If you want to see a number of different islands in a short time from the comfort of a mobile hotel don't hesitate, especially as the realistic option is a number of inter-island flights and the time this takes out of your holiday.
We're a married couple from the UK in our late 40's and have cruised with several different lines in a number of different parts of the world. Essentially we look to use the ship as a floating hotel to visit different places, so the port intensity and quality of stops is of far more importance to us than the ship.
We flew out via a couple of great days in Vancouver -- having experienced the unpleasantness of US immigration on previous trips, clearing immigration before reaching America in Vancouver was a pleasure with friendly border staff and a reasonable flight.
We'd pre-booked airport transfers to the Ramada Waikiki (hotel OK, breakfast poor) with Roberts Hawaii ($11 each) and they were very professional -- staff waiting before baggage collection with a list of customers they had booked off our flight -- there were plenty of Roberts staff around so if you had any problems I'm sure they would have sorted it out. Once they'd found everyone we went down to find the bags that were then passed to a Roberts porter with a luggage cart -- once everything was found they radioed for the van and we were away -- about 20 minutes. While the overall cost seems not much less than a taxi, the fixed price was an advantage as we were at the tail end of the rush hour and watching a taxi meter whirl round would not have been a good start to Hawaii!
I use Hertz for business travel in Europe so am in their loyalty club -- it works very well, but more later. In Waikiki they have a concession inside the Hilton Village (about 5 mins from the Ramada) where we picked up a car for a couple of days before the cruise -- they keep them in the multi-story car park on site and so are easy to collect and drop off.
On the Saturday afternoon we checked in for the cruise around 3-30 with no queues and went straight to our room, grabbed a quick bite in the Aloha buffet (all eateries close at 4pm ready for the safety briefing at 5pm). Before we got to the ship we had problems in finding the exact location the ship docks. It ties up (I think) on Pier 2 -- it's definitely the berth accessed via Channel Street off Ala Moana Bld -- the UK version of Google Earth has the ship moored up in the picture next to the large shed complex they use as an embarkation hall. Vehicles enter via Channel Street (one way) and leave via Forrest Ave. We saw a number of ship staff walking into Waikiki (guess about 50 mins?) and we walked over to the ship from the Aloha Tower -- about 20 minutes. Some cruise ships tie up directly next to the Aloha Tower -- the POA does not!
To take advantage of the great itinery we booked two weeks back-to-back -- an option not really advertised; all the agents push you to a week on the ship plus a hotel stay. In fact it was simple -- the cost was effectively double that for one week. Half way through the first week we asked at reception what we needed to do and they simply swapped our existing cruise cards for ones with later dates. As we had pre-booked the same cabin for the two weeks there was no need to pack or do anything else -- we simply treated the turnaround day as a port day (Pearl Harbour - bus from across the main road outside the port straight there $2.50 each).
Chatting to the ship officers (during a Latitudes party) they said the ship effectively sails full every week so the prices don't get big last minute cuts. This was very much our experience and so we eventually booked an inside cabin (for the first time). Other reviews have discussed the relative merits of balcony cabins verses inside -- all I can say is we couldn't justify the extra cost, though we were thrown by the lack of daylight to give a time clue. After a couple of days we took to leaving the TV on with the sound off and tuned to the bowcam channel! Also the inside cabins don't have facilities to make hot drinks -- but other than these two minor issues, the cabin was fine -- there was a safe and small fridge. As others have commented the ship spends lots of time in port and so if you're active you don't lose much by going for an inside cabin and you save a bundle. We did pick the location carefully (Deck 9 near the back) and this was ideal -- 2 flights of stairs up to the Aloha buffet (and on tap coffee) and 6 down to get off on Deck 3 -- to limit weight gain we have a policy of not using the lifts so getting back on at Deck 3 let us climb to Deck 6 via the midship stairwell, catch our breath walking through Deck 6 to the aft stairwell to cover the remaining stairs up to Deck 9!
Noted a few people commenting on the expense/poor quality of the on board wifi. If you have your own remote IT device not needing a plug in connection, there's no problem in finding high quality free (or the cost of a coffee) wifi ashore -- I kept up with data heavy work emails and booked our week two cars on line from various cafes with no problem.
Foodwise we ate in the Aloha buffet all the time and it was absolutely fine if slightly eclectic in options in the evenings.
