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Leeward — Restaurant in Portland

Name
Leeward
Description
Informal Italian restaurant serving pasta, seafood & meat dishes, plus desserts & a large wine list.
Nearby attractions
Cross Insurance Arena
1 Civic Center Square, Portland, ME 04101
SPACE Gallery
534-538 Congress St, Portland, ME 04101
Portland Museum of Art
7 Congress Sq, Portland, ME 04101
Maine Historical Society and the Wadsworth-Longfellow House
489 Congress St, Portland, ME 04101, United States
Monument Square
456 Congress St, Portland, ME 04101
State Theatre
609 Congress St, Portland, ME 04101
Mainely Frames & Gallery
541 Congress St, Portland, ME 04101
Mechanics' Hall
519 Congress St, Portland, ME 04101
Portland Stage
25 Forest Ave, Portland, ME 04101
Portland Public Library
5 Monument Sq, Portland, ME 04101
Nearby restaurants
Taco Escobarr
548 Congress St, Portland, ME 04101, United States
Marcy's Diner
47 Oak St, Portland, ME 04101
Nosh Kitchen Bar
551 Congress St, Portland, ME 04101
Empire Chinese Kitchen
575 Congress St, Portland, ME 04101
Tokyo Sushi Ramen & Bar
11 Brown St, Portland, ME 04101
REGARDS
547 Congress St, Portland, ME 04101
David's Restaurant
22 Monument Sq, Portland, ME 04101
Mister Bagel
539 Congress St, Portland, ME 04101
Asmara Restaurant
51 Oak St, Portland, ME 04101
Shays Grill Pub
18 Monument Sq, Portland, ME 04101
Nearby hotels
Holiday Inn Portland-By The Bay
88 Spring St, Portland, ME 04101
Portland Harbor Hotel
468 Fore St, Portland, ME 04101
Courtyard by Marriott Portland Downtown/Waterfront
321 Commercial St, Portland, ME 04101, United States
Canopy by Hilton Portland Waterfront
9 Center St, Portland, ME 04101
Hyatt Place Portland Downtown-Old Port Square
433 Fore St, Portland, ME 04101
Aloft Portland Downtown Waterfront ME
379 Commercial St, Portland, ME 04101
The Press Hotel, Autograph Collection
119 Exchange St, Portland, ME 04101
The Inn at Park Spring
135 Spring St, Portland, ME 04101
The Weldon Hotel
54 York St, Portland, ME 04101
Portland Regency Hotel & Spa
20 Milk St, Portland, ME 04101
Related posts
Keywords
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Leeward things to do, attractions, restaurants, events info and trip planning
Leeward
United StatesMainePortlandLeeward

Basic Info

Leeward

85 Free St, Portland, ME 04101, United States
4.8(202)
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Ratings & Description

Info

Informal Italian restaurant serving pasta, seafood & meat dishes, plus desserts & a large wine list.

attractions: Cross Insurance Arena, SPACE Gallery, Portland Museum of Art, Maine Historical Society and the Wadsworth-Longfellow House, Monument Square, State Theatre, Mainely Frames & Gallery, Mechanics' Hall, Portland Stage, Portland Public Library, restaurants: Taco Escobarr, Marcy's Diner, Nosh Kitchen Bar, Empire Chinese Kitchen, Tokyo Sushi Ramen & Bar, REGARDS, David's Restaurant, Mister Bagel, Asmara Restaurant, Shays Grill Pub
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Phone
+1 207-808-8623
Website
leewardmaine.com

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Featured dishes

View full menu
Peach Tart
Sweet Corn Gelato
Blueberry Custard Gelato
Plum Raspberry Sorbetto
Okay Fine
Tequila, cynar, coffee liquer, sweet vermouth, amaretti

Reviews

Nearby attractions of Leeward

Cross Insurance Arena

SPACE Gallery

Portland Museum of Art

Maine Historical Society and the Wadsworth-Longfellow House

Monument Square

State Theatre

Mainely Frames & Gallery

Mechanics' Hall

Portland Stage

Portland Public Library

Cross Insurance Arena

Cross Insurance Arena

4.2

(218)

Open 24 hours
Click for details
SPACE Gallery

SPACE Gallery

4.8

(113)

Open 24 hours
Click for details
Portland Museum of Art

Portland Museum of Art

4.6

(1.0K)

Open 24 hours
Click for details
Maine Historical Society and the Wadsworth-Longfellow House

Maine Historical Society and the Wadsworth-Longfellow House

4.4

(108)

