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2 days in Portland, first time

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2 days in Portland, first time

Howdy - I'm coming up w/2 friends for a semi-spontaneous weekend in Portland. Have never been, pretty excited...mostly looking forward to the food, esp a lobster shack. Below is my tentative itinerary. Any thoughts, esp re: sailing? Are these rides scenic/worth it or not so much? Other thoughts welcome. (Live music suggestions? Best lobster shack? Bikram alternative?) For context, we are about 30 yrs, female, and more into outdoors than museums, restaurants than clubbing.

Also, we are planning on staying w/ a friend...but that may fall through. I may need to make a backup reservation somewhere. Any suggestions for cheap but good place to stay?

Oh, and for Saturday dinner...we are looking for a good restaurant to celebrate, but that is not too expensive and vegetarian friendly. Too much to ask for?



1) 9:30 am bikram yoga http://www.mainebikramyoga.com/ (First place I found on quick search. If you know of others, holler!)

2) Sightsee and lunch in Old Port (or lunch alone, skip to below for time on beach?)

3) Crescent Beach, Two Lights State Park and dinner at The Lobster Shack in Cape Elizabeth

4) Drinks and live music?


1) Run (#s 1 and 2 on trails.org) and bfast

2) Bike rental? Sightsee Old Port, Peaks Island, or elsewhere?

3) Lunch at Duckfat

4) Sail (http://www.portlandschooner.com/ or http://www.silverliningsailing.com/ or something else?)

5) Dinner (Fore St? Caciola? Bresca? What's the hidden gem that won't be as expensive?!?)


1) Brunch and hit the road.

Portland, Maine
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1. Re: 2 days in Portland, first time

Looks like you've got a great schedule planned. Please enjoy Portland, I just moved away from it and am missing it terribly!

If it's a nice day, I'd hit up Crescent Beach for sure. Two lights is a GORGEOUS little sea side walk on rocky shores. Go to the Lobster Shack-- very very good lobster roll, but be prepared to pay a bit. you're really paying for the view, you won't find another one like it.

Dinner-- all of those are great restaurants, but allow me to let you in on the best little italian restaurant in portland that is an AMAZING deal-- Ribollita. Delicious. Fresh. And TOTALLY affordable. I think for the money, it's way better than Fore Street. If you're from NYC, you probably won't be too floored by Fore Streets pricing, but if you're going to go higher end, I'd go 555 on Congress St. Better food.

Brunch at Local 188 is supposed to be amazing, although I've never had it. I love Bintliff's American Cafe for brunch. Google it!

Cheers and enjoy!

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2. Re: 2 days in Portland, first time

You've done your homework :-)

Looks like Sunday will be the better day to do the beach, so I'd suggest switching that with a ride to Peaks Island & bike rental on Saturday. When "doing" the Old Port Saturday, you'll find a multitude of restaurants, and they'll all have vegetarian items on menu. Check them out for dinner as you wander, and you'll also see offerings for evening. I really like RiRa's for Irish music; a real pub feel and very friendly. A couple that come to mind that cost a little less than those are Walter's and David's restaurants. I often see the Portland Schooner boats out and they come recommended. For a hoot, luckycatch.com will get you a harbor cruise and a sampling of what it's like to haul lobsters.

If you end up needing a place to stay, you'd be able to find something out by the mall/airport without a reservation (all the chains are there.) A quick drive to everywhere you're headed, and no chance of losing your deposit upon canceling!

Central Maine
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3. Re: 2 days in Portland, first time

I agree w/ Maine-ah's suggestion of Walter's as a good "second tier" dinner. Well-executed food w/relaxed but professional service at good price/value.


You have Caiola's on your Sat dinner list...consider them for brunch on Sunday.

Pick up a Portland Phoenix (free weekly) for music listings or try mainetoday.com

Portland, Maine
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4. Re: 2 days in Portland, first time

Your itinerary looks great, and I second the restaurant recommendations that have been shared. I totally agree with Maine-ah and HD, Walter's would be a great choice for dinner. The food is amazing, and the prices are reasonable.

If you go out for a sail, I'd recommend Portland Schooner Co. on Commercial St. I looked at the web site for the other sailing group that you mentioned (Silversailing), and they're located in Ogunquit which mean sitting in traffic and that would eat into your schedule.

Casco Bay Lines Ferry on Commercial St. also offers cruises on Casco Bay. There is a 3 hour mail boat run that takes you around the islands. They also have a 2 hour sunset cruise.


Portland, Maine
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5. Re: 2 days in Portland, first time

I noticed that you're planning to catch some live music while you're in town. I'm not sure what kind of music you enjoy, but Chronic Funk is playing at Bull Feeney's on Fore St. on Friday night.

Southern Maine
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6. Re: 2 days in Portland, first time

This is such a great plan, I may join you! Have fun!

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7. Re: 2 days in Portland, first time

Thanks for all the replies! I forgot to mention...this is not for the upcoming weekend, but next weekend Aug 1. Nevertheless, thanks for reminding me to keep an eye on the weather and be flexible, Maine-ah. (Also, I love the luckycatch tip! Maybe we'll do that instead of sailing!)

MaineGirlAtHaert - Thanks for the color on Crescent Beach and Two Lights. I wasn't confident it'd be great, but now I'm looking forward to it and want to allot it sufficient time. Any suggestions for a better lobster shack? (Maybe we'll do a comparison!) Just peeked on the expansive menu for Bintliff's. That may be the place to go!

To everyone else, thanks a mil. Going to investigate Walter's, Casco Bay Lines, and get a free weekly! Yay!

8. Re: 2 days in Portland, first time

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