Wow. I couldn't even wait to leave the restauraunt to leave a review. Food is amazing. Service is amazing. The vibe is also amazing. We got the gnocco fritto, tagliatelle and the halibut. All were amazing. The halibut came on a bed of peas...never in my life have I said "wow, these peas are really good" but I did today. read more

My wife, two sons (20 yrs, 18 yrs), and I enjoyed a celebratory dinner at Leeward on the last night of our July 2026 visit to Portland. With an 8pm reservation for Wednesday, we were seated promptly at 7:50pm. This lovely restaurant has a young, welcoming vibe. It's a mix of high-end dining (Italian) with a somewhat casual atmosphere (blue jeans). If you seek a formal "suit and tie" dining establishment, Leeward is not ideal. Although it is pricey, Leeward has many pluses. First, the service here is outstanding. Second, the wood floors, cork decorated walls, open space, and candles provide a nice ambience. Third, the food is delicious and ideal for sharing appetizers. We ordered several items, including focaccia (the olive oil is wonderful), and the Maine Bluefin Tuna Carpaccio (our favorite!). The Gnocchi Fritto with prosciutto is a must-order appetizer for groups. We then each ordered a pasta dish. I devoured the tagliatelle, which had fava beans. My wife enjoyed the radiatore (with pine nuts). My sons both ordered the rigatoni (but one disliked the heavy Bolognese sauce). Glad we were able to enjoy a celebratory dinner in Portland! Leeward contributes to the strong "foodie" reputation of the city. read more

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Hot and highly rated, creative dining, EXCELLENT and attentive wait staff; this was just not the place for me, but MAY be for you. Reservations booked almost solid for days if not weeks, they do "allow" walk ins for high end bar seating. I was lucky to get a preferred bar seat that overlooked the theater of the cocktail creations at the center of the bar. Very entertaining indeed. Prior to that, we had to wait in line at the door before opening and then be assigned a specific seat. As one who hates standing in line for food and specifically avoids food trucks or food festivals for this reason, I was already slightly disagreeable. Obviously I would have had better humor with a long time reservation. Add to that, in order to park not too far away we street parked earlier and had to send one of us out to electronically feed the meter on this early evening experience. I do admit that the creative flavors of the dishes were appealing, if not a little too rich in dressings. I should have asked to have the dressing on the side of my lovely kale salad, but I WANT to trust the chef of a truly reputable high end establishment to not drown it. Still it was lemony delicious. The pea pesto was also creative , but again, slightly less sauce is MORE, it would keep me yearning for another bite. My partners steak was a bit chewy in the cut, we very much respected the bartenders suggestion that he have it rarer than he normally prefers. The potato "hash browns" (my quote) with horse radish sauce had a distinctive flavor and texture which was also crispy and delicious and allowed for a few bites each, again, super heavy on the sauce/ oil? Trendy techno play list was the background music and several tables were set for larger parties, so this does have a celebratory feel to it and you could easily spend your weekly pay check on an adult gathering here. Terrific wine list and stunning cocktails. read more

Leeward - Kale salad - Italian Near Me - Portland, Maine

Had reservations here on Wednesday evening and it was all pretty great. We arrived at 5pm as they were opening and got sat immediately. Our server was very attentive and provided some recommendations. We started with the focaccia which we expected would be fresh and warm but it was just a cold piece of bread. We added the fancy balsamic, but it went better with the pasta sauces. The lentils with brocolini were Amazing. The brocolini was crisp and the lentils were rich with flavor. The tonnarelli was cooked al dente, however it was a tad bit bland. The most delicious pasta was the bucatini. It had a bit of a kick and it was loaded with lobster. We ordered the rainbow trout and it was good just a little overcooked which made the fish a bit dry. Overall this place was good and the service was good as well. read more

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Another great meal here. We come every time we are in Portland for this basically once a year. The food is so well thought out and great service. Fair priced wine list too Totally recommend this place read more

