“There’s a sunrise and a sunset every single day, and they’re absolutely free. Don’t miss so many of them.”
― Jo Walton

Relax your shoulders, close your eyes and fill your lungs with that refreshing, salty sea air … the Cape in Massachusetts is a summer road trip destination that is hard to beat. 

Perfect for families, couples, and groups of friends, there is enough scenery and seafood to satiate everyone’s palette. Whether you are planning a trip to Cape Cod (the largest), Martha’s Vineyard (the choice of many a celebrity) or Nantucket (the slowest-paced) — or, lucky you, all three! — we’ve got you covered with favourite picks from our local photographers. Ready to feel that sweet sand between your toes? Let’s go!

Cape Cod

“When it comes to food, architecture, adorable town centers and beautiful beaches, you can’t beat a Cape Cod summer getaway. While you’re here you need to get a lobster roll from one of the many clam shacks where fresh lobsters are caught daily and try some local fish. Every town has a local art gallery to visit, cute shops and beautiful beaches. Just be sure to follow beach guidelines about sharks! ” – Caroline

“I love being active outside so Cape Cod summers are the best! My favourite things are the easy access to beautiful beaches, amazing local seafood, and riding along the Shining Sea Bikeway.” – Meghan


  • Betsy’s Diner (Falmouth): “I have been going to Betsy’s Diner as long as I can remember. This 50s diner is not one to be missed if you love all things vintage. Amazing food from their omelettes to their Belgian waffles, plus gluten-free breakfast options.” – Meghan 
  • BŌL (Wellfleet): Gluten and dairy-free smoothie bowls to start your day right! 
  • Young’s Fish Market (Orleans): Pick up the freshest seafood here as well as “some of the best lobster rolls you’ve ever had!” – Caroline 


  • Coffee Obsession (Falmouth): “I am a huge coffee shop enthusiast, so I love stopping in for a latte at Coffee Obsession. Their coffee and tea menu is massive, plus they do offer non-dairy milks and allergy-friendly baked goods. Their Woods Hole location is right by the Steamship Authority ferries so you can grab a drink before hopping on a ride to Martha’s Vineyard.” – Meghan 
  • Chatham Bars Inn (Chatham): “Their beautiful display of hydrangea at the front of the inn is a must-see if you are in the area in late July! Go grab a drink down by the water or stay the night if you’re feeling fancy!” – Caroline 

SEE/DO – Meghan’s Picks

  • Nobska Lighthouse (Falmouth): “There is nothing more nautical than going on a tour of lighthouses around the Cape. Built in 1829, the Nobska Lighthouse in Falmouth has been completely restored. The Keeper’s House will become a Maritime Museum and once the pandemic passes, the Tower tours will reopen to the public.” 
  • Old Silver Beach (Falmouth): “If you are looking for a public beach without needing a beach sticker, Old Silver Beach is the perfect option! It offers beautiful views of Buzzards Bay and has a jetty you can walk along as it juts out into the water. Sitting on the western shore you get amazing sunset views and it provides a great spot to go swimming!” 
  • Shining Sea Bikeway (Falmouth): “Whether you rent a bike or bring your own I love taking a ride on the Shining Sea Bikeway. This 10.7 mile paved path runs along the coast from Falmouth to Woods Hole and boasts beautiful ocean views.”  
  • The Knob (Woods Hole): “The Knob, located in the Cornelia Carey Sanctuary, is a beautiful little peninsula that juts out into Buzzard’s Bay. There is a small parking lot at the end of the dead-end road, but it does fill up quickly. There are multiple trails but when you come to the wooden sign just take the trail on the right the entire way and it will bring you to the Knob. There are small swimming beaches on either side too and a bench at the end to take in the stunning views of the ocean!” 

