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There are certain towns that capture the essence of simple pleasures on the water. Among them are Key West, Florida; Edgartown on Martha’s Vineyard and Nantucket town, Massachusetts; Laguna Beach, California and St. Michael’s, Maryland. They all have shingled cottages cheered up with bright paint colors or potted plants and gingerbread trim. Mixed in with the tourist shops selling t-shirts and flip-flops may be a surprisingly good antiques store, clothing boutique or art gallery. There is definitely an excellent ice cream or candy shop as well as at least one special hotel and some very good restaurants. And, perhaps, most importantly, there are annual visitors who flock to these places to cherish the laid-back atmosphere and sense of a return to summers of our childhood.

The most recent of these iconic American coastal towns that I have visited is St. Michael’s, where I stayed at the Inn at Perry Cabin. From the rooms are views of sailboats on the bay and herons cruising over the marshes. Bicycles can be borrowed for a ride into town or sailboats arranged for a day on the water with a picnic of sandwiches or lobster rolls on fresh-baked bread from the hotel bakery. Nearby attractions include the quaint town of Easton (be sure to eat at Mason’s, an exceptional restaurant in a converted two-story with an adjacent garden and chocolate shop) and Annapolis, only a forty-minute trip, best taken by boat. A five-minute walk from the Inn is the Maritime Museum (213 N. Talbot Street; 410-745-2916), an eighteen-acre campus of sea-related buildings where you can learn about oystering (the Eastern Shore is the world’s biggest source), waterfowling, crabbing and the history of sailing.

Summer is officially over but at any of these towns in late September and even into October, you can still savor sea breezes and warm days and probably the prettiest cloud-streaked skies of the year.

Read about Annapolis with kids

On Martha’s Vineyard stay at the Charlotte Inn

In Key West, stay at the Gardens Hotel

In Laguna Beach, stay at Montage

In St. Michael’s, stay at the Inn at Perry Cabin

On Nantucket, stay at the Wauwinet

More about the Eastern Shore coming shortly.