Somehow after 22 years of living in New England, and numerous trips to Maine, I had never spent any time in Portland. I was given the opportunity to go this past weekend for a bachelorette party (sorry, Toby!). It was too quick a trip and I definitely want to go back, but here were my thoughts on what I did get to do/eat/drink!

Where To Stay

We were a larger group (12 total) and at one point had the potential to be even more so we stuck with hotel rooms, as finding a house for up to 20 people can be a tough task! We opted for the Hilton Garden Inn Downtown Portland that was a great location – walking distance to a lot of shops, restaurants, bars and the ferry. However, I was blown away at the hotel prices – I know it’s August in New England but $425 a night? If I went again with Toby or a smaller group I’d definitely check out AirBnB.

Where To Eat

Roustabout – we dinner in a private dining room our first night. This was cool, but meant an additional $100 “dining room” charge and a set, family-style menu. The whipped ricotta, chicken marsala and eggplant parmesan were delicious. The Italian cookies for desert were not. They had creative drinks as well – I’d be open to checking it out again if I was able to order off the regular menu.

Union Restaurant – on day two we came here for brunch. You should too. I haven’t even looked at their dinner menu but I would go back for dinner in a heartbeat. The Orange Cinnamon Bun with smoked bacon maple syrup and whipped mascarpone that we got for the table was amazing. I also had the omelet with ricotta and peaches – seems weird but was delicious, and came with some yummy potatoes as well.

Sonny’s Bar & Famous Food – on night two we didn’t have dinner reservations and with a group this big it was difficult to find a place that could actually fit us all (even for an early seating!). Sonny’s had been recommended to us and after going, I see why. Lots of creative cocktails and yummy Latin food – not necessarily what you might be looking for in Portland, Maine, but their tacos, queso fundido and lobster stuffed avocado did not disappoint. Not in the mood for Latin food? I’d still definitely swing by for some cocktails.

What To Do

Sail! We did a two-hour windjammer sail with the Portland Schooner Co. You can bring your own booze and snacks and it’s a pretty relaxed couple of hours. If you’re really interested in learning a lot about what you’re sailing by though, I might pick a different company (assuming another one exists that is more informational).

Breweries! Unfortunately our self-made brewery tour never happened due to time constaints but we had planned on Rising Tide, Maine Craft Distilling, Bunker Brewing Co. and Oxbow Tasting Room, which are all very close to one another. Next time!

Bars! Being that we were on a bachelorette party (and are all in our early 30s) we hit the bars both nights after dinner. Bubba’s Sulky Lounge was perhaps one of the strangest bars I had ever been to – kind of like dancing the night away in the middle of a flea market (and cash only) but so much fun! It gets to be on the edge of more sketchy neighborhoods so taking a cab or uber might be a good idea. Our other hotspot of the weekend was the Pearl Nightclub, which was also a dive bar on one side so you could pick your poison depending on if you felt like dancing or not!

Too quick of a trip and I definitely will be back – if you have any recommendations for the next time I’m there let me know!

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Jocelyn
I've had a love for writing pretty much since I learned to write. My love for travel grew once I visited Europe in High School, lived in Italy in college, and really took off after a trip to Bali in 2009. Since then I've made it a goal to visit at least one country per year - sometimes a challenging feat when you have limited vacation time, income, and you want to see your family on the other side of the country. But, I've made it happen (in 2015 I visited 5 new countries!) so hopefully I can inspire you to get out there and travel too!