THE GREATEST 5 DAY ITINERARY FOR YOUR NEXT VACATION TO CAPE COD, MASSACHUSETTS
When people think about Cape Cod, I feel like they don’t realize just how big the area actually is. I know I didn’t when I first experienced it’s wonders back in September of 2020. I’ll be breaking down this guide by different Cape towns we visited, but first I’ll explain how each town and even villages within them are split up.
Cape Cod comprises the county of Barnstable which itself is comprised of 15 towns and each town has its own constellation of villages. This had me very confused when I first visited but once I learned about all the little villages in each town it made it a lot easier! The Cape is divided into three portions—the Upper, Mid, and Outer Cape. The Upper Cape towns are: Bourne, Sandwich, Falmouth and Mashpee. Hehe yes… I said Mashpee. How cool would it be to say you’re from Mashpee?! Then there’s the Mid-Cape towns which consist of: Barnstable, Yarmouth, Dennis, Harwich and Brewster. Finally, we have the Outer Cape towns of: Orleans, Chatham, Eastham, Wellfleet, Truro and my favorite, Provincetown or P-Town.
THE GREATEST 5 DAY ITINERARY FOR YOUR NEXT VACATION TO CAPE COD, MASSACHUSETTS
Where to go on Cape Cod
Cape Cod is rich with recreation, from the artistic to the adventurous. Did you know Cape Cod has been named as one of the top ten spots in the world for whale watching, paddle boarding, kayaking and windsurfing? There are numerous things to do on the Cape, especially when it comes to outdoor activities. Cape Cod has more than 125 trail heads providing access to more than 600 miles of conservation trails owned and operated by various town conservation trusts or conservation departments. The region is also ranked among the ten most popular destinations in the U.S. for beaches and golf. The beaches are absolutely stunning. The Cape has world-class bike trails for things to do biking, and some of the best shopping around. I definitely purchased a Cape Cod & Nantucket sweatshirt! The Cape’s sweatshirt game is on point. The Cape and surrounding Islands also have been named among the top 25 arts destinations in the country for its wealth of galleries, art studios, and museums!
FALMOUTH
See the beautiful gardens and special exhibits at Highfield Hall
Highfield Hall & Gardens is a must for all your history buffs or even those who like to get outside and enjoy trails and gorgeous flowers. It’s not your typical historic estate — Highfield is a vibrant cultural center surrounded by restored gardens, peaceful walking trails and conservation land.
The magnificently restored 1878 estate of the Beebe family has been transformed into a vibrant center of cultural and community life on Cape Cod. The story of this property is a dramatic one as it was, literally, saved from the wrecking ball in 1994 and lovingly restored, opening as a museum and historic site in late 2006. From 2011 to 2013, the property’s two magnificent gardens also underwent restoration.
DENNIS
Spend the day at West Dennis Beach
West Dennis Beach is a gorgeous 2 mile long beach with plenty to do. While on the Cape we went to West Dennis Beach 3 times — that’s how much we loved it. With the beach being as nice as it is, it does require fees. The fees are: $40 per year for residents, $20 on weekdays and $25 on weekends and holidays for non-residents, $75 for a weekly pass, & $300 for the season. To purchase passes you can head to the Dennis Town Hall at 485 Main Street. We were able to borrow a family friends pass while visiting which is probably why we visited this beach so often. I highly recommend hitting up a Trader Joe’s and creating a fun charcuterie board to enjoy on the beach. We loved just sitting on the beach, eating our yummy food, and listening to the waves roll in. Oh and definitely spend a morning watching the sun rise on the beach — it’s truly breath-taking.
CHATHAM
Explore the Chatham Lighthouse
Lighthouses on Cape Cod are kind of a big deal.. So of course, I would recommend going on a lighthouse trek across the Cape and even Martha’s Vineyard & Nantucket. What’s great about the Chatham Lighthouse is that it’s across the street from a gorgeous beach you can visit as well — best of both worlds. Did you know there used to be two lights in this location?! The Chatham Lighthouse has a rich history, as most places on the Cape. You can read all about that history here. Additionally, they have tours of the lighthouse, but unfortunately they were closed while we were visiting. Be sure to check their schedule here before your visit.
Watch the sunset on Lighthouse Beach
Lighthouse Beach is another one of my favorite beaches on the Cape because of it’s beauty, accessibility, and it’s free! While you’re visiting The Chatham Lighthouse absolutely head over to Lighthouse Beach quite literally across the street. There is a decent amount of parking on the street and then the stairs to the beach are right off of the street too. I will say, this is one of the beaches I do not get in the water at because of great white sharks. There are a decent amount of seals in the area so with that, comes the big girl sharks. I actually downloaded an app to see where the great white shark sitings are and they include photos — it’s so cool! However, you don’t need to get into the water to enjoy Lighthouse Beach’s beauty. We walked up and down the beach looking for shells, sea critters, and more.
EASTHAM
Learn about the Three Sisters who lit the way
The Three Sisters are kind of a big deal.. they are a trio of historic lighthouses off Cable Road in Eastham. The original three brick towers fell into the sea due to erosion in 1890 and were replaced with wooden towers on brick foundations in 1892. We were actually headed to see the Nauset Lighthouse which is the lighthouse on the front of the Cape Cod potato chips — but there wasn’t any parking. As we were headed to Chatham we saw a small little parking lot and pulled over to find these three lovely ladies. I highly recommend adding them to your lighthouse trek and if you’re up for a little walk you can head over to the Nauset Light.
