Transporting luggage Athans and the Islands

You will wheel your luggage onto the ferry and hand it off. It will be piled with others going to your destination. I can’t imagine taking luggage any larger than 22”. If that can’t be accomplished, perhaps you can find a tour to the islands. You can fly from Athens to several of the islands but not all of them. It is difficult to find flights between islands so you would have to fly back to Athens to connect..

Really, you have to be able to handle your own luggage to use the ferries.

I recall people who had mobility issues asking if there were services for help on the ferries on this forum without any luck.

I would say your wife has to pack lighter so she can wheel her own luggage or you won’t be able to very easily island hop.

You could fly to one island and use a taxi to get to your hotel and reverse that to fly back to Athens.

I'm not sure how much you two pack but the best policy is to travel lightly. Only take what you need. Dress in most of Greece is very casual even for going out at night. If you need anything buy it in Greece. No sense in dragging along multiple suitcase stuffed with clothes and other items you'll probably never need. One pair of good shoes will suffice for walking and a night out.

I have a small suitcase and 1 carry-on size backpack. I fit most of the clothes and important items in the backpack and jacket, rain jacket, hat, & toiletries in the suitcase.

The small suitcase is mostly taken to bring back gifts and souvenirs.

My normal time in Greece is 13 days and I found out you really don't need to bring a lot of extra items. You can get double use on clothes for exploring and a night out.

If you cannot downsize to a 21-22 inch roller bag as your primary bag, then hopefully you have a teenage grandchild you can bring along as your pack mule.

The answer is NOT finding some company or service to lug heavy bags, the answer is talking sense into a beloved partner. Would it help to show her some advice from another senior woman who has done 11 trips to Greece in May-June with one 20" suitcase plus a medium-size carry-on tote... and still manages to look respectable by day, and presentable for the evening? It might help if your wife could look at some typical online pack wardrobes will fit in a 20-21" rolling bag and provide outfits for every occasion. Here's one - https://www.flipandstyle.com/2014/06/packing-for-european-summer.html. (It needs some adapting for seniors & for personal tastes of course -- adding more bright colors for tops, for example)

Basically it involves using 3-4 basic colors that coordinate and minimizing any "dress-up" items -- Greece is simply NOT a dressy place in June & if that's what your wife wants, you need to choose another destination. Only on cruises do they wear long fancy dresses and white tuxedo tops... and nowhere will she want high heels! Even of an evening, nice flats r best. Another key is occasionally doing some hand laundry (almost all island hotels have little hanging racks on balcony, and things dry in an hour!); also hotels routinely have 1-day laundry service. That said; a woman can readily do 2-3 weeks with: TOPS - 5 knit tees, 1 LS shirt PANTS -2 lightweight long, 3 capri length; 1 patterned skirt, 1 pattern long pants; 2-3 pr shoes (sturdy walkers, midweight sandals, flats) 1-2 v. light cardigans, 1 SHORt windbreaker; 1 swimsuit, 1 nightie, underthings. Scarves & jewelry can doll things up. For you, forget the sport-coat, even in top athens restaurants. Also, no jeans; in June they feel too heavy. Maybe add a short sun-dress.

Believe me, this works; you both will be happier. Tell her to look at it this way -- if you will be island-hopping, you're on the move every few days, and no one on Naxos will know that you wore that T-shirt & Capri combo 2 days ago on Mykonos!