Plan Your New England Summer: Cape Cod and the Islands
The Insider's Guide to Cape Cod, Nantucket, and Martha's Vineyard
Cape Cod, Nantucket, and Martha's Vineyard offer the classic New England summer. Shingled cottages, seafood shacks, and breezy beach days make the whole region feel laid-back and easy. Each destination has its own personality, though.
Cape Cod has something for everyone, from family-friendly towns like Chatham to artsy enclaves like Provincetown. Martha's Vineyard feels relaxed but refined, with scenic bike paths, small towns, and a strong local vibe. Nantucket is the most polished of the three, known for upscale boutiques, cobblestone streets, and postcard-perfect beaches.
This region is great for couples, families, and groups looking for a coastal getaway with charm, character, and plenty of fresh seafood. Read on for where to stay, what to do, and how to plan a trip to the Cape and Islands.
Need to Know
Book your stay and activities at least three to six months in advance, especially for summer weekends and holidays. These coastal communities value their pace and traditions, so visitors are encouraged to keep beaches clean and quiet, follow local signage (especially around protected areas), and tip service staff generously.
Be mindful of ticks on trails and sharks in the water, and always use designated swimming areas. Beach access varies. Most of Cape Cod's beaches are public but may require parking passes. Martha's Vineyard has more private, sticker-only beaches, and Nantucket is a mix, so check before you go. And one more tip: lock your bike, even in the most charming towns.
Languages: English is spoken, but you will likely hear some unique vernacular from Bostonians and Cape Codders. A few key phrases to know:
- Down the Cape: traveling to or being on Cape Cod
- Wicked: used in place of "very" or "really"
- Bubblah: a drinking fountain
- Frappe: a milkshake
- Scrod: young Atlantic cod
Best time to visit: September through early November is ideal, when the summer crowds thin out but the ocean is still warm. May through August is peak season, with packed beaches and buzzy towns. Winter brings a quiet, residential feel best suited for peaceful retreats, with cold weather to match.
Ideal length of stay: All three make great long-weekend getaways from Northeast cities. If you have the time, a full week or more lets you settle into the slower pace and ferry-hop across the area.
Getting there: Most travelers fly into Boston (BOS) or Providence (PVD), then drive or take the train and ferries to the Cape and Islands. Cape Cod traffic gets busy on summer weekends, so arrive early or midweek when you can. If you are bringing a car on the ferry, book months in advance, or try a 6 am sailing or midweek for last-minute chances.
What to eat: Lobster rolls (warm with butter or chilled with mayo, and there is passionate debate on which is best). Clam chowder. Fried clams. Locally harvested oysters. Stuffed quahogs, known locally as "stuffies." Blueberry pie in late summer when the local berries hit their peak.
What to wear: Warm days with a relaxed, coastal feel. Pack swimsuits, breezy layers, sandals, and plenty of sun protection. A linen shirt or easy sundress is perfect for lunch or late-day drinks. Smart-casual works well for dinner, think boat shoes, a light sweater, or a collared shirt. Evenings get cool by the water, so bring a jacket or wrap.
Cape Cod: The Driveable Escape
Cape Cod offers a wide range of places to stay, from grand seaside resorts to intimate boutique inns. Most are found along the eastern shore, in or near Chatham. It is the ideal base for beach days, gallery hopping, and exploring the Cape's scenic byways.
Where to Stay
Chatham Bars Inn
A Cape Cod classic since 1914, Chatham Bars Inn blends historic charm with Atlantic views. Stay in a cottage by the sea, spend the day lounging on the private beach, and end with oysters and rosé on the veranda at sunset. Perfectly polished but relaxed.
Booked through me, you receive a $100 hotel credit, daily breakfast credit, a room upgrade when available, and extended check-in and check-out whenever possible.
Wequassett Resort and Golf Club
Set on Pleasant Bay, this resort delivers manicured grounds, multiple pools, and a championship golf course next door. Refined but family-friendly, with luxe rooms, waterfront dining, and kids' programming that lets adults have an afternoon at the spa.
As a Fora Preferred Platinum partner, when you book Wequassett through me, you receive a $100 hotel credit, a welcome amenity, daily breakfast, a room upgrade when available, and extended check-in and check-out whenever possible.
Salt House Inn
This adults-only boutique spot in Provincetown is all about minimalist design and curated touches. Whitewashed walls, vintage coastal décor, and a sun-drenched patio. It feels like staying in a stylish friend's beach house.
What to Do
- Beaches: Mayflower Beach is calm and family-friendly on the bayside. Coast Guard Beach delivers dramatic Atlantic-facing waves as part of the Cape Cod National Seashore. Catch the sunset at Race Point Beach.
