Cancel

    Open app

    Search

    Leeward

    4.5 (157 reviews)
    Closed Closed

    Leeward Photos

    Business Info

    LEEWARD ATMOSPHERE

    What's the vibe?
    Trendy
    Romantic
    Upscale
    Moderate noise

    You might also consider

    Recommended Reviews - Leeward

    Your trust is our priority, so businesses can't pay to alter or remove their reviews. Learn more about reviews.
    Yelp app icon
    Browse more easily on the app
    Review Feed Illustration

    Reviews With Photos

    Nero spagghettini.   Absolutely scrumptious - I'd say SUMPTUOUS.  But, bite-sized portion.  Sorry, this is just not enough for a $28 meal.
    Shaun T.

    The short of it: Really delicious (and expensive) food and cute atmosphere, with impeccable service. Food portions, however, are criminally small and lower the score to 4 stars. Definitely don't arrive hungry. We were seated on time and welcomed by our extremely awesome server. She was impeccable from start to finish - not hovering over us, but being attentive enough to know when to ask if we wanted more drinks, etc. She also (correctly) noted that it took way too long for the main dishes to come out and comped us a Meyer lemon sorbet dessert. This was a very professional and attentive note to the evening. We both ordered the citrus salad, which was amazingly delicious: fresh bites of citrus fruits of all varieties (oranges, grapefruits of a myriad of colors), with crispy endives, crunchy pistachios, tangy feta, and sweet dates. Really an amazing combination of tastes and flavors. The only problem? Too small! Even our wonderful waitress joked that she was glad that my spouse and I ordered the same thing and didn't need share plates because the portion is too small to share. It sure was! I don't expect copious amounts of food when I go out, but I do expect more than a child's size. It took some time for our main dishes to come out, but they were absolutely worth it. I got the black spaghetti (Nero spaghettini) with seafood and it was sumptuous: Bold, rich, expressive flavors with a delicious squid black ink spaghettini. The dish balances the briny flavor of the squid ink and seafood with the depth and grandeur of pork broth, the toasty texture of breadcrumbs and the pop of spice from bold chiles. Only problem? Once again, it was a minuscule portion. I mean really tiny. I sent my identical twin (yes, he likes the exact same things I do and will order the exact same thing as me - without even discussing it beforehand) a picture of my meal before I ate it and he jokingly wrote back "awwwww look at that cute kid's portion!" Indeed! It was devoured within a few minutes with a rumble of unsatiated discontent. Ah well. Dessert brought everything back up to a solid 4.5 stars: my spouse got the lemon crepes and I got the absolutely delicious cream cheese and date gelato. Perfection. All in all, I definitely recommend this place. But they really should look into their portion sizes. For the price, there really should be more in/on my (small) plate.

    Seating area near window.
    Nathan T.

    The menu was a little limited and is very seafood forward. The food was mostly tasty though the desserts were a disappointment. The atmosphere is fine, I thought it would be a little fancier inside based on the prices but it has more of a cafe vibe. Good service. Not a bad restaurant but we likely won't be eating there again as there are better options in town for the same price.

    marinated castelvetrano olives & roasted beets, salsa verde, capers, melogold grapefruit, puffed farro
    David Z.

    Perfect location to catch a quick bite before walking across the street to catch a Cross Arena event. It has been a bit since I have been in, but as I recall it is always amazing food, tip top service and a nice casual atmosphere to enjoy a meal. It wasn't too busy yet and was able to get a seat at the bar without reservation. Quick service and able to watch the drinks being made as the food made it out shortly thereafter. Everything on the menu sounded amazing and it was hard to choose but settled on the espresso tagliatelle which left me wanting to lick the plate clean! The crostone and cake were phenomenal as well. Perfect mix of complementary flavors to delight your taste buds in a casual setting. Great location go a date night out or just desire a good meal to enjoy!

    Antipasto dish
    Charles W.

    Talk about amazing Italian food. Was blown away with how good all of the dishes tasted. It explains why reservations are do hard to get in here. This is my favorite high end Italian food in Portland. Everything was so full of flavor and tasted great. Wonderfully service, stuff came out quickly. Highly impressed.

    Decor
    Jess B.

