Anna's Harborside Grille

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Plymouth, MA
Anna's Harborside Grille

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Cathedral ceilings give way to an exposed kitchen where customers watch with curiosity as dinner is being prepared. We hope to see you soon!

Perhaps it’s the smell of fresh herbs and spices being used for tonight’s dinner special or the intimate setting where patrons are engaged in conversation while enjoying one of our signature martini drinks. The outside patio is immersed with summer and there are ocean views as far as the eyes can see. However at its core, Anna’s Harborside Grille is more than just dining. In fact, it is an opportunity to slow down from the fast pace of life and take time to fully enjoy homemade authentic Greek Cuisine and Contemporary American Fare with family and friends…and very similar to how Anna herself hosted dinner at her own home.

11/03/2026

HAPPY TUESDAY FRIENDS….

Join us from 4-9 pm tonight..

11/03/2026

Who needs Tacos on Tuesdays when you can have a Prime Rib for $22.99! See you tonight 🙌

11/02/2026

Mondays are a whole lot more fun at Anna's! 🍻🧠

Join us tonight and every Monday at 7 PM for Trivia Night! Grab your smartest friends (or your funniest), enjoy some great drinks, compete for prizes, and have a few laughs along the way.

Good drinks, great company, a little friendly competition… what better way to spend a Monday?

See you tonight! 🍹🏆

10/31/2026

Live Music tonight..Cocktails & Desserts.. 8:30-11:30 pm

10/31/2026

🎉 𝗪𝗜𝗡 𝗔 $𝟭𝟬𝟬 𝗚𝗜𝗙𝗧 𝗖𝗔𝗥𝗗 𝗧𝗢 𝗔𝗡𝗡𝗔'𝗦 𝗛𝗔𝗥𝗕𝗢𝗥𝗦𝗜𝗗𝗘! 🎉

We're giving one lucky follower a $100 Anna's Harborside gift card! For your chance to win, simply 𝗦𝗛𝗔𝗥𝗘 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 𝘁𝗼 𝘆𝗼𝘂𝗿 𝗙𝗮𝗰𝗲𝗯𝗼𝗼𝗸 𝗳𝗲𝗲𝗱 𝗼𝗿 𝗥𝗘𝗣𝗢𝗦𝗧 𝗶𝘁 𝗼𝗻 𝗜𝗻𝘀𝘁𝗮𝗴𝗿𝗮𝗺!

And while you're at it, check out all the great reasons to visit Anna's throughout the week. We've got something happening almost every day!

🧠 𝗠𝗢𝗡𝗗𝗔𝗬 | 𝗧𝗿𝗶𝘃𝗶𝗮 𝗡𝗶𝗴𝗵𝘁
Grab your smartest friends and join us for Trivia Night every Monday at 7 PM!

🥩 𝗧𝗨𝗘𝗦𝗗𝗔𝗬 | 𝗣𝗿𝗶𝗺𝗲 𝗥𝗶𝗯 𝗡𝗶𝗴𝗵𝘁
Enjoy a delicious prime rib dinner with two sides for just $𝟮𝟮.𝟵𝟵 with the purchase of a cocktail or mocktail!

❤️ 𝗪𝗘𝗗𝗡𝗘𝗦𝗗𝗔𝗬 | 𝗗𝗮𝘁𝗲 𝗡𝗶𝗴𝗵𝘁
Dinner for two for just $𝟲𝟱! Enjoy a bottle of w**e and your choice of two entrées, including grilled ribeye, baked haddock, chicken Alfredo, braised beef, and more. Available 4–9 PM.

🍷 𝗧𝗛𝗨𝗥𝗦𝗗𝗔𝗬 | 𝗟𝗮𝗱𝗶𝗲𝘀 𝗡𝗶𝗴𝗵𝘁
Gather the girls for a Mediterranean charcuterie board featuring cheeses, hummus, tzatziki, pita, and more, PLUS a bottle of w**e from our Ladies Night selection, all for $𝟰𝟬! Available 4–9 PM.

🍸 𝗙𝗥𝗜𝗗𝗔𝗬 & 𝗦𝗔𝗧𝗨𝗥𝗗𝗔𝗬 | 𝗡𝗶𝗴𝗵𝘁𝗰𝗮𝗽𝘀 𝗮𝘁 𝗔𝗻𝗻𝗮'𝘀
Make a night of it with relaxing live music, martini flights, w**e, and dessert from 8:30–11:30 PM. The perfect way to unwind after dinner or finish off a night out!

🏈 𝗦𝗨𝗡𝗗𝗔𝗬 | 𝗙𝗼𝗼𝘁𝗯𝗮𝗹𝗹 𝗦𝗽𝗲𝗰𝗶𝗮𝗹𝘀
Catch the games in our heated tent from 12–6 PM and enjoy $𝟱 𝗰𝗵𝗲𝗲𝘀𝗲 𝗽𝗶𝘇𝘇𝗮𝘀 𝗮𝗻𝗱 $𝟱 𝗮𝗽𝗽𝗲𝘁𝗶𝘇𝗲𝗿𝘀! Great football, great food, and even better prices.

There's always a reason to get together at Anna's Harborside, and we'd love to see you!

𝗗𝗼𝗻'𝘁 𝗳𝗼𝗿𝗴𝗲𝘁 𝘁𝗼 𝗦𝗛𝗔𝗥𝗘 𝗼𝗿 𝗥𝗘𝗣𝗢𝗦𝗧 𝗳𝗼𝗿 𝘆𝗼𝘂𝗿 𝗰𝗵𝗮𝗻𝗰𝗲 𝘁𝗼 𝘄𝗶𝗻 𝘁𝗵𝗮𝘁 $𝟭𝟬𝟬 𝗴𝗶𝗳𝘁 𝗰𝗮𝗿𝗱! Good luck! 🎉

10/30/2026

Friday nights just got a little better at Anna's! 🍸🎶

Join us tonight for 𝗡𝗶𝗴𝗵𝘁𝗰𝗮𝗽𝘀 𝗮𝘁 𝗔𝗻𝗻𝗮'𝘀 featuring live music!

Unwind after a long week with martini flights, a glass of w**e, something sweet, and some great live music. It's the perfect way to wrap up dinner or keep your Friday night going a little longer.

No need to head into Boston for a great night out. We've got you covered right here in Plymouth! 🥂

10/29/2026

Start the weekend off early.. join us on the harbor font **e

10/28/2026

Wednesday nights are made for date night! 🍷

Join us at Annas Harborside for a delicious dinner for two, complete with a bottle of w**e, for just $65!

choose two entrées from seven favorites, including baked, haddock, chicken Alfredo, and broccoli, braised, beef, grilled ribeye, half chicken, stuffed peppers, or moussaka.

We are offering this promotion every Wednesday from 4 PM to 9 PM at $65 per couple

10/27/2026

Happy Tuesday everybody… 🍷❤️

Address

145 Water Street
Plymouth, MA
02360

Website

http://www.annasharborsidegrille.com/

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