The Complete Cape Cod, Martha’s Vineyard, and Nantucket Travel Guide
- Ryan Jones
- Jun 11
- 12 min read
Introduction to the Cape and Islands
Cape Cod, Martha’s Vineyard, and Nantucket are some of the most iconic and beloved summer destinations in the United States. This postcard-perfect region in southeastern Massachusetts captures the essence of New England charm, offering everything from sandy beaches and historic lighthouses to fresh seafood and quaint towns. Whether you're planning a romantic getaway, a family vacation, or a solo retreat, this comprehensive travel guide will help you make the most of your time in the Cape and Islands.
Steeped in history and brimming with character, each destination offers its own unique experience. Cape Cod enchants with its seaside villages and National Seashore, Martha’s Vineyard boasts rolling hills and pastel-hued cottages, and Nantucket exudes quiet luxury with cobblestone streets and iconic lighthouses. Let this guide be your one-stop resource for planning a seamless and memorable New England escape.
Best Time to Visit Cape Cod and the Islands
Peak Season: May through August
The summer months are the most popular time to visit Cape Cod and the Islands, with warm weather, vibrant events, and a full calendar of festivals, farmers markets, and beach days. During this time, the towns are alive with energy, and outdoor activities like whale watching, kayaking, and coastal bike rides are in full swing. However, accommodations fill up quickly, and traffic—especially on weekends—can be intense, so booking early is essential.
Families, couples, and friend groups will all find plenty to do in the summer, from seafood festivals in Cape Cod to surf lessons on Nantucket. The only downside? Crowds and high-season pricing. If you thrive on buzz and sunshine, this is your window.
Shoulder Season: September through early November
If you're looking for fewer crowds, better rates, and that quintessential fall charm, the shoulder season is ideal. The ocean remains surprisingly warm through September, and the cooler weather makes for perfect hiking and exploring. Fall foliage paints the landscape in vibrant reds and golds, adding a different kind of magic to the coastal views.
Many restaurants and shops remain open through October, and events like the Wellfleet OysterFest and Cape Cod Jazz Festival extend the fun into the fall. It’s the best time to savor the region without the peak-season pace.
Off-Season: December through April
Though most associate the Cape and Islands with summer, winter brings a peaceful, almost magical stillness. Towns like Edgartown and Nantucket light up with holiday charm, hosting events like A Very Vineyard Holiday and festive strolls. It’s the perfect season for quiet walks on the beach, cozy dinners, and off-the-beaten-path experiences.
Keep in mind that many businesses operate seasonally, so dining and shopping options are more limited. Still, for those seeking solitude, romantic winter retreats, or low-season deals, this time of year is worth considering.
Getting to Cape Cod, Martha’s Vineyard, and Nantucket
Flights and Airports
Most travelers fly into Boston Logan International Airport (BOS) or T.F. Green Airport in Providence (PVD), then drive or ferry to their final destination. Smaller regional airports include Hyannis (HYA), Martha’s Vineyard (MVY), and Nantucket Memorial Airport (ACK), offering seasonal and year-round flights from major hubs like New York, Washington D.C., and Chicago.
During summer months, seaplanes also fly into Provincetown and Boston Harbor, offering a scenic and efficient alternative to traffic-heavy routes. Booking early is crucial, especially if you're traveling during holidays or weekends.
Ferries and Train Options
Ferries are a scenic and classic way to reach the islands, with departures from Hyannis, Woods Hole, New Bedford, and even New York City. Book vehicle ferries months in advance or travel midweek for better availability. Fast ferries from Hyannis to Nantucket or Martha’s Vineyard offer a convenient option if you’re not bringing a car.
The CapeFLYER, a weekend passenger train from Boston to Hyannis, offers a relaxing and car-free way to reach the Cape in the summer. It’s a popular choice for those wanting to avoid traffic and enjoy the ride.
Cape Cod Travel Guide
Top Towns to Visit
Provincetown
At the northern tip of the Cape, Provincetown—or “P-Town”—is where the Pilgrims first landed in 1620. Today, it’s known for its vibrant LGBTQ+ community, art galleries, and lively atmosphere. Visitors can climb the 252-foot granite Pilgrim Monument for sweeping harbor views or take a guided Art’s Dune Tour to explore the Cape’s unique landscape.
Provincetown is also one of the best spots on the East Coast for whale watching, with daily excursions from spring through fall. The town’s walkable layout, quirky shops, and seafood eateries make it a must-see for any Cape Cod itinerary.
