Insider’s Guide to Cape Cod, Nantucket, and Martha’s Vineyard

Cape Cod, Martha’s Vineyard, and Nantucket offer a classic New England summer vacation. Shingled cottages, seafood shacks, and breezy beach days make it a laidback destination. 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 to learn where to stay, what to do, and how to plan a trip to the Cape and Islands.

Need to know

It’s smart to 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 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’ll likely hear some unique vernacular from Bostonians and Cape Codders.

• Key phrases: “down the Cape” (traveling to or being on Cape Cod), “wicked” (used in place of ‘very’ or ‘really’), “bubbler” (often heard as ‘bubblah,’ a drinking fountain), “frappe” (milkshake), and “scrod” (young Atlantic cod).
  

Airports: Most people fly into Boston (BOS) and Providence (PVD) airports. There are direct flights from Miami, Dallas, Atlanta, Los Angeles, Seattle, and many more cities. Travellers will then drive or take the train and/or ferries to Cape Cod, Martha’s Vineyard, and Nantucket. There are also smaller local airports with mostly seasonal connectivity.

Transportation: Cape Cod traffic gets busy, especially on weekends, so arrive early or midweek when you can. Ferries connect the Cape to the Islands, but schedules don’t always line up. Be prepared and plan ahead. If you’re bringing a car on the ferry, book spots months in advance, or try 6 am or midweek for last-minute chances. Watch for permit-only parking and small lots near beaches.

Best time to visit: The best time to visit Cape Cod is September through early November, 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, albeit very cold weather. Most businesses are only open from May to October, but residential areas have year-round offerings, especially on Nantucket, Martha’s Vineyard, and Block Island.

Ideal length of stay: Cape Cod, Nantucket, and Martha’s Vineyard all 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 around the area.

Signature dishes:

• Lobster roll: Served warm with butter or chilled with mayo—there’s passionate debate on which is best, so try both.
• Clam chowder: Creamy, hearty, and full of tender clams and potatoes.
• Fried clams: Whole belly or strips, you’ll find them at roadside shacks and sit-down spots alike.
• Oysters: Locally harvested and best enjoyed raw with lemon, mignonette, and the sea breeze.
• Blueberry pie: Especially good in late summer, when the local berries are at their peak.
• Stuffed quahogs (“stuffies”): A local favorite; chopped clams mixed with breadcrumbs, herbs, and spices, baked in the shell.
  

What to wear: Expect 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, while smart-casual works well for dinner. Think boat shoes, a light sweater, or a collared shirt. Evenings can get cool by the water, so bring a jacket or wrap. In fall and spring, and especially winter, layers are key.

Where to stay

Image courtesy of Chatham Bars Inn

Whether it’s a cozy seaside inn, a design-forward boutique hotel, or a historic resort with ocean views, Cape Cod, Nantucket, and Martha’s Vineyard have them all. Wherever you check in, expect local character, scenic surroundings, and easy access to beaches, restaurants, and bike trails.

Cape Cod

Cape Cod offers a wide range of places to stay, from grand seaside resorts to intimate boutique inns. Most are found along the Cape’s eastern shore, in or near Chatham. It’s the perfect base for beach days, gallery hopping, and exploring the Cape’s scenic byways.

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. It’s perfectly polished but relaxed.

• Our Perks include a £75 hotel credit, daily breakfast credit, an upgrade, and extended check-in/out whenever possible.
  

Wequassett Resort and Golf Club: Set on Pleasant Bay, this resort has manicured grounds, multiple pools, and a 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.

• Our perks include a £75 hotel credit, welcome amenity, daily breakfast, an upgrade, and extended check-in/out whenever possible.
  

Salt House Inn: This adults-only boutique spot in Provincetown is all about minimalist design and curated touches. With whitewashed walls, vintage coastal décor, and a sun-drenched patio, it feels like staying in a stylish friend’s beach house.

Nantucket

Image courtesy of Harbor View Hotel

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 provide a quieter, more residential feel close to beaches and bike trails.

Blue Iris: This chic, 12-room guesthouse downtown showcases bold interiors and an easygoing vibe. Expect curated design details, beach bags, and Turkish towels, plus a courtyard perfect for morning coffee or evening wine. It’s intimate and walkable to everything.

