Alaska Trip Planning

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We started our “decade of travel” with the kids in 2016 – the year my husband and I turned 40 and the year my oldest turned 8 (meaning he had 10 years left before leaving for college). Our goal during this time period is to take one big trip a year (preferably international) and as many small trips as we can fit in to explore locally and nationally. Alaska has long been on our bucket list, and we decided an Alaskan cruise leaving from Vancouver, Canada would fit the bill perfectly for 2019’s big trip.

2019 also happened to be the year my parents celebrated their 50th wedding anniversary. My mom had always wanted to take an Alaskan cruise. My dad was interested in Alaska as a destination in theory but not necessarily interested in a cruise. But part of what gets you to 50 years of marriage is compromise and doing things to make your spouse happy, so an Alaskan cruise it was. So thirteen of us (my family of 4, my parents, my sister and her family, and my brother and his family) all headed to Alaska in the summer in lieu of our regular annual Hilton Head trip.

As the designated family travel planner, I immediately got to work on the trip. I knew that we wanted to leave from Vancouver and that we wanted a round trip cruise, not one way. (While I would have loved to go on a one way cruise and tacked on a land portion at the end, we just didn’t have enough vacation time to work with for that.) We also determined that mid-August would work best for everyone’s schedules and would also be a good time of the year for wildlife viewing.

First up was picking a cruise line. We had been on one Disney Cruise and so had my sister and her family. My brother and his wife had been on one cruise, and my parents had never cruised before.  I started looking at the different cruise lines and soon discovered that Princess and Holland America are widely considered to be the best cruise lines for Alaska.

I eliminated Holland America right off the bat. HAL is known to cater to an older crowd, and with 5 kids between the ages of 4 and 11, it was important that we have a family-friendly ship.

Princess had some good options but the strongest point in their favor was that they are one of only four cruise lines with permits to sail into Glacier Bay. (Princess and HAL account for a whopping 123 of the 153 permits awarded in 2019.) Glacier Bay National Park encompasses some 3.3 million acres of stunning glaciers, snow-capped mountains, and gorgeous coastline, and a scenic cruise up to the glacier is the best way to see it. For many people, Glacier Bay is their main reason for taking an Alaska cruise.

So all signs were pointing towards Princess, but I just couldn’t pull the trigger. I was hesitant about the ships themselves (the design and layout, the condition they were in, the kids clubs) and the quality of service. Since my Dad was a hesitant cruiser, I didn’t want any surprises. I wanted to know exactly what we were getting, and I only knew that on Disney. The Wonder is the Disney Cruise Line ship that sails in Alaska, and we had sailed on her sister ship, the Magic. I knew the ship would be a good size and layout. I knew the staterooms. I knew the restaurants. I knew the service. I knew that Disney would provide a fantastic experience on a well run and wonderfully maintained ship. There were just too many unknowns on other cruise lines for a trip this important.

And of course the kids were a huge factor in the decision. My boys and my nephews had been on a Disney Cruise and absolutely loved it. We knew the ship would be kid-friendly, the staff would be accommodating, and the activities and clubs would be entertaining. Traveling with 5 kids, Disney seemed like a no-brainer. So in looking at the total cruise/vacation experience, the Disney difference won priority over Glacier Bay for our family.

Once we were decided on Disney, the rest was relatively easy.  In summer 2019, Disney offered one 5 day cruise, one 9 day cruise, and the rest were all 7 days. The 5 day was too short and the 9 day was too long (from a time-off-work perspective) so we zeroed in on the 7 day. The 7 day has a standard itinerary of Dawes Glacier, Skagway, Juneau, and Ketchikan, although 2 sailings swap Skagway for Icy Strait Point. We definitely wanted Skagway and fortunately all the August sailings went there. So we chose the August 12-19 sailing and booked on opening day for Silver Castaway Club member (read about booking opening day here).

Once the cruise was booked, the real fun began… booking excursions! There were two things on our Alaska bucket list that I wanted to be sure we fit in – whale watching and some sort of sled dog experience. For both financial reasons and personal preferences, we opted out of any helicopter excursions. With that limitation, the first two excursions fell into place. We focused on a “summer sled dog” experience in Skagway and whale watching in Juneau. Ketchikan was our wild card and we struggled a bit to figure out what to do there.

We opted to book our excursions outside of Disney. We felt confident that the outside vendors in Alaska could offer a better, more personalized experience at a lower price. With a group of 13, it even made financial and logistical sense to book private tours in 2 out of the 3 ports. Our excursions and vendors are listed below. Click on any of the links for full details.

With the Alaska portion of the trip settled, the final piece in trip planning was scheduling flights and planning our stay in Vancouver. The cruise sailed from Monday to Monday. I knew we wanted two full days in Vancouver beforehand so we picked Friday flights. For the return, Disney recommends not booking a flight before noon the day you disembark. Since we were flying back to the east coast (and did not have direct flight options to Charlotte), this essentially eliminated our ability to fly back on Monday since the huge majority of flights were in the morning. We could have taken a red eye Monday night but opted to stay another night and fly out Tuesday morning.

For hotels, we prioritized convenience and stayed at the Pan Pacific before the cruise and the Fairmont Vancouver Airport after the cruise.  (See my reviews here.)

So… our final itinerary is listed below. Click on any of the links to read the full trip reports.

Both Vancouver and Alaska are incredible destinations. No matter what you decide to see and do, it will be the trip of a lifetime!