Barnstable to Provincetown

Start your day by driving up the Cape to the red-banded Nauset Lighthouse, an icon of the Cape Cod National Seashore overlooking the dramatic cliffs of Nauset Light Beach. The light occasionally offers tours, but most visitors just stop by for a photo op before descending the wooden staircase for a walk on the beach.
Note: there is a parking fee June-September, and space may be limited during peak hours. Learn more at their official website.

Grab a bite of Cape Cod at Mac’s Market and Kitchen in Eastham, a busy seafood joint with a counter service selection of fried fish sandwiches, lobster rolls, clam chowder, and more. You’ll also find a range of prepared foods that you can grab to-go and enjoy at the outdoor picnic tables. Mac’s has several locations across the Cape, but the Eastham Market and Kitchen is the best bet en route to Provincetown.
Open daily year round from 10:00-19:00. Order in advance online at their official website.

Upon your arrival in Provincetown, spend some time wandering the windswept sands of the Dune Shacks Trail. This moderately challenging path leads to the shacks of Hill Bars, which are rented as artist residencies. Those up for a walk of about 2.5 miles can make it all the way to a secluded section of Race Point beach. Look for the amazing graffiti of “Shark Henge” on the way! You can find the map and trail description here. Information is also available at the Province Lands Visitors Center.

It’s hard to miss the Pilgrim Monument — this granite spire towers 252 feet above Provincetown and can be spotted from miles around. However, you haven’t really experienced the monument until you take the elevator to the tip-top. Road-trippers can also stop into the adjacent Provincetown Museum, which highlights Provincetown’s history as a maritime and theater hub.
The museum is open 10:00-17:00 Thursday-Monday. Reserve your tickets in advance online at the official website.

Get into the friendly coastal vibes of Providence at Irie Eats, a island-inspired joint housed in a tiny shack. What this restaurant lacks in size, it makes up for in flavor, with traditional Jamaican menu items like saltfish and ackee, curry goat, and jerk chicken. You’ll also find a compact market of Jamaican specialty foods, friendly counter service, and a few laid back picnic tables on which to enjoy your meal.

After dinner, grab a cocktail and unwind on the outdoor patio at the Shipwreck Lounge. This cool open-air courtyard serves beautiful beverages with a variety of elixirs, syrups, and infusions featuring fresh fruit, herbs, and exotic ingredients. They also have a number of fun, photo-worthy nooks, cozy firepits, and an all around relaxing vibe. Located inside the Brass Key Hotel.

Break away to the Breakwater Hotel where nearly every room is an oceanfront room. This nautical-themed space is nestled right against Provincetown Harbor Beach, providing excellent views and the opportunity to fall asleep to the crashing of waves. Outdoor spaces are lined with comfy couches and adirondacks, so you can grab a front row seat to the the bay.