Open 24 hours
Click for details

Things to do nearby

Hands-On Oyster Shucking Class in Portland
Hands-On Oyster Shucking Class in Portland
Sat, Dec 13 • 3:00 PM
Portland, Maine, 04101
View details
Birdwatch at stunning Biddeford Pool
Birdwatch at stunning Biddeford Pool
Sun, Dec 7 • 8:00 AM
Biddeford, Maine, 04005
View details
Portland, ME Murder Mystery: Solve the case!
Portland, ME Murder Mystery: Solve the case!
Mon, Dec 1 • 12:00 AM
1 Temple St, Portland, ME 04101, USA, 04101
View details

Nearby restaurants of Leeward

Taco Escobarr

Marcy's Diner

Nosh Kitchen Bar

Empire Chinese Kitchen

Tokyo Sushi Ramen & Bar

REGARDS

David's Restaurant

Mister Bagel

Asmara Restaurant

Shays Grill Pub

Taco Escobarr

Taco Escobarr

4.4

(1.2K)

Click for details
Marcy's Diner

Marcy's Diner

4.4

(608)

Click for details
Nosh Kitchen Bar

Nosh Kitchen Bar

4.4

(662)

$$

Closed
Click for details
Empire Chinese Kitchen

Empire Chinese Kitchen

4.6

(799)

Click for details
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Reviews of Leeward

4.8
(202)
avatar
1.0
2y

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.

My two friends and I arrived a few minutes early for our reservation, and we were greeted by a hostess, who was unfriendly from our first interaction. We went to the waiting area as instructed and noticed that another party of guests waiting to be seated had some cocktails. After no one approached us for our drink order, my friend tried to go to the bar to order espresso martinis. She was intercepted by the hostess, who said they only have "house" espresso martinis, that included tequila and amaro (but no real espresso because they don't have an espresso machine, which is inherently odd for an Italian restaurant). My friend ordered three of these, and then asked the hostess to come explain the drink ingredients, because she had never heard of a tequila espresso martini before and was not sure if she was relaying the ingredients correctly to us. Then the hostess listed the ingredients to us in an antagonistic manner, and when I tried to clarify if the tequila was forward tasting in the drink, she replied in a patronizing tone that "it tastes like all those things mixed together." We were taken aback by her attitude and lack of care / knowledge. She then notified us that the drinks were already being made, and so to cut this unpleasant interaction short, since she was visibly annoyed and did not seem to want to help us understand the drink or amend the order, we said we would be fine with them. A while later we received the drinks while still waiting to be seated, and sure enough they were disgusting.

We were then seated at our table with our awful cocktails, which none of us were drinking. We looked at the menu, asked the waiter some questions, and after he had taken our food order, we asked to order a bottle of sparkling wine. The waiter then said, "my manager told me not to bring you any alcohol for a while because you have been overserved." We were flabbergasted at this point and barely knew how to respond. He offered no additional information when asked why and for more details, and so we asked him to pause on placing the food order as we all felt deeply uncomfortable at this point. The interaction with this waiter also then felt disingenuous, as we would have hoped either he or his manager would have addressed whatever concern they had with us directly. As we were discussing what had just happened and trying to process what was going on, the same hostess came over to ask if we liked the drinks -- yet again in an unfriendly and, at this point, clearly also disingenuous manner. We were so uncomfortable at this point that we did not say anything about how horrible they were, as we wanted her to leave us as soon as possible.

After that interaction, we decided we needed to leave as soon as possible given the passive-aggression and underhanded hostility we were encountering. We politely told the waiter to please cancel the food order and please bring the bill for the drinks. As we waited, the hostess came yet again and asked if we liked the drinks and said she would comp them if we did not like them. Unfortunately, the hostess had made us feel so uncomfortable and stressed at this point that we did not think she would be receptive to the feedback on the drinks, and we did not want to experience any further hostility from her. So we said we would like to pay for the drinks please.

We paid for the drinks and left, and unfortunately this left a very black cloud over our night. I have honestly never felt so uncomfortable in a restaurant before, much less one in Portland, Maine. I genuinely hope this hostess and the manager and the waiter were just having a bad day, but this negative interaction was really unnerving, and I will certainly be warning any friends about going...

