For much of the year, Cape Cod is a quiet place, its tranquil beauty left for residents to enjoy, but Cape Cod in the summer months, the sleepy Cape awakens, welcoming travelers from all over the world. If your journey brings you here during the summer solstice, we want to be the first to welcome you to paradise! Offering stunning land and seascapes, fascinating historical landmarks, and a culinary landscape that you will dream about long after you have returned to your hometown, every day is an adventure in wonderful. We at Pretty Picky Properties love this land we call our own, and we can’t help but want to share its wonders with our guests. This guide to a Cape Cod Summer vacation is one way we do so.
Journey to Cape Cod for Summer Vacation
Day 1: Breakfast of Champions in Osterville
When your day begins with a hearty breakfast at the Pineapple Caper Café, it is impossible to be anything other than happy and excited. Located at 29 Wianno Avenue and offering a menu that serves breakfast all day, even their bright yellow coffee mugs will bring a smile to your face and a sigh of wonder at first sip, serving as the perfect accompaniment to your favorite morning meals. Their smoothies always delight, their breakfast sandwiches conquer the largest of appetites, and their foray into healthy foods will make you feel good about making the healthy choice, even as they taste so delicious it may be difficult to believe the meal is good for you!
Day 2: A Long Walk Not Spoiled in Marston Mills
Golf is the ultimate summer sport, and there is no better place to play on Cape Cod than at the Olde Barnstable Fairgrounds Golf Course, located at 1460 MA-149 in Marston Mills. Once a spot where children’s squeals of glee wafted through the air, where carnival food scented the breeze, and colorful lights brightened the night, today, the same acreage has been converted into a golf course that comes complete with a practice green, bunker, and chipping green, while also offering a driving range with 23 hitting bays in addition to the 18-hole course. Designed by Mark Mungeam, this course is definitely a summer must play for visitors and locals alike.
Day 3: Art and the Artist in Yarmouth
Edward Gorey was a multifaceted artist, playwright, author, puppeteer, illustrator, and resident of Yarmouth until his death in 2000, and today, the home in which he created many of his masterpieces serves as a museum honoring his work. Located at 8 Strawberry Lane in Yarmouth Port, closed on Mondays and Tuesdays, the Edward Gorey House may be an ideal way to play on a rainy day on the Cape.
Day 4: Epicurean Adventures in Eastham
Cape Cod has often been described as a foodie’s paradise, and your epicurean adventures in Eastham may end up being the highlight of your Cape Cod getaway. Start the day at Laura & Tony’s Kitchen Amazing Breakfast, located at 5960 US-6, enjoy a midday break at an authentic Cape Cod institution, Arnold’s Lobster & Clam Bar, 3580 US-6, and finish out the day at Brickhouse Restaurant, located at 4940 Mid-Cape Highway and offering an elevated seafood menu that you will dream about long after you have returned to real life. Every day will be a new adventure in culinary delights when you explore these and many other Eastham restaurants.
Day 5: Driving in for the Magic in Wellfleet
Most of today’s generation doesn’t know about the magic that could be found in a night at the drive-in, but if you have chosen one of our Wellfleet sanctuaries for your vacation accommodations, you can change that in your family! Wellfleet Cinema’s, located at 51 US-6, has kept that magic alive for nearly seven decades as the only drive-in theater on Cape Cod. Showing first run double features every weekend all summer long, the speakers still hang from posts between cars, the playground is still filled with fun-loving youngsters, and the smell of freshly popped popcorn still wafts through the air. During the daylight hours on weekends, the parking spaces serve as spots for vendors to set up tables for the Wellfleet Flea Market.
Day 6: Cold Beer, Sunny Days, and a Visit to a Brewery in Hyannis
The taste of a frosty beer on a hot summer’s day is a special treat that can be enjoyed during your Hyannis adventures with a visit to Cape Cod Beer, located at 1336 Phinneys Lane. This is Cape Cod’s original microbrewery, offering an outdoor beer garden that is only open from May through November. Providing live music as an accompaniment to the cold beers that are brewed onsite, they also offer wine, cider, and cocktails for those in your family with differing tastes.
Day 7: Toes in the Sand in Dennis
Saving the best for last, nothing says summer on Cape Cod more loudly than a day at the beach, and our Dennis guests may want to spend every day enjoying the views, the serenity, and the calmer waters at Mayflower Beach due to its bayfront location. Offering lifeguards, picnic areas, and public bathrooms, this beach may become your second favorite home away from home—after our Pretty Picky Properties Dennis sanctuaries, of course! Contact us to reserve your favorite property with us today. Search our rentals by amenity here.