The Definitive Cape Cod Travel Guide for Your Perfect Getaway

Here’s Your Guide to the Best Places to Stay, Eat, and Shop on Cape Cod

New York boasts the Hamptons, Rhode Island has Watch Hill and Massachusetts is home to Cape Cod. While each of these East Coast vacation destinations has its unique attractions, personally, I have a special preference for Cape Cod. There’s an almost otherworldly quality to the Cape; the moment you cross over the Bourne Bridge, a feeling of serenity washes over you. As the chaos of city life fades away, you can sense yourself transitioning into the easygoing vibe of life on the peninsula.

While you can indulge in lavish five-star accommodations and savor delectable seafood at upscale restaurants, the Cape Cod ambiance remains unpretentious, relaxed and unhurried. You don’t need to dress up in your most glamorous designer wear; simply don a crisp pair of white jeans and wedge heels and you’ll fit right in.

Amidst all the understated luxury that Cape Cod has to offer, there are also numerous hidden treasures to be discovered, such as a scenic 25-mile bike trail, local-favorite clam shacks and seafood markets, as well as secluded oceanfront lodgings. Whether you’re a first-time visitor to the Cape or seeking insider tips, you’ve come to the right place. As someone who spent every summer on Cape Cod growing up, I’ve compiled the ultimate guide showcasing all the must-visit destinations on the peninsula. Keep reading to uncover the very best of Cape Cod.

Where to stay in Cape Cod

Chatham Bars Inn

Chatham Bars Inn is a grand hotel that beautifully preserves the relaxed and easygoing charm of Cape Cod, making it one of the most distinctively stunning properties along the entire coast. The resort features tranquil and open rooms, as well as individual villas, with four dining options and a private beach. For an indulgent escape, treat yourself to a stay in one of the new Spa Suites. After settling in and unwinding, head down to the beachside eatery for a quintessential Cape Cod lunch, complete with juicy lobster rolls and crisp salads sourced from the resort’s eight-acre farm.

The Mansion at Ocean Edge

As someone who spent summers at the now-defunct Cape Cod Sea Camps, I may be partial, but Brewster is one of my absolute favorite towns on Cape Cod. It embodies everything that comes to mind when picturing this iconic destination: antique shops, strawberry fields and charming inns.

The Mansion at Ocean Edge sits atop a sprawling lawn complete with croquet, exuding grandeur with its red roof and accents flanking the stucco exterior. Inside, there are various wings housing classic rooms, suites or villas. Wander beyond the tennis courts and swimming pool to the tree-lined wooden bridge path, leading to a serene bay and beach bar.

Spend the day sipping refreshing cocktails in lounge chairs or savor a spritz or beer while watching the sunset over the bay in the evening. This location exudes rugged luxury, capturing much of what makes a Cape Cod vacation so special and exceptional.

If you’re traveling with family, consider booking at The Villages, a separate property area featuring renovated two- to four-bedroom villas for added space.

Red Jacket Beach Resort

If you’re looking for a family-friendly resort on Cape Cod, the Red Jacket Beach Resort is an excellent choice. Located in the heart of mid-Cape, this property boasts its own stunning stretch of private beach that’s perfect for swimming, sunbathing, and building sandcastles.

In addition to the beach, the resort offers tons of activity programming for kids, including arts and crafts, scavenger hunts, and even a supervised pirate-themed adventure camp. Adults can also enjoy a range of amenities and activities, such as a full-service spa, bike rentals to explore the scenic bike trails nearby, and both indoor and outdoor pools for a refreshing dip.

The accommodations at Red Jacket Beach Resort are spacious and comfortable, with options ranging from cozy rooms to multi-bedroom suites perfect for larger families. No matter what type of room you choose, you can expect modern amenities like flat-screen TVs, free Wi-Fi, and plush bedding for a restful night’s sleep.

Overall, Red Jacket Beach Resort is an ideal choice for families looking for a fun-filled vacation on Cape Cod, with plenty of activities and amenities to keep everyone entertained and relaxed.

Where to dine in Cape Cod

Brewster Fish House

For seafood lovers, the Brewster Fish House is a must-visit restaurant on Cape Cod. This eatery serves up some of the freshest seafood on the peninsula, all in a quintessential Cape Cod setting.

Indulge in homemade lobster rangoons, seared tuna, cured Scottish sea trout and lightly fried local squid, all with flavors that will tantalize your taste buds. Whether you prefer dining indoors or outdoors, the ambiance at this establishment is sure to impress.

It’s important to note that the Brewster Fish House doesn’t take reservations, so it’s best to come early or be prepared to wait for a table. However, the wait is well worth it to savor the delectable dishes and cozy atmosphere of this beloved Cape Cod restaurant.

The Ocean House Restaurant

For those seeking a more upscale, fine-dining experience, the Ocean House Restaurant in Dennis Port is a must-visit. Nestled right on the water, guests can relish in breathtaking views of the sea while savoring exquisite dishes such as charred octopus, lamb lollipops, grilled oysters and much more.

The restaurant’s white tablecloth ambiance exudes elegance and sophistication, making it an ideal spot for romantic dinners, special occasions, or simply treating yourself to a memorable meal. The attentive staff are knowledgeable about the menu and wine pairings, ensuring that each guest has a truly exceptional dining experience.

With a focus on locally-sourced ingredients and innovative cooking techniques, the Ocean House Restaurant is a standout destination on Cape Cod’s culinary scene. Be sure to save room for dessert, as the pastry chef’s creations are equally impressive and delicious.

