Country Mornings with Jonathan & Ayla

Country Mornings with Jonathan & Ayla

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There are a few places you can go to feel super fancy. Whether you're a frequent visitor, or crossing the bridge for the first time, here are some great places to feel bougie on the Cape!

If you want to feel fancy on Cape Cod, here are some great places to dress up, spend a little bit more money than usual, and feel totally bougie while doing it.

Cape Cod has golden beaches and a rich maritime history. It’s no surprise that this Massachusetts haven has become a sought-after vacation destination for many. But for those with a penchant for the finer things in life, Cape Cod offers some truly luxurious experiences. Whether you’re hoping to dine in opulence, sip cocktails in style, or shop in the chicest of boutiques, Cape Cod has it all!

History Of Cape Cod

From the early 20th century, Cape Cod transformed from a simple maritime and farming community to a hub for the American elite. Celebrities, politicians, and industrial magnates started flocking to its shores. Of course they began building summer cottages that would make any architectural digest cover. (Think of the Kennedy Compound!) This influx of affluence painted Cape Cod with a brush of opulence, a legacy that endures to this day.

Fast forward to the present, and Cape Cod remains a haven for those seeking a touch of extravagance. Strolling through the quaint villages, you can’t help but feel the historic allure that makes it a beloved vacation spot. The region’s cobblestone streets whisper tales of old money. The pristine beaches echo with laughter from glamorous 1920s beach parties.

Why Feeling Fancy Is Fun On Cape Cod

Sometimes, it’s worth loosening the purse strings a little to elevate the Cape Cod experience. Dine at an upscale restaurant where gourmet dishes are served with panoramic ocean views. Or perhaps enjoy a cocktail at an elite bar. The sheer joy of dressing up, stepping out, and feeling fancy for the evening is an experience in itself.

Ayla Brown and Rob Bellamy at a table eating oysters

My husband and I love going to the Cape. Ordering oysters makes us feel fancy, but luckily there are some places on the Cape that have Happy Hour Oyster specials! (This photo was taken when I was very pregnant so I ordered oysters Rockefeller).

To vacation on Cape Cod is to be part of a tradition—a tradition of seeking the best, of appreciating beauty, and of indulging in life’s finer pleasures. It’s a reminder that sometimes, it’s more than okay to be bougie, to celebrate life’s little luxuries, and to revel in the rich tapestry of experiences that this magnificent peninsula offers.

So, the next time you’re planning a trip, remember that Cape Cod awaits, ready to wrap you in its luxurious embrace. And trust me, it’s worth every penny.

Here’s 7 Places To Be Bougie On Cape Cod!

  • 1. Chatham Bars Inn

    297 Shore Rd, Chatham, MA
    Located in Chatham, this historic resort provides an unmatched coastal luxury experience. The oceanfront property boasts a private beach, a spa, golf, and a choice of elegant dining experiences. One could easily argue that it’s not just one of the best places on the Cape, but in the country. The Stars restaurant, with its gourmet dishes crafted from local ingredients, offers not just a meal but an experience.

    Ayla Brown standing in front of Chatham Bars Inn

    This is the place that my now husband took me to after he proposed. We celebrated with drinks outside at their beach restaurant. This is THE place to go on Cape Cod.

  • 2. Wequassett Resort and Golf Club

    2173 MA-28, Harwich, MA
    Another gem located in Chatham, this Five-Star luxury resort overlooks the serene Pleasant Bay. Beyond the lavish accommodations and the award-winning golf course, it’s home to Twenty-Eight Atlantic, Cape Cod’s only Five-Star restaurant, offering panoramic ocean views alongside its meticulously prepared dishes.

  • 3. The Captain's House Inn

    369 Old Harbor Rd, Chatham, MA
    A nod to the region’s history, this 1839 Greek revival mansion in Chatham is the epitome of elegance. The rooms are luxuriously appointed, the gardens are pristine, and the afternoon high tea experience takes you back to a bygone era of sophistication.

  • 4. Ceraldi

    15 Kendrick Ave, Wellfleet, MA
    Situated in Wellfleet, Ceraldi offers a seven-course, farm-to-table, ever-changing menu that showcases the bounty of Cape Cod. The intimate waterside setting and the art of the culinary journey here is all about sophisticated, authentic Cape Cod dining.


  • 5. Borsari Gallery

    524 Main St, Dennis, MA
    For those wanting to indulge in a shopping spree, Borsari Gallery in Dennis Village is a must-visit. This isn’t your average art gallery. It’s a vibrant collection of eclectic pieces, from contemporary art to vintage treasures, all showcased in a beautifully restored 1850s Cape building.

  • 6. The Ocean House

    425 Old Wharf Road, Dennis Port, MA
    Located in Dennis, The Ocean House is where the cocktail culture meets Cape Cod charm. The bartenders are mixologists, crafting signature drinks that are both innovative and classic. It’s the perfect place to start or end a bougie night on the Cape.

  • 7. Hot Chocolate Sparrow

    5 Old Colony Way, Orleans, MA
    This might be a surprise to some, but no visit to Cape Cod is complete without tasting some sweet treats. While it’s an espresso bar, candy shop, and ice cream parlor all in one, what makes the Sparrow standout in Orleans is its upscale take on confections and its chic, rustic interiors.

  • RELATED: Here's Where You Can Save Money On Oysters!

    Hope You’re Hungry! Here’s 7 Places On Cape Cod With $1 Oysters
  • RELATED: Here's ALL Of The Breweries And Wineries On Cape Cod!

    13 Cape Cod Breweries and Wineries You Have To Try

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