Retire Us to East Coastal, Island-Feeling Town
November 8, 2016 3:06 PM   Subscribe

Spouse is almost 62, I'm almost 55, and we want to retire to some town on the east coast of the U.S. that feels islandy, has a great community feel, and has great options for walking/hiking/biking.

We live in a wonderful spot now, in NH, in a home walkable to library, grocery, local college, stores, coffee shops, etc. We have lots of trails here to walk. We have lots of great friends. Lakes abound. We love our house (modern, big) and yard (3/4 acre, permacultured).

However, there are two things our current town does not have that are very important to me: the ocean, and public transportation. It may eventually get the latter, and climate change being what it is, perhaps the former but not likely in our lifetimes.

Given these hopes and goals, what town from Maine to northern Florida would you tell us to retire, and why?:


1. Island feel (subjective -- you know it when you feel it ... doesn't necessarily mean an island or peninsula per se)
2. Close to a beach on the ocean (walkable, bikeable)
3. Within walking or biking distance to a rail trail, trail system, and/or ocean walks. I like to walk/hike/snowshoe every day. I would learn to love biking if the rail trail were great.
4. Mainly a year-round place, not seasonal
5. Walkable or bikeable (within a couple miles, along sidewalks or trails) to some amenities (library, grocery, other stores, restaurants, college) Would be great if there is actually a defined town center, not mall sprawl.
6. Within striking distance (2 hours) of good medical care and hospitals
7. Cost of 2BR, 2BA home with garage and workshop space with 1/4 acres or more land (so not a condo), under $350K, preferably under $250K

1. Good health insurance options for pre-retirees (not on Medicare yet)
2. Good tax situation for retirees (getting income from dividends etc)
3. Local public transportation system and regional transportation system.
4. Also near fresh water (ponds, lakes, streams, brooks)
5. Within an hour of great public gardens
6. Liberal politically
7. Nearish (by bus or train) to a good big city (Boston, NYC, Savannah)
8. Near an Amtrak stop
9. No traffic lights in town and/or generally light traffic (like we have where we live now).

Here are the places in the running now (you'll notice some don't follow all the rules):
Boothbay, ME, Pine Point in Scarborough ME, Ogunquit ME, Cape Cod (Harwich and Brewster in particular), somewhere between Wilmington and Rehoboth DE, Jekyll Island GA, Fernandina Beach FL.

We're not sure how we feel about climate, whether we want 4 seasons (which we're used to) or mostly warmer temps.

I have Googled, Coastal Living'd, and City-Data'd this to death in the last three years. Help me, please. Thanks.
posted by mmw to Grab Bag (7 answers total) 9 users marked this as a favorite
Pine Point doesn't meet all of your criteria, but what about South Portland, Maine? South Portland is right on the ocean and beautiful, I hope to move there one day.
1. Yes, you know you are near the ocean. It smells like the ocean and there is fishing paraphernalia everywhere.
2. Willard beach is right in south portland, plus its a skip to pine point or higgins beach in scarborough.
3. The greenbelt goes right through south portland and there are trails everywhere.
4. South portland yes, pine point definitely not.
5. South Portland is walkable to a grocery store and tons of shops.
6. Maine med is right over the bridge in portland.
7. Doable under $350K, possibly even under $250K.

The cons are it's not super liberal but neither is Maine in general (says this vermonter). Traffic can be bad - especially in the summer and especially near pine point. Public transportation is as good as it gets in non-boston new england, which is not great.

It really seems like you'd like south portland!
posted by pintapicasso at 4:37 PM on November 8, 2016 [2 favorites]

If you are feeling more ambitious there is also peaks island, or long island, which are connected to portland via ferry at regular intervals. Cons - It's connected via ferry to portland which makes everything a bigger hassle. It can be quite isolating in the winter (says my husband who grew up there). Pros- it's gorgeous, affordable and a literal island.
posted by pintapicasso at 4:40 PM on November 8, 2016 [1 favorite]

Providence has a nice waterfront and access to state parks and the beach. I am not familiar with NH, but Providence has a classic New England vibe and does have a downtown center, though you would most likely need a car to live there. It's certainly very liberal and has an assortment of restaurants, stores, and a number of colleges/universities (URI, Johnson and Wales, Brown, RISD, etc). There is adequate healthcare in Providence. It is 3 hours from NYC (maybe a little less by Amtrak), 40 minutes to Boston on the commuter rail. I believe that the real estate in the area is within your budget as well. The main drawback might be the weather, though spring and fall are beautiful. My other gripe with Providence is that the airport is very small and it's generally more practical to fly out of Boston.
posted by gemutlichkeit at 5:00 PM on November 8, 2016

Chincoteague, VA, meets most of your crucial criteria; fewer of the desirable ones.
posted by missrachael at 5:37 PM on November 8, 2016

Check out Lewes, DE and those other points in southern Delaware you've been Googling. I am particlar to Broadkill Beach but it's probably a bit to seasonal and definitely off the beaten path.
posted by lstanley at 6:44 PM on November 8, 2016 [3 favorites]

Cape May NJ.
posted by fixedgear at 3:49 AM on November 9, 2016

Your list is largely northern Atlantic coast. Have you spent significant time south of the Outer Banks? It is a huge culture shift between New England and the southeast barrier islands.
posted by catlet at 7:23 AM on November 9, 2016

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