The Best Cape Cod Winter Getaways | Pretty Picky Properties
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Cape Cod Winter Getaways Journey

You came to Cape Cod this winter for fun, a four-seasons climate, and a wide and varied array of activities only available on Cape Cod. There are a variety of things to do and places to see to make your Cape Cod winter getaways to the cozy towns of Cape Cod one to remember for a lifetime!

Day 1:

First Encounter Beach

The Eastham beach is reportedly the site of the Pilgrims’ first encounter with the Nauset Native Americans upon arriving in the New World. They arrived in the spot after leaving Provincetown and before arriving in Plymouth. The mostly calm waters of Cape Cod Bay make it the perfect beach for families with young children. While you won’t be going in the water or sunbathing, the landmark of history offers a view like no other. There is handicap parking, boardwalk access to the sand, and more. Daily parking fee is $15 on weekdays and $18 on weekends.

Sightseeing Tours

The towns of the Cape are rooted in history. There are a variety of historic and other significant sights scattered across Cape Cod. Get in your car and plot your own course or book a sightseeing tour where someone else does the driving. There are a variety of companies in the towns across Cape Cod that offer guided tours of the area, hitting on all the hot spots. Your knowledgeable guide will take you to all the places you want to go and fill you in on local history and events. You can even select specialty tours that includes food or wine tastings, sunset tours, or night tours that offer a different perspective than any daytime tour can offer.

Day 2:


Anglers on a winter respite to Cape Cod won’t be able to resist some time with their favorite activity. The waters of the area are just bursting with great fishing spots, including great places for shore fishing, freshwater fishing, and of course, deep sea fishing in the Atlantic. You’ll hook catches like striped bass, flounder, bluefish, flatfish, smallmouth and largemouth bass, and many more. Check out shore fishing hot spots like Cape Cod Bay or Brewster Flats. Freshwater locales include Nickerson State Park, Long Pond, and Black Pond.

John F. Kennedy Hyannis Museum

Wander through the museum that is devoted to the life and legacy of America’s 35th president. It includes exhibits like a remembrance of the fateful day in 1963 when President Kennedy was assassinated, the presidential summer home, and personal belongings like his rocking chair – known as a Kennedy Rocker – on loan due to the renovation of The Towers of the Waldorf Astoria. Kennedy was known as the youngest person to be elected president, the youngest to end his tenure, and the first Catholic to hold the highest office in the U.S.

Woods Hole Science Aquarium

The aquarium is the oldest public aquarium in the U.S., having been established in 1875. It hosts approximately 80 species of marine animals native to the Northeast and Mid-Atlantic U.S. waters. It is designed for self-guided tours of the main exhibits, while visitors can also get a behind-the-scenes look at aquarium operations. There is also a seal enclosure hosting several residents. The upstairs gallery, touch tank, and other exhibits are currently closed for construction.

Day 3:

Cape Cod National Seashore

While you won’t be going in the chilly winter waters of the Atlantic, you won’t want to miss taking in the Cape Cod National Seashore on your Cape Cod winter getaways. Much of the seashore is accessed by the town of Wellfleet; over half of the designated land is there! The CCNS was created in August of 1961 by 35th President John F. Kennedy. It includes ponds, woods, and beachfront along the Atlantic coastal pine barrens ecoregion. The CCNS includes nearly 40 miles of seashore along the Atlantic-facing eastern shore of the Cape Cod region, encompassing the towns of Provincetown, Truro, Wellfleet, Eastham, Orleans, and Chatham.

Truro Vineyards

Set aside some adults-only time, on your last day or any other, for some good wine! Wine tastings are offered by the glass daily. There is also a pavilion with walk-up bar. The grapes are grown right on the five-acre vineyard and include Chardonnay, Cabernet Franc, and Merlot. Sample a large variety of reds and whites or try something from the “Lighthouse Wine Series” or “Limited Release Wines.” The vineyard offers a selection of spirits, including whiskey, gin, rum, and Amaro, too. The vineyards are open year-round, and hours vary throughout the year.

Cape Cod Winter Getaways

When planning your Cape Cod winter journey, make sure you choose accommodations provided by Pretty Picky Properties. We offer two-bedroom units for you and your small family or group all the way up to a ten-bedroom compound to house all your loved ones this winter.

Prepare a delicious home-cooked, soul-warming winter meal of your own in the fully equipped kitchen. Lounge inside in beautiful living spaces or enjoy the view from the private balcony or patio or spend some time near the pool at select rentals.

Explore a variety of vacation rentals in Cape Cod, including charming Marstons Mills vacation rentals, cozy Osterville vacation rentals, scenic Sandwich vacation rentals, and delightful Yarmouth vacation rentals.

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