Chatham
Chatham, located at the “elbow” of the Cape, is a picture-perfect New England town with a historic lighthouse, charming main street, and excellent dining. It’s one of the best spots for a leisurely day of boutique shopping and waterfront strolls.
Seafood lovers should stop by Mac’s Chatham Fish & Lobster for a laid-back meal of fresh lobster rolls and fried clams. It’s also a great jumping-off point for scenic drives or a visit to Monomoy National Wildlife Refuge.
Hyannis
Hyannis serves as the main ferry hub for reaching Martha’s Vineyard and Nantucket. It’s also home to the John F. Kennedy Hyannis Museum and the Cape Cod Maritime Museum, both offering insight into local history and presidential legacy.
Before hopping on the ferry, grab a bite at Spanky’s Clam Shack, a casual spot popular for its chowder and waterfront views.
Things to Do in Cape Cod
Cape Cod is packed with scenic activities. The Cape Cod National Seashore is a protected stretch of 40 miles of coastline, perfect for hiking, beachcombing, and taking in ocean vistas. For cycling enthusiasts, the Cape Cod Rail Trail winds through towns, marshes, and pine forests. Book a guided hike or tour like this one to lear more about the area and environment.
Heritage Museums & Gardens in Sandwich offers a serene spot for floral strolls and vintage car exhibits, while the Wellfleet Drive-In Theater is a nostalgic way to enjoy movies under the stars. Don’t miss the opportunity for a whale-watching tour from Provincetown or Hyannis—one of the most thrilling experiences on the Cape.
Best Places to Stay in Cape Cod
For luxury, the Chatham Bars Inn is an icon, blending historic charm with oceanfront views. It offers private beach access, boating excursions, and an upscale spa. The Wequassett Resort & Golf Club in Harwich is another polished option with manicured grounds, pools, and dining with bay views.
Couples looking for an adults-only boutique stay will love Salt House Inn in Provincetown, known for its whitewashed walls and sun-soaked patio. Each of these stays blends coastal elegance with prime locations.
Martha’s Vineyard Travel Guide
Top Towns to Visit
Edgartown
Edgartown is the island’s most polished and historic town, once a prominent whaling port. Today, it boasts white clapboard captain’s houses, charming streets lined with upscale boutiques, art galleries, and coastal dining spots. A stroll along its harborfront is the perfect way to soak up the Vineyard’s refined charm, and nearby Lighthouse Beach is a serene spot for sunset walks.
You’ll also find some of the island’s best dining in Edgartown, from farm-to-table cafés to elegant seafood restaurants. Whether you’re relaxing on a porch swing or exploring the town’s maritime heritage, Edgartown feels timeless and picturesque.
Oak Bluffs
Lively and colorful, Oak Bluffs draws day-trippers and families alike with its whimsical architecture and relaxed vibe. The famed Gingerbread Cottages in The Campground look straight out of a storybook, while the Flying Horses Carousel—the oldest operating platform carousel in the U.S.—delights visitors of all ages.
Ocean Park is the heart of the town, perfect for a picnic or simply soaking in the coastal breeze. Come evening, the town buzzes with energy thanks to beachside bars, live music, and the always-popular Back Door Donuts, which serves warm pastries from—you guessed it—the back door.
Aquinnah
On the island’s western tip, Aquinnah offers breathtaking natural beauty and rich cultural significance. It’s home to the Aquinnah Cliffs, a dramatic stretch of red clay bluffs overlooking the Atlantic Ocean. The adjacent Gay Head Lighthouse is a striking landmark, best viewed at sunset.
This area also honors the heritage of the Aquinnah Wampanoag Tribe. Visitors can learn about their history at the Aquinnah Cultural Center and respectfully experience the sacred lands through designated overlooks and trails.
Things to Do in Martha’s Vineyard
Sightseeing tours are a great way to explore the island, whether by bike, bus, or even kayak. Specialty routes include the African American Heritage Trail and the JAWS filming locations. Foodies will love the summer farmers’ markets in West Tisbury and the many small farm stands selling cheeses, jams, and baked goods made on-site.
Nature lovers should head to Felix Neck Wildlife Sanctuary for birdwatching and peaceful walking trails, or explore the tree-lined paths of Correllus State Forest. From harbor strolls to outdoor adventures, there’s something for every traveler.
