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This Cape Cod Road Trip Itinerary Will Make You Want to Pack Your Bags Now

Whether you’ve visited Cape Cod every summer since you were a child or you’re planning to go for the first time, you’ll discover that it is equal parts fresh and familiar. There’s something so unbelievably invigorating about the way that the natural light dances along the coast. Even more, the smell of the salty air seems to complement the gentle breeze that graces your cheeks perfectly. Read on for some great suggestions to include in a Cape Cod road trip itinerary.

17 Wicked Good Stops to Add to Your Cape Cod Road Trip Itinerary

A visit to Cape Cod is easily one of the most romantic getaways in New England!

1. Bourne

Bourne is the first town you’ll drive through on the Cape. Whether you’re trekking from Boston on vacation or planning a scenic drive from New York, you’ll appreciate stopping here to stretch your legs. The Cape Cod Canal is an excellent spot to walk around, ride your bike, or sit back and relax!

2. Falmouth

Falmouth Harbor is located on the south side of Cape Cod halfway between Newport, RI and Nantucket Island.

Falmouth radiates with an intriguing history, coastal charm, and New England vibes. Revel in a culinary scene that proudly boasts a sustainable, locally-sourced approach to cooking. There’s nothing quite like artisanally crafted meals prepared with the freshest seafood and produce that is found at restaurants such as Water Street Kitchen and C Salt Wine Bar and Grille. While you’re in town, you might also want to cruise the Shining Sea Bikeway, stroll through the Cornelia Carey Sanctuary, or visit the Nobska Point Lighthouse.

Stay at The Captain’s Manor Inn

the captains manor inn bedroom

One of many historic Captain’s homes turned into bed and breakfasts on the Cape, The Captain’s Manor Inn dates back to 1849! Enjoy the close proximity to the beach, well-manicured gardens, and beautiful accommodations.

Captain’s Manor Inn

Stay at The Palmer House Inn

Palmer House Exterior Victorian Style

The Palmer House Inn is a turn-of-the-century architectural marvel of a B&B. The Queen Anne style of this Cape Cod house, the gourmet breakfasts, and stylish bedrooms set the scene for an unforgettable getaway.

The Palmer House

3. Sandwich

Sandwich, Massachusetts, offers the perfect combination of arts & culture, and outdoor adventures. Peruse exhibits at the Heritage Museums & Gardens or the Sandwich Glass Museum. Stroll along the boardwalk with your sweetheart. Or, just relax on Sandy Neck Beach!

4. Mashpee

Mashpee, MA, is a small town you’ll drive through on your way through the Cape. For family-friendly fun, check out the Cape Cod Children’s Museum. Then, explore local shops and restaurants at Mashpee Commons.

5. Barnstable

The Long Pasture Wildlife Sanctuary in Barnstable will be a welcome change of pace from all the traveling. Sandy beaches meet beautiful marshland, butterfly-filled meadows, and woodland trails. You can even paddle out on your kayak if you’re feeling adventurous!

6. Yarmouth

Beach roses growing wild on the New England coast

Yarmouth is full to the brim with unique cultural attractions and beautiful beaches. Take a tour of author and illustrator, Edward Gorey’s house. Scour the shelves of antique shops for unique wares. Lay out under the warm sun on Seagull, Bass River, or Gray’s Beach. If you have kids with you, be sure to check out the Whydah Pirate Museum!

Stay at The Inn at Cape Cod

The Inn at Cape Cod Staircase

Have you ever wondered what it’s like to stay in a home that is on the National Register of Historic Places? The Inn at Cape Cod manages to capture the rich history of Cape Cod while offering all of the conveniences of modern lodging. The house sits on two acres of meticulously manicured gardens and overlooks a 100-acre nature preserve.

The Inn at Cape Cod

7. Dennis

In addition to an abundance of gorgeous stretches of pristine beaches, you will also find some one-of-a-kind shops, museums, and galleries in Dennis. Watch the birds soar overhead at Mayflower Beach. Then, check out the Cape Cod Museum of Art and Scargo Stoneware Pottery & Art Gallery.

