Exploring Cape Cod
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Exploring Cape Cod — Full Of Summer Fun

A Cape Cod 3 Day Itinerary

Exploring Cape Cod
Map of Cape Cod

Exploring Cape Cod for a long weekend (or mid-week) getaway is a wonderful way to enjoy summer in New England. There are any number of ways to enjoy The Cape, below are some of my favorite things to do when I’m there. This mix and match Cape Cod multi-day itinerary is a jumping off point to plan your own curated beach focused vacation.

Traffic can be an issue so selecting a home base should be based on your preferred activities, i.e. shopping, beach, hiking, etc. Below is a snapshot of beaches and fun things to do that will give you a jump start on your Cape Cod getaway.

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Cape Cod Rail Trail

Exploring Cape Cod
Cape Cod Rail Trail

The Cape Cod Rail Trail (CCRT) covers 25+ miles of an old rail bed from South Yarmouth all the way to South Wellfleet. You can spend the entire day wandering the walking trails and soaking up the pretty sights.

One summer I committed to walking the entire CCRT — not all at once of course!

From the Station Avenue parking lot in Yarmouth (which requires some backtracking to begin at the beginning) to Wellfleet, the trail is a treasure trove of scenic pathways, granite mile markers, and classic Cape establishments. Whether you are in the mood for a short hike or an extended biking adventure, the CCRT has beautiful gifts to bestow.

Cape Cod Baseball League

Exploring Cape Cod
Cape Cod Baseball League

Summer isn’t complete without taking in a baseball game. The Cape Cod Baseball League offers a long standing tradition of premier collegiate summer baseball. Replete with wooden bats, concession stands, and hometown pride, the Cape Cod Baseball League has been the showcase for many college players who move on to major league play.

Ten teams across The Cape play to a cheering crowd of happy vacationers and locals. One of the concession stand treats is the donut burger – a hamburger on a jelly or glazed donut. It’s an interesting ballpark dinner.

Lobster Roll Dining

Exploring Cape Cod
Sesuit Harbor Cafe Lobster Roll

I have several favorite spots where you can enjoy an excellent lobster roll. And, I always makes plans to have at least one while I’m on The Cape, you can’t beat the locally caught seafood freshness.

In Dennis, Sesuit Harbor Cafe is a beautiful spot along the channel near Northside Marina. Here you can enjoy a classic lobster roll and maybe a cup of clam chowder. Come prepared with USD, they are cash only and BYOB.

In Eastham, you will love dining at Arnold’s Lobster and Clam Bar. A wonderful spot to dine with kids, they have a mini golf course where you can spend a few hours as the kids can burn off some energy.

If you find yourself in Falmouth, motor on over to Quahog Republic Dive Bar for one of the best lobster rolls on the planet. It is a small, out of the way bar with killer cuisine.

Whale Watching

Exploring Cape Cod
Whale Watching

There are lots of great options when it comes to Cape Cod whale watching. The Cape Cod Chamber of Commerce has an extensive list of vendors. The proximity to the whale feeding ground Stellwagen Bank, a National Marine Sanctuary, almost guarantees whale sightings.

Check out my Tips on Whale Watching so you are well prepared before you sail.

A Day On The Upper CapeExploring Cape Cod

The Upper Cape is the Cape Cod closest to the mainland, comprising the towns of Bourne, Sandwich, Falmouth, and Mashpee. You only have to navigate over the bridge and you are ready for a glorious toes-in-the-sand experience.

Area Beaches

The lovely Monument Beach is one of the few beaches in Bourne with a daily parking fee option. Most of the other Bourne beaches require a resident sticker or a parking sticker for campers or rental stays.

Sandy Neck Beach in Sandwich and the next town, Barnstable, is blessed with beautiful high dunes along Cape Cod Bay. Off roading is a fabulous way to explore Sandy Neck, it will require a permit.

