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Wines on the Wing

A Couples’ Guide to Cape Cod in the Fall

by Barbara Rogers

Sep 6, 2019

Stillman Rogers

Age Specific / Adult Children

Off-season is the best time to enjoy a leisurely couples’ getaway on Cape Cod. In September and early October the summer crowds have left, but the weather is still warm enough to enjoy the beaches on a sunny day. The region’s many historic homes, museums and tourist attractions are still open, and the shops are having end-of-season sales, so it’s a great time for shoppers to visit.


Hotels and B&Bs are likely to have rooms available without reserving weeks or months ahead, and you have a good chance of scoring one of the coveted window tables or a romantic corner spot in the best restaurants.

Cape Cod Beach. Photo: Stillman Rogers

Game Plan

The Cape isn’t big — you can easily drive its length in a day with several stops. But you probably don’t want to because there’s so much to see and do there. If you have more than a couple of days, plan to split your stay between the two ends — the outer cape with the Cape Cod National Seashore and Provincetown, and the inner cape around Hyannis or Sandwich.


The Outer Cape

The most romantic place to stay in Provincetown, at the tip of Cape Cod, is high above the town at Land’s End Inn. Views from the verandah, where complimentary evening wine and cheese bring guests to relax and admire the inn’s the splendid Art Nouveau public areas, encompass the harbor, Cape Cod Bay and the Long Point lighthouses.

Provincetown, Land's End Inn.

Provincetown, Land’s End Inn. Photo: Stillman Rogers

Art Nouveau décor continues throughout the inn, with stunning guestrooms and suites filled with art, furniture, lighting, stained glass and accessories reflecting styles from the turn of the 20th century. Priceless collections include Tiffany and other art glassware. It’s like living in a museum, but a relaxed and comfortable one where you can kick off your shoes and sink into the chairs with a good book.


Savor the magnificent sunsets over the ocean from lounge chairs on a private balcony and stroll into town to eat at one of its’ many restaurants. Or just walk down the stairs through the garden to dine on Wellfleet oysters and fresh-from-the-sea lobster at The Red Inn. For a romantic dinner in the heart of town, choose Napi’s, where local seafood gets an international touch.


Shopping and gallery hopping are the favored pastimes in Provincetown, and miles of trails invite exploring the undeveloped Cape Cod National Seashore. For an up-close look at the magnificent dunes and the park’s natural and human history, join one of Art’s Dune Tours.


The Inner Cape

The waters of Cape Cod Bay, on the north shore, are calmer and warmer than those of the open Atlantic, and some of the best beaches are in the area around Brewster and Dennis. These towns are lined by fine old homes — and antiques shops, as well as more arts-and-craft galleries. Many of the historic homes are open for visitors, and beside the road you can spot historic grist mills, windmills and other places to stop. Hyannis is a good base, with the J.F. Kennedy Memorial and the Kennedy Heritage Trail recalling the days when the Kennedy beach estate was the summer White House. Dining tip: Tumi Ceviche Bar Ristorante in Hyannis combines Peruvian and Italian cuisines with brilliant results.

Sandwich, Belfry Inn

Sandwich, Belfry Inn. Photo: Stillman Rogers

Another good base for the western end of Cape Cod is the historic town of Sandwich, where you’ll find the Sandwich Glass Museum (the glassblowing demonstration alone is worth the admission price) and Heritage Museum and Gardens. The latter appeals to several interests with a fine collection of antique and vintage cars, a fully operating antique carousel you can ride on, collections of American art and antiques, beautiful gardens and an entire area for children, overlooked by a giant “tree house.”


The most romantic room in Sandwich’s Belfry Inn, the Tuesday Room, incorporates the large stained glass rose window at the front of the building, once a church. The beautiful woodwork and architectural details of the chancel have been carefully preserved in the restaurant, The Bistro at the Belfry. Even off-season, you’ll want to reserve a table here in advance.


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