Portland, ME trip suggestions

Neesy228

DIS Veteran
Joined
Apr 9, 2008
After much debate, my DH and I settled on a short trip to Portland, ME for our anniversary. We don't have many days (4), but we are hoping to see some sights, try some of their craft brews and explore their downtown.

We have never been there, so I was hoping to gather opinions on where to stay (prefer something that allows walking to shops/restaurants, or easy proximity to some of the breweries) and what to see/where to eat and what to skip.

Thanks for your help :)
 
I live close by, in Cape Elizabeth ME, I am not sure what your budget is but there is a ton to do in Portland and lots of hotel options. If you would like a nice dinner then check out Fore Street. It is great. There are tons of little shops and you can easily spend a morning just walking around. Try Gorgeous Gelato if you want a yummy sweet treat. They also have amazing espresso. You could take a day and go on a ride on the Casco Bay Ferry. Either a mail run, which will just ride around to the islands, or rent some bikes on Peaks and hang out for the day. (My parents live there, so if you want any info on Peaks Island, or any of the Casco bay Islands, just ask). If you want you can take a ride over the bridge to my hometown. We have the Portland Head light which has a nice little museum (for a small fee). It is also just nice to bring a picnic to and walk around. I am not sure when your trip is?

Other options that are fun is the Portland Art Museum, which is great. Maybe catch a Sea Dogs game, if you like baseball. It is a cheap and fun place to go. The Victoria Mansion is a cool place as well. You can hike to the top of the Portland Observatory and see the entire bay.

Portland is a great little city. I wish you the best trip and a ton of fun. Happy Anniversary!! And please, let me know if you have any questions about something around the area. I am more then happy to help.

ETA: Forgot to say, if you like sushi go to BenKay! It is my favorite sushi place. :)
 
We live right outside of Portland. As far as where to stay, there are tons of options in all price ranges. Lots of nice hotels right in downtown Portland. In fact 2 new hotels have just opened within the last few weeks.

I agree about Benkay - best sushi around. But I would personally skip Fore street - overpriced and loud. I know it has a good reputation but for the price there are so many better options in Portland. We love Street & Co. - great atmosphere and the best seafood ! We also love Salt Water Grill which is right over the bridge in South Portland. Sitting on their deck at night is just breathtaking. Right on Commercial Street in Portland is The Portland Lobster Company which is great for an informal night out. Good food and music. It is a real local hangout so is always packed but a lot of fun. I could go on and on - Portland is definitely a foodie paradise!

We have been to cities all over the US and Portland remains our favorite. Feel free to ask questions and have a wonderful time!
 
Depending on the time of year and whether you have a car, you can drive about 20 mins north and be in Freeport, home of the endless outlet. (There is also a vodka distillery just south of town that intrigues me!).

We like to go out to Portland Head Light and walk around; kind of a neat little park and an old fort-like area. I also am a fan of Duck Tours in any town, and Portland has one (although I haven't taken it).

There are many chain hotels in the downtown area, as well as out near the airport and mall- just depends on where you want to be and what you want to spend. Personally, I'd check out trip advisor and see what they recommend for both hotels and activities.
 
I don't know anything about Portland Maine, but there was recently an episode of Trip Flip that featured it. It looked like a cool place to hang out for a couple of days, maybe you can find it on Travel Channel's website?
 
I live in South Portland and I am just a few minutes away from the Old Port. That is such a fun place to walk around. I also second the suggestion of Ben Kay if you like Sushi. There are some nice museums around Free Street and tons of great restaurants.

Depending on what time of year you are coming, there are lots of free concerts happening this summer. There are also some towns that are offering free outside movies.

In South Portland, there is a great beach called Willard Beach. It is small but it never feels crowded. You could also travel South on Route 1 and hit up Old Orchard Beach.

Portland is far from Freeport if you are in the mood to go shopping. It also has the huge LL Bean store located there and you can visit the Big Hiking Boot.

That is what I can think off the top of my head.
 
I live close by, in Cape Elizabeth ME, I am not sure what your budget is but there is a ton to do in Portland and lots of hotel options. If you would like a nice dinner then check out Fore Street. It is great. There are tons of little shops and you can easily spend a morning just walking around. Try Gorgeous Gelato if you want a yummy sweet treat. They also have amazing espresso. You could take a day and go on a ride on the Casco Bay Ferry. Either a mail run, which will just ride around to the islands, or rent some bikes on Peaks and hang out for the day. (My parents live there, so if you want any info on Peaks Island, or any of the Casco bay Islands, just ask). If you want you can take a ride over the bridge to my hometown. We have the Portland Head light which has a nice little museum (for a small fee). It is also just nice to bring a picnic to and walk around. I am not sure when your trip is? Other options that are fun is the Portland Art Museum, which is great. Maybe catch a Sea Dogs game, if you like baseball. It is a cheap and fun place to go. The Victoria Mansion is a cool place as well. You can hike to the top of the Portland Observatory and see the entire bay. Portland is a great little city. I wish you the best trip and a ton of fun. Happy Anniversary!! And please, let me know if you have any questions about something around the area. I am more then happy to help. ETA: Forgot to say, if you like sushi go to BenKay! It is my favorite sushi place. :)

Awesome. Thank you so much!

Could you tell me a little bit more about the Casco Bay Islands? Does the ferry let you off at all of them or just certain one? How big are they? It sounds like a great way to spend an afternoon and I didn't even realize they existed!

Such great suggestions. :) I appreciate your help!
 
