@GolfSpy Stroker So now that the PGA is going back to Bermuda next year you really want to play Port Royal (even though it's on the other end of the island). GolfNow has it at $117 at noon every day next week which beats the $180 regular rate. Maybe GolfNow has a competitor with a better rate?
The place you want to go for your best chance at swimming with turtles is the Clearwater Beach area. They have bus service to the park in front of the beach or you can take a taxi. This is part of the old US military base that used to be at Bermuda and they still have a gate to restrict cars from going out to the end which is called Long Bay Beach at the end on the left (looking east towards St. David's lighthouse). It's a bit of a walk from the gate to the beach but we almost always saw turtles there this time of year. They like to hang out in the seagrass beds which start out at 20 to 30 yards away from shore. Just make sure to go when the water is fairly calm so your visibility is good otherwise you won't see a thing. We got snorkel gear at Costco before we moved there, there are no places to rent gear in the Clearwater area. Maybe Grotto Bay rents gear if you don't want to buy some? If you do end up snorkeling, bring a small (like 1 or 2oz) bottle of baby shampoo. This is what the dive boats use on their masks to minimize fogging. It worked better for us than the actual anti-fogging solution you can buy for way more $. One thing to caution you on is the lack of services in this area. The only bathrooms are a tiny building in the park close to the bus drop-off point.
The best place for snorkeling on the island is Church Bay which is on the South Shore past Horseshoe Beach (the best beach - they have rentals and food unlike the Clearwater area) and Fairmont Southampton (where they have the par 3 course - Turtle Hill). It's quite a ways from Grotto Bay though. If you decide to go there, you have to swim out to the rocks, that's where all the fish are. It's pretty amazing on a calm day when the visibility is good, it's like being in a giant fish tank, really cool.
For non-beach stuff, they have Harbour nights every Wednesday evening on Front St. in Hamilton. They usually have "Gombey dancers" performing along with some vendors selling food and crafts.
Fort Hamilton is at the east end of Hamilton and was probably the best fort that we visited (unless you make it out to Dockyard at the furthest point west). They have a moat garden which is pretty cool and you can take some stairs down into the fort and walk around. There is also a really nice view of Hamilton Harbor from the top of Fort Hamilton.
One of the cooler experiences we had was feeding sea anemones when we went Bell Diving. This starts out from Dockyard. It's very loud with your head stuck in a helmet but it was also very memorable. I also went on a 2 wreck dive experience for non-certified divers. Wish I had done more of that, it was really incredible.
For eating out, if you don't stay and eat at Grotto Bay the whole time there are some nice places to go around the island.
For eating with a view in Hamilton, we ate at Red's Steakhouse upstairs. Nice steaks and a good view. La Trattoria doesn't have a view but is one of the best values we found. Great food and great staff, my kids favorite place.
For eating outside of Hamilton, Gibb's Hill lighthouse near Fairmont Southampton was a nice outdoor dining experience. It's called "The Dining Room" and had really great views and good food. There were a few gnats but really not enough to deter us. Eating at Blu at Belmont Hills Golf Course and the patio seating at Port Royal G.C. are also really nice views. If you want to actually eat on the beach you can go to Elbow Beach resort. If you go to Dockyard, the Frog and Onion was good. Dockyard also has the best mini-golf place.
Be sure to check out the cave on the Grotto Bay Resort grounds, that's pretty neat. The swimming at Grotto Bay was OK, the water just wasn't as clear as some other places. They did sink a boat off the beach (seems like it was 70' to 100' from the beach, not far) and it's only about 10' or 15' down so pretty easy to free dive down to. A little bit of coral on the boat and some fish hanging out there.
Let me know if you have any questions.