How to create A life changing Cape Cod adventure TRIP 

There is so much to do on the Cape that it can be overwhelming to a newcomer. Where to stay? When to visit? There are tons of questions. As someone who has been visiting the area almost every summer for the last 25 years, I’m here to help. I suggest visiting during July or August and staying in Eastham. It is centrally located, close to both the beach and the bay, has ponds, hiking trails and much more. You will never be bored there! Once you find a great spot in Eastham, check out my guide below that covers fun, adventurous activities to do during your stay. Happy travels!

Sunset at Eastham's bay

Sunset at Eastham's bay

Day 1: Explore hyannis & cape cod foodie tour

Hyannis is the commercial and transportation hub of Cape Cod. Over the last 25 years the streets have become lined with unique restaurants, shops, art and museums. The area is also famous because of the Kennedy’s. As you walk through the village, you’ll notice Kennedy reference’s everywhere. Notably, a monument dedicated to John F. Kennedy on the Lewis Bay waterfront where he gave his President-elect victory speech. If you’re a Kennedy lover, check out the John F. Kennedy Hyannis Museum and the Kennedy Compound. Although I appreciate the love for one of our former commander-in-chief’s, we were visiting the area for their incredible cuisine.

Hyannis harbor

Hyannis harbor

We booked the Hungry in Hyannis experience through Cape Cod Foodie Tours. It is the first food tour on the Cape and was designed to support and showcase small owner operated businesses while answering the age old question, “where should we eat?”

Chunky Chocolate Pecan cookie from Good Butter Bakery

Chunky Chocolate Pecan cookie from Good Butter Bakery

The tour sure did answer that question! After stuffing our faces with cuisine from countries all over the world, we left full and smiling. To read more about the tour, check out our full article here.

Day 2: nauset beach

Popular Nauset Beach, not to be confused with Nauset Light Beach of the National Seashore, is a lengthy 10-mile expanse starting in Orleans stretching all the way to Chatham. It has beautiful sunrises, excellent bass and blues fishing, surfing, sunbathing and swimming in cool ocean waters. Despite its size, the massive parking lot occasionally fills up when the sun is strong. Arrive early or in the late afternoon if you want to claim a spot.

This beach is often a great spot for spotting seals from the comfort of your beach blanket. Seals are frequently found in groups, swimming and playing. We saw some that were about 15 feet from the shoreline. It was amazing!

Day 3: Heritage gardens, museum & adventure park

Heritage Museum & Gardens is comprised of three galleries and expansive gardens located in historic Sandwich, Massachusetts. It includes galleries for American Folk Art, a vintage carousel as well as automobile and traveling exhibitions. During our visit, there was an exhibit called "CUT! Costume and the Cinema" that featured tons of beautiful costumes from some of the greatest movies of all time.

The gardens feature a collection of thousands of rhododendrons, holly, daylily, herb, hosta and heather gardens. Also featured are more than a thousand varieties of trees, shrubs and flowers.

While exploring the grounds you’ll also find the Old East Mill, a restored windmill (1990-2000) built originally in Orleans, Massachusetts in the 1800’s. In 2002, a labyrinth was also added to the grounds, designed by Marty Cain, one of the best-known labyrinth designers in North America.

As an adventure lover, my favorite part was their aerial adventure ropes course in the forest. There are 5 separate trails of varying levels of difficulty. Each trail has zip lines but primarily consist of “bridges” between tree platforms made of rope, cable and wood configurations creating over 65 unique challenges. To see more of our experience, watch our video here.

Day 4: provincetown pub crawl

On a walk through Provincetown’s Commercial Street, the brick sidewalks, unruly rosebushes, gray shingle-lined cottages and thin streets called for exploring. Often called "P-town", the town is known for its beaches, harbor, artists, tourist industry and its status as a vacation destination for the LGBTQ community. Provincetown is packed during July and August, when the town’s population swells to more than 60,000, from about 3,000. To join the masses, my cousin, her husband, and my boyfriend decided to create our own bar crawl to taste the cocktail scene the area had to offer. Although my list had seven spots, we only made it to four and I blame that on the charming atmosphere of the bars and the booze. Our favorite find on the crawl was the newly opened Stangers & Saints. Located in the newly renovated 1850 home of Captain John Cook, the Mediterranean-influenced tavern offers Provincetown a unique and fresh dining option with incredible craft cocktails. This is a spot you need to visit. To see our full bar crawl click here.

day 5: cape kayaking

Staying in Eastham allowed us to be near some of the best kayaking locations the Cape has to offer. When I heard that Cape Kayaking offered a Kayaking and Clamming tour I booked it right away. Cape Cod is famous for their clamming throughout the country. With this tour we were able to get down and dirty, and forage for them along the mudflats and sandbars of the Nauset Estuary. While exploring the marsh our guide taught us about the various types of clams, their habitat and lifecycle, and showed us ways to find them using traditional techniques. To read more about our experience, see the full article here.

After our tour ended, we headed to a local pond to swim and relax. Eastham has many fresh water ponds to choose from and they are great to wash off after a day in salt water. My favorite spot is Great Pond. They have beautiful trails through the forest, a sandy beach, a playground and docks to jump into the water. It is a lot of fun! Beach stickers are required to park at either beach, but there are attendants who sell passes.

day 6: explore chatham & experience a biplane

See Cape Cod from a Bi-Plane! This was a truly unique and amazing experience that I will never forget. We headed to Chatham airport on a sunny afternoon to catch our 30 minute flight. In a biplane you will experience Cape Cod with a "bird's eye view" of the magnificent beaches, the newest ocean breakthrough, and the large volume of local harbor seals. If you look closely you may even see a Great White Shark (no guarantees on the shark though). Other sights include the wreck of the SS James Longstreet target ship sunken in the bay and the Provincetown Monument. Check out our video of the experience here.

For Dinner, head to Del Mar Bistro in Chatham. It is a friendly nightspot on Cape Cod for eating, drinking and socializing. It features local seafood, bistro cuisine, wood-fired thin crust pizzas and popular specialty drinks. In the Summer they have live Jazz from Tuesday through Thursday.

day 7: provincetown shopping & art's dune tours

To close out our week at the Cape, we headed back to Provincetown for a day of shopping. Commercial Street has tons of shops of all kinds. It is easy to spend 4-5 hours there at a time. For an afternoon snack, my favorite spot is the Provincetown Portuguese bakery. Their malassadas roll, a Portuguese fried dough, are light, fluffy and sweet. It is not dripping with oil like American fried dough. Every time I visit Provincetown I stop at the bakery to get one. Definitely worth it!

Before we left, we had to experience Art’s Dune Tours. Currently in their 70th year of operation, it is now run by Rob, Art’s son. Art’s Dune Tours started off in 1946 with a 1936 Ford Woody and has been taking thousands of people over the Cape Cod National Seashore dunes since then. We decided to do the sunset tour & dinner. To read about our full experience click here. After about a 45 minute tour of stunning dunes, we headed to the beach, had a clambake & BBQ dinner and watched the sunset. It was the perfect way to end our trip.

If you have any questions about our trip, please reach out to me at team@sarahfunky.com. Happy exploring!


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