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Finally made it back to Leeward after a couple of years, and it's just as delicious and incredible as I remember it. This time my husband and I brought a friend with us, which meant more sharing and trying a lot more of the menu. We started with the kale salad and the gnudi pasta, with the latter being the star of the night. The kale salad was delicious, incredibly light and refreshing. We accompanied these with some aperitifs from the never-ending and impressive cocktail menu. The gnudi pasta was listed as a main, but it made for an incredible app. For dinner, I ordered the tagliatelle, which was divine. My friend's rigatoni may have been the best out of all of the entrees, though. It was phenomenal. We finished our meal with dessert. It was this almond and fruit cake that was delish, although the dessert menu was a bit limited for what I expected. As always, the ambiance is just lovely. The dimly lit vibes make for a romantic and cozy time, especially during the winter. Our server was thoughtful and attentive and had great wine recs! read more

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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! read more

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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. read more

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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. read more

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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. read more

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Leeward took care of my notification request! I was happy to return again this year ! The decor and atmosphere is very nice! We had a wonderful server, Samantha. The menu was great! Too many choices! The pasta is excellent! My husband had the bolognese and I had pasta with lobster. We both had simple salads and shared a zucchini blossom as an appetizer! We ordered focaccia too. Enjoyed watching the people. There was a bachelorette party going on as well as many other cast of characters. It was interesting! We thoroughly enjoyed the experience and highly recommend it!!! read more

Amazing dinner as always, from the focaccia at the start, to the main pasta dish's, to cocktails and sweet ending of dessert everything was 10/10 read more

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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! read more

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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! read more

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I've been wanting to come here for so long and finally made it! We made a reservation for a Thursday night but it wasn't super busy. Our server was very patient with how indecisive we were being and offered great recommendations. We ended up sharing the gnudi, the tagliatelle, and the rigatoni. Everything was really solid but I enjoyed the tagliatelle the best! The pasta was fresh and the meat was really tender. The tagliatelle and rigatoni were maybe a little too similar to order together but no complaints. Overall a solid meal but there are other Italian places in Portland I'd likely try before coming back! read more

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! read more

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Restaurant seem off the beaten path from concentration of restaurants along the water and inland but actually not really and is an easy walk from center of hub of activity and worth it. Get the lobster pasta and dessert and asparagus appetizer. read more

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Still my favorite restaurant in Portland and top 5 in the US. Love coming with a group and ordering as much as possible off the menu. Favorite dish this go around was the spicy pork ragu pasta. Service and ambiance were just as good as always! read more

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. read more

Leeward - Shells with meat ragu while - Italian Near Me - Portland, Maine

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Fantastic meal. Grilled pork chops are just fantastic. Definitely coming back. Sat at the bar and was excellent

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. read more

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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. read more

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Once again, attentive and kind staff can make or break the night and we got blackjack! Super sweet and very knowledgeable, it enhances the evening when your server simply understands the assignment. Very well done! Open kitchen is really bad ass too! read more

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We had dinner here on a thursday night. I had to reserve it out two weeks. We were a party of four. We all had wine, there were not alot of single glass choices. The rose was very good. We ordered focaccia bread for the table. We should have ordered more appetizers as the pasta dishes were tiny! Maybe 3 oz of pasta for mine which was in a basic tomato sauce. It was good but I was still hungry. Decor was a calming design and wait staff attentive. read more

Pretty darn good and recommended by review dude. Hard to find, a little pricey but would go back

