40F in healthcare planning a slow solo trip to the islands. Looking for local advice on wildlife, ferries, and old-school hospitality.

I’m 40, single, and taking a long-overdue break from a demanding career in healthcare. I’m planning a solo trip to the San Juan Islands soon to experience the magic of the Pacific Northwest at a much slower, quieter pace. I’ll be renting a car, leaving the crowded tourist hubs behind, and I have three specific questions for the experienced locals here:

1. What is the best, most authentic way to catch a glimpse of the transient orcas and bald eagles without being stuck on a loud, commercial tourist boat? I’d love to find smaller local water taxi setups, quiet shore vantage points, or peaceful spots around Friday Harbor where I can just sit and watch the wildlife in silence.
2. Since I prefer a relaxed, spontaneous itinerary over a rigidly planned vacation, how seamlessly can a solo traveler navigate the ferry system with a rental car during this time of year if I don't pre-book weeks in advance?
3. If the mood strikes and the rhythm feels right, I’m even thinking about jumping on a luxury cruise further north towards Alaska. Any specific local recommendations for booking something like that from the area?

Beyond the travel logistics, I'm genuinely hoping these routes will lead to conversations with some of the more seasoned, mature locals—especially gentlemen who still value the art of old-school chivalry and hospitality. A former partner in his 50s once taught me a lesson that has always stuck with me: if you really want to know a person, you have to travel with them first to see how they navigate the road and take care of you when things get unpredictable.

I’m looking for that grounded, mature energy on this trip. If you know these waters and islands well and understand where a solo traveler can find genuine local advice, please share your thoughts. Thanks in advance!