
Photo courtesy of Ken Graham Photography
If you are new to Alaska, your first impression may be just how vast the state is. Put frankly — Alaska is huge, and things are really spread out. Alaskans love it this way, with lots of room to stretch out, and explore. But continue to read between the lines here and one will quickly realize that it takes time, and sometimes lots of effort, to access a specific destination. When visiting Alaska it is important to have a plan so you can maximize your time adventure-ing and less time worrying about how long it’s going to take you to get there. Don’t worry, we’ve compiled a guide here so you can make the most of a long weekend in Anchorage and Girdwood.

Photo courtesy of JodyO
DAY 1
Ok lots to do this weekend, so first things first is to make sure you are fueled up and ready to roll. Our go-to breakfast spots include Fire Island Rustic Bakeshop for The. Best. Pastries. Known to Man. They are epically delicious and worth the stop. And for a more hearty sit-down type meal, Snow City Cafe will have your mouth watering and your belly full with menu items like an Alaskan crab cakes benedict – whaaaaa? Say no more…..
Ok – belly full time to move and our recommendation for a beautiful sunny day in Anchorage is GET OUTSIDE! Don’t get us wrong, there are tons of wonderful indoor activities Anchorage has to offer, but you will also have LOTS of time in the Winter for those. You came to Anchorage to explore, and the first thing is to get a lay of the land. With trails and paths galore, exploring the Anchorage cityscape is choosing your adventure destination. Walking paths, bike paths, river paths, scenic coastal walks, quick and accessible hikes to lookouts, take your pick. Here’s a quick list to help you pick your passion:
- Head to Flattop lookout on the Glen Alps trailhead for a view of the city
- Walk along the Ship Creek Trail
- Bike along the 11 mile Tony Knowles Coastal Trail
- Explore Kincaid Park by either foot or bike
- Enjoy an urban tour of Anchorage via Campbell Creek Trail
- Hike up Rendezvous Peak for a view of the Chugach Mountains
- Hop on an Anchorage Trolley Tour
- Or you can combine this all with Moose Loop. a 32-mile looping path around the entire city.
Grab lunch and any of the incredible shops around town, and head over to Ship Creek to sit and eat. Just steps away from the urban core of anchorage you can watch anglers casting for salmon in a river that runs right through town. It’s an interesting mix of urban and wild and a truly unique Alaskan experience. While in the area, King’s Landing is a fun diversion, and if you happen to be around the weekend the Anchorage Market & Festival is a great way to check out unique products and food and support local small businesses.
As the day turns into the evening it’s now time to check off a bucket list item and start heading East to the Eagle River Nature Center for an otherworldly experience viewing the Northern Lights from the Chugach State Park. Only a quick 30-minute drive from downtown Anchorage, but feels remote and worlds away.
DAY 2
Up and at ’em, we got a big day ahead, and now that you’ve gotten a feel for the city, we are now going to widen our purview and get a feel for the region. Today we recommend an early start trip South to Seward, via the Alaska Railroad Coastal Classic Train route, which offers daily trips from Anchorage to Girdwood and incredible views of the Turnagain Arm, as it makes its way up to your final stop. Grab your overnight bag, we’re going for an adventure.
After the train ride, we recommend booking an overnight stay at Alyeska Resort, which offers exceptional accommodations and wonderful amenities. Before you rest your head, make sure to get out and explore by taking the gondola to the top of the mountain for incredible 360-degree views of the Chugach mountains. Once ready to go you can select an option for the journey back down, including the numerous hiking trails, or 2 knobby tires via the Alyeska bike park, a local summer hot spot for mountain biking and adrenaline.
Once back at the resort enjoy a glass of wine, and dinner with a view from Seven Glaciers Restaurant, named of America’s 100 Best Wine Restaurants of 2019, by Wine Enthusiast. A perfect way to unwind at the end of an adventurous day.

Photo courtesy of Frankie Flavin
DAY 3
On day 3 we continue to move, but not to worry, we’re going to take it easy today. Sleep in. Order room service. Sip a warm cup of coffee while enjoying the serenity of Girdwood just outside your hotel room window. Soak it all in, as today we head back into Anchorage. But this time by air aboard a flightseeing tour, including a stop along the way for some glacier exploring.
Make sure to book your seat with Alpine Air, for a scenic ride up into the mountains for the day. There are 60 glaciers all within 50 miles of Anchorage, and what better way to view them all, than by air. Book a 2-hour tour to get the ‘Best-Of’ tour of Anchorage’s magnificent peaks. You will head into the Chugach Mountains and we highly recommend opting for the touch-down stop at Punch Bowl Glacier.
At this pace, you will end up back in Anchorage by mid-afternoon, and with plenty of time before dinner to unwind and relax those sore muscles with a massage and relaxing spa treatments. We recommend the Sheraton Ice Spa set high in the sky overlooking downtown Anchorage with views of the mountain range as you lounge in their waiting room.
After operation Zen is complete, it’s your last chance to get your fill of that wonderful Alaskan seafood for dinner. Check out Kincaid’s Grill for an always fresh daily catch, or the local’s favorite – Glacier Brewhouse, which features seafood, game, and an ever-rotating mix of seasonal brews.
Well, you’ve done it! You ate, you drink, you walked, you hiked, you flew, you viewed, and you checked off a bunch of those bucket-list Alaska experiences you always wanted to do. And while we’re sure that had a wonderful time checking off that list, we also know you probably added a dozen more to-dos onto that list! We get it..its why we’ve been here for over a decade, when we came up here ten years ago ‘just for a weekend’ ourselves.
Let us know what other adventures you are looking to do, and our Toast of the Town team can help make them all happen.