White Elephant Nantucket: A Nantucket classic that pairs waterfront views with refined island luxury. Rooms, suites, and cottages are spread across this harborfront property with an on-site spa, lively brunch scene, and lounge chairs lining the lawn. 

The Brant: Just outside downtown, this retreat brings a playful, design-forward energy to the island. The atmosphere is social and fun, with lawn games, complimentary bikes, and a beach shuttle. It’s the perfect laid-back stay with easy access to town and surf.

• Our Perks include a welcome amenity, complimentary bottle of rosé wine, an upgrade whenever possible, and guaranteed late check-out.
  

Martha’s Vineyard

Image courtesy of The Brant

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, or the ferry hub of Vineyard Haven.

Harbor View Hotel: This iconic stay above Edgertown Harbor feels both timeless and refreshed. The wraparound porch is ideal for sunset cocktails, while rooms balance coastal charm with modern ease. It’s steps from the lighthouse, boutique shops, and the sailing scene.

• Our Perks include a £75 food & beverage credit, daily breakfast credit, an upgrade, and extended check-in/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. The spa and thoughtful service round out the experience.

• Our Perks include a £75 hotel credit, welcome amenity, an upgrade whenever possible, and guaranteed late check-out.
  

Home rental stays

The best summer rentals can book up 6-12 months out, especially around peak weeks and holidays like July 4th, Labor Day, and school breaks. Flexibility may be limited; most rentals require Saturday-to-Saturday stays, so plan your travel days with that in mind.

Stay HVN: Curated luxury rentals with vetted properties and on-the-ground support teams. A strong pick for upscale stays across coastal New England.

Plum Guide: Stylish homes that meet rigorous quality standards. Think dependable charm in Cape Cod, Nantucket, and Martha’s Vineyard.

Vacasa: A broad range of professionally managed homes, from laid-back beach cottages to high-end hideaways, all with 24/7 guest support.

Cruises

While plenty of New England cruises sail past Cape Cod, Nantucket, and Martha’s Vineyard, few actually stop there. The exception is American Cruise Lines, a small ship line built for coastal cruising. 

It’s ideal for travelers who prefer a relaxed pace, locally inspired cuisine, and an intimate onboard atmosphere with fewer than 200 guests. Staterooms are spacious and there’s no formal dress code. Expect easy access to port towns, onboard enrichment from local experts, and plenty of time to explore on foot.

Choose from one of four distinct itineraries around the Cape:

• Cape Codder (7 nights, roundtrip Boston): Visit Provincetown, Martha’s Vineyard, Newport, and New Bedford for art-filled towns, seaside mansions, and rich maritime history.
• New England Islands (7 nights, roundtrip Providence): Explore Nantucket, Martha’s Vineyard, Block Island’s dramatic Mohegan Bluffs, Bristol, Newport, and New Bedford to enjoy coastal views and classic New England charm.
• New England Explorer (10 nights, roundtrip Boston): Sail to Acadia National Park and five ports in Maine, plus Gloucester, Newport, and Martha’s Vineyard for historic shipyards, coastal landscapes, and old-fashioned lobsterbakes.
• Grand New England (14 nights, roundtrip Boston): Explore ports from Maine to Rhode Island and cross Cape Cod, Nantucket, and Martha’s Vineyard for historic harbors, charming seaport towns, and Gilded Age estates.
  

History and culture

Cape Cod, Nantucket, and Martha’s Vineyard are steeped in a layered and complex history. Long before they became beloved seaside getaways, they were home to the Wampanoag people. They’ve lived in the region for hundreds of years. On Martha’s Vineyard, the Aquinnah Wampanoag Tribe still resides near the clay cliffs of Aquinnah. It’s a sacred site that visitors can respectfully view from an overlook. 

The islands also later played pivotal roles in early American maritime history. Nantucket was once the whaling capital of the world. Its cobblestoned streets and saltbox homes are staples with ties to 18th-century sea captains, Quaker settlers, and global trade. At the Nantucket Whaling Museum, visitors can trace this storied legacy while also acknowledging the environmental and human costs of the industry. 

