Informal Italian restaurant serving pasta, seafood & meat dishes, plus desserts & a large wine list. Based on 222 reviews, the restaurant has received a rating of 4.8 stars. Price
✔️ Dine-in ✔️ No takeout ✔️ No delivery
Address:
85 Free St, Portland, ME 04101
Phone: (207) 808-8623
Website: https://leewardmaine.com/
Social Profile: 
Hours
| Monday
(Labor Day)
|
Closed |
| Tuesday | Closed |
| Wednesday | Closed |
| Thursday | Closed |
| Friday | Closed |
| Saturday | Closed |
| Sunday | Closed |
Menu
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Menu Photos
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Reviews
Kaitlin Altieri
Leeward is a good date night spot. They have an intentionally small menu with fresh ingredients that make it hard to choose from! Fresh, upscale Italian food! Their staff are friendly, knowledgeable and accommodating. The open kitchen makes for a fun and upscale atmosphere. I will certainly go back, but save this place for special occasions. I would recommend making reservations and save time for parking. It’s kind of off the beaten path in Portland with no off-street parking. If you are there for a more casual occasion, sit at the bar by the kitchen so you can watch and smell all the delicious things the chefs are cooking up!
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Stephy Miehle
Stunning meal! Yes, there was a wait for walk-ins, but the text waitlist was easy and efficient. We had ten minutes to head over and were a few blocks away, so it was no problem.
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TJ K
It took us way too long to try this place but decided to make reservations before the summer tourist season is in full swing. First, it’s a super cute establishment with a small cage vibe. We started with the Foccacia. It was fantastic and large than it appears in images. We shared a salad for a starter (sorry it was so good we forgot to take a photo), I’m not a fan of green goddess dressing, and this salad made me love it. Finally, the main meal. We fully enjoyed the fresh pasta. The menu changes often, which makes it hard to recommend a dish. We’d say you can’t go wrong with anything on the menu. Use Resy, make your reservation, and enjoy the freshest pasta in Portland!
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terri chau
Wonderful food, service and everything else. I went there twice in a week, that will tell you how much I like it. My friends that are from other countries loved it as well.
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Ava French
I had a poor experience I had at Leeward recently. When I messaged their establishment on Instagram regarding availability, I was informed that there was a no reservation policy. However, upon my arrival, I was informed that I should have called in advance and that there was no seating available and that there was an hour and a half waitlist for the bar. I was disappointed that this information was not conveyed to me earlier, as it would have saved me the inconvenience of driving two hours to their establishment. I hope that in the future, their team can communicate any pertinent information to guests in a clearer and more timely manner.
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Deth Khaia
The bar seating are popular. As soon as they open at 5pm all the bar seating was taken and it’s only Wednesday night. I highly recommended that you make reservation ahead. I was lucky to get a chef table seating. Food was good. Service is also fab. Definitely will go back and try their other dishes.
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Sandy “The Boozy Foodie Lady” Anania
Leeward is a pasta-centric Italian restaurant in Portland, Maine.
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Daniela Olivera
Amazing dinner, cannelloni was so tasty, the half chicken was so delicious! Omg I would go back for sure. Drinks were also delicious. Perfect place for a great meal!
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Diane Stowell
We had a wonderful dinner. Everything was excellent. The focaccia was light. Our table enjoyed the mussels, beet salad (very interesting combo with oranges and olives), and brussel sprouts with whipped feta (outstanding). The housemade pasta were all cooked to perfection. The gigli was simple but amazing. The balanzoni with black truffle was to die for. The only disappointment were the very limited dessert offerings (semolina cake, 2 gelato and a sorbet) so we went elsewhere. Our server was very knowledgeable and helpful. It is a very difficult restaurant to get into but well worth it.
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Elizabeth Gillespie
This is the first negative review I have ever posted online, and I hope it will be the last, but my experience at Leeward this Saturday was so unpleasant that it would be wrong not to say something. In fact, I’m sorry to say that it was the worst restaurant service I have ever experienced in my life.
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