Best Places to Stay in Martha’s Vineyard
For classic island elegance, the Harbor View Hotel in Edgartown offers coastal charm, wraparound porches, and easy access to shopping and sailing. Winnetu Oceanside Resort near South Beach caters to families and groups with its spacious suites, beach access, and outdoor amenities like firepits and lawn games.
Looking for something more intimate? Hob Knob, a boutique hotel housed in a 19th-century Edgartown home, offers cozy luxury and a standout breakfast spread. Many properties offer travel advisor perks like food credits, welcome amenities, or complimentary upgrades, so booking through a travel advisor can add value to your stay.
Nantucket Travel Guide
Overview of Nantucket
Nantucket is the epitome of quiet coastal luxury. Located 30 miles off the coast of Massachusetts, this island is known for its cobblestone streets, weathered shingle-style homes, and unspoiled beaches. Though it's often associated with upscale travel, Nantucket offers a welcoming charm that blends laid-back elegance with rich history and natural beauty.
Visitors will find a slower pace of life here—ideal for unwinding with long bike rides, boutique shopping, and seaside dining. Whether you come for the history, the views, or the lobster rolls, Nantucket is a destination that leaves a lasting impression.
Highlights of Nantucket
Nantucket Town
The heart of the island, Nantucket Town, is a preserved slice of New England history. Wander the cobblestone streets to discover a curated collection of boutiques, coastal bookstores, artisan shops, and cozy cafés. The Whaling Museum provides a fascinating look at the island’s 18th- and 19th-century legacy, once a global whaling capital.
Every corner of the town offers scenic moments—whether it’s the harbor views, ivy-covered inns, or flower-filled courtyards. It’s a great base for exploring the island on foot or by bike.
Beaches
Nantucket’s beaches are among the best on the East Coast. Surfside Beach is a favorite for wave lovers, while families enjoy the calm waters of Jetties Beach. For a quieter experience, head to Sconset Beach on the island’s eastern shore, where rose-covered cottages and the famous Bluff Walk add a dreamlike quality to the coastline.
Cisco Beach is popular with surfers and has a low-key, local vibe, often accompanied by food trucks and live music at nearby Cisco Brewers.
Iconic Landmarks
No visit is complete without a photo at Brant Point Lighthouse—one of the most photographed and accessible lighthouses in the U.S. History buffs will appreciate the 1686 Jared Coffin House and the Old Mill, the oldest functioning windmill in the country.
If you’re up for a cycling adventure, the Polpis Bike Path leads to scenic sites like Sankaty Head Lighthouse, Altar Rock, and the Windswept Cranberry Bog—each offering a snapshot of the island’s unique terrain and charm.
Things to Do on Nantucket
Biking is the best way to get around, with over a dozen paved paths crisscrossing the island. Rent a cruiser and explore at your own pace, stopping for beach views, art galleries, or a casual bite. Don’t miss a stop at Cisco Brewers, a local favorite for craft beer, live music, and lobster rolls served from onsite food trucks.
The Coskata-Coatue Wildlife Reserve is a haven for birdwatchers, hikers, and beachcombers. Drive or bike out to Great Point Lighthouse for solitude and sweeping ocean vistas. In the evenings, enjoy harborfront dining at places like Straight Wharf, or stroll the docks under a glowing island sunset.
Best Places to Stay in Nantucket
For a luxurious harborfront stay, the White Elephant is a beloved classic offering top-tier amenities, a serene spa, and unbeatable location. Just outside of downtown, The Brant brings a youthful energy with beach shuttles, complimentary bikes, and a playful design-forward approach.
The Blue Iris is a 12-room boutique guesthouse in the heart of Nantucket Town, offering
thoughtful design details, beach bags, and Turkish towels for a perfectly curated experience. Each of these properties caters to different traveler styles—whether you're seeking romance, adventure, or a refined retreat.
Signature Foods and Where to Eat
Signature New England Dishes
No trip to Cape Cod, Martha’s Vineyard, or Nantucket is complete without indulging in the region’s iconic coastal cuisine. Lobster rolls reign supreme—served either warm with butter or cold with mayo—and everyone has a strong opinion on which is best. Clam chowder is another staple, thick and creamy with plenty of tender clams and potatoes, perfect after a beach day or sunset walk.
Fried clams, especially whole belly clams, can be found at roadside shacks and sit-down restaurants alike, while oysters—fresh, briny, and local—are best enjoyed raw with a squeeze of lemon and a glass of chilled rosé. For something sweet, don’t miss the local blueberry pie, especially in late summer when the berries are at peak ripeness. And if you’re offered a “stuffie” (stuffed quahog), say yes—it’s a delicious baked shell of chopped clams, herbs, and spices.