There are a few restaurants in Portland that are able to bring an elevated dining experience, but keep it casual and almost neighborhood oriented - Leeward is one of those places. On any given day, you might see locals dining out for their weekly catch-up or visitors from out of town celebrating, all meshing together in a very casual but intentionally decorated space. Service was excellent as always. Our server paying close attention to cues for when we were ready to move onto the next course and was never pushy about thoughts/suggestions of what we should order. The focaccia, savoy cabbage and gnocco fritto were fantastic shareables for our table. With 7 folks, we had 2 orders of each and plenty of leftovers for people to continue picking at as we transitioned into next courses. The savoy cabbage was my favorite of the antipasto dishes: so crispy, bright and just the right amount of a satisfactory crunch in between bites. We tried several pastas: the pesto, rigatoni with beef/pork ragu, and the gigli - a vegetarian option with confit garlic and maitake mushrooms. My favorite? The pesto. I've never seen pesto coated that well or taste as spring/summer like as this one. Easily my favorite dish on the night and will be attempting to make this over the course of the summer as my basil comes in. We polished it off with shared dishes of apricot bread pudding. Bread pudding, not a very sexy dessert. The bread pudding from Leeward, however, was notable and a surprisingly sweet way to end the meal. For visitors of Portland, this is simply the top Italian restaurant you'll come across and one of the best restaurants in the city. read more

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. read more

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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. read more

Leeward - Pasta with chanterelle mushrooms - Italian Near Me - Portland, Maine

I had dinner at Leeward last night and was highly impressed. Started with the Joe formaggio cocktail because I was curious about it. A cocktail made with cheese? Definitely worthy of attention. It was really good and unexpectedly light. My only complaint is that, like a lot of Portland restaurants, they tend to feature local gin above more well-recognized brands. We started with the chicken liver mousse, which was generously portioned and accompanied by a plum and blueberry compote. It was really well done and one of the better prepared that I've had. The taste was outstanding. For our entrees, we had the pasta alla gricia and the butternut squash cannelloni. The alla gricia was the best that I've had outside of Rome, which is high praise. Roman pasta dishes don't feature a lot of ingredients but they are technically difficult to master. Leeward's execution was flawless and delicious. Like the alla gricia, the cannelloni was spectacular. The balance of sweet and savory flavors was perfectly blended and absolutely spectacular. We would have loved dessert but had no room for it. I had high expectation of Leeward since it has made a few notable top of Portland lists, and I was not disappointed. Quite the opposite, I was surprisingly pleased that it not only lived up to those expectations but exceeded them. Leeward is definitely on my short list of places to revisit. read more

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Had a two pasta dinner before a nearby concert. Lot of fun sitting at the chef's counter & watching them in action. Food was excellent - rivals the best Italian restaurants of San Francisco where I am from. Had interesting wine varietal not often seen in the US. Service friendly, attentive & efficient. read more

Leeward is the most 10/10 experience I've ever had! We had the most incredible experience from top to bottom:staff, vibe, drinks, food, bathrooms, dessert, decor! We go back frequently now! read more

The best pasta I've ever eaten. I've been all over the world. Had old world Italian men hand roll pasta in front of me that wasn't this good. It breaks my heart I don't live here and can't eat it every day. Chef Jake is an incredible man. And the restaurant looks and feels like home. It's the best restaurant I've ever been to. Period. read more

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We were visiting Portland for the weekend. Chose the Leeward for dinner first night. Sat at the bar. Food, service and atmosphere all wonderful. Definitely go again on next visit! read more

If I could give this place more than 5 stars I would! I've been here twice now and each time I've been blown away. Everything is perfect...the service, food and ambience. Price is fair for the quality of the food. Be adventurous here....one of my favorite things is the chicken liver mousse...so creamy and wonderful. Honestly...I've tried a lot here and the menu changes frequently but the food is on point. The wine pairings the server recommends have only made the food better. FYI the dessert is made in house and not to missed. Recommend a reservation...but they do have a bar with open seating and if you get there when the restaurant opens you should get lucky. read more

Really wonderful dinner tonight. Grilled little gems and Mushroom crostone were amazing. Sacchetoni pasta dish was warm and delicious. Cocktails were unique and flavorful. Service was very attentive without being overbearing. Loved everything about this quiet little hidden gem. read more

