I have never been to Key West. Well let me rephrase that. DH and I have never been. When I went it was with my parents and I did not do much. What is this about Bland Girraffe and fz chocolate dipped key lime pie on a stik. This sounds so good. And about the trolley does anybody know how much that costs. We want to go to the southern most point and DH would really like to see a light house.
We did the Trolley last year. I don't remember the cost off the top of my head, but for DW, DS and myself, I think it was $65.
The Trolley is a lot better than the train because it stops in more spots. You can get off when you want and within 20 minutes, another one will be there to pick you up. If they are full and you are waiting, they will call another trolley.
We got off and did the light house (cost extra - don't remember the price, but they do give AAA discounts. Ask ahead of time. Also, might have some discounts online) and Southern Most Point. They also give you some history of the island.
You could walk to both of those sites you are considering. Not sure exactly how far it is, but I think if you go right down Duvall street and hang a right, you'd be at Southern Most Point. I believe the Lighthouse is on the way. Check out a map. Maybe someone else on the thread knows the exact distance.