and teens, some Royal Caribbean ships offer flowrider, rock wall and basketball court, or check out the Norwegian ships with water slide and race track. While great for kids, these lines will feel a little more like a theme park, so adults may want to bring noise-canceling headphones or book a spa treatment.
Relaxing in Istanbul post-cruise
Cruises are also great for extended family trips, since there’s something for everyone. My first was taken with my mom and grandma when I was 21. And if you have a Nana who’s not quite ready for a care facility but ready to let go of the upkeep of a home, consider extended cruising. We met a nice lady in her 80s who had outlived her husband; she sold her home and booked a year of consecutive cruises. She had family visiting for a week here and there. All in, she said it was cheaper than the transitional care home she looked into, and she loved seeing the world!