    Leeward is amazing. From the staff to the food to the drinks, everything is amazing. No private parking lot but there is street parking and nearby parking garages. I would recommend setting up a reservation or trying to get bar seating without. The vibe inside is chill and welcoming. You can tell they care about their service and products. Sitting at the bar is great especially watching them make drinks. Our server gave us some good recommendations as to what was fresh. My mom got the sorrento spritz and I got the lady slipper for drinks. They were refreshing and delicious. My mom got the gnocco fritto which is almost like a fried dough (but savory) with a bunch of filling options (burrata, prosciutto, bresaola, and pickles) - this is fantastic and you can make it as you want. I got the fusilli pasta dish which has pesto, pine nuts, and cheese. I get this pasta every time and it's amazing every time. The decor is wonderful. The restaurant and bathrooms are handicap accessible. I can't wait to come back!

    Dinner menu
    Elena P.

    Leeward falls into the rare category of "dining experiences that haunt my dreams and places I'll wistfully think about if I ever move away". Every aspect of our experience was sensational from the moment we stepped through the door. The space is thoughtfully laid out with subtle sound dampening and an open kitchen. The service is very personal and anticipatory, they also truly work as a team and are a well oiled machine. Despite the restaurant being very busy for the duration of our experience, staff members noticed nuanced things (like me tasting my husband's wine) and stopped by the table to see if I needed a glass of my own. I wasn't thrilled about any of the cocktails on the menu (this is a me thing as I'm not a huge fan of gin or dark liquors), so I asked if I could choose a mocktail and have alcohol added. The bar-staff politely dissuaded me from my initial selection and suggested a different mocktail for them to customize. I said sure and WOW, it was the best drink I've possibly ever had in my life. I had the shrub and soda made with Tito's and it was wildly refreshing and balanced, bursting with fresh citrus and not overly carbonated. I was so impressed. My husband enjoyed both of his glasses of wine. Next the food, we had the squash blossoms, cucumber salad, bucatini, conchiglie, and for dessert - a dark chocolate tart, pistachio gelato, and a coffee. Everything was truly spectacular, though our favorites were the squash blossoms, conchiglie, and the chocolate tart. The flavors combined with the textures and presentation were interesting without trying too hard, and left nothing to be desired. The conchiglie with pork ragu, and the squash blossoms were our favorite bites of food we've had in the state of Maine by far (we relocated here at the beginning of the year). If it were societally acceptable, I probably would've licked my plate. Okay I'm raving a little now, but genuinely this was such a pleasant and shining dining experience top to bottom. The only thing we wished they had but they did not was an espresso machine to complement the dessert selection. We won't hold it against them, and will be back soon! Our compliments to the pastry chef - dessert can be hit or miss at great restaurants but that was not the case here. Much love to every hard working person at Leeward!

    Pasta with rabbit
    Olivia B.

    Came here for birthday dinner with friends. Molly took wonderful care of us and I would go back just to be waited on by her! The focaccia and olives are a MUST and do NOT miss the gnoccho fritto. The burrata is sooo creamy and the gnocchi are like beignets but not sweet. Everyone enjoyed their individual pasta dish and Molly recommended a great wine paring. Dessert was gelato and digestivos. Would come back again for any special occasion!

    Shells with meat ragu while
    Richard S.

    I feel this place was over hyped. Don't get me wrong, the food was good but not the best I've eaten good. We were seated at the chefs counter, which when I booked was exciting based on past experiences I've had. However, on arrival found that there was no view of the open kitchen due to height of the wall that was stacked with dinnerware. So what's the point of the chefs counter??? I had shells with a spicy meat ragu while my wife had the tagliatelle which was probably the winner. We started with the focaccia, which again was nice but is free in most restaurants but was $12 including the balsamic dipping vinegar. Next time I'll try someplace else...there are too many options here.

    Allison H.

