Hi Heather and thank you for the great questions!
Yes a cruise is really nice but it really only gives you a snap shot of the different areas. By flying directly and staying a few days in both areas of interest, would definitely give you more time and a better taste of what each place has to offer. Flying into Charlottetown or Halifax would be ideal, that way you could rent a car at either location and begin your adventure.
I can only speak for Prince Edward Island but I find if you have a car, following the three scenic routes around the Island gives you the best opportunity for seeing the most and hitting the majority of the neat attractions. Of course, you will always find a few treasures off those routes as well. We have some really great sample itineraries on our website too. It's a really good starting point to get a feel for what is out there and help you decide how you'd like to start.
Most people find spending two or three days doing each coastal route a perfect amount of time. To find the perfect place to meet your needs, Tourism PEI offers a convenient online accommodation search engine called "Places to Stay". With this search engine you can define the type of accommodations you are looking for, in your case a cottage.
A visit to PEI wouldn’t be complete without a visit to "Anne's home" - The Green Gables Heritage Place - located in the heart of Cavendish on the Island's beautiful north shore. You can walk the grounds experienced by the author, Lucy Maud Montgomery, which inspired her to write this world famous book. There is a small movie theatre on the grounds offering you a taste of the time as well as beautiful trails including the Haunted Woods, Balsam Hollow and Lover's Lane. For a full list of all things Anne of Green Gables on Prince Edward Island, please visit the Anne of Green Gables page on our Tourism PEI website.
For good walking areas, I would suggest checking out the new Bonshaw Hills Provincial Park trails. There are at least 14 kilometers of hiking trails there. My other suggestion would be the PEI National Park as it has scenic look outs and beautiful walking areas. Being a small island, nothing is really ever far away. We are surrounded by amazing beaches from one end of the Island to another. They are great for exploring and looking for seashells, pretty rocks or starfish.
Local music and festival and events can be found at many locations across the Island. You can check out the Festival and Events site for information on ceilidhs and other musical performances while you are here.
I truly hope you and your mother have a wonderful stay on Prince Edward Island.