Meanwhile, Cape Cod’s historic charm is anchored in its shipbuilding towns, clapboard cottages, and lighthouses, many of which date back to colonial times. Provincetown, located at the tip of the Cape, marks the landing site of the Mayflower in 1620, predating Plymouth. Today it thrives as a vibrant, welcoming community known for its artistic spirit and LGBTQ+ pride. Across all three destinations, local traditions like summer agricultural fairs, oyster festivals, and bonfires on the beach persist. The area invites travelers to visit and experience its historical charm, whether for a weekend or summerlong stay.

Cultural celebrations & events

• Nantucket Wine and Food Festival (May): Chefs, vintners, and food lovers descend on Nantucket for a weekend of tastings, oceanfront dinners, and culinary conversations.
• Provincetown Pride (June): Parades, beach parties, drag shows, and community events in one of the most LGBTQ+-friendly towns in the country.
• Juneteenth Jubilee (Martha’s Vineyard, June): This island-wide celebration honors African American freedom and culture with live music, educational panels, local vendors, and family programming.
• Fourth of July Celebrations (all locations, July 4): Parades, fireworks, and small-town Americana charm, from Edgartown’s harborfront show to parades in Chatham and festivities in Oak Bluffs.
• Cape Cod Jazz Festival (July to August): Hosted at the Wequassett Resort, this summer series features weekly performances from top jazz musicians.
• Wellfleet OysterFest (Cape Cod, October): A fall favorite on the Outer Cape with shucking competitions, shellfish tastings, and art vendors.
• A Very Vineyard Holiday (Martha’s Vineyard, December): Caroling, shopping strolls, tree lightings, and plenty of hot cocoa as Martha’s Vineyard transforms into a winter wonderland, especially in Edgartown.
  

What to do

Whether it’s a beach day, scenic bike rides, or boutique shopping, Cape Cod, Nantucket, and Martha’s Vineyard have no shortage of ways to spend your days.

Cape Cod

• Beaches: Relax on miles of public beaches. Mayflower Beach is a calm, family-friendly option on the bayside. Dramatic Atlantic-facing waves can be found at Coast Guard Beach, part of the Cape Cod National Seashore. Catch the sunset at Race Point Beach.
• Whale watching: Go whale watching from Provincetown, one of the best spots on the East Coast to see humpbacks and minkes.
• Hiking and biking: Explore scenic bike trails like the Cape Cod Rail Trail, or hike the rugged Great Island Trail in Wellfleet for secluded shoreline views.
• Chatham and Hyannis: Stroll through Chatham to find 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 its bold art scene, quirky shops, and lobster rolls with a harbor view.
  

Nantucket

• Beaches: Cliff Beach offers gentle waves and a family-friendly feel, while Surfside Beach is ideal for bodysurfing, long walks, and a breezy day by the sea.
• Town of Nantucket: Wander Nantucket Town for cobblestone streets, historic inns, and boutiques that blend timeless charm with modern flair.
• Sconset: Head out to Sconset, where 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 for a glimpse of America’s oldest functioning windmill.
• Museum: Dive into island history at the Whaling Museum, where maritime exhibits bring 19th-century Nantucket to life.
• Surfing: Catch waves at Cisco Beach, the island’s favorite surf spot with a laid-back scene and postcard-worthy views.
  

Martha’s Vineyard

• Menemsha Beach: Watch the sunset at Menemsha Beach, a working fishing village known for its easygoing feel and freshly caught seafood from the nearby market.
• Museum: Browse the Martha’s Vineyard Museum for a thoughtful mix of island history, seasonal art exhibits, and panoramic harbor views.
• Oak Bluffs: Meander past the colorful gingerbread cottages in Oak Bluffs, or head to Felix Neck Wildlife Sanctuary for birdwatching and quiet coastal trails.
• Walking and biking: Walk or bike through the peaceful, tree-lined paths of Correllus State Forest—14 miles of shaded trails that feel a world away from the beach crowds.
• Landmarks: Take in the sweeping coastal views from Aquinnah Cliffs and Gay Head Lighthouse, then unwind with a cold beer at Bad Martha’s Brewery in Edgartown.
  