    Leeward is certainly my favorite restaurant in Maine, if not all time. The ambiance, service, and quality is incredibly deserving of its accolade), and yet this restaurant is also incredibly homey, familiar, and accessible in terms of its flavors and price point. It's amazing how deceptively simple Leeward's offerings are-- focaccia with just olive oil, cured meat with fried dough, fresh cheese, and pickled vegetables, pistachio ice cream. They specialize in farm-to-table offerings, so their seasonal menus highlight the natural flavors of each ingredient used. I'm absolutely floored by how delicious every single element in the dishes I tried are. For it's price point, no restaurant in LA can compare to what I've tried (in comparison, they'd just come across as pretentious). Come here for the talent, but stay for food presented in its best (and most authentic) light. If you don't have a reservation, wait outside at least half an hour before Leeward opens-- it's likely that you'll get a seat.

    Butter Lettuces
    Candi M.

    Leeward was a wonderful experience. From the modern interior to the pleasant service, I would definitely return. We shared the butter lettuces and the chicken liver pate, which was the best texture of any spread I've had before. We also shared 2 pastas. The fusilli with pea pesto was refreshing and light and the counterpoint to the rigatoni which was smothered with a delicious bolognese and Parmesan. Loved them both.

    Focaccia
    Samantha J.

    Stopped in with a friend on a Saturday night. Restaurant was busy and we couldn't make a reservation online but we got a seat at the bar right away. Staff was very friendly and answered all the questions that we had. We ordered the focaccia, gigli, and the rigatoni. Everything was very yummy! The space was nice and would recommend for some good pasta in the area! Prices were reasonable as well, compared to other restaurants in the area they all seemed to run you $20-30 for an entree.

    Pasta with chanterelle mushrooms
    Eydie Q.

    What a pleasant surprise this place was. We couldn't get a reservation at another restaurant so we went to this place which was available for the dinner time we wanted. We were so happy with everything we ordered. The pasta with chanterelle mushrooms was so great and light. Best mushroom pasta dish I've ever had. Super rich in flavor but did t feel heavy at all. Two of my friends had the lobster Fra Diablo and loved it. Huge amount of lobster. My other friend had a gluten free pasta that she enjoyed as well. Excellent service to complement our excellent meal. Now I know why Portland is a foodie town. Very highly recommend this place.

    Pasta alla gricia

    See all

    2 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    2 months ago

    Helpful 1
    Thanks 1
    Love this 1
    Oh no 0

    13 days ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Shaun T.
    132
    70
    14

    2 months ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    24 days ago

    Helpful 0
    Thanks 1
    Love this 0
    Oh no 0

    2 months ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    7 months ago

    Helpful 1
    Thanks 1
    Love this 1
    Oh no 0

    2 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    3 months ago

    Helpful 1
    Thanks 1
    Love this 1
    Oh no 0

    9 months ago

    Helpful 3
    Thanks 2
    Love this 2
    Oh no 1

    1 year ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    10 months ago

    Helpful 1
    Thanks 0
    Love this 1
    Oh no 1

    10 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    1 year ago

    Helpful 1
    Thanks 0
    Love this 2
    Oh no 2

    1 year ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 1
    Photo of Amy C.
    277
    619
    1984

    7 months ago

    Helpful 4
    Thanks 0
    Love this 0
    Oh no 0

    2 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    1 year ago

    Helpful 3
    Thanks 2
    Love this 2
    Oh no 1

    1 year ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    2 years ago

    Helpful 2
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Joe Z.
    0
    58
    13

    7 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    1 month ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    5 months ago

    Helpful 1
    Thanks 1
    Love this 1
    Oh no 0

    10 months ago

    Helpful 2
    Thanks 1
    Love this 2
    Oh no 0

    1 year ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Dan G.
    7
    12
    4

    11 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    6 months ago

    Great Italian food and an enjoyable atmosphere in the heart of Portland. Highly recommended.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Marc B.
    420
    483
    3296

    2 years ago

    Helpful 2
    Thanks 2
    Love this 2
    Oh no 0

    2 years ago

    Helpful 1
    Thanks 0
    Love this 1
    Oh no 0
    Photo of Ron B.
    0
    128
    0

    5 months ago

    Solid pasta and experience. Pretty hyped though and I'm not sure I'd say it lived up to that. Would return

    Helpful 0
    Thanks 0
    Love this 1
    Oh no 0

    9 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    3 years ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 1

    2 years ago

    Helpful 0
    Thanks 1
    Love this 1
    Oh no 1

    4 months ago

    Freakin delicious. I was practically licking my plate clean. Will definitely be going back.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    3 years ago

    Helpful 2
    Thanks 1
    Love this 1
    Oh no 0

    3 years ago

    Helpful 2
    Thanks 0
    Love this 2
    Oh no 0

    10 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    3 years ago

    Helpful 1
    Thanks 1
    Love this 1
    Oh no 2

    3 years ago

    Helpful 4
    Thanks 1
    Love this 1
    Oh no 0

    2 years ago

    Helpful 2
    Thanks 1
    Love this 1
    Oh no 0

    Page 1 of 4

    Ask the Community - Leeward

    Is this place quiet, moderate, or noisy? We want serious eats and serious talk?

