If you are going to head out on the ocean to see the world and its whales, you might want to do it from a nice, warm place. The closer you get to the equator, the higher the temperatures are in general and the more rain there is as well. Places like these are great for older folks suffering from rheumatism and anyone else who wants to get away for a while. Portugal comes to mind as a warm but not overmuch hot place, easily accessible and open to much water.
Among the Azores there will surely be a good city for you to set up in, maybe get a hotel and check out the town while waiting for your tour to set sail.
Because they are volcanic islands, the Azores could be dangerous to stay on for a long time. You might not want to sleep there for fear of an eruption but that could be just the kind of thing that draws you to the islands, too. The waters are going to be warm for all the thermal venting nearby so you can expect to see lots of fish and more importantly whales any time of the year. That makes the Azores a popular destination for travelers seeking warm places. Remote islands really seem to draw people in from all around.
The Azores are beautiful and fit to visit any time of the year because of the fair weather and sights to see. You could stay at the Residencial Arcanjo in Lagoa or Solar do Conde in Sao Miguel, two great hotels for less than £30 a night. Regardless of where you choose to sleep, groceries should be cheap compared to eating back at home and if you’d rather not try restaurants every night, you might be able to prepare something at your hotel. Cooking with new foods for the first time can be exciting but you shouldn’t expect your results to be great on only the initial attempt. If you can keep your meals small, you should be able to eat at restaurants for most of your time away from home.
Good food won’t be hard to find on the islands of the Azores, but just in case you needed a little help, check out O Gato Mia for some authentic, ethnic food. If you want to know what Portuguese food is supposed to taste like, that’s the place you need to dine. It won’t cost much either; even their most expensive meal choices only approach £30. You can get something good to eat after a long day of whale watching or start your day off in a great way with food good enough to put a smile on your face.