A Two Week Winter Cruise To Hawaii

A cruise ship can be a very economical way to see a lot of places in a relatively short amount of time. Check in once, unpack once, and your meals and transportation from city to city are all included. 12 – 14 day Baltic, European, South American and many other itineraries will often hit multiple major cities, allowing from a few hours to a few days to get a taste for each.  Ideal if your vacation time is limited.  (I wrote about my Alaska cruise adventure here.)


After a few months of pretty intense land travel, I was happy to join a friend for a low key, relaxing two week, mostly sea day itinerary to Hawaii.  Prices were pretty amazing, and given the last minute, ridiculously low off peak pricing, we opted to go with the higher priced balcony cabin, which ended up costing less than $100 day.  I loaded up my kindle, and hopped on an American flight to San Francisco (booked with 4500 Avios,) where our ship would depart.  The pier is super easy to get to with BART, even with luggage.  The journey took about an hour.

San Francisco Style Send Off

We set sail at sunset, making our way under the Bay Bridge and spending four days at sea, ultimately arriving at the Big Island for our first stop on the itin.  We would stop on each major island for a day.  The trip was mid-February, so the average passenger age skewed –  older.  I had no agenda for the two weeks other than to catch up on some reading and enjoy the nice tropical weather.

The weather at sea was perfect, and as we got closer to the islands, it warmed up significantly.  The cabins were pretty small, but I really enjoyed the balcony splurge!

Cabin With A View

Food was included in the cost of the trip, and it was plentiful.  We mostly opted for sit down dining room meals, though the buffet option on the Lido was convenient for a snack or meal if getting to the dining room was too much trouble.  In addition there was a 24 hour room service menu, though I didn’t use it this trip. One day, one of the restaurants on board was transformed into an English pub, serving traditional English fare.  One thing is for sure, you won’t go hungry on a cruise ship!

Traditional English Pub Food For Lunch
Fish N’ Chips In The Specialty Restaurant

Thankfully there was a promenade deck on the Grand Princess, which ran the circumference of the ship.  Three laps around was the equivalent of one mile.   Between reading, lounging, and consuming food, I completed many laps.  The scenery was beautiful and the fresh air divine.

The Promenade Deck Rescuing Waistlines And Outgrown Clothing

This particular ship was massive, holding just under 3000 passengers and crew.  There were plenty of places to lounge and with eight total sea days, people did just that.

Relaxing By The On Board Pool

The sunsets throughout the journey were stunning.


There were several laundry rooms on board.


Our first stop was Hilo.  While most took tours and helicopter rides to the volcano and other places, I had been twice before and had already seen and done most of those things.  I had a relaxing day wandering downtown a bit and reading on the peaceful near empty boat.

Next was Honolulu and having been multiple times before, ended up meeting up with an equally points and miles addicted  friend who happened to be on a layover at HNL for dinner and some VR hunting!

I had never been to Kauai or Maui, so I was really looking forward to these two stops.   I had booked a helicopter ride for Kauai but the weather wasn’t cooperating on the day we were there, so it was cancelled.   Our backup was to rent a car and drive around the island.  But those had sold out.  So I set off to explore on foot, hitting a few touristy shops, a Hawaiian bakery, and a beautiful orchid nursery


There was also a museum, but it was closed on the day I was there.


Each island has its own massive Walmart, and in every port there was a shuttle available to take passengers to and from their local superstores.  Since there wasn’t much to do because of the rain, I  partook in an excursion to one in this port.

Free Walmart Shuttle

We had pre-reserved a rental car in Maui and were looking forward to exploring the island.  Given the shallow water in this port, the ship was unable to pull into the harbor and dock properly, and so had to use the tenders to get to the port.  Princess used the emergency lifeboats in this case to shuttle people back and forth.

Tender Boats Taking Passengers To and From The Port in Maui

The cruise lines tend to offer first boarding to those passengers having booked tours with them, making the wait to get to port long and boring.  With lots to see and limited time before the boat set sail again, we managed to sneak on early.  After a bit of paperwork, we were on our way in our rental car.  The drive around the island is beautiful and the weather made it even more perfect.  Our first stop was a two hour hike up to a beautiful waterfall and swimming hole.


We then drove back down the coast, stopping at several parks for the views and some snacks.

Maui Bob’s Hawaiian Shave Ice

After a little shopping in port, we got back on the tender boat, and settled in for the next four days at sea.  We sailed away with whales breaching all around us and one of the most beautiful sunsets I’d ever seen.


Our only stop on the way back was in Ensenada, Mexico which was necessary due to some old maritime regulations.  Most people didn’t get off the boat, as we were greeted by armed guards, it was a Sunday, and there wasn’t much to see or do here.

Armed Guards Looking After Our Boat In Mexico

I got off the boat to wander around a little in town, but  most shops were closed.

The Grand Princess Preparing To Set Sail From Ensenada

After a  final relaxing day at sea, we arrived early in San Francisco, just in time to watch the sunrise over the Bay Bridge.


I jumped back on the BART train to and headed to the airport to catch my AA flight home, relaxed and ready for my next travel adventure!


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