Barnaby'sDad
Contributor
If her business conference runs from June 19 to June 23, why not join her for a day or two in Orlando at the end of her trip and then both of you can drive down to southern Florida for a few days and fly home from Miami or perhaps Fort Lauderdale/West Palm. She's going to be busy anyway and there's not much of interest to you around Orlando.
That will lose the advantage of the free hotel nights, but you can shop around for a decent place to stay at a reasonable price and it may allow you to save money (and precious vacation time) in other ways. The dive op you pick may be able to suggest a reasonable hotel option.
It will cover the price of airfare for her, and it should reduce the ground transportation costs and avoid spending so much of your limited time on the road. It might also shave a day or two off the pet-sitting fees at the start of the trip since you will still be home.
If you head down on the weekend at the end of her trip, it might even save a couple of vacation days for you.
If your girlfriend is a non-diver, there are lots of things of interest in southern Florida during the day, she might enjoy some relaxing beach time or a spa day and you can both figure out how to spend time together and still manage some good diving.
Just my opinion.
I want to be able to bring all of my stuff and come and go as I please, so I'm going to pass on flying down.
If I fly down, I have to rent a vehicle ($50+/day for something comfortable), rent tanks for all dives (including a pony bottle), not dive in the last 24 hours prior to the flight home, etc. It didn't cost me much (fuel wise) to drive down last time, so I wouldn't be saving anything (other than a few hours time each way) by flying down.
If I'm not burning the vacation days on the front end (ex. Thursday and Friday), I'll have to burn them on the back end (ex. Monday and Tuesday). I don't see a scenario in which I go down there for 4+ days and do not end up using 2+ vacation days.
She's a non-diver and she is not a fan of the heat, so she's going to be ready to leave when her scheduled trip is up. If I ended up staying past when she flies home, i'll be solo. That being the case, I should probably explore cheaper accommodation options. ex. Camping.
Edit: On the pet sitting fees and logistics...I could do what you suggested, delay my departure for two days, and just stick around for a few extra days. That's a good idea. Thank you.