8. Brewster

point of rocks beach brewster ma

Brewster is one of the most recognized coastal towns on Cape Cod. Grab a lobster roll for lunch or check out a five-star dining establishment for a unique spin on New England clam chowder. Hunt for seashells and look out for natural wonders along the Cape Cod National Seashore. Then, pedal your troubles away on the Cape Cod Rail Trail. You might even enjoy hunting for a special souvenir along Highway 6A to bring home for yourself or a loved one.

Stay at Candleberry Inn on Cape Cod

Candleberry Inn Room beautiful window

There’s a light air of regency that accompanies a stay at a historic New England inn. Since 1790, Candleberry Inn served as a home to a sea captain, a senator, an author, and a painter. It was even a boys’ school at one point. Now guests from around the world can revel in the luxurious comfort of the modern world that so perfectly complements the historic charm.

Candleberry Inn

Captain Freeman Inn of Cape Cod

BrewsterRoom beautiful bed frame white linens

Stay in one of Captain Freeman Inn of Cape Cod’s upscale guest quarters. Natural light beams throughout the halls of the property, giving off a clean and refreshing air of sophistication. They pride themselves in their green, farm-to-table philosophy which is present in their delicious breakfasts. While you’re there, say hello to their labradoodle, Harrison!

Captain Freeman Inn

Old Manse Inn

Also nearby is the Old Manse Inn. Offering 12 deluxe rooms, all with private ensuite baths, air/heat, and some with fireplaces and jetted tubs. This beautiful romantic antique sea captains manor offers detailed amenities to ensure a delightful guest experience. The expansive outside gardens offer many areas to enjoy and it is just a stroll to Breakwater Beach.

Old Manse Inn


9. Harwich

Some would argue that it’s the small fishing villages that make Cape Cod the pleasant locale that it is! As you drive through Harwich, admire colorful boats rocking in the harbor and the sound of seagulls calling out over the ocean sky. One of the major attractions to check out in this town is the Cape Cod Lavender Farm. Find unique lavender products such as chocolate, body wash, room sprays, and more!

10. Chatham

chatham lighthouse with brilliant sunset paining the sky

Once you reach the easternmost point of Cape Cod, stop to check out Chatham! This 300-year-old town is surrounded by water on three sides. Explore the past of Cape Cod when you visit sites and museums such as the Chatham Lighthouse, one of the most romantic things to do in Massachusetts, or the Marconi Maritime Center. Keep your eyes peeled for seals and horseshoe crabs at Monomoy National Wildlife Refuge. Or, simply spend some time breathing in the fresh air on Chatham Lighthouse Beach.

Stay at Captain’s House Inn

Lady Hope 4 room beautiful new england charm decor

Stay in a quiet, sea captain’s estate that is now a quaint inn in Chatham, MA! Captain’s House Inn sets the scene for a dream-worthy romantic getaway on the Cape. Choose between sixteen guest rooms and suites that feature top-notch amenities such as whirlpool tubs and fireplaces. You will also enjoy waking up to a gourmet breakfast each morning!

Captain’s House Inn

nantucket massachusetts lighthouse

Miles of pristine beaches, delicious food, and serene landscapes await in Nantucket! Leave your worries behind and take a moment to let the natural surroundings rouse your senses. Colorful flowers, steep cliffs, the ocean wind; all of these things paint a vivid reality that you can live in even if just for a moment. Step back and take in the views of the water. Count the lighthouses that adorn the shores. Additionally, you’ll find so many exciting attractions to keep you busy in Nantucket! Check out the Whaling Museum and admire the 46-foot-long sperm whale skeleton. Peruse artworks at the East End Gallery. Or, simply grab a milkshake at the old Pharmacy on Main.

Stay at Seven Sea Street Inn Bed & Breakfast

seven sea street inn bedroom

Seven Sea Street Inn Bed & Breakfast prides themselves on providing attentive service in addition to their elegant accommodations. Lookout over the Nantucket Harbor from the Widow’s Wall deck in the morning after finishing a hearty breakfast. Then, grab complimentary beach towels and chairs and make your way to the ocean. You’ll feel right at home when you stay here!

