Samantha's South Portland/Portland Proper Guidebook

Samantha
Samantha's South Portland/Portland Proper Guidebook

Sightseeing

Dog friendly all day during the fall and winter months, easygoing folks, beautiful views of surrounding islands like Peak’s Island.
135 locals recommend
Willard Beach
135 locals recommend
Dog friendly all day during the fall and winter months, easygoing folks, beautiful views of surrounding islands like Peak’s Island.
Walking distance and the history behind it is interesting!
105 locals recommend
Bug Light Park
105 locals recommend
Walking distance and the history behind it is interesting!
Beautiful! There’s usually a lobster roll truck there, provided the weather is good. Parking can be slightly challenging on really nice weekends. You can also do a nice long there-and-back 5 mile walk and pick up Scratch on the way!
346 locals recommend
Portland Harbor Museum
12 Captain Strout Circle
346 locals recommend
Beautiful! There’s usually a lobster roll truck there, provided the weather is good. Parking can be slightly challenging on really nice weekends. You can also do a nice long there-and-back 5 mile walk and pick up Scratch on the way!
Gorgeous views and a nice walk. There are coal BBQ grills nestled into the hills if you want to grill and take in the views.
144 locals recommend
Two Lights State Park
7 Tower Dr
144 locals recommend
Gorgeous views and a nice walk. There are coal BBQ grills nestled into the hills if you want to grill and take in the views.
Walking distance and awesome!
45 locals recommend
Spring Point Ledge Lighthouse
2 Fort Rd
45 locals recommend
Walking distance and awesome!
Magical!! It's pretty busy on weekends, so try and get there early to get a parking space.
130 locals recommend
Mackworth Island State Park
U.S. 1
130 locals recommend
Magical!! It's pretty busy on weekends, so try and get there early to get a parking space.
Use this to walk to Bug Light and places like Foulmouthed Brewing!
Greenbelt Walkway
Greenbelt Walkway
Use this to walk to Bug Light and places like Foulmouthed Brewing!
124 locals recommend
Crescent Beach State Park
109 Bowery Beach Rd
124 locals recommend
Reminds me of Coney Island, if you're into that.
185 locals recommend
Old Orchard Beach
185 locals recommend
Reminds me of Coney Island, if you're into that.
Get there early to rent a bike or a golf cart to cruise around the island! We strongly encourage to not only book your bike/golf cart reservations in advance and also purchase your ferry ticket as early as possible.
176 locals recommend
Peaks Island
176 locals recommend
Get there early to rent a bike or a golf cart to cruise around the island! We strongly encourage to not only book your bike/golf cart reservations in advance and also purchase your ferry ticket as early as possible.
Just a beautiful place - dog friendly and sometimes the tide goes out so far that you can walk on the sand bar!
208 locals recommend
Popham Beach State Park
711 Popham Rd
208 locals recommend
Just a beautiful place - dog friendly and sometimes the tide goes out so far that you can walk on the sand bar!
We've done this twice! We learned SO much about the fascinating lobstering industry here in New England. We also got the chance to catch our own lobsters and bring them straight over to Portland Lobster Company to eat! You can bring adult beverages onto the boat as well ;)
40 locals recommend
Lucky Catch Cruises
170 Commercial St
40 locals recommend
We've done this twice! We learned SO much about the fascinating lobstering industry here in New England. We also got the chance to catch our own lobsters and bring them straight over to Portland Lobster Company to eat! You can bring adult beverages onto the boat as well ;)
YOU GET TO HIKE WITH GOATS! The hosts are super nice and it's such a fun experience.
Ten Apple Farm
241 Yarmouth Rd
YOU GET TO HIKE WITH GOATS! The hosts are super nice and it's such a fun experience.
Beautiful town about an hour north of here!
184 locals recommend
Camden
184 locals recommend
Beautiful town about an hour north of here!
About an hour north from here. It’s almost ONE MILE of breakwater which is mind blowing. It’s like you’re walking I in the middle of the ocean. Be prepared to get splashed! Wear sturdy shoes.
99 locals recommend
Rockland Breakwater Light
99 locals recommend
About an hour north from here. It’s almost ONE MILE of breakwater which is mind blowing. It’s like you’re walking I in the middle of the ocean. Be prepared to get splashed! Wear sturdy shoes.
Really easy walking and a fun place to camp !
123 locals recommend
Wolfe's Neck Woods State Park
426 Wolfe's Neck Rd
123 locals recommend
Really easy walking and a fun place to camp !
93 locals recommend
East End Beach
Eastern Promenade Trail
93 locals recommend
They have live events here and it's a fun place to catch a concert - near Bissell Brewing!
28 locals recommend
Thompson Point
Thompsons Point
28 locals recommend
They have live events here and it's a fun place to catch a concert - near Bissell Brewing!
39 locals recommend
Scarborough Marsh Audubon Center
92 Pine Point Rd
39 locals recommend
About an hour and a half drive, but so worth it in the Spring and Summer.
163 locals recommend
Coastal Maine Botanical Gardens
105 Botanical Gardens Dr
163 locals recommend
About an hour and a half drive, but so worth it in the Spring and Summer.

