Which is precisely what we did during Aiden's spring recess this past April, as almost everywhere else are packed with kids during the break. I could not believe the $450 flight cost when I tried to book flights to Orlando.
Portland's main attraction to me is FOOD, and more FOOD! It is amazing how many good restaurants are in this small city.
Breakfast/Brunch - definitely my favorite meal of the day, and proven to be the best in Portland, ME
Five Fifty-Five - yum!!!
Bintliff - Best Brunch EVER!! The pictures may not look as the best brunch, but this bloodymary is the best we've had, and this egg white omelette is so perfectly done that I am trying to make it at home myself.
Duckfat - sandwich place with everything made in duck fat. It's a small place with long line especially during lunch hour. But, if weather is nice, you can have the sandwich to go and walk to a park or water front nearby to enjoy.
Lobster Shack at Two Lights - Not only this is one of the best lobster roll places in Maine, it is also located right by the water with spectacular view of Casco Bay.
Street&Co - great seafood restaurant in a small alley in Old Port. This fish dish we had was really amazing!
The main attraction in Portland is the Portland Head Light, it is one of the most photographed lighthouses in the country and maybe the world.
The old port is full of good eats and boutique stores that are fun for stroll for everyone. Here are few fun stops.
I also recommend stopping in to the seafood market to check out the variety of Maine seafood or go on a lobstering tour with Lucky Catch.
We also spent half day at Peeks Island. There are 7 islands near Portland, I think Peeks Island is most visited. You get to ride a ferry to and from the island with great view of Casco Bay, and spend a relaxing day at the beach, why not? There is a little shop on the island that sells things made from the local artist which are very cool and why not support starving artists right? There is also an umbrella cover museum, it was closed when we were there, but definitely fun to stop in and good for kids. You can also rent bikes on the island, which is the best way to tour the island.
Portland Museum of Art, Children's museum (next to Portland Museum of Art) and Victoria Mansion are good stops if you have time.
Maine Mead Works - honey winery, if you like honey, this can be a nice stop
Maine Brewery Tour - we didn't go on this tour since we had kids, but we saw people having lots of fun on this tour
Where to Stay
We stayed at the Westin Portland Harborview Hotel, very comfortable with a top floor lounge and great view of the city.