Long Weekend Escapes: “How-To” Cape Cod & Islands

Anyone that has called our brainstorming line knows that we get as excited as you about planning your future travel plans. You may have heard us say, why not take an extra day and make it a long weekend? We know there are a lot of people in need of or ready for a long weekend.  Luckily, every state has amazing tourism regions that are perfect destinations for your next getaway. Leisure travel has become slightly more complicated due to travel restrictions, so, for our recent trip, we stayed closer to home and chose the Cape Cod & Islands region of Massachusetts.

Cheat Sheet for a Classic New England Experience

World-Class Resorts

There are a few terms that you’ll hear often while visiting Cape Cod, one of the most common being “Cape Casual.” This region is truly a place to unwind and relax with the entire family. For relaxed lodging options, there are hundreds of boutique properties, including classic hotels and motels up and down Cape Cod. When we are asked about high-end lodging, our short list of three includes the Chatham Bars Inn, Ocean Edge Resort & Golf Club, and Wequassett Resort & Golf Club.

Beaches, Two Ways 

Most people know that the Cape is a narrow strip of land bordered on either side by the Atlantic Ocean and Cape Cod Bay. There are dozens of beaches to explore along both the ocean and the bay, each of them unique and worth exploring. The beaches within the Cape Cod National Seashore are very popular, as they are accessible to everyone, while some of the town beaches require resident beach passes.

Fresh Seafood

There are many fantastic dining options on the Cape, and you really can’t go wrong with one of the many established seafood restaurants. For fresh seafood, seek out the restaurants near the town harbor. Another great indicator is the size of the cue— we are creatures of habit and willing to stand in line, summer after summer, for a great meal.

Wellfleet Drive-In

The only drive-in theater on Cape Cod has been welcoming carloads of vacationers since the late 1950’s. This is a classic Cape Cod thing to do and one that you will never forget.

Small Town Shopping

People are often surprised by the number of small towns in the various regions of the Cape— Upper, Mid, and Lower Cape Cod. A few of our favorite towns with unique boutique stores and art galleries are Chatham, Hyannis, and Provincetown.

Scenic Drives

The two main roads that run the length of Cape Cod are Route 6 and Route 28. If you want to find some hidden gems, spend time driving through the towns and coastal roads. Route 6A is another pleasant drive through the quaint towns of Sandwich, Barnstable, Yarmouth, and Dennis. The drive to Provincetown is also a must-do, you know you are almost there when the sand dunes start encroaching on the road in the town of Truro.

The Islands

Martha’s Vineyard and Nantucket are great destinations for day trips while visiting the Cape. Ferry Service is available from Woods Hole, Hyannis, and Harwich Port. The islands have different vibes, and everyone has their favorite. You will want to plan for a return trip to spend a few nights on the islands after your first visit!

Museums & Historical Societies  

If there are a few showers during your stay and you are looking for an indoor activity, many of the towns have a historical society or local museum. A few of the more popular museums that are worth a visit are the Chatham Marconi Maritime Center, Falmouth Museums on the Green, Sandwich Glass Museum, and the Whydah Pirate Museum of Cape Cod.