Food scene

The sea salt bagels are amazing and they have rotating savory and sweet pastries. As of April 2022, this location is still under construction, but they have another location nearby called Toast Bar.
164 locals recommend
Scratch Baking Co
416 Preble St
164 locals recommend
The sea salt bagels are amazing and they have rotating savory and sweet pastries. As of April 2022, this location is still under construction, but they have another location nearby called Toast Bar.
Walking distance!
52 locals recommend
Willard Scoops
429 Preble St
52 locals recommend
Walking distance!
The peanut butter sundae is *chef's kiss.* Parking can be really difficult so be prepared - it's popular!
36 locals recommend
Red's Dairy Freeze
167 Cottage Rd
36 locals recommend
The peanut butter sundae is *chef's kiss.* Parking can be really difficult so be prepared - it's popular!
Gets REALLY busy in the summer and parking is tough to find. But if you're patient and wait it out for a spot, it's definitely work the visit. Amazing food and views.
136 locals recommend
The Lobster Shack at Two Lights
225 Two Lights Rd
136 locals recommend
Gets REALLY busy in the summer and parking is tough to find. But if you're patient and wait it out for a spot, it's definitely work the visit. Amazing food and views.
Get the lobster rolls! Oysters are also amazing.
272 locals recommend
Eventide Oyster Co.
86 Middle St
272 locals recommend
Get the lobster rolls! Oysters are also amazing.
You can't go wrong here. Everything is good. I recommend splitting a sandwich if you're not starving - they're more filling than you'd expect!
173 locals recommend
Duckfat
43 Middle St
173 locals recommend
You can't go wrong here. Everything is good. I recommend splitting a sandwich if you're not starving - they're more filling than you'd expect!
Connected to oxbow!
17 locals recommend
Duckfat Friteshack
43 Washington Ave
17 locals recommend
Connected to oxbow!
This is such a fun place just to hang out and listen to great live music on the water and have a couple of drinks on the water. If you book a Lucky Catch Cruise to catch your own lobsters, this is where you'll bring them. They cook them however you'd like!
131 locals recommend
Portland Lobster Co
180 Commercial St
131 locals recommend
This is such a fun place just to hang out and listen to great live music on the water and have a couple of drinks on the water. If you book a Lucky Catch Cruise to catch your own lobsters, this is where you'll bring them. They cook them however you'd like!
Get the soup dumplings! Everything else is also equally amazing. on weekends, be prepared to place your order for pickup 2 hours earlier than you'd like to eat. This place is popular!
102 locals recommend
Empire
575 Congress St
102 locals recommend
Get the soup dumplings! Everything else is also equally amazing. on weekends, be prepared to place your order for pickup 2 hours earlier than you'd like to eat. This place is popular!
Get the burritos! The tacos are just OK. If you're craving good Mexican, the burritos will definitely hit the spot. We prefer El Corazon/Casita :)
62 locals recommend
Taco Trio
60 Ocean St
62 locals recommend
Get the burritos! The tacos are just OK. If you're craving good Mexican, the burritos will definitely hit the spot. We prefer El Corazon/Casita :)
Super popular!
145 locals recommend
Central Provisions
414 Fore St
145 locals recommend
Super popular!
Very close to the Airbnb with nice views of the marina. Food is pricey and just okay in our opinion, but it does the trick.
13 locals recommend
North 43 Bistro
1 Spring Point Dr
13 locals recommend
Very close to the Airbnb with nice views of the marina. Food is pricey and just okay in our opinion, but it does the trick.
Great grocery to find fresh local goods.
223 locals recommend
Rosemont Market & Bakery
40 Pine St
223 locals recommend
Great grocery to find fresh local goods.
Yum!! Fair priced oysters and you can even take some home - they sell gloves and knives and will show you how to shuck them yourself if you decide to go this route.
42 locals recommend
The Shop by Island Creek Oysters
123 Washington Ave
42 locals recommend
Yum!! Fair priced oysters and you can even take some home - they sell gloves and knives and will show you how to shuck them yourself if you decide to go this route.
Omg - SO good, you won't regret the chocolate sea salt donut. They also sell these at Hannafords!
220 locals recommend
The Holy Donut
194 Park Ave
