Cape Cod Vacation Planning Guide + Itinerary

Sharing is caring!

Cape Cod is a popular family beach vacation destination located off the eastern coast of Massachusetts. After just one visit, it quickly became one of our favorite places to date. The miles of beaches, sea life and adorable towns make it a great place to both relax and explore. Whether you’re looking for where to stay or things to do, this Cape Cod vacation guide will help get you started with planning the best trip for your family.

We’ve also included our itinerary from our recent family vacation in Cape Cod to help you plan the best trip!

One Week Cape Cod Itinerary 

  • Day 1
    • Drive to Cape Cod 
    • Check into Sesuit Harbor Hotel in Dennis, MA
  • Day 2
    • Breakfast at Grumpy’s Restaurant
    • Walk to Princess Beach
    • Lobster rolls at Sesuit Harbor Cafe for lunch
    • Cape Cod Museum of Natural History
    • Dinner at The Pheasant in Dennis Village
  • Day 3
    • Brunch at Hangar B in Chatham
    • Atlantic White Shark Conservatory
    • Seal Watching at Chatham Harbor + Shopping in Chatham
    • Dinner at Old Yarmouth Inn
    • The Ice Cream Smuggler 
  • Day 4
    • Donuts from Village Coffee
    • Mayflower or Corporation Beach
    • Check into The Soundings beachfront resort in Dennis Port
    • Fish and Chips at Kream N Kone
  • Day 5
    • Captain Baker Donuts 
    • Beach and pool day
    • Pizza takeout 
    • Ice cream at Sundae School Creamery in Dennis Port
  • Day 6
    • Monomoy Island Seal Cruise from Harwich Port
    • Shopping in Harwich Port + lunch at Cape Roots
    • Dinner on the patio at Pelham House Resort
  • Day 7
    • Whydah Pirate Museum (rainy morning)
    • Tide Pooling/ Beach in Dennis Port
    • Dinner at The Oyster Company
  • Day 8- Leave Cape Cod via Breeze Airways from Providence, RI

Getting to Cape Cod

Cape Cod is located south of Boston in Massachusetts, making it easily accessible from several major cities in neighboring states. Driving to Cape Cod is one of the popular ways to access this family beach destination. If you’re coming from Boston or New York, however, you can also travel to Cape Cod via ferry.

If you prefer flying into Cape Cod, there are several airports to choose from. While there are some small airports in Cape Cod that fly regionally, the Martha’s Vineyard airport is one of the only major airports located in Cape Cod. 

For more flight options via a short drive, you can fly to Cape Cod from the Boston Airport or Providence, Rhode Island airport. The distance from the Boston airport to Cape Cod is about 75 miles or 1.5 hours. If you prefer to fly into Providence Airport from Cape Cod, it’s an hour and 45 minute drive. (About 90 miles.)

Harwich Port Cape Cod Vacation Toddling Traveler
Harwich Port

The Best Time of Year to Visit Cape Cod

With Cape Cod’s coastal location in the Northeast part of the US, the winters are cold and the summers are a little milder than some east coast beaches further south. Cape Cod in the summer is one of the best (and also the busiest) times to visit Cape Cod. 

If you’re looking to avoid the crowds but still enjoy the warmer weather and ocean temps, we found early September in Cape Cod to be perfect. The temps were high 70s, the ocean warmed up enough for swimming and the summer crowds have mostly dispersed. 

Cape Cod Towns

The Cape Cod area is made up of several different towns, all of which have so much to offer in terms of restaurants, beaches and other activities. One of our favorite parts about Cape Cod was exploring the different towns while we were there.

Cape Cod is over 60 miles wide and is split up into the Upper Cape, Mid Cape and Lower Cape.

