I wasn't intending to go to Alaska in the near future, but when the points redemption from Chicago to NYC was high, I looked at a few other places out of curiosity. For 34.5k United miles R/T per person, I thought why not go on a short trip to Alaska at the end of March with one of my kids, who had vacation. The only downside was I only had 2 full days on this trip. This required careful research to identify our main sights without too much driving. A wildlife cruise and dogsledding were our daily picks.
Getting there: Direct flights from Chicago to Anchorage didn't start until April, so we connected through Denver. We asked for trading cards on each of our flights. On the first leg on the 757, the pilot only had a 767 card, and the pilots had none on the 737-Max. We rented a car from National/Enterprise for $70 / day including taxes. There was no emerald row in Anchorage, and we had to wait for about 10 minutes until we could pick up the car.
Night 1: Fell asleep pretty quickly, as we got in just before midnight. Stayed at Hyatt House anchorage for 9K hyatt points. Clean, quiet hotel close to the airport with a number of kosher-friendly options at Breakfast.
Day 1: Drove 2.5 hours from Anchorage to Seward. There are lots of great turnoffs on the Seward highway to check out waterfalls and other beautiful scenery. I'm glad I gave ourselves an extra hour and half, because we stopped multiple times for photos and short walks. All of the hiking parking lots were empty, and there were no concerns whatsoever with winter weather driving. The road was wet but was maintained and not snow-covered.

We booked a 4 hour wildlife cruise through Major Marine. The spring cruises start in mid-March. Since we booked early, we took advantage of a 30% discount ($142 total). We ended up seeing multiple glaciers, bald eagles, sea otters, a few species of seals and sea lions, 2 mountain goats, lots of seabirds, and my daughter even caught a rare glimpse of a whale. The crew did say that the day before was rainy and poor wildlife viewing conditions, so your experience may depend on the day's weather. The boat was barely 1/3 full. If you go in the summer, you're almost guaranteed to see whales and puffins (not in the area in Spring). The crew were great, and the boat had a pleasant heated indoor deck, outdoor spaces, and free binoculars for guests. Bonus of traveling at this time of the year is free and easy parking across the street from the harbor.



We spent the night in an AirBNB near downtown ($136, the same Airbnb is over $300 in the summer). In the evening, we took a short hike on part of the Tonsina Point trail and on the Two Lakes trail, which is right in town. There's kosher food basics to be found at the Safeway and health food store in town.
Day 2: We drove to Anchorage to pick up food for lunch and get souvenirs before our main excursion of dogsledding. Polar Bear Gifts downtown has a big selection of all the cheap things, magnets, you might need. This is the first time I've ever got a discount for being Jewish at a store. Owned by a Jewish person, the staff said the owner appreciates when they come to make purchases. I was not impressed with downtown Anchorage. It's a bit run down, and if you do happen to spend the night there, the midtown hotel district is a better bet. The Fernandez Fish Hatchery is just outside of downtown, free, and has lots of tanks of fish being reared to be released in Alaskan waters. The exhibits had lots of interesting displays and photo-ops. We were the only visitors.
Snowhook dogsledding is an hour and 20 minutes North of Anchorage. My child and I had a blast here. The introduction to dogsledding was a bit long, and there was about 50 minutes of actual dog-sledding on the 2 hour tour. Before starting the tour, you get to meet the dogs and puppies being trained for mushing. It was almost too warm for dogsledding, as the trails were a bit slushy. It's best if you go with an even number of people in your group, or you may be paired with a stranger. 1 person will sit, and the other will stand on the rear of the sled. There's also a guide with you who will let you take turns. Total cost before tipping the guide was $290. Very fair price compared to other dogsledding outlets in the Lower 48, which will often only have full day or overnight excursions.

On the way back, we stopped at Thunderbird falls. This pleasant trail was right off the highway and about 1.5 miles. We bought ice chains for our shoes at REI in Anchorage earlier in the day, as we heard the trail was supposed to be icy. These were helpful for the downhill viewing point. Without the chains, there were a few areas that would be very slippery. If you go hiking at this time of year, better to have ice spikes or chains just in case.

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We had a few hours to spare before the midnight flight back to Denver and stopped at the indoor-ice skating rink at the Dimond Mall. Very reasonable price and had a nice conversation with one of the Israelis at a mall kiosk. There's a baskin robbins in the mall too. Northern Lights conditions were forecasted to be strong for the night, and we went to Point Woronzoff, which is right next to the airport. You could see Northern Lights around 10 PM, although using the night vision function on a camera made them clearer. There are better Northern Lights viewing points outside of Anchorage, but you can't beat a 5 minute drive from the Airport for Northern Lights watching.
The flight from Denver to Chicago was on a Boeing 777, and we found a very reasonable upgrade for $90 / person. The product is just ok, but a lie-flat seat on the 2 hour flight was pleasant after a red eye in economy. So much leg room! And the crew found 777 trading cards for us.
Is 2 days too short? Yes, but it is still possible to see a lot with the right planning. If the choice is 2 packed days or no trip, choose the 2 days. We accomplished everything we wanted to other than seeing wild moose. The weather was quite pleasant. If you're expecting warmth, you won't get it. If you already live in a place with winter, the weather will be fine. 40 - 50 degrees in the daytime, and it only rained lightly in Seward. The weather can be a wild card at this time of year. There will be snow/ice in the mountains, but the lower elevations were snow-free. At this time of year, hotels and car rentals are half the price compared to the peak season, and you will have almost 12 hours of daylight. Alaska is not cheap, but you can have a great time and save on the costs by visiting during the off-season.