In Falmouth there are three popular beaches that offer day passes. Surf Drive Beach with views of Nantucket and Martha’s Vineyard is a beautiful option. The soft sand of Old Siver Beach is the perfect spot to spend a day relaxing on your beach blanket. Menauhant Beach is less crowded than the other Falmouth beaches, but the sand can be a bit rocky.

Cape Cod Winery

Exploring Cape Cod
Cape Cod Winery

Resting in a pretty little spot in East Falmouth is Cape Cod Winery. Know for their Dry and Semi-Dry Rose – Mermaid Water, the winery is a perfect spot for a quiet afternoon to enjoy a fight and a nosh.

Sandwich Glass Museum

Exploring Cape Cod
Sandwich Glass Museum

The Sandwich Glass Museum offers guests a delightful mix of old and new. Stunning modern blown glass exhibits seem perfectly at home next to vintage glassware on display. Be sure to plan your visit to include a live glass blowing demonstration. They are scheduled on the hour every day beginning at 10 a.m.

Woods Hole Science Aquarium

Exploring Cape Cod
Woods Hole Sunset

A visit to Woods Hole is a fun alternative to the beach. Home to the Woods Hole Oceanographic Institution, where marine science is the study focus. It is also home to the Woods Hole Science Aquarium, a charming aquarium where you can view local marine life.

A Day On The Mid CapeExploring Cape Cod

When you consider the Mid Cape, it is composed of the towns of Dennis and Yarmouth. It also includes the city of Barnstable with it’s seven villages: Barnstable Village, Centerville, Cotuit, Hyannis, Marstons Mills, Osterville, and West Barnstable. Filled with historic homes, this area has charming old town appeal.

Area Beaches

The beaches on the Mid Cape rest on Nantucket Sound in the south and Cape Cod Bay in the north. While many beaches are resident sticker only, there are several beautiful beaches that have day parking.

A popular Centerville beach is Craigville Beach. Even though there is a large parking lot, you need to arrive early to secure a spot at this beautiful beach.

If your destination is Hyannis, there are a few beaches that have day parking options. Sea Street Beach is a public beach in Hyannis Harbor. It is withing walking distance to many downtown rentals. On Ocean Street is the family oriented Veterans Beach. At the end of Ocean Street is Kalmus Beach, known for outdoor activities and a great windsurfing beach.

In West Yarmouth the most popular beach for the 20 something crowd is Sea Gull Beach. Other West Yarmouth beaches include Bay View Beach, Colonial Acres Beach, and Englewood Beach.

A wonderful, family friendly beach is Smugglers Beach (aka Bass River Beach) in South Yarmouth.

Sunset aficionados will love Bass Hole Beach (aka Gray’s Beach) in Yarmouth port.

Dennis has some of the prettiest beaches on Cape Cod. Chapin Beach is one of The Cape’s best kept secrets (or it was once upon a time). A gorgeous sandy beach with long tidal flats. One of my favorite beaches is Mayflower Beach; a long stretch of soft white sand. It is the best way to spend the day soaking up summer sunshine, especially at low tide when the beach is wide. A great family beach is Corporation Beach.

A Day On The Lower CapeExploring Cape Cod

The eastern side of The Cape is known as the Lower Cape, it includes Harwich, Brewster, Orleans, and Chatham.

The Beaches

In the beautiful town of Orleans, you will find two beaches. Nauset Light Beach is part of the Cape Cod National Seashore. The pretty Skaket Beach is another family friendly beach.

Brewster Beaches include the popular Breakwater Beach and Crosby Landing Beach. A beautiful sandy location, Ellis Landing Beach, offers very little parking. And like most Brewster beaches, Robbins Hill Beach offers little in the way of amenities.

A visit to Cockle Cove Beach in Chatham is perfect for a family beach day. Also, Hardings Beach is a great option offering restrooms and lifeguards.

Red River Beach and Pleasant Road Beach are two Harwich Beaches that are perfect for spending a day in the Nantucket Sound sunshine.

