5-Day Cape Cod Itinerary for the Perfect Trip

Where to Stay in Cape Cod

Cape Cod is the land of sun, sand, and picturesque sunsets. But where to rest your head after a glorious day of beach-hopping?

We’ve got you covered with the coziest and most charming spots to lay your weary head.

Kick off those flip-flops, take a deep breath of that salty sea air, and let us guide you to your perfect home away from home on the Cape.

Chatham Bars Inn: This historic luxury resort is a seaside sanctuary that’s been welcoming weary-minded folks since 1914.

A true Cape Cod classic, the Chatham Bars Inn offers breathtaking ocean views and top-of-the-line amenities.

Grab a morning coffee on their beautiful veranda while you soak in some sunshine, or indulge in their on-site spa for some well-deserved pampering.

The Old Harbor Inn: Located in the heart of charming Chatham, The Old Harbor Inn is a cozy and inviting bed and breakfast that will quickly become a cherished coastal classic.

With homemade breakfast, plush bedding, and harbor views, you’ll feel like royalty in your waterfront oasis.

A Little Inn on Pleasant Bay: This delightful spot will live up to its name, we promise! The Little Inn on Pleasant Bay offers an intimate atmosphere with a touch of European flair.

Situated between Chatham and Orleans, it’s prime beachfront real estate, with easy access to all the sights and sounds of Cape Cod.

Soak in the stunning bay views while sipping on afternoon tea and daydreaming of seashells.

Do You Need More Than 5 Days for Cape Cod?

First off, 5 days in Cape Cod might sound like an eternity to some, but trust us, this delightful destination has so much to offer that you’ll feel like time just flew by.

For first-timers, a 5-day vacation is recommended to truly appreciate the captivating beauty of Cape Cod.

While a weekend getaway might work for a quick recharge, you’ll need at least 5 days if you want a full immersion into the Cape Cod magic.

Cape Cod is brimming with picturesque beaches, scrumptious seafood, vibrant culture, and enchanting activities. As such, it can be a struggle to fit everything into a limited time frame.

But hey, that’s where the magic of a well-planned 5-day itinerary comes in. With that, you can be sure to catch all the highlights this spectacular destination has to offer while also leaving some room for spontaneous adventures.

Now, if you’re privy to the idea of extending your trip beyond 5 days, more power to you! Cape Cod still has a wealth of hidden treasures waiting to be uncovered.

While 5 days in Cape Cod is absolutely a reasonable starting point, the bottom line is that the ultimate length of your trip depends on your own pace and preferences. After all, it’s your journey, and you get to shape it just the way you like.

Day 1: Arrival and Exploring Hyannis

Stay tuned as we dive deeper into the fantastic adventures that await you on Cape Cod. Rest up and get ready!

Check-In and Unwind

You’ve just arrived at beautiful Cape Cod, ready for an awesome 5-day adventure; time to check in and unwind in the comfort of your lodging.

Put on some comfy clothes, kick off your shoes, and relax for a bit. Trust us, you’ll want to be fresh and rejuvenated to fully enjoy the fun that lies ahead.

Hyannis Harbor Walk

Once you’ve got your energy back, it’s time to start exploring! Begin with a leisurely stroll along the Hyannis Harbor Walk.

This picturesque walkway offers stunning views of the harbor and leads to some fabulous local attractions.

Keep an eye out for the JFK Memorial and picturesque boats bobbing in the water – they’re charming sights you won’t want to miss.

Explore Main Street

After your harbor walk, make your way to Hyannis’ lively Main Street! Bursting with an array of shops and eateries, walking along this street is a treat in itself.

Do yourself a favor and savor some mouth-watering seafood or swing by a vibrant art gallery to admire the works of local artists.

Who knows? You might even find a little treasure to take home as a memento of your fabulous Cape Cod journey.

Day 2: Nantucket Adventure

By the end of your Nantucket adventure, you’ll feel like a true islander; you might just find yourself singing a sea shanty as you board the ferry back to Cape Cod.

Ferry Ride to Nantucket

All aboard! Today’s the day for an epic Nantucket adventure. Start your day by hopping on a ferry from Cape Cod to the picturesque island of Nantucket.

Feel the sea breeze tousle your hair as you enjoy the sights and sounds of the ocean during your journey.

Island Tour

Once your feet touch Nantucket’s shores, get ready to explore its bountiful beauty. Hop on a guided island tour and take in the breathtaking scenery, from the idyllic beaches to the quaint, cobblestone-lined streets.

Keep your camera handy as you’re bound to spot Instagram-worthy photo ops at every turn.

A few highlights to check out during your island tour are the famous Nantucket lighthouses, historic homes, and stunning gardens. Do take a leisurely stroll or rent a bike to soak in Nantucket’s charm.