  • Upper Cape is the area you first enter when driving into Cape Cod, and it’s the closest to mainland Massachusetts. The towns here include Bourne, Falmouth, Mashpee and Sandwich. 
  • Mid Cape is centrally located and one of the best places to stay in Cape Cod if you plan to explore several different towns in Cape Cod. Barnstable, Dennis and Yarmouth make up the Mid Cape. 
  • Lower Cape includes the eastern towns in Cape Cod and extends all the way up to the tip of Cape Cod in Provincetown.  In addition to Provincetown, towns in the Lower Cape include Brewster, Chatham, Eastham, Harwich, Orleans, Truro and Wellfleet.
  • Martha’s Vineyard and Nantucket are two Cape Cod islands off the southern coast.

If you’re looking for the best Cape Cod towns for families, there are so many great options to choose from. We found Dennis, Harwich Port and Chatham to be some of the best towns to visit in Cape Cod, and each town is super charming in it’s own way. 

Cape Cod Towns- Captain Baker Donut Shop Toddling Traveler

Cape Cod Family Friendly Hotels & Resorts


There are a wide range of hotels in Cape Cod, from budget motels to luxury resorts. During our recent Cape Cod family vacation, we stayed at a few different Cape Cod family hotels to get a feel for different beach towns on the Cape. Our recommendations for Cape Cod kid-friendly hotels and resorts are below.

To find Cape Cod kid-friendly resorts, search here on Booking.com and filter by family friendly properties in Cape Cod. 

Sesuit Harbor House

For a great family-owned hotel in Dennis, MA in a quiet setting near the bay, be sure to check out Sesuit Harbor House. It offers breakfast with local coffee and pastries, a pool, fire pit and other activities. One of the highlights of this (kid friendly hotel in Cape Cod) was the little petting zoo area with 4 super friendly goats. You can get food to feed them and they are so friendly to kids of all ages. 

Search more hotels in Dennis, MA here

Sesuit Harbor House Cape Cod Hotel Toddling Traveler
Sesuit Harbor House

The Soundings Resort

The Soundings Resort by BlueGreen Vacations is the perfect option if you’re looking for timeshare rentals in Cape Cod. It’s a beautiful oceanfront resort in Cape Cod, located right by the Dennis Port harbor. The rooms have been recently updated, and our 2 bedroom vacation rental in Dennis Port also included a full kitchen, living area, two bathrooms and a balcony with ocean views. The resort also has an indoor and outdoor pool as well as games and fire pits. 

Search vacation rentals and hotels in Dennis Port, MA here.

Chatham Bars Inn

If you’re looking for Cape Cod luxury hotels, Chatham Bars Inn is the perfect option. Set on the Chatham harbor, the resort boasts a beautiful pool, beachfront access and one of the best waterfront restaurants in Chatham. There are also a variety of room sizes for every family, and it’s perfect if you’re looking for Cape Cod hotels with family suites. (It would also be great if you want a Cape Cod weekend getaway without kids!)

Search more resorts and hotels in Chatham, MA here



Booking.com

Beaches in Cape Cod

One of the things that made Cape Cod different from other east coast beach vacations we’ve taken before is the variety of beaches in Cape Cod.  The Cape Cod beaches on the northern coast vary significantly from the southern coast in terms of sand texture, roughness and temperature of the water and even sea life. (Even though it’s only about 8 miles from the ocean to the bay!) 

  • The southern part of Cape Cod borders the Atlantic Ocean, and the shoreline tends to be rockier and filled with shells. The water is also cooler throughout the summer. Many of the beaches on the ocean side are accessible via private access from resorts in Cape Cod, but there is public beach access as well.
  • The beaches on the Cape Cod Bay (the Northern part of Cape Cod) generally have softer sand. They are also calmer than the beaches on the ocean side and have some of the best Cape Cod beaches for kids of any age.  We loved Mayflower Beach and Corporation Beach, two great beaches in Dennis, MA.
  • There are also several beaches along the eastern side of Cape Cod, including the Cape Cod National Seashore. The National Seashore in Cape Cod includes some of the best Cape Cod beaches for families and spans about 40 miles from Chatham up to Providence. 

