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Best Restaurants for People Watching in South Portland

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6 restaurants available nearby

How are Featured results ranked

A photo of Old Port Sea Grill restaurant
1. Old Port Sea Grill
new
4.6
Exceptional(579)
$$$$
• Seafood • Portland
Booked 22 times today
The Old Port Sea Grill, located in the heart of the Old Port, serves fresh seafood prepared simply so that you can taste the flavor and quality of the product. We offer a selection of Maine oysters on the half shell, steamed Maine lobster - lazy style...we do the work for you, clam chowder and one of the best lobster rolls in Portland. Take in the city streets from our picture windows while relaxing with friends, entertaining business associates or watching our flat screen TVs. We have sixty four seats in our dining room and over fifty in our bar and lounge area. Our bar and lounge is open for walk-ins all day long. We always feature local micro brews on tap and have a specialty cocktail menu that changes seasonally. Be sure to check out our 500 gallon aquarium.
A photo of The Garden Cafe, at The Portland Regency Hotel & Spa restaurant
2. The Garden Cafe, at The Portland Regency Hotel & Spa
4.4
Awesome(11)
$$$$
• American • Portland
Booked 2 times today
The Garden Café, at the Portland Regency Hotel and Spa - In the warmer months (and weather permitting), we invite you to dine al fresco across the street from the hotel at our enchanting Garden Café. Open for lunch, dinner, cocktails, or dessert, the café is framed by flowers, trees, and gentle ocean breezes; it’s a fabulous destination for catching up with friends or colleagues over delicious fare. During inclement weather we will serve inside at the Armory Lounge.
A photo of The Burleigh restaurant
3. The Burleigh
4.7
Exceptional(921)
$$$$
• American • Kennebunkport
Booked 4 times today
Experience culinary excellence at The Burleigh, a delightful tavern-style restaurant located at the Kennebunkport Inn, named in honor of its original owner. Revel in the inviting ambiance, featuring warm red walls and polished wood that create a cozy dining atmosphere. Treat your taste buds to a diverse menu that includes locally sourced seafood, hearty burgers, and innovative cocktails. Enjoy elevated pub fare with delicious gluten-free and vegan options expertly prepared by Chef John Shaw. For an unforgettable dining experience in the heart of Kennebunkport, visit The Burleigh.Discover The Burleigh Botanical Bar: Step into The Burleigh Botanical Bar and immerse yourself in a whimsical oasis adorned with organic florals, herbs, and candlelit charm. Relish herbaceous spring cocktails and delightful bites in this enchanting botanical haven, open until September 1st. Open Wednesday-Sunday 4-8 PM. OpenTable Reservations are for the dining room only.
A photo of C2-Congress Squared Restaurant restaurant
4. C2-Congress Squared Restaurant
new
3.9
Excellent(161)
$$$$
• Contemporary American • Portland
Congress Squared Restaurant's cuisine is Contemporary American with an emphasis on New England ingredients and local favorites. The menu features New England sourced seafood. The bar is stocked with Maine Beers and Maine Spirits. The intimate dining room seats 70 guests and the bar accommodates an additional 20. Congress Squared welcomes walk-in guests nightly in the dining room and the bar. Best Happy Hour in Town! Seven days a week 4-6pm Happy Hour! The restaurant is on the street level of The Westin Portland Harborview Hotel.
A photo of Napoletana Pizzeria and Bar restaurant
5. Napoletana Pizzeria and Bar
4.3
Awesome(125)
$$$$
• Italian • Portsmouth
Booked 9 times today
Right in the heart of Market Square, featuring Neapolitan style pizza, artisan Italian dishes and craft cocktails, our dining room and bar provide the setting for a unique and memorable experience
A photo of Two-Fifty Market restaurant
6. Two-Fifty Market
3.8
Excellent(168)
$$$$
• American • Portsmouth
Booked 1 time today
Two-Fifty Market is a one of a kind dining experience located in the Sheraton Portsmouth Harborside Hotel inspired by local ingredients and the culinary expertise of our professional team. Two-Fifty Market provides our guests with an authentic Portsmouth dining experience in the heart of the city.Our food is made with local ingredients, and our restaurant has really transformed into a place where families, businesses associates, and friends can gather and enjoy the experience. The menu offerings include Award Winning Clam Chowder, shareable delights, locally inspired entrees and other seasonally inspired dishes.

See what locals rave about

From verified diners like you
From verified diners like you
  • Dennis
    New Hampshire •4 reviews
    5.0
    Dined 4 days ago
    Very friendly and hospitable staff, ample and excellent food at a fair price.
    More info
    Old Port Sea Grill$$$$• Seafood• Portland
    •
    4.6
  • Jean
    5 reviews
    5.0
    Dined on 24 May 2026
    We had such a wonder dinner the day before we came back tonight to try different options. Shoutout to Kayla for her knowledge on their local beer options. My husband was very happy with her recommendations. Food was wonderful and Damian was able to make our dessert request happen. Please give their blueberry compote a try. It is so good. Don’t miss your chance to dine here. Highly recommend.
    More info
    The Burleigh$$$$• American• Kennebunkport
    •
    4.7
  • Deborah
    Greater Boston •2 reviews
    5.0
    Dined on 16 May 2026
    Wonderful graduation lunch for 8! Excellent and attentive server, delicious pizza and salads, outstanding drinks!!! Highly recommend
    More info
    Napoletana Pizzeria and Bar$$$$• Italian• Portsmouth
    •
    4.3
  • Dan
    Maine •1 review
    5.0
    Dined on 28 Aug 2025
    We were there at the Regency for a 2 day conference and this was very convenient for us with a short lunch break. The food came fast and was very good. It was a beautiful day and very pleasant. The noise level was what I expected for a summer day in the Old Port with the background music blocking most noise.
    More info
    The Garden Cafe, at The Portland Regency Hotel & Spa$$$$• American• Portland
    •
    4.4
  • CarolR
    Greater Boston •2 reviews
    5.0
    Dined on 25 Nov 2021
    Came for your Thanksgiving meal. It was delicious! Great selection of food on your menu. Will definitely be back.
    More info
    C2-Congress Squared Restaurant$$$$• Contemporary American• Portland
    •
    3.9

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