Chatham MA, Port boats in the harbor on cape cod

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

Select Registry -

Travel and Industry Resources

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. If you’re planning a trip with your sweetheart, then check out our Romantic Getaway Guide for tips on how to make your vacation extra special!

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 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

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

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

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

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

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

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

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

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

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

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

Stay at The Carriage House Inn

The Carriage House Inn stands out in that it is owned by a professional chef who trained in France and Switzerland. Here, you will be treated to 3-course menus, gluten-free options, French pastries, and artisan eats. You don’t want to miss out on this premier foodie experience!

The Carriage House Inn

Stay at Chatham Gables Inn

Chatham Gables Inn is a historic mansion by the sea that embodies coastal charm and hospitality. After a busy day of whale-watching, beach-bumming, and sightseeing, return to your home away from home for an exceptional night’s rest. Then, arise in the morning to the pleasant aroma of a delicious, made-to-order, country breakfast.

Chatham Gables Inn

11. Orleans

Visit some of the Cape’s most popular beaches in Orleans! Nauset Beach and Skaket Beach serve as gorgeous backdrops for watching the waves crash on the shore. You’ve never seen a sunrise like this before. The sky paints itself shades of peony pink and marigold orange as the sun peeks out from behind the Atlantic Ocean.

12. Wellfleet

Wellfleet boasts an eclectic culinary scene that is sure to appeal to any palate. For veggie-friendly plates, check out Ceraldi. Van Rensselaer’s Restaurant boasts an authentic, raw bar where you can indulge in Wellfleet’s world-famous oysters and clams. Sometimes you just want to grab a quick bite to eat. In that case, Moby Dick’s makes for a great lunch spot where you can try fried shrimp or New England chowder!

13. Eastham

While you are in Eastham, you might feel drawn to visiting the beautiful Nauset Light! This famous landmark stands out against the blue sky with its vibrant red painted stripe. Additionally, you could easily spend a day at Coast Guard Beach, soaking in the natural beauty of the Cape.

14. Truro

Whether you’re making a point to visit every lighthouse on the Cape or you’re just stopping to see one or two during your road trip, consider checking out the Highland Light in Truro. This lighthouse is the oldest and tallest lighthouse on Cape Cod!

15. Provincetown

There are so many amazing things to do in Provincetown! Lounge around on Race Point Beach. Shop for unique souvenirs on Commercial Street. Stroll along Provincelands Trail to take in the sights of kettle ponds, marshlands, cranberry bogs, and the Race Point Lighthouse. Visit MacMillan Pier where you will encounter art shacks, museums, and more. Attend a production at the Provincetown Theater. If you have a sweet tooth, you don’t want to miss out on Cabot’s Candy of Cape Cod! You’ll come across an array of art museums and galleries here. Additionally, seafood lovers can take comfort in knowing there is an array of dining establishments that feature fresh, local seafood such as The Canteen and The Mews.

16. Nantucket

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 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