Mac’s Seafood

If you’re looking for a more laid-back dining experience, Mac’s seafood shack is a must-visit. The Chatham location is my personal favorite, offering picnic benches outside where you can relax while waiting for your order.

One of the most popular dishes on the menu is the locally caught lobster roll, served with a side of crispy fries and coleslaw. Alternatively, if you’re in the mood for something other than traditional seafood, try their sushi, tuna poke bowl or fried chicken salad.

Mac’s has multiple locations scattered throughout Cape Cod, including Provincetown, Wellfleet, Eastham, and Dennis, making it easily accessible no matter where you’re staying. With its casual ambiance and delicious food, Mac’s is an ideal spot to grab a quick bite while exploring all that Cape Cod has to offer.

Where to drink in Cape Cod

Old Colony Tap

If you’re in the mood for a lively atmosphere, head down to Commercial Street in Provincetown. This vibrant area is a thriving hub of the LGBTQ+ community and boasts numerous historical fixtures.

One of our favorite spots is Old Colony Tap, a popular dive bar that serves an extensive beer selection and features a classic jukebox. It’s a great place to grab a drink and mingle with locals and visitors alike.

Provincetown is also home to many other bars and clubs catering to the LGBTQ+ community, making it a welcoming and inclusive destination for all. Whether you’re looking to dance the night away or simply enjoy a few drinks with friends, there’s no shortage of nightlife options in P-Town.

Cape and Islands Distillers

For those interested in tasting locally distilled spirits, the Cape Cod Distillery tasting room is a must-visit. Located on Cape Cod, this tasting room is only open on Fridays, Saturdays, and Sundays, using only raw materials and ingredients sourced from the peninsula.

The distillery offers a range of unique and delicious spirits, including vodka, rum, gin, and whiskey, all crafted with care and precision to highlight the flavors of Cape Cod. Friendly staff are on hand to guide visitors through the tasting process, providing insight into the distilling process and the history of the area.

Overall, the Cape Cod Distillery tasting room is a fun activity that’s sure to delight your taste buds and provide a unique experience during your time on the Cape.

What to do in Cape Cod

Hyannis Whale Watcher Cruises

No visit to Cape Cod is complete without taking the opportunity to see some whales up close. One of the best ways to do this is by booking a spot on one of the Hyannis Whale Watcher Cruises, which depart from Hyannis.

During your cruise, you’ll have the chance to see majestic creatures like Humpback, Finback, and Minke whales, as well as playful dolphins swimming alongside the boat. Even if you don’t spot any whales, you’ll still get to enjoy a few hours out on the water, taking in the stunning views of the Cape’s coastline.

The knowledgeable crew on board will provide commentary throughout the trip, sharing fascinating information about these incredible marine animals and the surrounding ecosystem. This experience is perfect for families, couples, and anyone looking to add a unique and memorable activity to their Cape Cod itinerary.

Cape Cod Rail Trail

For biking enthusiasts, the Cape Cod Rail Trail is a must-do activity. Spanning 25 miles and weaving through six different towns on the peninsula, this trail offers stunning views of the Cape’s natural beauty and charming towns.

With various entry points along the way, you don’t have to bike the entire length of the trail if you’re not an experienced cyclist. This also gives you the opportunity to explore different towns on the Cape, including Dennis, Harwich, Brewster, Eastham, Orleans, and Wellfleet.

When you stop in Brewster, be sure to visit Cobies Clam Shack for a quick bite. Their fried clams are a local favorite and a delicious treat after a day of biking.

Overall, the Cape Cod Rail Trail is a fantastic way to get some exercise while taking in the sights and sounds of this beautiful region. Whether you’re a seasoned cyclist or just looking for a leisurely ride, this trail is an ideal way to experience the best of Cape Cod.

Where to shop in Cape Cod

Chatham, Main Street

Chatham’s Main Street is a shopper’s paradise, overflowing with charming boutiques, memorabilia shops, antique stores, home decor shops, bookstores, and bustling restaurants.

If you’re in the mood for some retail therapy, be sure to check out Jackie’s, The Black Dog, and Cook’s Nook – all fantastic shops that offer unique gifts and souvenirs. And don’t forget to stop at Candy Manor, where you can indulge in some of the best fudge on Cape Cod.

In addition to shopping, Main Street also offers numerous dining options, with a variety of cuisine ranging from classic New England seafood to international fare. Whether you’re grabbing a quick bite or indulging in a multi-course meal, there’s something for everyone on Main Street.

Overall, Chatham’s Main Street is a must-visit destination on Cape Cod, offering a delightful mix of shopping, dining, and local flavor that’s sure to delight visitors of all ages.

Mashpee Commons

If you’re in need of some big box shopping, Mashpee Commons is your go-to destination on Cape Cod. This sprawling outdoor shopping complex offers a wide range of stores, including popular chains like Lululemon, L.L. Bean, and Pottery Barn, as well as smaller boutiques.

Once you’ve finished shopping, be sure to head to Bleu for a chic French meal. This elegant restaurant offers a menu filled with classic French dishes made with fresh, locally-sourced ingredients. The cozy atmosphere and attentive service make it an ideal spot for a romantic dinner or special occasion.

In addition to shopping and dining, Mashpee Commons also offers a range of entertainment options, including a movie theater and outdoor events throughout the year. Whether you’re looking for a day of shopping, dining, or relaxation, Mashpee Commons has something for everyone.