10 of the Things You Need to Have on Your Cape Cod Road Trip Itinerary

Are you ready for the trip of a lifetime? Pack your bags, fuel up the car, and embark on an incredible adventure with our Cape Cod road trip itinerary! We go beyond simply telling you the best attractions in the area. With our help, you can enjoy some of the most scenic drives on Cape Cod as you travel to each destination. Read on to find out how to make the most of your journey through our beautiful area! Plus, you can always explore our free Vacation Guide to customize your itinerary! It’s full of local tips and information on our beautiful beaches, iconic lighthouses, fascinating museums, and more. You won’t want to start your road trip without it!

Plan the Ultimate Cape Cod Getaway!

Craft the Best Cape Cod Road Trip Itinerary With These Ideas!

1. Begin Your Adventure at the Captain Farris House

Once you arrive on the Cape, make your way to the Captain Farris House. At our charming South Yarmouth inn, you can stretch your legs with a leisurely stroll along Pleasant Street in the historical Bass River Village or have a seat in our gardens while enjoying complimentary treats, fresh from the oven. And, our central location on Cape Cod makes it the perfect jumping off point on your way to the various attractions nearby. After one night in our luxurious guest rooms, you’ll wake up refreshed and ready to continue your Cape Cod road trip. We even serve homemade breakfasts each morning to fuel your adventures!

2. Take Route 28 to Chatham

After a delicious morning meal at the Captain Farris House, you can hop in the car and continue your scenic tour of the Cape. Chatham is just 30 minutes away via Route 28, making it the ideal next option on your itinerary. Here, you can take a stroll through quaint shops along Main Street, snap a picture of Chatham Light, and check out Lighthouse Beach. You might even spot a few seals as you walk along the shoreline or stop at the Chatham Fishing Pier!

3. Next Stop, Orleans!

After a peaceful morning in Chatham, you can continue north on Route 28 until you reach Orleans. Located on the eastern end of the Cape, this charming town is known for having great restaurants as well as a beautiful, 10-mile stretch of shoreline, Nauset Beach. If you happen to be visiting during the holidays, you can even check out their popular Christmas festival throughout town!

4. Journey Along the Cape Cod National Seashore

The Cape Cod National Seashore features 40 miles of natural beauty, and your road trip is the perfect opportunity to experience it all. Route 28 eventually merges with Route 6 past Orleans, which is your pathway to a variety of attractions along the coast. At the Salt Pond Visitor Center in Eastham, you can explore a museum, catch a film in the theater, or check out the walking trails nearby. Afterward, feel free to stop at several beaches as you continue your drive northward.

5. Grab a Glass of Wine in Truro

There’s nothing like an exquisite glass of wine to pair with the famous Cape Cod scenery, and Truro Vineyards is the perfect spot for it. Their wines have won several medals over the years, and now it’s your turn to see what makes them so award-worthy! You can even check out their new on-site distillery. Stop in for a tasting as you pass through town!

6. Enjoy the Charm of Provincetown

Before you know it, you’ll be in Provincetown, a local treasure at the tip of Cape Cod. It’s famous for being the site of the Pilgrims’ landing in 1620, and there’s no shortage of history here. Save some time to check out the Pilgrim Monument during your visit. In addition to simply marveling at this 250-feet tall structure, you can go inside and walk up to the top! The views there are well worth the 10-minute climb! Depending on the season, you might also be able to enjoy a whale watching tour at Provincetown Harbor!

7. Make Your Way to Brewster Via Route 6A

On your way back from Provincetown, you can turn onto Route 6A, one of the most popular scenic drives on Cape Cod. This beautiful roadway takes you on a journey through Cape Cod’s past with several historical sites. One of these fascinating attractions is in Brewster, MA. At the Cape Cod Museum of Natural History, you can take your mind on a journey as you learn about the past, present, and future, of our local animals and ecosystems. Make sure to stop at the Lemon Tree Village Shops as well!

8. Continue Your Road Trip in Dennis

As you follow Old King’s Highway on Cape Cod, you’ll soon find yourself in Dennis, MA. This seaside town is home to several historic sites, top-notch restaurants, and stunning beaches. There are also some excellent opportunities for shopping along Cape Cod’s Route 6A here! For a unique souvenir from your road trip, be sure to check out the Antique Center of Cape Cod. Along the shelves, you can find collections of artwork, furniture, jewelry, and more! Before leaving Dennis, we also encourage you to explore the breathtaking exhibits by local artists in the Cape Cod Museum of Art!

9. Return to the Beautiful Town of Yarmouth

Make sure you save some time and energy for Yarmouth, another exceptional destination on your Cape Cod road trip! For a relaxing, scenic experience, you can take your pick from several local beaches. Or, visit the Taylor-Bray Farm for a bit of history and a lot of fun. The Farm offers unique tours and even hosts some exciting festivals! Before your road trip, make sure you also take a look at the upcoming events at the Cultural Center of Cape Cod. It’s right across the street from our inn and offers cooking classes, concerts, trivia nights, and more!

10. Rest, Relax, and Recharge at the Captain Farris House

After enjoying one of the best drives on Cape Cod, you’re going to need a comfortable place to rest. Luckily, the Captain Farris House is here, and we’re always happy to make you feel at home. From our freshly baked treats to our elegantly designed guest rooms, you’ll be wishing you could stay here forever!

Spend a night in the Captain Farris Suite to discover the epitome of luxury. As you step inside, you’ll find yourself in a beautifully decorated living room with a gas fireplace. When you’re not lounging on the couch in here, you can treat yourself to a restful night’s sleep in the antique, queen-size bed. This charming, private space offers the perfect atmosphere for romantic getaways on Cape Cod!

Book your stay with us and start looking forward to an adventure you’ll remember for years to come! We hope to see you soon!

When it’s time to return home, you can still add a few more memories to your visit by checking out Sandwich, MA, on your way out! The Heritage Museum and Gardens and the Glass Museum are must-see attractions for beautiful scenery and fascinating histories!