When the well-traveled look to plan their next destination, their minds jump to the most notorious of cities: Los Angeles, Paris, New York City. Even as a travel writer, I am no exception to this rule. I relish in visiting a new city, where I can book my hotel, grab a guidebook and go exploring without any complications.

However, when recently planning my first visit to Cape Cod, I wasn’t completely sure where I should start. Since Cape Cod is a region, even sometimes considered an island, it isn’t immediately obvious in what city one should book their hotel, what attractions one should partake in, what restaurants one should visit, or even how one should arrive. The only foolproof way to ensure that, as a traveler, you truly get all highlights of Cape Cod is simple: Enlist the help of a local. Unfortunately, this is much easier said than done.

I was lucky enough to have a companion who has been vacationing in the area for over ten years. But for those who are visiting this historic locale without the help of an accomplished Cape Codder, below are must-see municipalities of the legendary region to help make your travels to Cape Cod a little more manageable.

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Brewster Bay Beach ©Jenna Intersimone

Brewster, a town of about 10,000 located on the south end of Cape Cod Bay, has a significant makeup of tourists’ summer homes. But it had a decidedly intimate and friendly feel, making it an excellent spot to rest my head after a long day wandering. Although the town didn’t nest the biggest attractions of the Cape, it was picturesque, quiet and centrally located within other popular towns in the area.

If you pass through or stay in Brewster, make sure you grab a lemon square at Hopkins House Bakery, a bakery only open four days a week, since everything is prepared completely homemade. Grumpy’s, is a choice breakfast restaurant with a line wrapping around the building to prove it. Cape Cod Bay beach is a favorite sunbathing spot for locals, with opportunities for fishing and boating as well.

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Brewster Bay Beach ©Jenna Intersimone

Provincetown is a notoriously quirky community, reminiscent of Key West, located at the most northern point of Cape Cod. After driving 30 miles from Brewster to Provincetown, my companions and I rented beach cruisers and headed off for a leisurely drive to and around nearby beaches. We soon arrived in Herring Cove, a bright and quiet untamed beach. After some time spent relishing in the sunshine of this clean and wild beach, we got back on our bikes and delved deep into the scenic trails surrounding Clapps Round Pond and Province Lands Road.

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Herring Cove ©Jenna Intersimone

Back in Provincetown, night descended quickly, which meant that it was high time for Commercial Street, the “Main Street” of the town, filled with galleries, boutiques, packed seafood restaurants, dive bars and shows. Rainbow flags flew overhead the endless train of excited people who paraded the streets. This town is a must-visit, especially those looking for a night out on the town, an amusing show or some stellar seafood.

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Provincetown ©Jenna Intersimone

Hyannis is the largest of the seven villages of Cape Cod, an urban and historic district known for its shopping and hub of transportation. Of course, it’s also the home of the Kennedy Compound. It served as the locale for our Hyannis Whale Watching tour, an obvious must-do for a trip to New England. During the four-hour boating trip starting from Lewis Bay and traveling outward, our boat spotted several humpback whales and their calves, at the tail-end of their season in New England.

This “Capital of the Cape” tends to be the favorite spot for those looking for some bustle in their trip to Cape Cod. It often features concerts and other forms of entertainment alongside some of the Cape’s best restaurants and shops. Due to its location, it’s also where many tourists head for ferry and whale watching tours.

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Hyannis Whale Watching ©Jenna Intersimone

Chatham is like the scaled-down version of Provincetown, perfectly equipped for families, due to Friday night low-key bands as well as shopping and fine restaurants. While there, we went to Chatham Pier and Fish Market for lunch, a specialty shop known for its quality seafood and fine views of the busy Chatham Fish Pier.

If you find yourself passing through Chatham during your Cape Cod trip, make sure you visit the Chatham Lighthouse, established in 1877 and known as one of the most famous and scenic of Cape Cod lighthouses.

Cape Cod can be a daunting trip to book, especially without the help of a seasoned local, due to its many tempting destinations that are impossible to hit completely in one trip. Part of the intrigue of Cape Cod is that, unlike visitation of a single famous city such as Miami or Florence, every vacation to Cape Cod will be different due to endless possibilities enveloped in this legendary locale.

To read the Luxe Beat Magazine version of this article click on the title The Many Municipalities Of Cape Cod