Dolphin/Swan Upgrades

Not necessarily. Hotels upgrade for many different business reasons. If they have some club level or other higher-cost rooms that haven't been booked, they won't automatically upgrade guests just to fill those rooms.

Also 'larger than other resorts' doesn't have to mean 'more empty rooms in club level than other resorts'. The Dolphin hosts a lot of conventions and meetings, they must run at pretty high occupancy.
 
It is probably best to book what you want and then you want be disappointed.
We stayed at the Dolphin once before and got a small upgrade to resort-view but I had heard that if you are a Starwoods member that you automatically get an upgrade? Maybe I misunderstood. We got a great rate for our trip anyway.
I can't complain. We were very lucky to get some "pixie dust" at BWI on our 30th anniversary last year.
 
It is probably best to book what you want and then you want be disappointed.
We stayed at the Dolphin once before and got a small upgrade to resort-view but I had heard that if you are a Starwoods member that you automatically get an upgrade? Maybe I misunderstood. We got a great rate for our trip anyway.
I can't complain. We were very lucky to get some "pixie dust" at BWI on our 30th anniversary last year.

I'm a starwoods member and we didn't get an automatic upgrade. It was okay, because the room was nice and we didn't spend any time in it. BTW the view was of the dumpster area.
 

It is probably best to book what you want and then you want be disappointed.
We stayed at the Dolphin once before and got a small upgrade to resort-view but I had heard that if you are a Starwoods member that you automatically get an upgrade? Maybe I misunderstood. We got a great rate for our trip anyway.
I can't complain. We were very lucky to get some "pixie dust" at BWI on our 30th anniversary last year.
You have to be at the Platinum, Gold or Preferred Plus level of SPG to receive the upgrades, which are based on availability. There are also certain promotions that include upgrades to the next room category level, such as the Sunsational Savings Promotion.

That said, if it's not an especially busy time of year, you can always inquire at check-in about the possibility of obtaining a room with a view, balcony, etc.
 
I would book what you want and not expect an upgrade. Swan / Dolphin are popular resorts for conventions. I was at the Dolphin last Sept with 800+ people!! All in our own rooms! We took over the lounge/bar area in the lobby every night, the restaurants at lunch and dinner times and the function rooms. The good news is that we were not in the parks or at the pool (awkward!!)
 

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