Great Ideas to Get a Jump on Your Cape Cod Vacation Planning

Start planning your Cape Cod vacation NOW so you don't miss a thing, like a Cape Cod Family Fishing Charter trip out of Barnstable Harbor. CCFFC photo.

Although there is still snow on the ground, it is never too early to start thinking about coming to Cape Cod for a visit in the summer. If you haven’t been to Cape Cod before or if it has been a while (or if you are just looking to visit a different part of the Cape), you may have questions about the different towns.

Beaches and Water Activities

While every town has beaches, consider what you are looking for from your beach. If you are looking to try out a new activity (or partake in an old favorite), different towns have different things to offer. Dennis and Wellfleet both have kite boarding outfits. If you like stand-up paddleboarding, towns from Sandwich to Orleans have places to participate in SUP. If you want to parasail or jet ski, there are locations that offer both in Dennis and Yarmouth, as well as a strictly parasailing outfit in Provincetown.

If you want something a bit less strenuous, kayak outfits are located in almost every town. There are also several locations that offer sailing on Cape Cod, from boat rentals to lessons.

If you are a real thrill-seeker, try tandem skydiving out of Chatham. This is a great way to get a completely different view of the Cape, as well as an adrenaline rush.

Fishing charters run out of many of the towns and are a fun way to spend a day (as well as a great way to bring home dinner). Most of the charters offer cleaning services as well, so there’s no hassle with scales once you get your fish home.

If you aren’t into fishing charters, but still want to get out on the water, consider going on a whale watch or seal watch. You can try Hyannis Whale Watcher Cruises, Dolphin Fleet of Provincetown, or seal tours with Blue Claw of Orleans.

Coming with small children or looking for a less intense beach experience? Cape Cod Bay has dramatic flats and great water for wading in and finding small critters. Towns with Bay access include Brewster, Dennis, Sandwich, Orleans, Eastham, Wellfleet, Truro, Provincetown, Yarmouth, and Barnstable, so there are great options up and down the whole peninsula.

Towns on Nantucket Sound include Falmouth, Sandwich, Mashpee, Harwich, Dennis, Yarmouth, and Barnstable. Nantucket Sound is part of the ocean side of the Cape, but is protected from the stronger breakwater.

If you are looking for some fun waves to toss and turn in, consider heading to one of the National Seashore beaches in Eastham, Orleans, Wellfleet, Truro, and Provincetown.

Chatham has beaches that are unique in their own respect because the town is in such a unique position on the Cape. There are beaches here for everyone, so if you want to sample beaches, consider staying in Chatham.

For more on beaches, click the following links for information about the best beaches on the Outer, Lower, Mid, and Upper Cape, as well as the best Cape beaches for a sunset.

If you are thinking about doing a day trip to Martha’s Vineyard, Falmouth is closest to the Vineyard and ferries run out of Woods Hole. If you want to go on a day trip to Nantucket, the closest ferry runs out of Hyannis (and ferries to the Vineyard run out of Hyannis as well).

Of course if you crave fresh water, the Cape has plenty of gorgeous ponds to swim and boat in. Towns especially well known for their beautiful ponds are Brewster (Sheep Pond, the many ponds of Nickerson), Mashpee and Sandwich (Mashpee and Wakeby Ponds), and Falmouth (the Punch Bowl in the Beebe Woods), Long Pond and Hawksnest in Harwich, Goose Pond in Chatham, Great Pond in Wellfleet, Flax Pond in Dennis, and Orleans (Pilgrim Lake, Bakers Pond).

Another thing to keep in mind is that hiking (nature walks) and swimming tend to go hand in hand, with many of the nature trails leading either to ponds, the Bay or the Ocean.

Shopping, Art Galleries, Museums, and More

The Cape has no shortage of wonderful local businesses, offering everything from avant garde to luxury items. The local Main Streets are some of the best places to explore, although the local flea markets can sometimes hold real gems, while the local farmers markets offer a personal interaction with the artisans. While Main Streets are up and down the Cape (and towns from the Upper Cape to Outer Cape have farmers markets in the summer), flea markets are a bit more limited, so if perusing through the treasures of the ages is up your alley, consider going to a town near where one of the flea markets are held. There are flea markets in Wellfleet, Dennis, and Sandwich, as well as sporadic events at churches and historical societies, so keep your eye on the calendar.

Of course, most of the towns have their own historical societies, as well as other museums (Mashpee has the Children’s Museum, Dennis has the Cape Cod Museum of Art). There are also fun places such as the Green Briar Nature Center in Sandwich (part of the Thornton Burgess Society), Heritage Museums and Gardens in Sandwich, and the Pilgrim Monument in Provincetown.

For art lovers, there are galleries that explore all sorts of different mediums up and down the Cape, as well as plenty of local theatre groups that put on spectacular shows, from family friendly affairs to performances that make for a great night out. And never to be out done, the Melody Tent always has a terrific summer line-up, with something for everyone.

Are you interested in golf? The Cape has plenty of stunning courses that are a great time.

If rain begins to fall, there are several great bowling alleys to visit, perfect for families and couples. Another fun thing to do during a bout of bad weather (or even when the weather is nice)--tour a local winery or brewery.

If you’re looking to get more familiar with the area, consider going on a tour (different towns have different companies offering tours, all offering a unique view of the Cape).

Kids Stuff

Of course, when planning your stay, if you are bringing kids, you will want to know the best places to go to keep them entertained (in addition to beaches and museums).

From playgrounds, to mini-golf, an inflatable park, and more (laser tag, go-karts, ice skating, et cetera), there is plenty to tucker kids out on Cape Cod. And after all the fun? Head out for a cone of delicious ice cream.

So when trying to find a rental or hotel, just remember to go through a checklist of what you want to do and cross-reference it with which towns offer the most to you and your family.  

About the Author

Contributing Writer

Mati Brown holds a Journalism degree from the University of Massachusetts – Amherst. She has written for several publications, including the Berlin Reporter, EDGE publications, and the Falmouth and Mashpee Bulletins. A current resident of Brewster, she is glad to be writing about the area she grew up in.