220 locals recommend
Omg - SO good, you won't regret the chocolate sea salt donut. They also sell these at Hannafords!
YUM! Pricey but easily the best sushi you'll find in Portland.
8 locals recommend
Mr. Tuna
28 Monument Sq
8 locals recommend
YUM! Pricey but easily the best sushi you'll find in Portland.
There is a location in South Portland and one in Old Port! Very good pizza and they also deliver!
192 locals recommend
OTTO
576 Congress St
192 locals recommend
There is a location in South Portland and one in Old Port! Very good pizza and they also deliver!
You can walk here (0.7 miles away) and they have outdoor seating. You can bring your pup!
80 locals recommend
Elsmere BBQ and Wood Grill
448 Cottage Rd
80 locals recommend
You can walk here (0.7 miles away) and they have outdoor seating. You can bring your pup!
67 locals recommend
The Honey Paw
78 Middle St
67 locals recommend
The closest thing to an “authentic” California burrito that we’ve found on the East Coast. Their taquitos are amazing, chips and salsa are super fresh. This is a weekend staple for us for sure! They also opened up Casita which is super close and walking distance :)
10 locals recommend
Restaurante El Corazon
190 State St
10 locals recommend
The closest thing to an “authentic” California burrito that we’ve found on the East Coast. Their taquitos are amazing, chips and salsa are super fresh. This is a weekend staple for us for sure! They also opened up Casita which is super close and walking distance :)
Outdoor seating and they take over the phone reservations. Pricey but nice to treat yourself!
48 locals recommend
Saltwater Grille
231 Front St
48 locals recommend
Outdoor seating and they take over the phone reservations. Pricey but nice to treat yourself!
Amazing brisket tacos and margs! Outdoor seating and they take online reservations!
77 locals recommend
Terlingua
40 Washington Ave
77 locals recommend
Amazing brisket tacos and margs! Outdoor seating and they take online reservations!
We haven't had the food here yet but the patio is nice and the cocktails are decent!
19 locals recommend
The Thirsty Pig
37 Exchange St
19 locals recommend
We haven't had the food here yet but the patio is nice and the cocktails are decent!
Excellent sandwiches
8 locals recommend
Ramona's
98 Washington Ave
8 locals recommend
Excellent sandwiches
Fun, big bar with great bar food.
76 locals recommend
The Great Lost Bear
540 Forest Ave
76 locals recommend
Fun, big bar with great bar food.
I believe they take reservations via the Resy app!
51 locals recommend
Woodford Food & Beverage
660 Forest Ave
51 locals recommend
I believe they take reservations via the Resy app!
REALLY popular especially on weekends. Just a good 'ole diner in Old Port.
88 locals recommend
Joe's Boathouse Catering
88 locals recommend
REALLY popular especially on weekends. Just a good 'ole diner in Old Port.
Very close to the house and super good!
6 locals recommend
Cafe Louis
173 Ocean Street
6 locals recommend
Very close to the house and super good!
AMAZING pasta!
14 locals recommend
Leeward
85 Free St
14 locals recommend
AMAZING pasta!
Really good fancy grilled cheese!
Cheese Louise Portland
363 Fore Street
Really good fancy grilled cheese!
We like to order this via the DoorDash app when we’re feeling lazy. Really really good!
6 locals recommend
Kuno
166 Cumberland Avenue
6 locals recommend
We like to order this via the DoorDash app when we’re feeling lazy. Really really good!
Super yum, small plates, a little pricey, but worth it and it’s on Washington ave, which has a lot of good food and drink spots!
41 locals recommend
Cong Tu Bot
57 Washington Ave
41 locals recommend
Super yum, small plates, a little pricey, but worth it and it’s on Washington ave, which has a lot of good food and drink spots!
Literally the best pizza I think we’ve had in Maine. Reminds of of a classic NYC pie.
Pizza Joint
239 Ocean St
Literally the best pizza I think we’ve had in Maine. Reminds of of a classic NYC pie.
A ~5 minute walk from the Airbnb. Awesome Mexican food.
El Corazón Casita
A ~5 minute walk from the Airbnb. Awesome Mexican food.
SoPo Seafood
Cafe Louis
27 locals recommend
Cia Cafe
72 Ocean St
27 locals recommend
13 locals recommend
Verbena Eat Right Now
103 Ocean St
13 locals recommend
Crispy Gai
Really good smash burgers on Sunday nights. Their apps and cocktails are amazing.
Wayside Tavern
Really good smash burgers on Sunday nights. Their apps and cocktails are amazing.