SEE/DO – Caroline’s Picks

  • Chatham Fish Pier (Chatham): “Watch the commercial fishing boats come in with their catch in the morning and you’ll see a seal or two! It’s cool to watch the fish being unloaded, and then you can walk across the parking lot to the Chatham Pier Fish Market to buy the freshly-caught fish! Great free activity for kids.”
  • Nauset Lighthouse (Eastham): “The Nauset Light is a beautiful old lighthouse with a great history. Take a tour, visit the Three Sisters Lighthouses while you’re there and spend the day at Nauset Light Beach. Check your bag of Cape Cod Potato Chips and you’ll see the Nauset Light!” 
  • Cape Cod National Seashore: “Created by President JFK, the Cape Cod National Seashore is home to some of the most beautiful beaches on the Cape, from Provincetown down to Chatham. With 40 miles of beach to explore, you can hit a new beach every day and stay on the CCNS!” 
  • Grey’s Beach (Yarmouth): “Grey’s Beach has free parking, a big sectioned-off swimming area, boat launch and a long boardwalk that goes right out over the marsh and into the ocean. It is a beautiful spot to explore, take photos and spend the day.” 
  • Rock Harbor (Orleans): “Come watch the fishing boats leave in the mornings or charter one of the boats for a day of deep-sea fishing! This peaceful harbor attracts artists who you can find painting along the boardwalk most days. While you’re there, check out Skaket Beach (my pick for best kid-friendly beach on the Cape!) and Young’s Fish Market for some of the best lobster rolls you’ve ever had. Take a photo in front of the Cap’t Cass Restaurant with its iconic buoys.” 
  • Crosby Mansion (Brewster): “A beautiful mansion-turned-museum perfect for visiting on a rainy day. The grounds are beautiful, especially during hydrangea season!”  
  • Uncle Tim’s Bridge (Wellfleet): “The bridge itself is a beautiful spot to stop and take some photos, but cross the bridge to Hamblen Island and you’ll find walking trails that are perfect for kids. The trails lead out to the beach near Wellfleet Harbor and are not to be missed! While you’re there, stop at BŌL in Wellfleet for the best smoothie bowl breakfast!”  


  • Commercial Street (Provincetown): “Commercial Street has everything: beautiful homes, shops, history, galleries and great food. Make sure you check out The Lobster Pot for lunch!” – Caroline 
  • Main Street (Falmouth): “If you are looking for restaurants, gift shops, and local boutiques, Main Street Falmouth covers all your needs. Chocolate enthusiasts, be sure to stop in Ben & Bill’s Chocolate Emporium to fulfill your sweet tooth dreams!” – Meghan 

Martha’s Vineyard


  • Larsen’s Fish Market (Menemsha): Don’t miss the lobster rolls and clams fresh from the dock! It’s also the perfect place to watch the sunset.  
  • Alchemy (Edgartown): Fine dining at its best.  
  • Lookout Tavern (Oak Bluffs): A huge menu of the freshest seafood, including sushi. 
  • Artcliff Diner (Tisbury): Cooking up Americana since 1943. Come early to avoid long lines! 
  • State Road (West Tisbury): High-end offerings with ingredients straight from the restaurant’s gardens. 
  • Scottish Bakehouse (Vineyard Haven): Hearty breakfast fuel-up options at this café bakery.
  • Back Door Donuts (Oak Bluffs):  Find the purple door at the back and get in line for sweet treats from heaven!


  • Behind the Bookstore (Edgartown): Get your coffee here in the morning and your cocktails in the evening in this friendly open-air hotspot.
  • The Port Hunter (Edgartown):  Fresh oysters and modern cocktails — need we say more?  
  • Bad Martha Brewery (Edgartown & Falmouth): Enjoy a freshly brewed beer in the outdoor garden patio and support the brewery’s efforts to donate profits to a local hunger-relief charity.


