The Porthole (20 Custom House Wharf): Where Portland spends its Sundays. This sister establishment to the Comedy Connection has a huge deck right on the harbor. It is rumored that a few people have fallen through the rickety boards that separate patrons from the water below, but things seemed pretty stable upon last visit. The outside bar is fully operational for Reggae Sundays, which runs from 3 to 7pm. Wide open and very dog friendly.
Joes Boat House (One Spring Point Drive – South Portland): As if Marina Bay in Quincy, MA was cloned and plopped down in SoPo. The food is reasonably good, though the beer selection is lacking. No signs of any summer ales on the brief list. The deck is sun splashed until about 3 and you can look out on the outer harbor. Off the beaten path and hard enough to find that most tourists won’t make the journey.
Silly's (40 Washington Ave): Tucked behind this Washington Street institution is what may be the most unique patio in town. The tables are crafted from large rope spools and each is equipped with its own survival kit. The contents of which are menus, napkins, other dining accessories and a deck of cards. Not that they are needed. A pitcher of sangria helps pass the time while waiting for your food. The sweet wine is served in half and whole sizes. The half pitcher is enough for 2 or 3 people to get a bit loopy before/during dinner. The food is as eclectic as the décor. The chicken in a boat, which is essentially a Pad Thai chimichanga, is a must order, as are the fired pickles. There is a little garden abutting the patio that is open for pre or post meal wondering. This is the type of place that you hope stays around for a long long time. It has already persevered for 19.9 years.
Eve’s at the Garden - Portland Harbor Hotel (468 Fore Street): The patio is sizable, though fairly sterile. Surrounded by the Portland Harbor Hotel on 3 sides and an office building on 1, the patio is sunless by 6pm or so. Still, a nice place to spend a post work happy hour. Appetizers are half price from 5 to 7pm each day. They are clearly making up for the loss of gross margin on the food through a boost in cocktail prices. Specialty drinks are up between $10 and $14 and a standard cocktail is pushing $9.
Amigo's (9 Dana Street): Part of the all star line up of dives on Wharf Street. They may have the worst bathroom in all of Portland, but beers are cheap and they have a decent little patio. It has picnic tables, an outside bar and there is generally the haze of cigarette smoke in the air. When you need relief, head inside, play a trek on Safari Edition Big Buck Hunter and feast off of candy and nuts from the vending machines bolted the posts throughout the bar.
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