Breweries/Bars

Outdoor seating during the warmer months, their food is also great and you can get it delivered. It’s a quick bike ride away on the Greenbelt. Also dog friendly if you sit outdoors!
47 locals recommend
Foulmouthed Brewing
15 Ocean St
47 locals recommend
Outdoor seating during the warmer months, their food is also great and you can get it delivered. It’s a quick bike ride away on the Greenbelt. Also dog friendly if you sit outdoors!
Easily the best beer you'll have. Pickup only during COVID - follow their instagram to see their latest releases.
102 locals recommend
Bissell Brothers
38 Resurgam Pl
102 locals recommend
Easily the best beer you'll have. Pickup only during COVID - follow their instagram to see their latest releases.
If you're a fan of farmhouse ales.
106 locals recommend
Oxbow Blending & Bottling
49 Washington Ave
106 locals recommend
If you're a fan of farmhouse ales.
In our opinion a little overhyped, but it's a staple with decent food!
138 locals recommend
Rising Tide Brewing Company
103 Fox St
138 locals recommend
In our opinion a little overhyped, but it's a staple with decent food!
Outdoor seating for COVID - super friendly staff and superb beers. Dog friendly! One of our favorites.
49 locals recommend
Bunker Brewing Company
17 Westfield St
49 locals recommend
Outdoor seating for COVID - super friendly staff and superb beers. Dog friendly! One of our favorites.
Try and get a seat outside so you can be on the water!
34 locals recommend
Liquid Riot Bottling Company
250 Commercial St
34 locals recommend
Try and get a seat outside so you can be on the water!
Good brews, nice people. Outdoor seating but in the colder months it's a little tough to bear — there are outdoor heaters but it can get pretty windy. It’s next to rising tide
70 locals recommend
Austin Street Brewery
115 Fox St
70 locals recommend
Good brews, nice people. Outdoor seating but in the colder months it's a little tough to bear — there are outdoor heaters but it can get pretty windy. It’s next to rising tide
Must go! It's SO beautiful inside and very spacious so you can feel safe inside during COVID. They also have heated outdoor seating and I believe you can reserve tables for larger parties. They also have a contactless pickup system if you just want to swing by and pick up beers. Their pizzas are also pretty good!
86 locals recommend
Maine Beer Company
525 US-1
86 locals recommend
Must go! It's SO beautiful inside and very spacious so you can feel safe inside during COVID. They also have heated outdoor seating and I believe you can reserve tables for larger parties. They also have a contactless pickup system if you just want to swing by and pick up beers. Their pizzas are also pretty good!
37 locals recommend
Goodfire Brewing Co.
219 Anderson St
37 locals recommend