- Whale watching: Provincetown is one of the best spots on the East Coast to see humpbacks and minkes
- Hiking and biking: Explore the Cape Cod Rail Trail, or hike the rugged Great Island Trail in Wellfleet for secluded shoreline views
- Chatham and Hyannis: Stroll Chatham for glassblowing studios, small galleries, and postcard-perfect lighthouse views. Visit the JFK Museum in Hyannis for a dose of local history
- Provincetown: Head to "P-town" for the bold art scene, quirky shops, and lobster rolls with a harbor view
A practical note: summer is shark season along the Outer Cape. Stay aware of posted beach guidance and follow lifeguard instructions.
Where to Eat
- Water Street Kitchen (Woods Hole): Tiny but mighty. Locally sourced dishes in a cozy harbor setting.
- The Pheasant (Dennis): Seasonal, modern New England cooking with a cool, rustic vibe. Feels like dining at a chef friend's chic farmhouse.
- Fishermen's View (Sandwich): Seafood so fresh it is often from their own boats. Great canal views, a buzzing raw bar, and casual upscale energy.
- The Ocean House Restaurant (Dennis Port): A favorite for a polished night out. The oceanfront setting is hard to beat.
- Mac's Chatham Fish and Lobster (Chatham): Simple, fast, and consistently good. Grab a lobster roll and eat outside. It does not get more Cape Cod than this.
- The Lobster Pot (Provincetown): An icon with a massive menu, bold flavors, and harbor views. Constantly packed for a reason.
Nantucket: Cobblestones and Cedar Shingles
Nantucket blends classic New England charm with elevated coastal style, from boutique hotels in historic buildings to harbor-view inns. Staying near town offers walkable access to shops, restaurants, and the ferry, while out-of-town options give you a quieter, more residential feel close to beaches and bike trails.
Where to Stay
Blue Iris
This chic, 12-room guesthouse downtown showcases bold interiors and an easygoing vibe. Curated design details, beach bags, Turkish towels, and a courtyard built for morning coffee or evening wine. Intimate and walkable to everything.
White Elephant Nantucket
A Nantucket classic that pairs waterfront views with refined island luxury. Rooms, suites, and cottages spread across this harborfront property with an on-site spa, a lively brunch scene, and lounge chairs lining the lawn.
The Brant
Just outside downtown, The Brant brings a playful, design-forward energy to Nantucket. The atmosphere is social and easy, from lawn games to complimentary bikes and a shuttle to the beach. The perfect laid-back stay with quick access to town and surf.
Booked through me, you receive a welcome amenity, a complimentary bottle of rosé, a room upgrade when available, and guaranteed late check-out.
What to Do
- Beaches: Cliff Beach offers gentle waves and a family-friendly feel. Surfside Beach is ideal for bodysurfing, long walks, and a breezy day by the sea.
- Town of Nantucket: Wander cobblestone streets, historic inns, and boutiques that blend timeless charm with modern flair
- 'Sconset: Rose-covered cottages and quiet beaches deliver major storybook vibes and a slower pace
- History: Snap a photo at Brant Point Lighthouse, one of the oldest in the US, and swing by the Old Mill, America's oldest functioning windmill
- Whaling Museum: Maritime exhibits bring 19th-century Nantucket to life
- Surfing: Catch waves at Cisco Beach, the island's favorite surf spot
Where to Eat
- The Nautilus: Always buzzing. Bold, globally inspired small plates and inventive cocktails.
- Galley Beach: Tables right on the sand and front-row seats to the sunset. A cocktail effortlessly turns into a long, lingering dinner.
- Cru: A harborfront favorite for oysters, lobster rolls, and chilled rosé. Laid-back luxury with serious Nantucket polish.
- Millie's: Baja-style tacos, breezy beach vibes, and spectacular sunsets
- Bar Yoshi: Sushi with a waterfront view, sake to sip, and a menu perfect for something lighter
- Sandbar at Jetties: Beachside and breezy with tropical cocktails and fresh seafood
Martha's Vineyard: Laid-Back Island Life
Martha's Vineyard is home to a mix of charming inns, refined hotels, and cottage-style stays. Each town offers its own distinct feel, from lively Oak Bluffs to elegant Edgartown to the ferry hub of Vineyard Haven.
Where to Stay
Harbor View Hotel
This iconic stay above Edgartown Harbor feels both timeless and refreshed. The wraparound porch is built for sunset cocktails, and rooms balance coastal charm with modern ease. Steps from the lighthouse, the boutique shops, and the sailing scene.
Booked through me, you receive a $100 food and beverage credit, a daily breakfast credit, a room upgrade when available, and extended check-in and check-out whenever possible.
Winnetu Oceanside Resort
A short walk from South Beach, Winnetu blends classic resort amenities with a laid-back luxe feel. Spacious suites and private homes make it perfect for families or groups, while firepits, lawn games, and Jeep rentals keep days full and easygoing.