Nantucket Whaling Museum

Conclude your day by stepping back in time at the Nantucket Whaling Museum. This treasure trove of whaling history and artifacts awaits you, a mid-1800s candle factory turned must-visit destination.

Uncover the nautical tales that shaped Nantucket’s heritage and feel a connection to its seafaring past.

Get up close and personal with the impressive, 46-foot-long sperm whale skeleton hanging overhead in the museum’s main exhibit.

Spend time browsing the galleries, marveling at scrimshaw art, and, if you’re keen, attend one of their engaging and informative presentations.

Day 3: Martha’s Vineyard Getaway

On your thrilling island getaway, you’ll be immersed in an array of picturesque beauty, charming towns, and lighthearted fun that can only be found on Martha’s Vineyard.

With these exciting stops in your 5-day Cape Cod itinerary, you’ll undoubtedly have tales to tell and memories to treasure for a lifetime.

Morning Ferry to Martha’s Vineyard

Rise and shine, it’s time for a maritime adventure Get ready to hop on a ferry and set sail for the enchanting island of Martha’s Vineyard.

With the crisp morning air in your lungs and the salty sea breeze on your face, prepare to embark on a day full of exploration and excitement.

Visit Edgartown and Oak Bluffs

As you step off the ferry, you’ll be greeted by two stunning towns that invite you to uncover their hidden treasures.

Marvel at the quaint charm of historic Edgartown, where you’ll find fascinating museums, unique boutiques, and delightful eateries. Don’t forget to grab a locally-inspired snack to fuel your escapades.

Next on the list: Oak Bluffs, a whimsical wonderland just begging to be explored. Stroll through streets adorned with colorful gingerbread cottages and capture that perfect Instagram-worthy moment.

Swing by Ocean Park for a peaceful picnic or simply soak up the glorious sea views. The world is your oyster, and Martha’s Vineyard is the pearl waiting to be discovered.

Aquinnah Cliffs and Lighthouse

Now brace yourself, because your Vineyard venture is about to reach new heights! Make your way to the breathtaking Aquinnah Cliffs, a geological masterpiece that’ll leave you in awe.

Marvel at the stunning scenery, snap a few photos, and then prepare for the cherry on top: the Aquinnah Lighthouse.

Climb its winding stairs for panoramic vistas, and don’t forget to give yourself a pat on the back for conquering these captivating Cape Cod wonders.

Day 4: Charming Provincetown

Ready to sort out day four of your itinerary? Go ahead and have a blast exploring charming Provincetown.

Discover Provincetown

Provincetown, a short one-hour drive from Chatham, is a delightful mix of art, culture, and history.

With 60,000 annual visitors, this buzzing coastal town is perfect for strolling through galleries, hopping into quirky cafes, and just soaking in the vibrant atmosphere. Did we mention the mouthwatering seafood options?

Activities at Race Point Beach

Get ready to soak up some sun at the stunning Race Point Beach in Provincetown on your fourth day at Cape Cod.

Bring your sunscreen and get ready to make a splash as you dive into refreshing waters or walk along the soft sand.

Make sure to sneak a glance at the mesmerizing sunset as the sky turns into a palette of colors – it’s a must-see!

Province Lands Bike Trail

Feeling adventurous? Grab your helmet and conquer the scenic 5.45-mile loop on the Province Lands Bike Trail.

This picturesque trail weaves through the woodlands, ponds, and beaches, offering breathtaking views and countless opportunities for picture-perfect memories.

After a day of biking, you’ll feel like a total champ as you look back at a trail well-traveled.

Day 5: Departure and Last-Minute Shopping

Oh, how time flies! It’s already your last day in the beautiful Cape Cod. But worry not, we’ve got you covered with some last-minute shopping and strolling around, soaking it all in before you bid this lovely place goodbye.

Final Stroll in Hyannis

Rise and shine! Let’s seize the day by taking a leisurely walk in the lovely town of Hyannis. Stroll along the picturesque Main Street, savoring the vibrant atmosphere one last time.

Hyannis is packed with quaint shops, cafes, and galleries perfect for last-minute souvenirs or just for that perfect selfie with “Cape Cod” written all over it.

Cape Cod Mall Shopping

Now it’s time for an action-packed shopping adventure at the Cape Cod Mall. This is the place to be for that last-minute retail therapy you’ve been craving, stocking up on all the Cape Cod goodies you want to take back home.

Be it cute little trinkets, artisanal products, or even locally themed clothing, you’ll find it all here. It’s your day, so treat yourself like the Cape Cod King or Queen that you are!

Farewell and Departure

As the sun begins to set on your epic 5-day Cape Cod adventure, it’s time to pack your bags, squeeze in those last-minute purchases, and prepare for the journey back.

We understand that saying goodbye is not easy, but Cape Cod will be waiting for you with open arms for your next visit. So, until next time!