Leeward - Pasta - Italian Near Me - Portland, Maine

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Wow. Having been to Leeward three times, I continue to be impressed with the service, food, wine selection and overall experience at Leeward. On our most recent visit to Leeward, my partner and I ended up sitting at the chef's counter (which I highly suggest if you are able to). Sitting at the chefs counter allows you to get a close-up look at the chefs in action, and we got the chance to actually talk to the head chef, which was an added perk. The other times we have gone to Leeward, we have sat at the bar and at a table, and we continue to love the bar and chef's counter. The drinks/wine menu are extensive, with creative cocktails and rare wines. Ask your server about the wines, and their knowledge on the different offerings is always impressive. As far as the food, you can't go wrong with any dish, and the menu changes frequently. Some of the staples that we have had was a cabbage caesar-inspired salad...I know...salad...but seriously, it was amazing. On a recent trip, there was a cacio e pepe tortellini that was out of this world. Additionally, we have tried the bolognese and we had a seafood pasta dish. All were incredibly flavorful and worth every penny. Speaking of costs, the price point for the various dishes are incredibly reachable, in my opinion. Many of the dishes are in the $20+ range, so you are not totally breaking the bank for a great experience with amazing food. Overall, Leeward will continue to be a frequent spot for us. I highly recommend to anyone who is looking for a great pasta spot in the Portland scene. read more

We had the most spectacular dinner and Jenny provided exceptional, personable service. We sat at the chef's counter and enjoyed the focaccia, the gnocco Fritto (not to be missed), summer salad and the bolognese and fra diavolo. Perfect amount of food, so many fresh ingredients. Would absolutely return and try more pastas! read more

Leeward - Gnocco Fritto & focaccia - Italian Near Me - Portland, Maine

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

Yes, Leeward is worth the hype! We did not have a reservation but we were able to grab 2 seats at the bar. There was a line when we arrived just before opening but I think you could snag a seat at the bar after the first round of diners, you just have to time it right. I appreciated that they had a decent mocktail selection. The bartenders are attentive and knowledgeable of the menu. We started with the Grilled Peach Crostone and the Cucumber Salad. The Grilled Peach was quite large, we could have only ordered this for an appetizer but the peach and ricotta combo was delightful! The Cucumber Salad is light and perfect for a hot summer day. The fried capers are very crispy and not too salty and pairs well with the dill. The eel is smoky and salty and the yogurt helps to neutralize that. For the main entree, I went with the Spaghettini Nero and my fiancé got the Bucatini. I was deciding between the Spaghettini and another dish but I am glad I went with the Spaghettini. The bartender told me that they only make 5-6 of these dishes a night too! Both pastas were perfectly al dente and seasoned so well without being bland or overly salty. Leeward does a great job at letting the seafood be the main seasoning and not adding more in to cover up the fresh seafood taste or have it be too fishy. I love squid ink pasta and this dish has taken the #1 spot. The Bucatini is a bit spicy so beware of that. There were large chunks of lobster and the tomato added freshness. Highly highly recommend Leeward and I will be thinking of the Spaghettini dish until I return! read more

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Last night I returned to Leeward. It had been a while - maybe a year or so. And, every time I come, I wonder why I don't come more. And last night was no exception. As always, the food was top notch. My cousin and I enjoyed a lovely baby artichoke appetizer along with some delicious sea salt and rosemary focaccia bread. For my entrée, I had the special which was a gnudi stuffed with spinach and goat's milk ricotta. It was so yummy! But, the reason I wanted to update my review is that we had the best service I've had a restaurant in quite some time. Our server, Paige, was delightful, engaging, and very helpful. Both my cousin and I ordered wines that they didn't have, so she brought over bottles of various types she thought we might like. Two different options till I found one, but four for my cousin. And, not the slightest hint of being annoyed with us!! If you are going here and can request a server - ask for Paige. You won't be disappointed!! read more