Where to eat

From clam shacks to fine dining, seafood is fresh, local, and at the heart of New England’s dining scene. Here are some favourite restaurants across Cape Cod, Nantucket, and Martha’s Vineyard.

Cape Cod

• Water Street Kitchen (Woods Hole): Tiny but mighty, this creative spot serves up 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’s 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, with a globally inspired seafood menu.
• Mac’s Chatham Fish & Lobster (Chatham): Simple, fast, and consistently good, grab a lobster roll and eat outside. It doesn’t get more Cape Cod than this.
• The Lobster Pot (Provincetown): An icon with a massive menu, bold flavors, and harbor views. This place is constantly packed for a reason.
  

Nantucket

• The Nautilus: Always buzzing, this energetic spot is known for its bold, globally inspired small plates and inventive cocktails. 
• Galley Beach: With tables right on the sand and front-row seats to the sunset, this is the spot for a cocktail that effortlessly turns into a long, lingering dinner.
• Cru: A harborfront favorite for oysters, lobster rolls, and glasses of chilled rosé. It’s laid-back luxury with serious Nantucket polish.
• Millie’s: Baja-style tacos, breezy beach vibes, and spectacular sunsets make this casual favorite an easy repeat stop.
• Bar Yoshi: Sushi with a waterfront view, sake to sip, and a menu that’s perfect for something lighter but elevated.
• Sandbar at Jetties: Beachside and breezy with tropical cocktails, fresh seafood, and a laid-back vibe that works for families or happy hour.
  

Martha’s Vineyard

• Morning Glory Farm (Edgartown): Beloved by both locals and visitors, this farmstand bakery is your spot for fresh muffins, scones, and just-picked produce.
• Rosewater Market (Edgartown): A cozy corner café perfect for grabbing a quick breakfast sandwich or lingering over a cappuccino outside.
• L’étoile (Edgartown): One of Edgartown’s fancier splurge spots 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 and salty ocean air.
• Nomans (Oak Bluffs): Equal parts beer garden and beachy hangout, this is 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.
  

Trips to add on

Make it a longer getaway by adding these nearby cities and coastal towns to your trip. They’re easy to pair and add even more culture, food, and coastal beauty to your itinerary.

Newport, Rhode Island: Gilded Age mansions, sailing culture, and a sophisticated harbor town where you can tour cliffside estates by day and sip cocktails on the waterfront by night.

Providence, Rhode Island: Creative and compact, Providence is known for its arts scene, riverside walkways, and standout restaurants. Don’t miss WaterFire, a local tradition that brings the whole city to life.

Boston, Massachusetts: With its mix of Revolutionary history and world-class dining, stroll the cobblestone streets of Beacon Hill, catch a Red Sox game, or take a sunset cruise in Boston Harbor.

Montauk, New York: The Hamptons’ laid-back cousin, Montauk has rugged beaches, a big surf culture, and seafood shacks worth the trip.

New York City, New York: If you’re flying in or out of NYC, spend a few days soaking up the iconic museums, Broadway shows, rooftop bars, and vibrant neighborhoods.

If not Cape Cod, Nantucket, and Martha’s Vineyard…

Looking for a coastal escape with a similar vibe? These destinations offer charming beach towns, rich history, and an easygoing appeal.

Ipswich and Rockport, Massachusetts: These working fishing towns are all about local art galleries, harbor views, and fresh lobster rolls on the dock, both an easy drive from Boston.

Maine: For something more wild and outdoorsy, head north to Maine’s rocky coast. Camp in Acadia National Park, kayak between islands, and explore charming towns like Bar Harbor.

Lake Placid, New York: Set in the Adirondacks, this mountain escape combines lake days with hiking, cozy lodges, and a luxury-meets-rustic setting perfect for couples and families.

Charleston, South Carolina: For Southern charm with a coastal twist, Charleston has cobblestone streets, colorful homes, and fantastic restaurants. Nearby beaches like Folly and Sullivan’s Island are perfect for laid-back lounging.

Saint Lucia: For a completely different pace, this Caribbean island is mountainous, with excellent hiking  and beach resorts tucked into jungle-covered coves.

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