The Aloha restaurant covers a large part of the back of Deck 11 running right through to include an outside dining area. At breakfast time the main (inside) buffet opens about 7am with a smaller area (under a cover outside) duplicating the main buffet opening at 7.30. During evenings, only the inside buffet is opened (at 6pm), though you can easily carry food through to the outside dining area. Oddly no trays, but the plates are way oversized! We ate outside all the time and never had a problem finding a table. Plenty of veggie options inc soya milk if you asked.
The food is laid out in island units that you wouldn't think would work but do -- they seem to minimise queues -- the only ones queues we saw were for the carvery and salad at peak times. Otherwise there was always pizza/burgers/pasta as well as Indian food if the main options did not appeal.
Helpfully free coffee/tea/fruit tea/water/lemonade (or similar) plus ice was available all the time in the Aloha Buffet either in the main area or in the smaller buffet area on the outside deck.
Can't comment on any of the other eating areas (or indeed the on board entertainment) as we never visited - except the Cadillac Diner we tried once -- you had to order and it was slow!
Trip wise we hired cars at all the stops in the first week and some during the second. I'd strongly urge you do this and book in advance -- we got better prices on line and on a couple of occasions I heard people trying to book on the day being told there was no spare cars. This also worked out much much cheaper than taking ship trips. At all the ports the mains car hire companies were running automatic courtesy shuttles to and from the airport rental locations. Thrifty and Dollar seemed to be getting most of the business, but we were well served by Hertz. The only exception was Kona (the tender port) were we rang after waiting for an hour and they sent a shuttle -- evidently the airport is further away and lots of people don't bother with a car as the port itself is nice -- would have been helpful if they'd said this beforehand..
Port wise Kahului is an industrial area and while there are beaches you can walk to either way they aren't great and quite exposed -- you really need a car or trip to the other parts to the island.
Hilo again is quite industrial, though the nearby beaches are nicer with some pretty coves and a shopping centre not too far away -- still a car is helpful as you can cover these areas on the way back.
Kona is the tender day and the only time you get dropped right into the middle of a nice tourist area with a mix of beaches shopping and a historic area.
Nawiliwili again is an industrial port, though with beaches and shops about a 10 minute walk away -- there are free shuttles. Just about enough entertainment for half a day.
We struggled to find any ship specific info on disembarkation (to inform us in booking our own flights) so you may find the following useful;
A few days before the end of the cruise they put colour coded labels out near reception -- they don't get delivered to your cabin. These are timed for disembarkation from 8am in 15 minute groups through to (I think) 9-30.
You put these on your bags the night before disembarkation and the cases are ready batched inside the pier terminal ready to be collected according to colour when you get off. On the Saturday morning they announce the colour codes for you to get off -- in reality each time was called about 15 minutes early (8am called at 7-45 etc) -- this doesn't really matter as you can still get off when you want.
They also have a self-walk off option where you carry off your own cases starting at 7-45 -- in fact they announced this was open from 7-30. Be aware if you choose this option you need to navigate the ship walkway and two sets of stairs (with lifts/escalators etc) before you pass the luggage collection point, so unless the 15 minutes is critical it's easier to let them take your bags off the ship for you.
Getting off the ship was very slick with sufficient card scanning points for the queues to be small and fast moving -- the only delay was dodging round dawdling passengers. As the ship never leaves US waters there's no immigration, customs or Government formality -- once you leave the ship (and general Port security) you're back in Hawaii -- it's as quick as that. There are no walk up transfer points from the pier to the airport so we got a cab --well marshalled and as it's a weekly event plenty of cabs ready for your business - $30 (inc tip and as it's Saturday morning no real risk of traffic delay).
We were at the airport easily by 9am (if pushed I think you could guarantee 8-30 for flight planning purposes.) We were booked with United and they use the modern method of a single queue for all flights meaning a long queue as there were earlier flights as well. Be warned that before you join the queue they have some scales and if any bags weigh more than 50 pounds you need to re-pack before they let you join the line -- about 1 in 10 passengers were caught out in this way - interestingly they never seemed to weigh hand luggage so any excess baggage just got shifted around -- but I can't guarantee! Finally the security check was very slow (about an hour) so don't cut it too fine!
In conclusion if you want to visit a number of islands without the hassle of internal flights this is the option for you. Also the Pride of America (being US flagged) is the only ship allowed to have an interisland itinerary so if you want to avoid the multi-day sea transfer it's the only option.