San Francisco can be a bit cold going into October, But weather in Orlando or Miami should be very nice that time of year and plus it's only a 2.5 hour flight vs. a 5 hour flight, if that matters to you. I'm not sure you even care if you are in the city at all and since you mentioned the beach, it sounds more like you want to get away from the City. From Orlando, there are quite a few beach communities on the coast Daytona Beach has 3* hotels on the beach with Ormond Beach and Palm Coast as rebid zones where you can stay and you can use priceline to bid and hopefully land something in the $45-$85 range per night for 3*, giving yourself a weekend getaway that's not too far and not too expensive. If you feel more like SoBe, then South Beach in Miami will cost a few more dollars more, but definately more beautiful people and lots of clubs and stuff to visit if you think that's romantic. Bid 3* South Beach with North Miami and SW Miami as rebid zones starting at $70-$110?? per night, and you'll have the hip SoBe getaway. 2 other places that come to mind, but are a bit more remote, so you'd need to rent a car... Kill Devil Hills in the Outer Banks of Virginia (Newport News, VA) South Padre Island by Corpus Cristi, TX Let us know where you decide to go...