The Nautical Whimsey is located in downtown Tupelo along Main Street. This spot serves comforting Italian food with very generous portions and a decent bar selection. THE FOOD The Highlight: The Tiramisu was the star of the evening--moist, semi-sweet, and rich. A tasty end to the meal. Starters: The freshly fired Cheese Bread was another win, topped with fluffy, warm cheese. A comforting start. The Entrees: The portion sizes for the Gnocchi, Lasagna, and Fettuccine Alfredo were enormous. You get a massive amount of food for the price. * Note: The execution didn't match the size. There were issues with texture and flavor depth across the main dishes. For example, the Fettuccine Alfredo sauce was watery and bland rather than creamy and rich. SERVICE & ATMOSPHERE The dining area has a homey, casual feel. The hostess and server were patient, and the waitress immediately swapped out a glass of red wine that had oxidized, which was appreciated. PARKING Plenty of streetside parking is available. OVERALL The Nautical Whimsey provides a large amount of food for the cost. It is a solid choice if you need to feed hungry teenagers who value quantity over culinary precision, but foodies looking for high-quality Italian might want to look elsewhere. read more

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Food: excellent food with very large portions We got the filet, lasagna, and my son got the grilled cheese Service: the service was wonderful and very prompt Ambiance: we sat outside and very much enjoyed it! They had music playing and the weather was wonderful! We will definitely be back!! read more

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It had been over a decade since my last visit to Nautical Whimsey--and to be honest, I didn't remember much about it. So when a friend suggested we go while I was in town, I figured it was time for a reintroduction. I ordered the 12oz filet mignon (medium), which came with their stuffed baked potato--loaded with alfredo sauce and plenty of cheese. The steak leaned more toward medium-well, but it was still tender and flavorful. And that potato? Totally indulgent in the best way. Cheese and potatoes rarely miss. I paired the meal with the Honeysuckle Mule. It was beautiful but very sweet. If you're into sugary cocktails, you'll probably enjoy it, but I'd personally go with something else next time. Service was friendly and relaxed. We sat outside, which they offer both in a quaint little alley or street-side. We ended up on the street side, which was a bit loud thanks to passing cars and the occasional bass-thumping teenager. Still, the atmosphere was fun and casual. Overall, a solid dinner with good food and friendly service. I'd come back--maybe next time, I'll try the alley seating and a less sweet drink. read more

Plus: The servings are HUGE! Never seen such big fried cheese. Nachos were well seasoned. Entrees tasty! Service was good, atmosphere family-friendly. Cons: Would come back, although the temp in the restaurant is cold. Bring a jacket! They did not clear dishes from the table so stacked appetizer plates to get them out of the way. read more

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This was our first time eating here. I ordered the Caesar salad it was so delicious. For entree had the flounder well prepared and tasty, my friend order the lobster ravioli it was overcooked tomato sauce had no flavor and about 6 pieces of lobster sprinkled throughout. Our server gave us very nice service. The ambiance is very pleasant and comfortable. read more

If you want the best steak you've ever eaten... give this place a try. I was told this was the place for a filet, yet was somewhat hesitant, since it's primarily Italian food. So glad I gave it a shot! I've had steak all over... and this won top spot! I got the Cajun baked potato and my wife got the Italian. Either choice is a win for sure! It's not cheap... but well worth it! read more

The food was amazing. The service was awesome. I like the location, we got our food in a timely manner.

Huge, can I say HUGE portions...lasagna as big as my head, eggplant Parmesan that is crunchy and serve red over a huge plate of spaghetti marinara (pasta was a bit over done), gnocchi is delicious. Great service and variety of Italian dishes. Appetizers of fried mozzarella is fried breaded cubes of deliciousness, fried ravioli looked good too! Casual ambience and great service, each dish is enough for 3 people, we all needed doggy bags!!! read more

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The service was incredibly nice and attentive, and our wait time for food was almost non-existent. Everything came out piping hot, fresh, and beautifully presented. It all tasted amazing. The appetizers and main course was enough to have leftovers to enjoy later. read more

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The food portions are huge! Bring your appetite. The restaurant is nice, and the staff are great! read more

We ordered the Around Italy dinner for two and it was amazing. Definitely more than enough for two. We took home a box of leftovers! The fried cheese is a great app and the house wines are good too! We had the house cab. Definitely will be back! read more

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Food, service & drinks were all excellent! Portions are huge! The seasonal martini flight was delicious! read more

Nautical Whimsey - Fall Martini flight- espresso, peach & apple cider - Italian Near Me - Tupelo, Mississippi

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Everything about the food, including the portions are awesome great service and cool ambience

Service was great. Food is ok. It's not a top 20 place in Tupelo. Maybe the hype skewed my opinion?

The appetizer with the sauce 10/10 Half caesar salad delicious and very fresh! The lasagna was so ginormous, I could only take 2 bites, but more for the next day right! Our server Ashton was Amazing! He took really great The ambiance was ok, it was a little loud due to a birthday party of 40+ people. However, the hostess sat us in as quiet area as she could. read more

Nautical Whimsey - Greek salad - Italian Near Me - Tupelo, Mississippi

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This place was amazing ! We had one of the best lunches of our lives here. We were in town for a wedding and after searching Yelp for the help we needed to find this place we decided to give it a try. My wife had the filet and baked potato which was baked to perfection and I had the shrimp alfredo which was enough for 3 people to eat. The food was amazing and the portions were enormous so come hungry and bring a friend to help eat it all ! read more

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Delicious food. Generous portions. Locally owned by the best of people!! I've not had one bad meal or experience ever!! read more

The food is always delicious and I have never had bad service. A great locally owned restaurant that everyone should try!!! read more

