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Spend a Day in the Life of a Cape Codder with Our Insider Itinerary

Jul 10 2019

Cape Cod is a magical place. So magical in fact, that more than 4 million people visit the peninsula at the edge of Massachusetts each year. From spending the day at the beach, to eating some of the best ice cream in the country, there are endless reasons people pick the Cape for their vacations. As insiders who live here year-round, we’ve got the scoop on what visitors should do and see during their vacation and we’ve rounded up our top picks to help you plan the perfect Cape escape. 

8 a.m. Get Your Fill of Local Cuisine

Eating a hearty breakfast is the perfect way to start your vacation day and the Cape’s breakfast scene is rich with from-scratch options. Four out of five Red Jacket Resorts on Cape Cod offer breakfast, with menu options for diners of every age. If you’re staying at Red Jacket Beach Resort, our favorite way to start the day is with our namesake sandwich, the Red Jacket Breakfast Sandwich. It’s no ordinary sando, with ingredients like a farm-fresh egg, American cheese, tomato, avocado and bacon, served open-faced on grilled sourdough with home fries. If you’re staying at Green Harbor, our only resort that doesn’t have on-site dining, all of the units have kitchens where you can cook breakfast with the beach as your backdrop.

If you feel like venturing beyond the resorts, start the day at a local favorite spot like Yarmouth’s Keltic Kitchen, where you can dine on an Irish farmhouse breakfast, or Ann & Fran’s Kitchen, where cinnamon french toast with ricotta cream awaits. The Red Cottage Restaurant in South Dennis is a Red Jacket favorite, thanks to its Chesapeake Bay Breakfast, complete with two scratch-made crab cakes. If you’re willing to travel a bit further, try Hyannis’s Sea Street Cafe, where the Cape Cod benedict comes atop mini lobster cakes, or the Daily Paper on Main with the quaintest diner seating on Cape Cod. Be prepared to wait for a table wherever you go (the earlier you go, the better). Don’t worry, the reward will be worth it. 

Child on the beach holding a kite made at Kids Club.

9:30 a.m. Head for the Beach or the Pool

If you’re staying at a Red Jacket Resort, you’ll be happy to know that you can access any of our private beaches throughout your stay (even if you’re staying at Blue Rock Resort without beachfront). Every beachfront resort, including Red Jacket Beach Resort, Blue Water Resort, Riviera Beach Resort and Green Harbor Resort, offers complimentary towels, lounge chairs and umbrellas to build the perfect sandy set-up. The beaches are also steps from our pools, so you can go back and forth at your leisure.

Beyond Red Jacket beaches, there are ample options to explore the Cape’s oceanfront. Most of the beaches require day passes, like Yarmouth’s town beaches which charge $20 per car per day, so bring cash with you when you head out. Gray’s Beach is one of our favorites if you’re looking for a priceless view. The beachfront itself isn’t expansive, but there’s a lengthy boardwalk with marsh life that provides the perfect backdrop for a day at the beach. Outside of Yarmouth, beaches like Mayflower in Dennis ($20 per weekday, $25 per weekend day) and Kalmus in Hyannis ($20 per day) are great for a morning (or day) at the water’s edge. Both offer snack bars and restrooms and have plenty of space to spread out. Bonus: Kalmus is known for its prime windsurfing conditions so there’s always plenty of action on the water.

No matter what beach you find yourself at, remember to bring: 

  1. Beach toys

  2. Sunglasses

  3. Hats

  4. An outdoor Bluetooth speaker

  5. A good book

  6. Lots of sunscreen!

Diners at the Blue Water Resorts Surfside Bar and Grill.

12 p.m. Enjoy Lunch By the Water

One of our favorite parts of staying at Red Jacket Resorts on Cape Cod is the fact that you don’t have to leave the resort to have a stellar meal. When you stay at Red Jacket Beach or Blue Water, your beach chair (or pool chair) is steps from outdoor patio dining at the Ocean View Grill and Surfside Bar & Grill (pictured above), respectively. You can order outside and take the food back -- and you don’t even need to put on shoes if you don’t want to. Riviera Beach Resort guests can take advantage of the close proximity to Blue Water and Surfside (they’re next door neighbors) and venture over for a bite, too. Menu items include summer favorites like lobster rolls, and frozen drinks (with or without adult-only additions). 

We also love the menus and waterfront views at Baxter’s Boathouse Restaurant and The Black Cat Tavern -- both on Hyannis Harbor, Brax Landing Restaurant at Saquatucket Harbor in Harwich, Sesuit Harbor Cafe in Dennis (which is BYOB), and Osterville Fish, Too at Barnstable Marina. Each offer fresh seafood (fried and otherwise), reasonable prices, killer views, and close proximity to other area attractions, like Hyannis’ Main Street (if you choose Baxter’s or the Black Cat), which is chock full of shops to explore. 

