Pretty Picky Properties Blog

As temperatures fall and leaves change colors, the new season on Cape Cod changes our vibe. We locals love our visitors, but by summer’s end, we love the thought of fall even more, and if your journey brings you to our doorstep at this time of year, we can promise a different kind of vacation experience. This local’s guide to Chatham is an opportunity to share our love for our...

Cape Cod is different from many other vacation destinations, and part of that is due to how it governs itself. Divided into 15 self-governing towns, each with its own series of villages, it is also divided into four distinctly different regions: Upper, Mid, Lower, and Outer Cape. Today, we at Pretty Picky Properties are going to take you on a tour of the towns on Cape Cod (and their villages...

Not every traveler wants to do what every other traveler does when on vacation on Cape Cod. For some intrepid explorers, finding the hidden gems of Cape Cod provides a vacation experience that is both fulfilling and exciting. If you are a Pretty Picky Properties guest who prefers to march to the beat of your own drum, this guide to unique activities and attractions for 2026 will make it easy...

Some of the best vacation memories revolve around the food you eat, and your visit to Cape Cod (and stay in our Pretty Picky Properties Cape escapes) will be no exception. To get a taste of the Cape, add this tour of the best waterfront restaurants on Cape Cod to your adventures in comfort and luxury! Waterfront Dining on Cape Cod: Why Views Matter There are plenty of wonderful restaurants...

Road trips are always a good idea in our mind, and if you feel the same, you’re sure to love the following collection of the best Cape Cod scenic drives. Each one is short enough to fit into a day trip, and impressive enough that you will never forget them. It’s time to hit the road during your Massachusetts vacation! Why Driving Is One of the Best Ways to See...

A Cape Cod vacation is something that the whole world dreams about. Aren’t you lucky to be in the planning stages of yours? Offering history, fun, and dreamy beaches, there are always unique things to do on Cape Cod, even if you take the beaches out of the equation. Today, we at Pretty Picky Properties want to take you beyond the beach with this guide to the best things to...

Spring on Cape Cod brings the beauty of flowers blooming, trees budding, and the sun shining. We can’t wait to get outside and play, enjoying the soft warmth of spring and a landscape free of snow and ice. This guide to the best outdoor activities on Cape Cod in March and April offers a variety of things you will be able to do, quite possibly convincing you that these early...

If you’re thinking about a Cape Cod getaway before summer crowds arrive, early spring is a great time to go. With cooler temperatures and fewer visitors, it’s easier to explore the area, enjoy local dining, and experience the Cape at a more relaxed pace. Browse our Lower Cape Vacation Rentals Here! A Prime Season for Whale Watching Spring marks the return of whale watching season on Cape Cod, and it’s...

Spring Break on Cape Cod feels like a breath of fresh air. The weather begins to warm, seasonal businesses reopen, and the Cape shakes off winter without the summer crowds. It is an ideal time to explore at a slower pace, enjoy the outdoors, and experience the charm that makes Cape Cod such a popular destination. Whether you are traveling with family, friends, or planning a quieter escape, Spring Break...

A vacation on Cape Cod is a dream come true for travelers who flock to our sandy beaches from all over the world, and although summer is prime vacation time, spring on Cape Cod may be the vacation that fulfills all your wishes. Quiet days and even quieter nights, beaches that are pristine and empty, and the chance to experience the authentic Cape Cod will make your trip wonderful, and...