Cranberry Bog

Exploring Cape Cod
Cranberry Bog

At one time, cranberries were widely farmed across Cape Cod. Today only a few working cranberry bogs still exist. You can tour Cakounes’ cranberry farm and learn why a bog requires a full 12 months of tender loving care.

Chatham Marconi Maritime Center

Exploring Cape Cod
Marconi Maritime Center

History buffs will be enchanted with the Chatham Marconi Maritime Center. STEM enthusiasts of all ages will enjoy exploring the 1921 ship-to-shore radiotelegraph station and the history of the Marconi/RCA-Wireless museum.

Nickerson State Park

Exploring Cape Cod
Nickerson State Park

If you love to camp, Nickerson State Park is a great spot for outdoor activities. Sections of the park run along the CCRT. It has waterfront lake swimming, excellent hiking trails, and over 400 campsites. You can even rent a yurt, so you don’t have to pack your tent.

A Day On The Outer CapeExploring Cape Cod

The Outer Cape comprises five towns: Provincetown, Truro, Wellfleet, and Eastham. This area is part of the stunning Cape Cod National Seashore.

Area Beaches

Explore Cape Cod
Cahoon Hollow Beach

Most of the beaches in Wellfleet require a sticker for parking. Cahoon Hollow Beach, a sandy haven for the college crowd, has a daily parking fee. Nestled next to the Beachcomber restaurant and bar, a popular gathering spot. White Crest Beach is another public beach with an extremely steep climb down the dunes to the beach — not the spot to be lugging all the beach toys. A wonderful National Seashore option is Marconi Beach.

Provincetown, the very tip of Cape Cod has two National Seashore Beaches, Herring Cove Beach and Race Point Beach.

Commercial Street

When you visit Provincetown, a stroll down Commercial Street, the main drag, is the first thing on everyone’s to do list. The sidewalks and road are jammed with locals and tourists wandering in and out of the many shops and restaurants. From inviting art galleries to ice cream shops, you can immerse yourself in the LGBTQ bustling enclave.

Provincetown, P-town to locals, is a day trip from everywhere on Cape Cod. It is also easily accessible by ferry from Boston.

Pro Tip: Fur babies are welcome almost everywhere!

Travel Itinerary: 3 Days on Cape Cod

Exploring Cape Cod
Hydrangea Landscaping

A getaway vacation Exploring Cape Cod can take on a variety of itinerary goals — fine dining, beachy days, fun filled nights, or simply enjoying the sun and surf. Whatever your vacation style, visiting Cape Cod most likely has just what you need for a wonderful vacation break. As you explore Cape Cod, you will find more ideas on how to enjoy your vacation day and night adventures.

Happy Travels



Exploring Cape Cod


Don’t you just hate it when your phone battery is in the dreaded red zone? I always carry Fuel Rods with me. They give me a battery boost, they are rechargeable, and they work with iphones and androids. 

Travel health insurance when you are heading out of the country is an important consideration. Many policies don’t fully cover you outside of the US. I use Safety Wing for my international travels.

If you know me, you know I love a glass of wine (or two). My favorite mail order wine company is Naked Wines. I order a case every month or so – no judgment please. I love that they work with small independent winemakers and I get to choose what wine I want and when I want it delivered. 

Don’t forget to download my free packing list! It’s the perfect jumping off point to get your adventure started.

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  1. We have been to many beach communities along the East Coast, but somehow we have missed Cape Cod. You’re three day itinerary looks great: sign me up for a whale watch and a lobster roll!

  2. So much fun reading about Cape Cod and looking at your beautiful photos! I’ve always wanted to visit Cape Cod and still have it on my bucket list. I think I would beeline for the first place serving lobster rolls as soon I got there! 🙂

  3. We did an East Coast road trip last summer, and we considered trying to fit in Cape Cod, but in the end, we just couldn’t make it work. We’ll have to visit next time! I loved the parts of the East Coast we did see, and I can’t wait to do more exploring in the future! This looks like such a fun place to explore.

  4. There’s a lot to explore at Cape Cod. I like the beaches. pretty flowers and whale watching would be cool.