A journey to Cape Cod can be the most fun, the most relaxing, and the most wonderful journey of your life, especially as each day on a Cape Cod getaway will end in our Pretty Picky Properties sanctuaries. Offering the comfort you crave, the style you admire, and the luxuries that will make your travel experiences that much more special, our properties are designed to be an integral part of your vacation experience. And although we suspect that you already have many ideas on how you are going to fill many of the blank spots on your vacation itineraries, we have created this guide to a seven-day Cape Cod trip, adding to your list of activities that absolutely should not be missed.
Seven-Day Cape Cod Trip
Day 1: Breakfast in Brewster
Yes, our vacation rentals all come with fully equipped kitchens, but no one wants to cook every meal while on vacation, especially when the Cape Cod landscape is decorated with some of the best restaurants in the world. Starting your journey the right way can mean a breakfast at the Kitchen Café, located at 2671 Main Street, not far from your Brewster retreat. This is a newer restaurant on the culinary map of Brewster, and we tend to prefer tradition, but we have to admit the Kitchen Café slid neatly onto the scene, fast becoming one of our favorite spots for breakfast. They offer reasonably priced meals and hearty servings of their classic breakfast dishes. Eat “dessert” first and try their chocolate chip pancakes—you’ll thank us later!
Day 2: Christmas Card Photos at the Chatham Lighthouse
The Chatham Lighthouse, located at 37 Main Street, was constructed over 200 years ago in 1808 and is an iconic landmark in a town known for its rich maritime heritage. Standing tall above the landscape, you may be surprised to learn that is more than just something pretty to look at; it is still used by sailors to avoid being smashed upon the rocks. Your Cape Cod adventures are sure to include more than a few visits to local lighthouses, but we think this one will make the perfect backdrop to your next Christmas card photo, and if your visit brings you here during the summer months, tours can be taken every Wednesday in July and August.
Day 3: Something Scentful in Harwich
Not every adventure has to be a grandiose one. Some of your favorite Cape Cod activities may be the simpler ones, such as a visit to Cape Cod Lavender Farm. Located just off Weston Woods Road in Harwich, a visit during its peak months (June through mid-July) will be a prize for all the senses, including, of course, your sense of smell. There is no sense of urgency at this serene spot, and guests are invited to explore the fields, soak in the ambience, and take a peek in the gray clapboard cottage in which lavender-themed gifts await purchase. Also offering an online shop, if you find something you really love, you can stock up from the comfort of your recliner at home.
Day 4: A Midday Meal to Remember in Orleans
As you spend your Cape Cod days hanging out at the beaches, hiking on scenic trails, and exploring all the unique attractions that make this place so special, you will soon discover the importance of not missing a meal, so when the sun hovers straight above your head, we suggest you stop by The Knack (5 MA-6A in Orleans) and fill up on lobster rolls and homemade lemonade. Offering an authentic Cape Cod experience, there is a second location in Hyannis at 1120 Route 132, giving you twice the opportunity to enjoy some good old fashioned Massachusetts meals.
Day 5: The Magic of Mid-Cape
The towns of the Mid-Cape offer a magic all their own, including that which can be found in our Pretty Picky Properties that are located in that region. Laugh at the antics of comedians onstage at the 100+ year old building that houses the Barnstable Comedy Club, 3171 Main Street, create your own souvenirs or buy beautiful art from the Cape Cod Museum of Art, 60 Hope Lane in Dennis, or exploring the world of the Kennedy’s in the Cape’s most famous town, Hyannis Port. Magic can be found in all these places and in so many more towns in Mid-Cape.
Day 6: Savoring a Sunset Supper in Sandwich
Although there are a plethora of inland restaurants that offer exquisite dining experiences, we recommend that at dinner you choose patio dining with a harbor view with a visit to the Pilot House Restaurant & Lounge, 14 Gallo Road. Offering locally sourced seafood, refreshing cocktails, and for our guests who are staying in a Pretty Picky Properties pet friendly escape, they offer a small section outside where dogs are permitted. Cape Cod is a dog-loving place, and those tables go fast, so be prepared for a wait during busy times.
Day 7: Stay Close to “Home” in Yarmouth
Real life is filled with have-to-do’s and must-do’s but during your Cape Cod journey, you only need to consider the things you want to do, and if that means staying close to home in your seaside Yarmouth sanctuary, all the better! Relax, rest, and let the ocean recharge your drained batteries in the most beautiful spaces on Cape Cod. Contact us to reserve your favorite escape today! Search our rentals by amenity here.