Seven Sea Street Inn B&B

17. Martha’s Vineyard

Martha’s Vineyard is a romantic haven for New England enthusiasts. In addition to gorgeous beaches, you will also encounter various natural wonders such as Aquinnah Cliffs. Here, you can stand in awe of the beautiful clay cliffs that were carved by glaciers millions of years ago. Go island hopping and spend part of your day on Chappaquiddick, where you can explore walking trails, a Japanese garden, and the Cape Poge Wildlife Refuge. The Edgartown Lighthouse is small but beautiful and definitely worth a visit. For a unique experience, head to the Island Alpaca Company where you can interact with these gentle creatures.

Stay Select

Regardless of where this itinerary takes you on your Cape Cod road trip, rest assured that your vacation will be one worth remembering when you Stay Select. Once you experience the luxury of staying at one of our quality-assured bed and breakfasts, inns, or boutique hotels, you will never go back to staying at a boring chain hotel. We understand the time and money that goes into planning the perfect vacation, which is why our properties work hard to ensure that your getaway is just right.

Browse All Properties

Best Places to Stay in Brewster

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Guest room with fireplace
Candleberry Inn Guest Room
Candleberry Inn Guest Room
Canelberry Inn Guestroom
Guest rooms with sitting area
Guest room
Sitting area with Fireplace
Dining Room
Breakfast Service
breakfast spread
fruit salad

Candleberry Inn on Cape Cod

Brewster, MA

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sitting room
guest room
front door
guest room
guest room
living room
living room
outdoor pool
wine by fire
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table by the pool

Captain Freeman Inn of Cape Cod

Brewster, MA

Exterior front facing dinning room and main house
Interior - Living Room with Wine and Cheese Reception
Interior - Guest Bedroom Bass River
Exterior - Outside Dinning Porch
Interior - Old Chapel Dinning Room
front entrance sign to inn
Exterior - Gardens with Fire Pit
Exterior - Lewis Bay Suite Private Outdoor Patio
Exterior - Brick Patio with Fire Pit and Adirondack Chairs
Interior - Highland Light Guest Room
Interior - Highland Light Guest Bathroom
Interior - Guest Room Bass River Luxury Bathroom
Interior - Guest Room Wood End Light
Exterior - Old Manse Inn Twilight

Old Manse Inn

Brewster, MA

Best Places to Stay in Chatham

Chi 2016 Summer 05
Lady_Hope_4_room beautiful new england charm decor

Captain's House Inn

Chatham, MA

Best Places to Stay in Falmouth

front entrance
dining room
dining room
the captains manor inn bedroom
kitchen seating
sitting room
green room

The Captain's Manor Inn

Falmouth, MA

front entrance
Emily Dickinson Room
palmer house inn
Firepit at sunset
Palmer House Exterior Victorian Style
suite with fireplace
palmer house
Beautiful gardens
Relaxing porch seating
Porch rocking chairs
Harriet Beecher Stowe Room
Robert Frost Room
Theodore Roosevelt Room
Walt Whitman Room
Walt Whitman Bath
Henry Thoreau Cottage

Palmer House Inn

Falmouth, MA

Best Places to Stay in Martha's Vineyard

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nobnocket table

Nobnocket Boutique Inn

Martha's Vineyard, MA

Best Places to Stay in Nantucket

front entrance
guest room
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guest room
guest room
guest room
dining room
sitting room
back patio

Seven Sea Street Inn Bed & Breakfast

Nantucket, MA

Best Places to Stay in West Harwich

Platinum Pebble Front Entrance
Platinum Pebble Front View
platinump ebble sitting area
Platinum Pebble Bathroom
platinum pebble room 7
paltinum pebble room 7 patio
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The Platinum Pebble Boutique Inn

West Harwich, MA

Best Places to Stay in Yarmouthport

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