  • Lighthouse Beach (Edgartown): Miles of soft golden sand surround the iconic black and white Edgartown Lighthouse, one of five historic lighthouses on the island.
  • Lucy Vincent Beach (Chilmark): Formerly known as Jungle Beach, this is one of the most popular hangout beaches, with a nude beach section at the far end for the adventurous and free-spirited. 
  • Gay Head Lighthouse (Aquinnah): The lighthouse’s interior is closed for now due to COVID precautions, but you can still enjoy the incredible views of the clay cliffs, designated a national landmark.
  • Lobsterville Beach (Aquinnah): A perfect stretch for a day of fishing, leisurely walks on the sand, or letting the kids run wild.
  • The Carnegie (Edgartown): Get your fill of island history surrounded by the beauty that is the newly-renovated Neoclassical former home once owned by the Carnegie family.
  • The Campground (Oak Bluffs): Enjoy a stroll around this famous area to get your Insta-worthy snaps of the island’s unique and utterly charming gingerbread cottages.  
  • Island Alpaca Farm (Vineyard Haven): Visit a family-friendly alpaca farm — new babies arriving this summer! 


  • Portobello Road (Edgartown): Book lovers rejoice! The sweetest bookshop that offers accessories and gift ideas. You won’t escape empty-handed.
  • Slate (Edgartown): Look for the cheery striped awning that will lead you to a treasury of unique and local fashion finds.
  • Alley’s General Store (West Tisbury): The oldest retailer on the island with a post office and all the supplies you could possibly need. 
  • The Allen Farm Sheep and Wool Company (Chilmark): A family-run farm offering beautiful handmade preserves, woollens and meat.  
  • North Tabor Farm (Chilmark): Gorgeous bouquets of flowers and baskets of fresh fruit and veg are grown and sold at this family farm stand.  


“Nantucket is known for its idyllic New England scenes, quaint cobblestone streets, gorgeous beaches and great restaurants — it’s a true summer vacation destination. As a local, I love never having to be more than 5 minutes from the ocean. I also love how happy everyone is when they’re here. It truly does feel like a fairytale!” – Emily


  • Nautilus (Downtown): “Such amazing food. Shared plates with an Asian flare and some of the best food on the island.” – Emily 
  • Something Natural (Downtown): “Really good sandwiches! Perfect spot to eat in or to grab sandwiches to bring to the beach.” – Emily 
  • Handlebar Café (Downtown): Friendly and fun atmosphere with a “secret garden” to enjoy your morning cuppa.
  • Roastd (Mid-Island): “Really cute coffee shop with specialty lattes.” – Emily
  • Cisco Brewers (Mid-Island): “The best day spot to hangout. It’s family and dog friendly with an outdoor courtyard and live music. As it’s a brewery, distillery and winery, there are lots of drink options! Food trucks often stop by too.” – Emily
  • CRU (Downtown): End your day with a glass of bubbly overlooking the marina at this popular oyster bar.
  • The Club Car (Downtown): This colourful piano bar mixes innovative cocktails alongside the freshest Mexican-inspired menu.


  • Steps Beach: A quiet local beach boasting beautiful stretches of sand and surf. Find the path off Cliff Road, between Jetties Beach and Dionis Beach — but as the name implies, be prepared to descend a multitude of steep steps to access it.
  • Whaling Museum: Pay tribute to the island’s 400-year-old seafaring history with a visit to this display-rich museum.
  • The Oldest House: Also known as the Jethro Coffin House, it was built in 1686. The interior is currently closed due to COVID precautions, but it’s lovely to explore the grounds and gardens. 
  • Sconset: “This is the east end of the island with the only other small town on Nantucket. It is so gorgeous out here. Adorable flower-covered cottages, bluff walk, and a couple small markets and restaurants.” Emily


  • Toujours Midi (Downtown): Bring a piece of Nantucket home from this tasteful gift and decor shop. 
  • The Skinny Dip (Downtown): Large selection of men’s and women’s fashion and lifestyle that features emerging designers. 
  • Murray’s Toggery Shop (Downtown): Find all the prepster classics for the whole family at this fashion outlet on Main Street. 
  • Bartlett’s Farm (Mid-island): Pick up the freshest fruit, veg and flowers at the island’s largest and oldest family-run farm.
  • Sconset Market (Sconset): Food for your picnic, wines, books, clothing, gifts, ice cream and more … it’s all here in this charming market.

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