Bikes near beach and swings

2 p.m. Get to Know the Cape

From the abundant ecosystem to the art history, there is a museum or attraction for everyone to get to know Cape Cod while on vacation. Young families will enjoy the Cape Cod Natural History Museum in Brewster or the Thornton Burgess Society Green Briar Nature Center in Sandwich, where native Cape Cod wildlife are the stars of exhibits and special shows. Art buffs will enjoy stops at Dennis’s Cape Cod Museum of Art, which is steps from indie-airing Cape Cinema and lively theater at the Cape Playhouse

If you’d rather explore outdoors, our hiking, biking and golf options are pretty fantastic. The Cape Cod Rail Trail’s new trailhead in Yarmouth is a short bike ride from Blue Rock Resort (where you can rent e-bikes!), and if you don’t mind starting in the middle of the trail you can enter from White’s Path and North Main Street (a short 5-minute ride from Blue Rock). The Rail Trail, built on the former Cape Cod railroad tracks, is more than 20 miles long, winding its way through towns like Dennis and Brewster before ending in Wellfleet. Hikes abound with options close to our resorts, like the Botanical Trails at the Historical Society of Yarmouth. And if the golf is your thing, you’ll be happy to know that our award-winning par-3 Blue Rock Golf Course offers preferred pricing for Red Jacket Guests for rounds of golf and even for lessons. It’s open to the public, so if you have friends on the Cape, they can join, too.

Go on an adventure: The Yarmouth Chamber of Commerce’s annual Sand Sculpture Trail, featuring 33 sand sculptures throughout the town, is running a photo contest this year and prizes in three different categories include gift cards to local businesses. Check out the Chamber’s website for contest information. 

4 p.m. Relax ⁠— You’re on Vacation

Don’t forget to take some time for yourself while you’re here. Whether it’s stealing away to a spa (like the Spa at Red Jacket Beach, which offers a multitude of massage options), or simply sitting on the patio enjoying a good book, this is a great time of day to kick back and unwind. You can even take a nap, you’re on Cape-Cod time.

Cape Cod Baseball League players line up for the national anthem. via Flickr

5 p.m. See the Next Best in Baseball or Try Your Hand at Mini-Golf

The Cape Cod Baseball League has hosted some of Major League Baseball’s biggest names (can you say, “Jason Varitek?”), and while you’re here you’ll have the chance to scout out the next big names in the major leagues. The Y-D Red Sox home games are held at Red Wilson Field at Dennis-Yarmouth Regional High School, which is less than 10 minutes from any of our properties. The games typically start between 5 p.m. and 7:30 p.m. and you can check out the full league schedule online.

Other fun fields to check out include McKeon Field, home of the Hyannis Harbor Hawks (behind Hyannis Harbor) and Lowell Park, the idyllic home of the Cotuit Kettleers. Spectators can enjoy classic baseball snacks like hot dogs and popcorn at the games, and if you’re feeling lucky, you can enter 50/50 raffles that deliver a hefty purse to the winner. 

When you go to a CCBL game, make sure to pack a blank baseball. Players are typically more than happy to sign memorabilia following the outing!

If you have little ones who can’t sit still (or you’d simply prefer to simply prefer trying your hand at 18 mini-holes), Yarmouth is the epicenter of mini-golf on Cape Cod. We have our very own course at Green Harbor, which is open to all guests (pictured above), and courses like Skull Island, Pirate’s Cove (which has a back and front course), Putter’s Paradise and the Wild Animal Lagoon are practically in our backyard. We even offer a themed pirate package that includes mini-golf tokens for Skull Island and admission to the Whydah Pirate Museum!

Photo of a child holding an ice cream cone.

7:30 p.m. Get Dinner — and Save Room for Ice Cream

If you don’t fill up on hot dogs and popcorn at the Cape League game of your choice, then you’ll be happy to know that restaurants across the Cape are known for their culinary prowess. Our resorts offer offer tons of options, including themed buffets, casual seated dining and patio dining. You can’t go wrong with an on-site meal, but we’ve also rounded up some of our favorite picks for upscale and family dining, too.

Our picks for upscale dining:

Our picks for family dining:

Special night out: Sesuit Harbor is home to the Cape’s Lobster Roll Cruises which run throughout the spring and fall in Sesuit Harbor. Departure times include brunch, lunch, dinner and sunset options and the menu is highlighted by the company’s namesake lobster roll, which comes with a hint of celery and mayo, letting the lobster steal the show.

After dinner, ice cream can be found in every Cape Cod nook and cranny. Cape Cod Creamery (Yarmouth, Dennis and Hyannis), Sundae School (Dennis Port, Harwich Port and Orleans), Four Seas Ice Cream (Centerville) and Katie’s Ice Cream (Hyannis) are some of our favorites, but you can’t go wrong at any outpost you pick.

HyArts Artist Shanties in Hyannis, MA.
Marie Grady Palcic

9 p.m. Finish the Night Right

If you’re traveling with kids, the Cape’s Main Streets in areas like Hyannis and Chatham typically keep shops open until 9 or 10 p.m., allowing for sweatshirt and souvenir shopping as the evening chill rolls in. Even Cuffy’s, home of some of our favorite Cape Cod gear (in West Dennis), stays open until 10 p.m. in the summer!

Must-visit shopping stop: The HyArts Artist Shanties (pictured above) are technically open until 8 p.m. but a lot of artists will stay later, showcasing their goods and even making new pieces right in front of visitors. The Shanties are the perfect place to find something one-of-a-kind to remember your vacation.

If you’re still feeling adventurous post-dinner and traveling sans-kids, the Cape’s nightclubs and bars are open until 1 a.m. (with last call sometime around 12:40 a.m.). There are Uber drivers ready to whisk you to your location of choice, whether it be a DJ’d dancefloor, like that of Torino Restaurant and Bar in Hyannis, or a lively pub with live music, like Red Jacket Beach’s Asa Eldridge Pub or Blue Water’s Jonah’s Pub.

These are our picks for the perfect Cape Cod day. Ice cream, the beach, fried seafood, a little education, some downtime and a memorable meal -- nothing can beat that combo.