In addition to the ocean and bay side beaches, Cape Cod is filled with almost 1,000 ponds, many of which have sandy beaches available for either private or public access. These lakefront beaches in Cape Cod are another great option for playing in the sand with littles.  We loved Princess Beach, which is walking distance from the Sesuit Harbor House.

Dennis Port Beaches Cape Cod Vacation- Toddling Traveler
Dennis Port Beach

More Things to Do in Cape Cod 

There are so many fun things to do in Cape Cod besides the beach, that it can be hard to know where to start! From museums to sea life and shopping, a Cape Cod, MA vacation is perfect for anyone who enjoys sightseeing on a beach vacation. Below are a few of our recommendations for things to do on vacation in Cape Cod, Massachusetts. 

Visit One of Many Cape Cod Museums

Cape Cod is a place that’s rich in history, making it perfect for museum goers. Whether you’re visiting Cape Cod with kids or without, there are several museums in Cape Cod for every age and interest.  (In fact, Cape Cod has over 80 museums!) These are also perfect if you’re looking for Cape Cod indoor activities on a rainy day. 

  1. Cape Cod Museum of Natural History is a great place for families to explore. There are several indoor exhibits that showcase the people and animals native to Cape Cod and also explore hands-on. Outdoors, you can take a nature walk through the marshes or reserve a time for the butterfly house. 
  2. Whydah Pirate Museum in Cape Cod is perfect for those wanting to learn about the Whydah shipwreck and Cape Cod’s history of piracy. (Full disclosure, it was a little too crowded here for us.)
  3. Chatham Shark Center is essentially a shark museum that covers the history and types of sharks found in Cape Cod. The Atlantic White Shark organization also focuses on recovery of Atlantic White Sharks (like the movie Jaws!) and grey seals. 
  4. John F Kennedy Museum in Hyannis captures JFK’s legacy in Cape Cod, a place he has a strong connection to. 
  5. Heritage Museum and Gardens in Sandwich, MA is a unique museum for families with several different indoor exhibits (including a carousel) and beautiful gardens to explore. 
Cape Cod Museums Natural History Toddling Traveler
Cape Cod Museum of Natural History

Book a Whale or Seal Watching Cruise

Monomoy Island is located off the coast of Chatham and is known for the Cape Cod seals that gather around it. The Monomoy Island Seal Cruise is a fun way to see seals up close and learn more about Cape Cod as you go. It also takes you by the scenic Wychmere Harbor and a few lighthouses in Chatham. 

Wondering where to see seals in Cape Cod without the boat ride? Chatham Pier is one of the best places to go seal watching in Cape Cod.  It overlooks the harbor and there’s a great upper deck area for watching the seals and boats go by.

There are also several whale watching cruises in Cape Cod that depart from Provincetown or Barnstable. Popular whale watching tours from Cape Cod include:

Monomoy Island Seal Watching Cruise Cape Cod Toddling Traveler
Monomoy Island Seal Cruise

Go Shopping in Cape Cod

There are so many cute towns in Cape Cod that it’s worth spending a few afternoons exploring and visiting the local shops in Cape Cod. Our favorite towns to visit during our trip were Harwich Port, Dennis Village and Chatham.  If you’re looking for locally made clothing and unique gifts in Cape Cod, Buoys on Main in Harwich Port was one of our favorite stores.

Provincetown and Hyannis are two Cape Cod towns that are on our list for a future visit. For more commercialized shopping in Cape Cod, there’s also the Cape Cod Mall in Hyannis.  

Search for Lighthouses

Cape Cod has about 14 lighthouses surrounding the coast of Cape Cod. Most of the lighthouses in Cape Cod were built in the 1800s, and each comes along with its own history. There are several operational lighthouses in Cape Cod like Long Point Light, while others like are privately owned. One of the best lighthouses to visit in Cape Cod is Nauset Lighthouse. (If you’re a fan of Cape Cod potato chips, you may recognize the lighthouse from the bag!) You can tour the Nauset Light while visiting the adjacent Cape Cod National Seashore, making it one of the most popular Cape Cod tourist attractions.