We live right outside of Portland. As far as where to stay, there are tons of options in all price ranges. Lots of nice hotels right in downtown Portland. In fact 2 new hotels have just opened within the last few weeks. I agree about Benkay - best sushi around. But I would personally skip Fore street - overpriced and loud. I know it has a good reputation but for the price there are so many better options in Portland. We love Street & Co. - great atmosphere and the best seafood ! We also love Salt Water Grill which is right over the bridge in South Portland. Sitting on their deck at night is just breathtaking. Right on Commercial Street in Portland is The Portland Lobster Company which is great for an informal night out. Good food and music. It is a real local hangout so is always packed but a lot of fun. I could go on and on - Portland is definitely a foodie paradise! We have been to cities all over the US and Portland remains our favorite. Feel free to ask questions and have a wonderful time!

Thank you for these suggestions. The Portland Lobster Co. looks like it would be great! If you think of any others, please let me know. :)
 
http://www.themainebrewbus.com/ I can't vouch for any of the hotels (as I've not stayed there or had friends stay there) but these are some of the downtown hotels (lots in town so you can walk around): https://www.google.com/maps/place/Portland+Harbor+Hotel/@43.6581606,-70.2478348,15z/data=!4m5!1m2!2m1!1shotels+downtown+portland+maine!3m1!1s0x4cb29c3f9305952f:0x5e76266d949a181d I love me some Flatbread Pizza--located right on the water http://www.flatbreadcompany.com/FlatbreadPortland2010.html

I've looked at the brew bus website. Have you done it before? It looks like. It could be fun or horrible depending on the group you're with.
 
I live in South Portland and I am just a few minutes away from the Old Port. That is such a fun place to walk around. I also second the suggestion of Ben Kay if you like Sushi. There are some nice museums around Free Street and tons of great restaurants. Depending on what time of year you are coming, there are lots of free concerts happening this summer. There are also some towns that are offering free outside movies. In South Portland, there is a great beach called Willard Beach. It is small but it never feels crowded. You could also travel South on Route 1 and hit up Old Orchard Beach. Portland is far from Freeport if you are in the mood to go shopping. It also has the huge LL Bean store located there and you can visit the Big Hiking Boot. That is what I can think off the top of my head.

We are coming next month. Thanks for the beach suggestions. I was wondering if there were any nearby. And I think we are going to have to try to sushi after all the recommendations!
 
I have a friend and her hubby who did the brew bus tour. They enjoyed it and even made a couple good friends. For perspective they are in their 40's and so was the other couple.
 
Awesome. Thank you so much!

Could you tell me a little bit more about the Casco Bay Islands? Does the ferry let you off at all of them or just certain one? How big are they? It sounds like a great way to spend an afternoon and I didn't even realize they existed!

Such great suggestions. :) I appreciate your help!

The ferry just lets you off at one. There are several to choose from. Peaks is the easiest as far as ferry schedule and times. It is about 5 miles around, so not very big and easy to bike on. You can rent bikes on the island from Brad's bikes, which is a 5 min walk from where the ferry lets you off. Or you can just walk to the back shore or various beaches and skip the bikes if you prefer. Not sure if you like kayaking but if you want something else to do for half a day you could try a kayak tour around the islands. Maine Kayak company is based off Peaks Island as well. Another company is Portland Paddle. I got my dad a GC for a sunset tour with them for his birthday and he really enjoyed them. We have been to all the Islands and they are all great. The others are a bit more quiet then Peaks and take a bit more time to get to, but if you look at them and decide you would rather try another, let me know and I can try to help give you some suggestions on those ones. Peaks does have a few places to eat and they do have a few little inns as well. Happy planning!!
 
There are so may great restaurants in Portland but I agree with Salt Water Grille in South Portland. The food is great and the view is amazing. If you go out to Peak's Island, The Peak's Island Inn has a nice restaurant. (One of the best Bloody Mary's I've ever had!). Head down to Pine Point Beach if you get a chance. It's probably one of the prettiest beaches around the area. There's also a couple of great seafood places around that area. Ken's is right on Pine Point Rd as is The Clambake (much bigger and I prefer Kens). There is also Baileys Lobster Pound which is excellent. Walking around the Old Port in Portland and going in and out of the shops is always a nice afternoon. Of course there is always Kennebunkport and Ogunquit if you're looking for quaint little shops. Portland has a lively nightlife as well. Not sure of your age but for us, when we head out for a night out we like to hit RiRa's on Commercial St. It's a hopping Irish pub and they usually have a live band on Friday and Saturday night. It tends to be an older crowd. There's a ton to do around here in the summer!!!!

Oh and if you get a chance, take a drive out to Cape Elizabeth. There's a few spots there that are beautiful! Portland Headlight of course, Two Lights State Park and also Kettle Cove. All gorgeous spots! Great photo ops!!
 
Take a harbor tour. We really enjoyed the boat ride and the tour guide was very informative.
 
Thanks to everyone for the great suggestions. :) we have lots to choose from and can't wait for the trip! Now I wish it was a little longer!
 
Here is another great option. There is a restaurant on Great Diamond Island called Diamond's Edge. We always go once or twice a summer. We actually went last night. We took the 5:45 ferry out to Diamond's Cove. (Make sure you take the Diamond Cove one not the Great Diamond one) Anyway, the trip out is beautiful. We had reservations for 7:00. The food and atmosphere are fabulous. Most years we can sit out on the lawn overlooking the water. The weather wasn't great last night so we sat inside but still had a great time. We finished just in time to catch the 9:15 ferry back to Portland.The trip back is just as nice with all the lights and views along the way. Check out the website for Diamond's Cove restaurant. It is a little pricy but well worth it. I also like that it is informal and you can dress pretty casual. If you decide to go just make sure you get reservations. Have a great time in Portland.
 
The Regency is a beautiful but pricey hotel - I've stayed there over a dozen times and have never had a bad stay. It's in the middle of all the great shops and restaurants.
 

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