Chart House, Cannons and Wind and Sea are all boring surf and turf places with great views... and kinda beat up. Surf and Sand Resort is nicer and is right on the water. Ritz and Montage are nicest. Las Brisas has a great view, but is not nice unless you are already drunk. If you go further north, there is Javier's which has a good ocean view, but a very Real-Housewives-of-the-OC feel to it.
I agree with previous post.
Chart House and Cannons are the two in Dana Point that are the destination restaurants for special events. Haven't been to Cannons in years, but go to Chart House occasionally. Expect to wait at least half an hour beyond your reservation time for an oceanview table. People tend to linger over their coffee so assume it hard for hostesses to know exactly when a table will clear.
Menu is rather pricey, heavy on seafood as one would expect. You won't leave hungry as portions are large, especially if you have an appetizer or other starter. Menus all alacart.
Usually they ask if it is a birthdy or anniverary when making the reservation. If they don't ask, and you want a free slice of coffee ice cream sundae pie, just let them know then that it is an event. Sometimes it also triggers a menu presenttion that says "happy anniversary" on it. . (They don't sing or anything like that.) That is a bit inconsistent sodon't count on the special menu label.
As for reservations, in the holiday and summer periods suggest you make one at least three weeks ahead to get the time you want. Valet parking is $4 (or maybe $5) and street parking is almost nonexistent.
There are more casual restaurants along the harbor with nice views of the boats at Dana Point Harbor. Harpoon Henry and Wind and Sea are two suggestions.
For a casual brunch try El Torito - wait can be long there, too. But if you don't mind wandering around the harbor picking out that yacht you want to buy , it can be a nice wait.. Happy anniversary.
You can go on the cliffs of Dana Point to Cannons or Chart House, I wouldn't recommend either too strongly. There are great restaurants in Laguna and Dana but oceanfront is tough as those are unfortunately restaurants where you pay mainly for the view (i.e. Las Brisas in Laguna).
The best would probably be 162 in the Ritz or one of the restaurants in the Montage hotel, though Studio is higher than the price your looking for.
Plenty of recommendations can be found walking distance to the beach if you look around.