Scargo Tower, although not a lighthouse, has some of the best views and is easy to climb up. We recommend stopping here as well if you’re looking for things to do in Dennis, MA or happen to be in the area.

You can find a map of Cape Cod lighthouses and more information here

Chatham lighthouses in Cape Cod Toddling Traveler

Enjoy the Beautiful Sunrises and Sunsets 

With Cape Cod being a relatively narrow body of land, it’s easy to enjoy both sunrises and sunsets in Cape Cod. The best places to watch the sunrise in Cape Cod are typically on the southern and eastern part of the Cape. Dennis Port in particular had the most beautiful sunrise we saw on our trip, and the way the light hits the shoreline is so pretty. 

Rock Harbor in Orleans is known as one of the best places to watch the sunset in Cape Cod, but we also enjoyed the sunsets in Dennis as long as we had a good angle.  (Although when traveling with a baby and toddler we tend to catch more sunrises than sunsets!) 

Dennis Port Best Sunrise in Cape Cod Toddling Traveler

Take the Ferry to Martha’s Vineyard or Nantucket

If you’re not staying on one of Cape Cod’s islands but still want to explore them, it’s very doable! Both MV and Nantucket are islands south of Cape Cod that are popular New England summer destinations for families.  They each have a number of unique shops, restaurants and places to stay, along with their own unique history since being founded in 1602. 

You can take the ferry to Martha’s Vineyard from Cape Cod from Woods Hole, MA. The schedule for the Martha’s Vineyard ferry can be found here

The ferry from Cape Cod to Nantucket also runs daily from several locations in Cape Cod. (There’s even a ferry from NYC to Nantucket!) The Nantucket ferry schedule can be found here

Looking for more ideas for day trips from Cape Cod? Boston, Plymouth Harbor and Newport Rhode Island are all great options.

 

Best Places to Eat in Cape Cod

With Cape Cod being mostly surrounded by water, it’s no surprise that seafood is super popular. From lobster rolls to fish and chips and more, you certainly won’t go hungry while vacationing in Cape Cod!  Below are a few recommendations for some of the best restaurants in Cape Cod. 

  • Sesuit Harbor Cafe for one of the best lobster rolls in Cape Cod. It’s BYOB and cash only with scenic views of the harbor. The long line goes pretty fast.
  • Kream N Kone in West Dennis for some of the best fish and chips in Cape Cod in a casual setting.
  • The Pheasant in Dennis is a foodie hotspot in a casual outdoor setting. 
  • Grumpy’s Restaurant for the best breakfast in Cape Cod with a huge menu to choose from. 
  • Hangar B Eatery in Chatham for some of the best brunch in Cape Cod.  You can grab a coffee at the counter and watch planes take off as you wait to be seated. 
  • Pelham House Restaurant for fine dining in Cape Cod that’s still very family-friendly. The beach front patio has live music and is great for littles who want to run around.
  • Old Yarmouth Inn for a mix of seafood and steak in Cape Cod. (The outdoor garden patio is perfect during the summer in Cape Cod!)
  • The yummiest donuts in Cape Cod at Captain Baker Donuts in West Dennis or Village Coffee Shop in Dennis, MA

Ice Cream Shops in Cape Cod

No Cape Cod family vacation is complete without trying at least one of many places for ice cream in Cape Cod. There were so many great ice cream shops in Dennis, and some the best ice cream in Cape Cod includes:

Note: Many restaurants and ice cream spots in Cape Cod are cash only. It’s also not uncommon to eat a really nice dinner on a picnic table. It’s part of the charm!

Have you been on a Cape Cod family vacation before? Please share any of your favorites in the comments below. It’s a family beach destination we’ll definitely be back to!

Related Posts

Like this post? Click on the image to save it for later!

Itinerary for Cape Cod Vacation Guide- Toddling Traveler

Leave a Comment