Homer
One of the more active arts communities in Alaska, Homer is 5 hours south of Anchorage and located on the lovely Kachemak Bay. Unusually for a cute coastal town in Alaska, no cruise ships stop here (because the harbor is too shallow). There’s a scattering of restaurants and galleries and in the summer they host a summer writing retreat. Note too the drive from Anchorage is longer than most people expect - four to five hours depending on stops – and only the first 2.5 hours and the last 10 minutes are scenic – the rest goes through rough towns and flat land.
You can also fly there pretty cheaply from Anchorage but renting a car in Homer won’t be cheep.
Best Place to Eat: Three Sisters Bakery has the best eats in our opinion.
Best Bar: The Salty Dog on the Homer Spit is one of the coolest bars in Alaska, even if it knows it.
Best Places to Stay: Though not necessarily a great value, Alaska Adventure Cabins has a landlocked boat and a railroad car you can stay in that both have great views. We stayed in the boat during the off season when it was cheaper and had a great time.
If you really want to splurge, we hear from multiple sources that these condos at the end of the spit are fantastic – hot tubs, amazing views, multiple bedrooms.
There is also a lighthouse you can rent at the base of the Homer spit – though next to the highway, it is kind of funky and cool.
Otherwise, there are heaps of bed and breakfasts in town. There are enough of them that you can probably prioritize having a view without having to pay too much extra.
There aren't many good camping options in walking distance of town. Camping on the spit is allowed but directly next to the highway.
A Note on Lands End Resort: Also at the end of the spit, this place seems to attract a lot of folks but we feel it’s kind of rundown and could be much cooler given its location.
Day Trips: Halibut Cove across the bay has a famous restaurant - the Saltry - and is supposed to be great, though we haven’t been there.
Seldovia [link] is also nice as a day trip, especially if you fly one way and take a water taxi another.
A Note on Kachemak Bay Wilderness Lodge: One of the most expensive lodges in Alaska, they probably do a nice job, but again, who can’t do a nice job at $1,750 a night? Also, for such a spendy place they sure have a shitty website.
Hiking: Across the bay there are endless coves, islands, and trails to be explored via kayak or foot in Kachemak Bay State Park. Though the snow seems to retreat here late, definitely a highlight for many visitors.