    Unless there is an obnoxious party (haven't seen in my visits) this venue is on the quieter side. Perfect for conversations over a great meal be it two at the bar or a larger party at a table. Highly recommended!

    Don’t See Your Question? Ask Away!

    You might also consider

    Via Vecchia - Must try salad!

    Via Vecchia

    4.2(454 reviews)
    0.3 miOld Port
    $$

    EXCELLENT pastas & dishes, and perfect for a night out! Reservations are highly recommended - we…read morecame on a Friday night during the off-season and had about a 25 min wait still. Via Vecchia was definitely worth the wait, and this was one of the most surprising restaurants during our trip. We ordered the brussel sprouts, grilled octopus, campanelle, and radiatori. The brussel sprouts was the one dish that I was most hesitant about, seeing that it was paired with a blueberry agrodolce. Not a typical combination, but this ended up being a favorite. The sweetness & tartness of the sauce worked SO well with the sprouts - it's an excellent dish. The octopus had the perfect char, and all of the flavor pairings were really cohesive. I had never heard of either of the pastas, but I loved the textures of both. The campanelle with nduja cream was delicious, but did get to be a little heavy about halfway through. Radiatori with bolognese was a classic but well executed dish. Service is attentive without being overbearing. Prices are super reasonable.

    Note: if you come in the winter (which includes March) there will be no ivy growing on the building…read more. The Inside is gorgeous. The mocktails and cocktails are truly inspired. The food was very small plates for the price. You'll leave feeling not stuffed, just right. But the American in you will feel like you may not have got your moneys worth. They didn't offer Parmesan and I felt our food looked different than the picture we had seen. Service was fast and kind. What did bother me was that despite the fact the place was mostly open, they sat everyone right next to, practically on top of eachother, and this definitely made things feel less intimate and more like a crappy Applebees. It was Good, I would come back, but rarely.

    Photos
    Via Vecchia - More seating

    More seating

    Via Vecchia - Awful Bread

    Awful Bread

    Via Vecchia - Back lounge area

    See all

    Back lounge area

    Roma Cafe

    Roma Cafe

    4.0(185 reviews)
    0.6 miParkside
    $$$

    Amazing atmosphere, amazing food!…read more Went here for a date night and highly recommend. All servers were very nice and planning on going back!

    We chose Roma Cafe for our wedding anniversary dinner since Italian is our tradition each year, and…read morethe setting really did feel special. The cozy, romantic atmosphere made it easy to settle in for a long meal. Sitting by the window overlooking the street, it honestly felt like a scene out of an old romance set in a brownstone in NYC. There was so much to love about the food, too. The pasta tasted fresh and perfectly cooked, my pesto had a great balance of flavor, and both of our drinks were beautifully made. You can tell the kitchen puts care into the ingredients and preparation. Unfortunately, my husband's chicken parmesan came out undercooked. The chicken was clearly raw in the center. It was disappointing, especially on a special occasion, and food safety issues like that are hard to overlook. I do want to highlight that our waitress was outstanding. She noticed something was wrong from across the room and stepped in right away. She handled the situation with professionalism and kindness, and we truly appreciated her attentiveness. What left us surprised was that no one else came by to acknowledge what happened. With something as serious and easily preventable as raw chicken, we expected at least a brief apology or check-in from a manager. It was less about getting something for free and more about feeling taken care of after a pretty significant mistake. Overall, there were some really lovely parts of the experience, but the food issue and lack of follow-up made the night feel more mixed than we had hoped for a celebration dinner.

