I’ll be going to bed in a bit after my usual nightly watching of Golden Girls.

But before I do, talk me up or talk me down.

So here’s my tentative itinerary. You’ll need to do read the itinerary to understand my question. Here goes…

Sat: 6 hour flight MSY to OAK

Sun: OAK…24hrs free

Mon: 5.5 hour flight OAK to HNL, arrive Honolulu

Mon, Tue,Wed,Thurs: Hotel #1. I wanted to be Oceanfront on my B-day). No car for this segment. I’ll be using public transportation whenever possible. From what I’ve read The Bus in Honolulu can get you everywhere.

Thurs,Fri,Sat: Hotel #2. I didn’t want to keep paying oceanfront price, so I’m moving to a hotel farther from beach, but still walking distance and I also will rent a car on for this segment, so I can explore the island more.

Sat, Sun, Mon: 51min flight to HIlo. I really wanted to see Volcano National Park. I’ve rented a car for the duration of this trip. From my reading, public transportation in Hilo is not up to the same standards as Honolulu, so a rental car is better.

Sun: Full day in Hilo. I’ll use the majority of the time at VNF, and maybe check out some places in Hilo later in day.

Mon: Flight Hilo to HNL and then HNL to OAK. This day is ALL flights. I’ll arrive in OAK late, check into my hotel for the night and then next day head back to NOLA.

Tues: 5 hour flight from OAK to NOLA

My question is about baggage. So, all my “mainland” flights will be on Southwest. Southwest still doesn’t charge for bags. The complete Hawaiian leg of the flight will be on Hawaiian Airlines and they charge $25!!!!!! for each checked luggage! I calculated that I will have paid an extra $100 just to check a bag!!!!

So my question is simple, anyone think I can manage to bring EVERYTHING I’ll need in my carryon luggage. I have a carryone suitcase that can fit in the overhead and I can get a bag that is big enough to hold my purse (I plan to bring the small one) and maybe toiletries?

Anyone think it’s possible to do?