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avatar
3.0
1y

I Wanted to Get It So Much, But I Didn't For a few weeks we were looking forward to experiencing Leeward based upon recent reviews. Later we learned about its James Beard award nomination. But I will say - I just don't get it. I want to get it but I don't. To be direct and more specific. I will address the vibe first, then service and then food. The vibe was intense, serious and without any soul. The staff seemed focused on performing and not making a mistake. So much so, that they appeared very phony and transactional. We sat at the counter and the cook staff were there, but not there. The music was a bit too loud - you would think talking should not be challenged by the music. The decor and layout was great - but that was it. Regarding the service, when we arrived - no welcome. I shared we had a reservation. The person at the front of the room looked around said they have to do something else and left. We had no idea what that meant. Someone else showed up, grabbed menus and seated us. There was no pleasantry, no comment such as have a nice evening or thank you for coming have a nice meal. Just a walk away. The waitress was not a good experience at all. There was no welcoming, just an arrival and asking us if we want a drink - very curt and transactional. The smile seemed fake and there was an interest in leaving as soon as she arrived. We ordered a bottle of wine, She came back to show me the bottle and then said she had to leave to have the wine checked. I have no idea what that was about. She reappeared with the bottle and I said I did not need to try it - I am of the mindset if it is corked we would know, and asked her to kindly pour - we would be fine. She said they tried it too and it was okay. So do you try the wine in the bottle before serving it? That is weird. Next we said we would be sharing our appetizers and entrees but that we only settled on the appetizers for now. We were told we had to order everything at once. But once she took our small plate order, she disappeared. I guess that was not true, but why say it? We did order two main meals. The food was just okay. As someone who is an avid cook with flavors, textures, balance and presentation, I cannot tell you what I was eating and explain how it tasted. I was left very disappointed. The artichokes were okay. We got what we expected with some caramelization, but the overall dish was very dry. The best experience of the night was the burrata, charcuterie meats and wonderful pillows of fried dough. The burrata was the best I've had - a real depth of creaminess. Everything together blended well and we savored each bite. As for the main dishes, the ravioli was overwhelmed by the lemon zest. We could not taste the egg yolk, the fresh pasta or the pureed bean. We could taste the texture of the white beans, but not the flavor. A+ for the technique of serving a raw egg inside the ravioli - that was cool. Our other entree was the gnudi. This dish was so disappointing. They were bland, and only with sauce was there flavor. I couldn't believe I made myself put sauce on the gnudi in order to have a flavor in my mouth. The sauce was tasty, but the gnudi felt like I put food in my stomach and cannot tell you what I ate. Lastly, it was strange to experience the staff. At the end of the entrees, the waitress eventually came back and dropped of dessert menus. She never asked if we were interested in dessert or if we would like something else. When she came back we told her we were passing on dessert. It felt like everyone was so focused on performance and not making a mistake that they left their joy and passion behind. I would have rather had a dish where no cotton was used to clean the rim before presenting if it meant the staff could be more relaxed, would engage authentically and the food was cooked with passion and soul. We were very bummed out from the experience. I still left a 20% tip because the staff works hard and deserves to be paid for their efforts. However, the culture means we...

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avatar
1.0
4y

My girlfriend and I arrived at Leeward at 6:30 for our reservation and were greeted by a nice hostess. Our server came with water immediately and asked if we were ready, but we told her that we need a few minutes since we literally just sat down. Over the next 15 minutes, she proceeds to serve a few other tables, including the one right next to us for whom she retrieves the bill, comes back to grab their card, charges their card and bring it back to their table all before coming back to us to ask what we would like. I did notice that this couple happened to be two white people (I’m latino), but I assumed it was coincidence and gave our server the benefit of the doubt. We gave our server our entire order (wine, appetizers, and entrees) at once since we had plenty of time to think about it and didn’t know when we would get her attention again. When she brings out the bottle of wine, she tells us that she’s going to bring it back inside so that SHE can taste it to make sure that it’s okay. I’ve never been anywhere that didn’t let ME taste the wine that I was paying for to make sure that I thought it was okay, but we let her do her thing and then bring the wine back. We also never received anything to keep our white wine chilled which we’ve also never experienced at a place charging these kinds of prices. After waiting for a full hour from when we ordered, we received our two small plates of pasta that left us about as hungry as we were when we arrived. When our server came to take the plates away, I asked for the check so that we could leave ASAP (at this point it was 8pm and cold outside which I didn’t prepare for since we sat down at 6:30). We saw the server serve multiple tables of white people before handing us our bill (I had my card in hand to continue to try to speed up the process) and then check on several more tables including the two next to us before handing us our paid bill. Pretty different from the way she seemed to be treating everyone else. We finally got to leave at 8:15pm still hungry after spending more than $140 and had to stop at a nearby pizza joint to make sure we didn’t go to sleep hungry. Lazzari treated us very well even though they could probably tell that we were visibly frustrated walking in and the food was truly amazing. We made sure to tip them as much as we did at Leeward because we got better service there for almost 1/10 of the price. Lastly, after doing more research when I got home, I realized that the only other non-5 star review for this restaurant on Google was also given by a...