11 locals recommend
Batson River Brewing & Distilling - Portland
82 Hanover Street
11 locals recommend
Amazing beer selection and some good eats in the heart of Old Port.
85 locals recommend
Novare Res Bier Cafe
4 Canal Plaza
85 locals recommend
Amazing beer selection and some good eats in the heart of Old Port.
Really good!
10 locals recommend
Belleflower Brewing Company
66 Cove Street
10 locals recommend
Really good!
Super cool ambiance with an indoor fireplace in the colder months.
11 locals recommend
Batson River Brewing & Distilling - Portland
82 Hanover Street
11 locals recommend
Super cool ambiance with an indoor fireplace in the colder months.
Fun bar with great music.
21 locals recommend
Maps
64A Market St
21 locals recommend
Fun bar with great music.
Exactly a 1 mile walk from the Airbnb - great beers and atmosphere.
Mast Landing Brewing Company - South Portland Taproom
Exactly a 1 mile walk from the Airbnb - great beers and atmosphere.
A really sweet crafty spot that does occasional craft tutorials and has Prosecco on tap. The owner, Lisa, is lovely.
Knitting Nook
124 Sawyer St
A really sweet crafty spot that does occasional craft tutorials and has Prosecco on tap. The owner, Lisa, is lovely.
Amazing food and drinks
12 locals recommend
The King's Head
254 Commercial St
12 locals recommend
Amazing food and drinks
Wayside Tavern
Super fun hard seltzer spot
Après
Super fun hard seltzer spot
68 locals recommend
Lone Pine Brewing Company
219 Anderson St
68 locals recommend
16 locals recommend
The Portland Zoo
41 Fox St
16 locals recommend

Groceries

280 locals recommend
Hannaford Supermarket
295 Forest Ave
280 locals recommend
223 locals recommend
Rosemont Market & Bakery
40 Pine St
223 locals recommend
29 locals recommend
CVS
51 Market St
29 locals recommend

City/town information

Original LLBean flagship store is here and lots of outlet shopping.
202 locals recommend
Freeport
202 locals recommend
Original LLBean flagship store is here and lots of outlet shopping.

Hiking within 1 hour of Portland

124 locals recommend
Bradbury Mountain State Park
528 Hallowell Rd
124 locals recommend
37 locals recommend
Pleasant Mountain Summit
37 locals recommend
22 locals recommend
Douglas Mountain
22 locals recommend
16 locals recommend
Rattlesnake Mountain
16 locals recommend
109 locals recommend
Mount Agamenticus
109 locals recommend

Traveler advice

Getting around

Download the “passport” app to pay for meters in old port.

The existing meters no longer take coins or card - it’s all done via the passport app.
Getting around

Download local food delivery apps

2Dinein, carhop, Uber eats, DoorDash!
Getting around

Uber and Lyft can take a while!

Ubers and Lyfts run here, but you may want to request one ~15 minutes before you want to leave. They can take a while!