Best cruise company and time of year for Alaska cruise

I used to work for Holland America and still have a few friends in the business, so hopefully this will help!

As others have said, June is the best (and most expensive) time to go. If you're not concerned about funds, do it then.

If you're interested in doing a land tour of Alaska and/or only sailing one way, why not start with a flight to Anchorage and the land tour before your cruise? I hear consistently from friends in the biz that this is the cheaper option and less likely to be packed on the ships.

As for companies, it depends on the personality of your travelers. Holland America is much more 'old money,' Princess tailors to a more 'yuppie' crowd, Carnival and Royal Caribbean are aimed more for the fun-lovers, and Disney has just started cruises aimed at families. Those are the biggest companies, I think...

As someone who grew up in Southeast Alaska, it's my duty to strongly advise against taking a cruise. Instead, I wholeheartedly second Tony's suggestion for taking the ferry.

So... If you're game for that route, you can tailor your own trip based on where you'd like to go and how long you'd like to spend there. This is definitely a less "luxurious" option but the best one to see and experience the area you'll be traveling through.

All ferries have a cafeteria, bar, and staterooms. Alternatively, if you're looking to rough it/budget you can pitch a tent and/or snag a lounge chair on the top deck/solarium and bring along some groceries. If you have the time (and money), bring a car along for further travels..

http://www.dot.state.ak.us/amhs/

Sitka is easily the most charming city in Southeast AK, (and with the strongest Russian roots). Ketchikan is the first port on the way up and I'd recommend stopping there if you're interested in getting out to Misty Fjords National Monument (which I strongly recommend you do). This can be done via flight-seeing (take Taquan Air) or via a boat trip if you have more time. Juneau's a good stop to see/hike the Mendenhall Glacier. While there, be sure to get out to Glacier Bay National Park If you're game for more and up for tackling the Chilkoot Trail then head on to Skagway. 

If you're sticking with the Southeast only, grab a flight home from Juneau. If you have more time (and no car), from Juneau you can connect up with the Cross-Gulf ferry route to Whittier, continue on the Southcentral ferry route to Seward, and grab a train to Anchorage. If you have more time (and do have a car), just drive from Whittier on to Seward, Homer, Anchorage, Denali National Park...

Once you get further north (ie, out of SE) the weather is much better but Southeast Alaska contains one of the world's largest (temperate) rainforests (Tongass National Forest) so there it's always a gamble. If you don't mind chancing a strong likelihood of chilly, rainy, grey days then anytime late May to early September will do. If you want the best bet for sunshine go in July or August. Honestly, go in July.

I think you can't go wrong with either Celebrity or Princess.  I personally like Celebrity more, but Princess is great too.

Timing-wise, August and September are great weather wise, August being most crowded.  

As far as land tours, there are so many to choose from, its hard to narrow down, but here are some things that I really enjoyed on my 3 or 4 Alaskan cruises:

• In Ketchikan i've done a sea plane trip to see bears, which was amazing and also gone to the Misty Fjords National Monument, both of which are great.  For a great, quick bite to eat in town, grab a Halibut Burger at the Burger Queen.  Phenomenal.
  
  
• In Juneau, visiting Mendenhall Glacier is a must. I've taken a helicopter to hike on the ice, gone by car, and gone by bikes and they are all worthwhile.  The bike ride we did through the ship and you visit the glacier, then ride back for a stop at the Alaskan Brewing Company which was a lot of town.
  
  One place that I would personally avoid is the Red Dog Saloon, which is an old-west type bar in town with very expensive drinks. Its worth popping your head into, but if you want a beer, walk down to the The Alaskan Hotel and Bar, which is in an historic building with a GREAT bar that really makes you feel like you are in the wild west and it isn't touristy at all.  Even if you don't like beer, its worth visiting.

We took the Emerald Princess on its second voyage and its first Alaskan Inside Passage cruise.

It was great. We went in late June and it was expected to be a tad chilly so I spend too much money on the LL Bean website. Wasted might be a better term as during the whole week of the cruise there was a record setting heat wave where during the day it was in the middle 80s, in Alaska.

We had our teen and preteen daughters with us and we hardly ever saw them - unless we went looking for them or it was dinner time or we were taking in a show together.

Early one morning we woke up to find the ship doing 360 degree turns in the Tracy Arm Fjord just so everybody on board could see the many splendors...I never forget the stunning blue ice which was thousands of years old. And it was cold, finally it was cold in Alaska.

I was not crazy about some of their stops especially Juneau Port. No thank you, I do not need any Tanzanite jewelry. The stop in Victoria was great and Ketchikan  had a entertaining lumberjack show and a smoked salmon barbecue.

I'd go back and do it again but I have too many other places to visit! Most of them are in climates that are supposed to be warm and are accessible by a private charter on a catamaran sailboat.

You will have a fine time!

I've been to Alaska twice and both times I went the end of May. Both trips were on Princess Cruises and both were outstanding. The prices are cheaper in May plus school is in session so there weren't many children on the cruise. There is so much to do...white water rafting in Denali National Park, ATV tours, sea kayaking and I'm a "senior"

Holland America had some great cruise options when my wife and I went a few years ago. If you are looking for a great deal, look at the very beginning of the season (Mid-April). It's a tad chilly, but much cheaper than the mid-summer peak prices. 

We've cruised with four cruiselines, and our favorite is Holland America, hands down. Our favorite times to go to Alaska are September and October.

The only Alaska cruise i've been on is Royal Caribbean, they were pretty good. I have been on Princess down in Mexico -- I have heard Norwegiain Cruise Lines is pretty good too

In terms of time of year, it really comes down to price -- start and end of seasons are going to be cheaper, but the prime is July/August

Land Tours range from town tours, to helicopter rides, and climbing glaciers. Lots of outdoors!

I like to go north in June; almost endless daylight. Best Cruise Line? Maybe you mean least costly. Try Vacations-to-go for a good list of Alaska cruises.  (I'm not an employee)

Alaska is beautiful year-round but I assume you're aiming for summer months.  You'll get the best deals early or late (May, Sept/Oct), but you'll get the warmest weather and most daylight in late June/early July.  Given that most cruises hit Southeast Alaska (Juneau/etc), you'll do better from a rainfall perspective if you aim for May/June.

There's often an imbalance of customers heading north vs. south, so consider flying up to Anchorage and grabbing a cruise SOUTH versus the more normal northern route.

If you want some adventure, consider the Alaska Marine Highway System.  It's a little more spartan (there are staterooms but also are camping areas) but you can do cool stuff like get off at a port you like and catch the NEXT ferry boat (versus the 8hrs you get on a cruise). 

http://www.dot.state.ak.us/amhs/

Also consider some time in SouthCentral area before or after your cruise.  Talkeetna, Seward, and Homer are all lovely towns worth a visit.  Anchorage is also a pretty cool town.

In terms of companies, Cruisecritic has a pretty good breakdown:

http://www.cruisecritic.com/articles.cfm?ID=1424