Nautical Whimsey - 8oz Fillet with potato covered in cheese and Caesar salad - Italian Near Me - Tupelo, Mississippi

Everything could improve...especially the food & ambience The portions are huge but not worth it read more

There's going to be a bit of a wait but it's well worth it. The portions are huge! The fried cheese is amazing. I love their marinara. It's got a sweet flavor. Will be going back if I find myself back in Tupelo. read more

The food was absolutely amazing, the portions were huge!!!!! Definitely shareable. My husband and I left stuffed. The wait was very long, and the service was slow. The steak was nice and tender, but it did has a sweeter tasting sauce on top. All in all, really good place to eat!! read more

Nautical Whimsey - Filet mignon & Italian cheese baked potato - Italian Near Me - Tupelo, Mississippi

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Don't believe the reviews, this is the BEST restaurant in Tupelo. Never had anything but the best food and servixe.

Large portions, delicious food, and awesome waitress. Definitely recommend the lasagna and the fried cheese appetizer. Great place to go in downtown Tupelo! read more

I have drove 4 times from Arkansas (5 hours) to eat here. If you call or look on their Facebook they say they're open, but they ALWAYS close early. They need a new manager. If you ever get to eat here the food is great, but they will never be open. read more

This place has the best Italian food, we always have the best time! Service is always wonderful! read more

Nautical Whimsey - Happy plates - Italian Near Me - Tupelo, Mississippi

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Great service...waitress was nice and attentive. Great food...steak was sooooo tender, I cut it with my fork. Cheese sauce on baked potato was ooey gooey delicious. My only issue was time, it took over an hour to get our entrees. read more

Nautical Whimsey - Summer Martini Flight 5/5 - Italian Near Me - Tupelo, Mississippi

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Small place with a cool vibe. The food was delicious, especially the eggplant parm. Good thing too because we all had leftovers. Portions are very generous. And a pretty good Manhattan. Waitstaff also above average. Two enthusiastic thumbs up. read more

HUGE portions and delicious. Bring friends to share plates. So Yummy! Ask about the specials and wear your stretchy pants. read more

Lasagna is definitely enough for 2 maybe even 3 people. Food is awesome we traveled over 100 miles and worth every mile. Awesome food love the staff and the food. read more

Nautical Whimsey - Menu - Italian Near Me - Tupelo, Mississippi

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I've eaten here many times and twice last week. If you are considering lunch, just keep considering and go somewhere else. You can't order from the menu during the week and your only option is the buffet. The nicest thing I can say about the buffet is that it is mediocre. Just go somewhere else. Or, go here knowing that nothing you eat will be delicious. If you are looking for an evening meal, there is potential for better-than-buffet food. The Mozzarella balls are huge. They are my favorite thing on the menu. The marinara sauce that comes with them is good. However, the red sauces are consistently not good. I don't know why they don't use the marinara on everything and toss the red sauce recipe. The wait staff is never great. The bartenders are not great. Cleaning is not a priority. It's just feels like the owners don't care any more. read more

My husband and I were in Tupelo for his job! He and I found this place on Yelp! It was amazing We had fried cheese as an appetizer! It was even better the next day! My hubby had the Gnocchi with shrimp... I couldn't stop stealing a bite. Only problem was the shrimp was really salty, but it was still great. I had the cheese stuffed ravioli and I ate in it for 3 meals. Such amazing food. The place is a little bit of a dive, but who doesn't love a dive. There is really cool out door seating but no heaters so we couldn't sit out there. Our waitress was adorable and very attentive. All in all a great place to eat. read more

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Good food but not great, had the Egg Plant Parmesan. Also, share a plate with someone. Was enough to feed 3 people just on my plate alone. All in all, would try them again if ever in the area. read more

One of the best restaurants in town. Best Italian food around! Love the fried cheese and eggplant parmigiana. My wife loves their filet special. read more

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Our first time to eat here... Very friendly staff and very attentive... the cheese and sausage appetizer was good, I had the Greek salad with added steak which was very good.... The wife had the lasagna that was excellent.... All these items were large portions... my wife had enough lasagna for her meal, and enough for her, our daughter, and granddaughter the next day... A very good dining experience!!! We will be back.. read more

Our server was super sweet on a very busy night. We had the fried cheese and had to share it with the neighboring table as it was so big! The marinara was excellent. Split a pizza and glad we did. The filet/potato dish was way too much food for me to have eaten. We love local places such as this. read more

The gnocchi is one of the best I've had----perfectly prepared! Tasty! My sons ravioli--he ate it all! (A rarity) the portions were huge! The bruschetta was ...different. There's a sweet flavor that seems to overpower the essence of bruschetta's traditional flavors... This will be my gnocchi go to when on the road for sure! read more

One of our favorite spots on Tupelo. You sit in the front in the bar area or there is a small area of seating in the back and an outdoor area in the alley. read more

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The portions are big enough to feed a small army, and they're amazing! I had the lobster ravioli with vodka sauce (amazing) and my fiancé had the prosciutto fettuccini which was also very good. It's small so expect to wait, but the wait is worth it. read more

Very disappointing. Went for dinner and sat at bar. I was torn between several entrees, so asked the bar tender/server. She recommended the Egg Plant Parmesan and so I ordered it. Also, ordered wine that they ran out of. Meal came out, except it was the egg plant that I ordered it was chicken parm. When the server came back around, offered half heartedly to take it back, not wanting to be that person, I said I'd he eat. I should have sent it back...appeared to be chicken fingers with cheese over it. I will say, the sauce was very good. Very bad experience, very bad food, very bad service. Such a disappointment; just go to the Olive Garden... read more

Great food and great portions! We try to visit Whimsy as often as we can. One of our favorites in Tupelo.