Dennis & Yarmouth Port - Cozy, classic Cape Cod (home base)

Why Visit: Your home base filled with cute shops, amazing beaches, and great food
Breakfast & Pastries: Red Cottage, Village Coffee Shop, Lighthouse Keepers Pantry, Ann + Fran’s, The Mercantile, Underground Bakery
Lunch & Ice Cream: Sesuit Harbor Café (BYOB), Captain Frosty, Cape Cod Creamery, Smugglers
Dinner & Drinks: The Pheasant, Baleine, Leonessa, Encore, Scargo Café, Fin, Chapin’s Bayside, Inaho, Lune, Clean Plate, Pizza Shark
Provisions: Dennis Public Market, Dunn & Sons Wine, Cape Abilities Farm, Ring Bros., Rory’s, Big Rock Oysters
Beaches & Hiking: Mayflower, Corporation, Howes, Chapin’s, Crowes Pasture, Rail Trail, Grays Beach
Other Activities: Taylor Bray Farm, Cape Cinema & Playhouse, East Dennis Hot Yoga, Oyster shucking and wine tasting classes (Email Adam @ The Pheasant)

Brewster - Charming artsy, and community focused

Reasons to visit: Leisurely but beautiful hikes, our favorite cafes, bookstores, and local provisions 
Breakfast & Pastries: Snowy Owl Coffee Roasters, The Kitchen Café
Shops: Brewster Book Store, Brewster General Store
Provisions: Chatham Bars Inn Farmstand, ACK Gioia
Beaches & Nature: Paine’s Creek, Crosby’s Landing, Wing Island Trail, Cape Cod Museum of Natural History (great for kids), Rail Trail
Nightlife & Cocktails: The Woodshed, Oceans Edge Beach Bar

Orleans — Wellness-forward community with spectacular beaches

Reasons to visit: Beaches and a main street with cafes, bookstores, and provisions
Food & Provisions: Viv’s Kitchen, Orleans Whole Food Market
Beaches & Hiking: Skaket Beach, Nauset Beach, Rail Trail
Shops: Sea Howl Bookstore, The Weekend, Main Street Wines,  Supple Apothecary

Chatham - Classic New England Summer Charm

Reasons to visit: Strolling Main Street for classic Cape Cod Goods (candy, swag, and beachy trinkets), upscale resort vibes, and beautiful coastlines
Coffee & Breakfast: Hangar B Eatery, Snowy Owl
Lunch & Burgers: Mom & Pops, Chatham Bars Inn (Try the Poolside restaurant for drinks or the veranda restaurant for seaside views)
Provisions: Chatham Pier Fish Market, Mac’s Seafood
Sunset Tip: Grab burgers from Mom & Pops and head to Hardings beach with a bottle of wine for a beautiful sunset (don’t forget the bug spray 🙂).

Wellfleet & Truro — Edgy coastal towns with massive dunes, great seafood, and creative energy.

Reasons to visit: The best oysters, incredible hikes, wild landscapes, and great shopping in a delightful fishing village (our favorite rainy day excursion)
Breakfast & Cafes: Bagelhound, PB Boulangerie, The Blue Willow, Flying Fish
Lunch & Dinner: Mac’s Shack, Bookstore & Restaurant, Pizza Spinello, Wicked Oyster, Winslow’s, Moby Dick’s (BYOB), Blackfish
Drinks & Vibes: The Beachcomber, Truro Vineyards Provisions: Hatch’s, Mac’s, Wellfleet Farmers Market
Beaches & Hikes: Great Island Trail, Whitecrest, LeCount Hollow, Duck Pond, Rail Trail
Shops: Salt, Sailor, Isabel Souza, Wellfleet Flea Market
Fun: Wellfleet Drive-In, OysterFest (October)

Provincetown (Ptown) — Eclectic, colorful, and full of life

Reasons to visit: Vibrant and diverse, incredible food, design-forward shops, and one-of-a-kind hikes
Eat & Drink: Squealing Pig, Ceraldi, Sal’s Place, The Lobster pot, Mac’s Fish House, Portuguese bakery, The Canteen, Cafe Heaven, Liz’s cafe
Shops: Clove & Creek, John Derian, Captain’s Daughter
Hikes & Nature: Dune Shack hike, Longpoint Shuttle, Whale watching, Sailing

Other Excursions

Day Trip to the Islands: Catch a ferry from Hyannis to Nantucket or Martha’s Vineyard for a full day of exploring. There’s plenty to do and see right near the ferry, or rent a bike to cruise around the different towns and beaches. (Martha’s Vineyard has a great public transportation system, so getting around is easy.)

Charter a Boat: We like doing a fishing trip once a summer. It’s easy to charter a boat out of Sesuit Harbor Marina for full-day or half-day trips, and we always catch plenty of sea bass for the perfect summer-night dinner at Whig. Also check out the Lobster Sunset Cruise for a classic Cape tradition. There’s also a sailboat charter out of Ptown we’ve been wanting to try.

Shellfishing: Grab some waders and a shellfishing permit (super easy to get) and experience some of the best oysters in the world, fresh out of the water. Every town has slightly different regulations, so be sure to check them wherever you're heading. (Can’t shuck oysters? Try an oyster shucking class with Adam from The Pheasant.)

Fire and Oysters on the Beach: Newcomb Hollow Beach in Wellfleet allows dogs and fires on the beach (you may need a permit in summer). We love bringing fresh oysters, wine, and a couple baguettes for the perfect summer night.