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Posts

Maggie JMaggie J
Been thinking about Leeward since my first visit 3 years ago. Since we were going to be a larger party of 6, I set an alarm for 1 month out to make sure that I could snag a Saturday night reservation. We were seating in a back booth upon arrival and were quickly greeted with waters and menus. We placed our drink orders along with an emergency appetizer order for the gnocco frito and focaccia all of which came out promptly. For our mains we literally just ordered all of the pastas. Unfortunately they were already out of the mushroom pasta but we were able to try all of the rest. Each pasta was beautifully al dente with fresh seasonal ingredients. If I HAD to choose a favorite at the table it was probably the cannelloni but they were seriously all winners. If you made me choose one not to order it would probably have been the rigatoni. It was still great, just not our favorite of the bunch. Anytime people ask me for Portland recs this is absolutely the top of my list. You must make time to go here. Italian food is my bread and butter and this has to be one of the best Italian restaurants in the country. Until next time!
Calvin NgCalvin Ng
Leeward is really busy on a Saturday night, so we had to wait for 40 minutes. We didn't make a reservation. The place is modern. The staff are really nice and attractive. The food came out pretty quick. We got the housemade focaccia. It was soft and cold. I wished it was crispy. We also ordered Rigatoni and Crispy Polenta. Have you ever eaten something on your first bite and say to yourself this is really good! Well, the Rigatoni and Crispy Polenta were a big disappointment. Both were not authentic Italian food. It's a more high-end Italian fusion. The Rigatoni noodles were cooked just right, but the beef and pork ragu bolognese, dandelion green, paramigiano reggiano wasn't anything special. The Crispy Polenta Tuscan pork was tender, but again, it wasn't what I was hoping for. I guessed I had high expectations with all the great reviews here, but it was a big disappointment. They price for three dishes came to 73 dollars with tips. The portions are small. If you're looking for authentic Italian, this isn't it.
Audrey DAudrey D
Leeward was such a delightful treat! Reservations are recommended as they fill up fast. We loved their flavorful and fun mocktails. The menu is small and constantly updated based on what is in season. It made it easy to decide what to order. For appetizers we got the focaccia and fried artichoke hearts. The focaccia was soft and balanced with a saltiness that paired beautifully well with the olive oil. The artichokes were tender and lightly battered. I ordered the mushroom ricotta pasta and my husband ordered the braised rabbit pasta. This place is known for their pasta dishes and did not disappoint! My favorite dessert was the hazelnut tart. We had such a good time overall. Service was efficient, the waitstaff was prompt and helpful, and we left having had a perfect amount of food for a fun night out. I highly recommend Leeward!
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Been thinking about Leeward since my first visit 3 years ago. Since we were going to be a larger party of 6, I set an alarm for 1 month out to make sure that I could snag a Saturday night reservation. We were seating in a back booth upon arrival and were quickly greeted with waters and menus. We placed our drink orders along with an emergency appetizer order for the gnocco frito and focaccia all of which came out promptly. For our mains we literally just ordered all of the pastas. Unfortunately they were already out of the mushroom pasta but we were able to try all of the rest. Each pasta was beautifully al dente with fresh seasonal ingredients. If I HAD to choose a favorite at the table it was probably the cannelloni but they were seriously all winners. If you made me choose one not to order it would probably have been the rigatoni. It was still great, just not our favorite of the bunch. Anytime people ask me for Portland recs this is absolutely the top of my list. You must make time to go here. Italian food is my bread and butter and this has to be one of the best Italian restaurants in the country. Until next time!
Maggie J

Maggie J

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Leeward is really busy on a Saturday night, so we had to wait for 40 minutes. We didn't make a reservation. The place is modern. The staff are really nice and attractive. The food came out pretty quick. We got the housemade focaccia. It was soft and cold. I wished it was crispy. We also ordered Rigatoni and Crispy Polenta. Have you ever eaten something on your first bite and say to yourself this is really good! Well, the Rigatoni and Crispy Polenta were a big disappointment. Both were not authentic Italian food. It's a more high-end Italian fusion. The Rigatoni noodles were cooked just right, but the beef and pork ragu bolognese, dandelion green, paramigiano reggiano wasn't anything special. The Crispy Polenta Tuscan pork was tender, but again, it wasn't what I was hoping for. I guessed I had high expectations with all the great reviews here, but it was a big disappointment. They price for three dishes came to 73 dollars with tips. The portions are small. If you're looking for authentic Italian, this isn't it.
Calvin Ng

Calvin Ng

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Leeward was such a delightful treat! Reservations are recommended as they fill up fast. We loved their flavorful and fun mocktails. The menu is small and constantly updated based on what is in season. It made it easy to decide what to order. For appetizers we got the focaccia and fried artichoke hearts. The focaccia was soft and balanced with a saltiness that paired beautifully well with the olive oil. The artichokes were tender and lightly battered. I ordered the mushroom ricotta pasta and my husband ordered the braised rabbit pasta. This place is known for their pasta dishes and did not disappoint! My favorite dessert was the hazelnut tart. We had such a good time overall. Service was efficient, the waitstaff was prompt and helpful, and we left having had a perfect amount of food for a fun night out. I highly recommend Leeward!
Audrey D

Audrey D

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