    Photos
    Roma Cafe - Vibe

    Vibe

    Roma Cafe - Mussels

    Mussels

    Roma Cafe

    See all

    Il Leone

    Il Leone

    4.5(31 reviews)
    3.1 mi

    I have to caveat my three star review with the fact that I have had Il Leone multiple times before…read morethis review and the pizza is always tasty. It's unique and it's simple -- but the flavors created are something to keep coming back for. In my most recent visit, we had a pretty bad experience leading up to the pizzas actually being served. We had some friends visiting and decided to go to grab pizza after sending a small group back to the mainland on the 6 o'clock boat. Our order must have been placed maybe 5 or 10 minutes after 6... we weren't served our first pizza until after 8 PM. And our second pizza lagged behind that one by nearly 10 minutes. I can understand how, taken out of context, this can be seen as a petty complaint. However, it really was a discouraging experience because we had multiple (at least half a dozen) other groups order well after us and enjoy their entire dining experience all around us. The group ordering behind us enjoyed their pizzas, bottles of wine and chit chatted for nearly a half hour after their indulgences... and still rode off in their golf cart before our pizzas even made it into the oven. The part that really baffled me was that we took the opportunity to speak with the staff about what was causing the delay -- simply asking if our pizza order had been started or not yet and the explanation was "our team has made several mistakes this evening and we don't have a good estimate on how long it'll take for your pizzas to be ready". We got the same explanation after waiting for 45 minutes and again after nearly an hour and a half. It seemed like a pretty inadequate answer when their wood-fired oven was often not full of cooking pizzas and their entire staff was dancing to the music playing on their speakers. In the end... the pizza was good (same quality as expected). But my experience left something to be seriously desired.

    This was the best lunch on a gorgeous trip out to Peaks! They are literally a couple trailers and…read moresome picnic tables so if you need a bathroom look elsewhere. My friend and I decided to split a pizza and it was a good sharing size. We got the burrata and it was delicious! The cashier told us it would be about 45 and I think it was a bit less than that but expect a bit of a wait on a busy weekend. The crust is super thin and floppy but good texture and taste! The sauce was flavorful and the burrata was perfect.

    Photos
    Il Leone - The counter

    The counter

    Il Leone
    Il Leone - Pizza Bianca

    See all

    Pizza Bianca

    Quanto Basta - This is what a Neapolitan pie should look like.

    Quanto Basta

    4.3(36 reviews)
    0.6 miEast Bayside

    This was our first time to Quanto Basta. They don't take reservations and the place is tiny, so I'd…read morerecommend going on the early side. I had a margherita pizza, which I thought was really good. As others have mentioned this pizza is not "American" style, it's Napolitano, which I think translates literally on Google to "don't drown your pizza in mozzarella, this isn't Domino's stuffed crust." My friend had a salad to start, that had a lot of different flavors to it -- a mix of fruit and greens and fennel and... and... For my taste, it was a little too-too. But it was fresh as everything else we had was. Server was super nice and accommodating - we chose to sit outside, and it started raining. Heads up -- only a few of the outdoor tables fit under the glass awning, and the covering doesn't cover completely. So I'd definitely recommend going when there's a lower chance of rain. One other thing I'll add around ambiance is that the area for dishes/plates is right by the back door, and the sprayers are loud. Made it a bit difficult to hear at times but I imagine it's not an issue (or is less of an issue) if you sit inside. But for the pizza itself? Go.

    How did I not eat here before? Nathan and Emily created some classics but also some unlike any…read moreavailable locally such as the leek and bottarga or limone (yes, limone). Sit at the bar - best seats in the restaurant and a great place to watch pizza maestro Emily rank out pizza after pizza! Everyone's favorite was the Diavola...the pickled peperoncini was a nice change to this standard pizza. I liked the salsiccia & bitter greens, but wish it was also available with red sauce. I'm adding Quanto Basta to my heavy rotation and if you love great pizza, you should as well!

    Photos
    Quanto Basta - This is what a Neapolitan pie should look like.

    This is what a Neapolitan pie should look like.

    Quanto Basta - Rice balls

    Rice balls

    Quanto Basta - Summer special pie & sausage and broccoli

    See all

    Summer special pie & sausage and broccoli

    Leeward - italian - Updated May 2026

    Loading...
    Loading...
    Loading...