Hob Knob
This intimate 19th-century home turned boutique hotel in Edgartown feels like a cozy, elevated escape. Each room is individually styled and the porch is made for slow mornings with house-made pastries.
Booked through me, you receive a $100 hotel credit, a welcome amenity, a room upgrade when available, and guaranteed late check-out.
Oak Bluffs: The Cultural Heart
To stay in the center of the island's heritage and vibrant porch life, consider these boutique options:
- Inkwell Beach Cottage: Located directly across from the historic Inkwell Beach
- Summercamp: A high-end, fully renovated property overlooking the harbor with a nostalgic vibe
- Narragansett House or The Morgan Hotel: Boutique options that put you steps from the ferry and historic sites
What to Do
In Oak Bluffs, visit Inkwell Beach, a central gathering place for the African American community since the late 1800s. Explore the African American Heritage Trail, which includes sites like Shearer Cottage, the first inn on the island to welcome Black guests in 1912.
Across the island:
- Menemsha Beach: Watch the sunset at this working fishing village known for freshly caught seafood from the nearby market
- Martha's Vineyard Museum: A thoughtful mix of island history, seasonal art exhibits, and panoramic harbor views
- Oak Bluffs gingerbread cottages: Meander past the colorful storybook houses, or head to Felix Neck Wildlife Sanctuary for birdwatching and quiet coastal trails
- Walking and biking: Walk or bike the peaceful, tree-lined paths of Correllus State Forest, 14 miles of shaded trails that feel a world away from the beach crowds
- Aquinnah Cliffs and Gay Head Lighthouse: Sweeping coastal views, then unwind with a cold beer at Bad Martha's Brewery in Edgartown
Where to Eat
- Morning Glory Farm (Edgartown): A farmstand bakery beloved by locals and visitors. The spot for fresh muffins, scones, and just-picked produce.
- Rosewater Market (Edgartown): A cozy corner café perfect for a quick breakfast sandwich or a lingering cappuccino outside
- L'étoile (Edgartown): A splurge spot with a creative, seasonal menu served in a charming old house and under a romantic tent
- Larson's Fish Market (Menemsha): Grab a lobster roll or steamers from the counter and enjoy dockside dining with harbor views
- Nomans (Oak Bluffs): Equal parts beer garden and beachy hangout. The go-to for live music, picnic tables, and easygoing eats. No reservations, just vibes.
- Back Door Donuts (Oak Bluffs): Late-night donuts from an actual back door. Go after 7 pm for warm fritters and people-watching.
Cruising the Cape and Islands
Plenty of New England cruises sail past the Cape and Islands, but few actually stop there. The exception is American Cruise Lines, a small ship line built for coastal cruising. It is ideal for travelers who prefer a relaxed pace, locally inspired cuisine, and an intimate onboard atmosphere with fewer than 200 guests. Staterooms are spacious, there is no formal dress code, and you get easy access to port towns, onboard enrichment from local experts, and time to explore on foot.
Four distinct itineraries cover the region:
- Cape Codder (7 nights, roundtrip Boston): Provincetown, Martha's Vineyard, Newport, and New Bedford
- New England Islands (7 nights, roundtrip Providence): Nantucket, Martha's Vineyard, Block Island's Mohegan Bluffs, Bristol, Newport, and New Bedford
- New England Explorer (10 nights, roundtrip Boston): Acadia National Park, five ports in Maine, plus Gloucester, Newport, and Martha's Vineyard
- Grand New England (14 nights, roundtrip Boston): Maine to Rhode Island, including the Cape, Nantucket, and Martha's Vineyard
If a cruise itinerary interests you, this is one of my specialties. I plan celebration cruises across premium and luxury lines, and American Cruise Lines is one of the strongest fits for travelers who want New England specifically.
Make It a Longer Trip
Pair the Cape and Islands with one of these nearby destinations to extend the experience:
- Newport, Rhode Island: Gilded Age mansions, sailing culture, and a sophisticated harbor town
- Providence, Rhode Island: A creative, compact city known for its arts scene, riverside walkways, and standout restaurants
- Boston, Massachusetts: Revolutionary history, world-class dining, Beacon Hill, and Red Sox games
- Montauk, New York: The Hamptons' laid-back cousin with rugged beaches and surf culture
- New York City: If you are flying through, spend a few days with the museums, Broadway, and rooftop bars
Ready to Escape?
Planning a trip to the Cape and Islands is more than booking a room. It is curating each detail, securing the right rooms before they are gone, and layering in the perks that turn a vacation into something memorable.
Let's design your next New England summer. Reach out to me at yannicke.collins@fora.travel.