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Boston to portland in October

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Clarksville...
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Boston to portland in October

My husband and I are flying into Boston on a Wednesday and plan on driving up the coast of Maine for a few days. I am tentatively planning on flying out of Portland on Sunday so we can squeeze in more sights without back tracking back down to Boston.

As of now, I am planning one night in Portsmouth, one or two nights in Kennebunkport and a night in Portland. I am torn on whether it is a good idea to stay the night in portsmouth or should we see the sights and move along. I also need help determining how long to stay in Kennebunkport. Is one day enough? What are must see stops and sights along the way? We want it to be a some what restful trip but want to see the sights!!

Any advice that will help me make these hard decisions would be greatly appreciated!!!

Maine
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1. Re: Boston to portland in October

I can't advise on Portsmouth, as when we go it is usually just to take the kids to Strawberry Banke, I don't know if it's worth an overnight or not.

As for 2 nights in Kennebunkport vs. 2 nights in Portland, it probably won't make a huge difference. They are within 30 minutes of each other so if you do 2 nights in Kbunkport and run out of things to do, then you are within easy driving distance of other southern Maine places.

Alternately if you only do 1 night and wish you had more time, it's an easy drive from Portland to finish your sightseeing.

One thing to consider is when in October you are going. After Columbus Day many of the seasonal places start closing up, which will have more of an impact on Kennebunkport than either Portland or Portsmouth.

For Portland area things to do/see......go to Portland Head Light and Two Lights in Cape Elizabeth. Wander around the Old Port section of Portland (an area of rehabbed old buildings/warehouses packed with shops and restaurants, cobblestone streets, right along the waterfront), take a ride out to the islands on the Casco Bay Ferry, you can get off and explore the islands or just remain on for a cruise of the bay. Go to the Porltand Observatory for great views of the city and the bay, extra bonus if there is foliage.

Edited: 1:39 pm, July 12, 2011
Clarksville...
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2. Re: Boston to portland in October

Thank you so much for your reply. We will be going after Columbus Day. Thank you for pointing that out!

Clarksville...
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3. Re: Boston to portland in October

Also, after comparing the costs, it looks like we will be flying into and out of Boston.

Manhattan Beach...
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4. Re: Boston to portland in October

We spend two nights in Kennebunkport when visiting each Oct., flying from LAX to Boston. There are so many restaurants around Dock Square, places to visit, and we like one full day in between the 2 nights. It's usually our first or last night, flying in or out of Boston.

There is the Seashore Trolley Museum, Kylie's Chance, to go on a lobster cruise, the Bush Compound, walks on the beach, etc.

They hold a Gathering of the Scarecrows, that weekend ending on the grounds of the Nonantum Resort.

For a real splurge, dining at the 5* White Barn Inn is something you'll never forget. It's two 1800's barns put together, for a rustic feel, with farm equipment used for decoration, but you will dine with white tablecloths and by candlelight.

whitebarninn.com/kennebunkport-maine-restaur…

Clarksville...
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5. Re: Boston to portland in October

Thank you so much for your reply. I have made dinner reservations at the White Barn Inn. I am looking at booking 2 nights at the Captain Lord Mansion in Kennebunkport but I had better do it soon before there is no availability. Out of curiosity, where have you stayed?

As of now, I think I have decided to fly into Boston, spend the first night in Portsmouth, the next 2 nights in Kennebunkport and the final night in Portland. I decided to spend the extra money and fly out of Portland. We may never be back to this part of Maine again. So, I didn't want to do any back tracking. We do, however, hope to go back sometime for Lobsterfest in Rockland and during the same trip do Bar Harbor and Acadia.

I wish I was not a perfectionist. It really makes planning a trip to a new location more tedious than it should be! I bet I have gone back and forth on whether to stop in Portsmouth for a night as opposed to heading straight to Kennebunkport a million times. Thanks again for your input.

Manhattan Beach...
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6. Re: Boston to portland in October

We've stayed at the WBI about a dozen times, but wanted to try something new after a while and sleeping in different rooms or suites, so stayed at their sister Beach House Inn, across from the beach, and really enjoyed that about 6 times. Also have stayed at their sister Breakwater Inn and Yachtsman Lodge on Ocean Ave. as we like walking to Dock Square. A few other places over the years too.

If we stay in K our first night, we like the casual Alisson's for dinner. Might have the Lobster dinner where they tie a bib around your neck, and their lobster roll is pretty good, too. At lunch we always have a lobster roll at Mable's. It's where Bush likes to go they say.

http://www.alissons.com/

Newburyport...
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7. Re: Boston to portland in October

Just FYI - the season in Kennebunkport extends later than Columbus Day -- foliage season keeps things busy through the third week of October so everything is basically open until November 1. Captain Lord is an excellent choice for a very opulent traditional inn...excellent service and luxury. Next door there are two other fantastic inns, Captain Jefferds Inn and Captain Fairfield Inn. They both offer beautiful rooms and exceptional hospitality. At CLM and CJI, you are offered breakfast at a common gathering table and at Captain Fairfield you can enjoy your breakfast at your own table. While CJI and CLM are more traditional in regards to design, Captain Fairfield is more of a boutique Inn -- the property was just re-designed by a noted Boston interior designer. Bottom line is that you will be happy at any of these great Inns who are known for their outstanding hospitality. Enjoy!

8. Re: Boston to portland in October

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