WELLFLEET
Atlantic White Cedar Swamp Trail at The Cape Cod National Seashore
For my trail walkers and even hikers, this one’s for you! The Cape Cod National Seashore is an absolute must visit while on the Cape. The National Seashore consists of forty miles of pristine sandy beach, marshes, ponds, and uplands support diverse species. It’s kind of wild seeing the sandy beaches and then hiking through the forest and coming upon marsh and swamp lands. The Atlantic White Cedar Swamp Trail is a 1.2 mile loop and takes about one hour. I will say, wear bug spray.. if you can find environmentally friendly bug spray wear that. Once we got to the swamp part of the trail the mosquitos were out full force. We actually ran through the swamp part because they were so bad, however, it was a beautiful trail. Additionally, it could have been the time of day we were there that brought out more bugs than normal. Haha, basically I’m saying check it out but be warned!
Marconi and the South Wellfleet Wireless Telegraph Station
While we were in the parking lot of Atlantic White Cedar Swamp Trail at The Cape Cod National Seashore we saw a bunch of people walking to the opposite side so we grabbed our bathing suits and walked over. We initially thought the beach was around the corner but come to find out it was a long way down… as you can see from the photos. However we stumbled upon something really cool we never would have sought out — the site of the first United States Transatlantic Wireless Telegraph Station. Then we immediately understood how high up we were, haha! While we were up there they had plaques walking you through the history of the wireless telegraph station which I personally love. I’m a big fan of visiting museums and historical sites while on trips or even vacations.
BONUS! While we were there Ana mentioned she saw something down in the water bobbing
PROVINCETOWN
Commercial Street
When you visit Provincetown you absolutely have to take a stroll down Commercial Street. It’s essentially the main street of P-Town. All the main shops, restaurants, and art galleries are off Commercial. You can walk a little off Commercial and find some cool places too. We did walk a block or two off Commercial to go to a restaurant that looked super cute but the wait was an hour and a half so we passed BUT what I’m trying to say is experience Commercial Street as a tourist then explore more if you have the time.
Bob Gasoi Memorial Art Alley
Provincetown is kind of known for their art galleries and even art alleys like this one. While walking on Commercial Street you’re sure to come upon Bob Gasoi Memorial Art Alley. This alley is full of whimsical and eclectic art pieces that are sure to amuse! This is one of the reasons I love P-Town so much you can just be walking down the street and see a cool place like this or a fun shop selling cool gifts or t-shirts.
Catch a ferry over to Nantucket or Martha’s Vineyard
What’s great about Cape Cod is that you’re only a ferry ride to Nantucket or Martha’s Vineyard! Every time I visit the Cape, I like to spend at least a day popping over to the other magical islands that make Cape Cod so amazing too. The Hy-Line Ferries are awesome boats that can take you to Nantucket or Martha’s Vineyard or even both in one day. You can purchase your tickets online ahead of time, which I recommend because the ticketing office can get a little crowded. Additionally, you can purchase parking tickets ahead of time. One thing I will mention is that if you leave on day A and return on day B you have to buy a paring pass for 2 days which kinda blows but our car was safe and locked in while we stayed the night on Martha’s Vineyard. I’ll be writing a post all about these special islands too so stay tuned for that.
Where to eat on Cape Cod
Cape Cod is definitely not lacking in the food department… They have everything when it comes to seafood and it’s extremely fresh. From Provincetown to Sandwich, there are numerous options for casual dining to oyster shacks and of course luxury dining as well. We ate fresh oysters, some of the most delicious pizza I’ve ever eaten, and of course fresh lobster rolls! We even found out that $26 for a lobster roll is relatively cheap!
I’m sharing a full blog post dedicated solely to dining on the Cape! You’ll absolutely want to read all about that here.
Where to stay on Cape Cod
The Lighthouse Inn
Situated on nine secluded oceanfront acres, this resort offers a private sandy beach, heated pool, tennis courts, family activities and a full service restaurant with panoramic ocean views. It’s truly a great place to relax and just soak in the sea breeze. Lighthouse Inn is welcoming guests for their 83rd season and Bass River Light is 160 years old — which is pretty cool. As a travel blogger, I try to stay at hotels and resorts that have a rich history and Lighthouse Inn isn’t lacking in that department. Be sure to read all about it here. This resort will take you to a time gone by…secluded and relaxing, with refreshing ocean breezes to rejuvenate your spirit. Situated on nine secluded oceanfront acres, this resort offers a private sandy beach, heated pool, tennis, family activities and a full service restaurant with panoramic ocean views and delicious cocktails.
Be sure to check out my full blog post on The Lighthouse Inn here.
Bayside Resort Hotel
Bayside Resort Hotel is located in close to beaches, restaurants, shopping, ferries, and various other Cape Cod attractions in West Yarmouth. We came in from the ferry dock in Hyannis and the drive from there to Bayside Resort Hotel was a short 8 minute drive. What makes Bayside Resort Hotel so special is that they’re locally owned and managed with the all amenities of the newest chain hotels plus the look, feel and charm of the Cape.
Be sure to check out my full blog post on Bayside Resort Hotel here.
Are you ready to start planning your trip to the Cape? Let me know if you have any questions!
XOXO
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