Top Restaurant Recommendations
Cape Cod
Cape Cod’s dining scene blends casual charm with high-quality seafood. Water Street Kitchen in Woods Hole offers creative, locally sourced dishes in an intimate harbor setting. The Pheasant in Dennis has a rustic-farmhouse feel and a modern New England menu that changes with the seasons. For a canal-side view, Fishermen’s View in Sandwich serves seafood fresh from their own boats.
For upscale dining, The Ocean House Restaurant in Dennis Port provides global seafood dishes with panoramic ocean views. And no visit to Chatham is complete without a lobster roll at Mac’s Chatham Fish & Lobster, where you can eat outdoors and watch the boats come in. In
Provincetown, The Lobster Pot is a legendary stop, known for bold flavors, harbor views, and a bustling atmosphere.
Nantucket
Nantucket offers everything from elevated dining to breezy beachside bites. The Nautilus is one of the island’s most popular spots, dishing out inventive small plates and a buzzing atmosphere. For sunset dining, Galley Beach places your toes in the sand as you sip cocktails and savor fresh seafood.
If oysters and rosé are your vibe, Cru on the harborfront delivers with laid-back luxury and unbeatable views. Millie’s, known for its Baja-style tacos and stunning west-end sunsets, is a casual favorite, while Bar Yoshi offers fresh sushi and waterfront views. Families love Sandbar at Jetties, where you can enjoy beachside eats with a tropical cocktail and let the kids play in the sand.
Martha’s Vineyard
The Vineyard’s food scene leans into its farm-fresh identity. In Edgartown, Morning Glory Farm is a beloved stop for muffins, scones, and just-picked produce. For breakfast or a relaxed lunch, Rosewater Market is a cozy café with excellent coffee and sandwiches.
For something upscale, L’étoile offers a refined seasonal menu served in a charming Edgartown home or under a romantic tent. In Menemsha, Larson’s Fish Market is a must—grab a lobster roll or steamers and eat dockside with harbor views. For live music, picnic tables, and a laid-back scene, Nomans in Oak Bluffs is a favorite. And if you’re up late, Back Door Donuts serves warm pastries from—you guessed it—the back door, starting at 7 p.m.
Travel Tips and Insider Advice
Practical Considerations
Planning ahead is key when visiting Cape Cod, Martha’s Vineyard, and Nantucket—especially during peak summer months. Book accommodations, ferry tickets (especially for vehicles), and popular dining reservations three to six months in advance if possible. Ferries can fill up quickly, and schedules don’t always align perfectly between the islands, so be flexible with your travel times and consider traveling midweek for more availability.
Keep in mind that beach access varies: many Cape Cod beaches are public but may require parking passes, while Martha’s Vineyard and Nantucket have a mix of public, private, and sticker-only beaches. Be sure to check local rules before heading out for the day. Also, don't forget to lock your bike—even in the most charming towns!
Local Etiquette and Safety Tips
Respect local customs by keeping beaches clean, observing signage in protected areas (like dunes and conservation lands), and tipping generously at restaurants and tours. When hiking or walking wooded areas, be cautious of ticks by wearing long clothing and using repellent. If swimming, always stay within designated areas and be aware of occasional shark advisories, especially along outer Cape beaches.
Locals use fun regional terms, so don’t be surprised if someone points you to the “bubbler” (water fountain) or invites you for a “frappe” (milkshake). And remember—“down the Cape” is how locals refer to heading to Cape Cod.
Add-On Trips and Nearby Destinations
Extend Your Coastal Getaway
While the Cape and Islands are magical in their own right, nearby New England destinations make excellent additions to your trip. In Newport, Rhode Island, explore opulent Gilded Age mansions and enjoy sunset sailing excursions. Providence offers a walkable arts scene and riverside charm—perfect for a cultural detour.
Heading north? Boston is rich with Revolutionary War history, vibrant neighborhoods, and world-class dining. Or venture up the coast to Rockport or Ipswich, Massachusetts, for lobster rolls on the dock and coastal art galleries. Looking for something more adventurous? Maine’s rocky coast and Acadia National Park offer stunning outdoor experiences. Even Montauk, New York, provides a surfer-friendly alternative with beachy restaurants and rugged charm.
Why Book with a Travel Advisor
Booking your trip through a professional travel advisor means peace of mind, insider knowledge, and exclusive perks. From finding you the best ferry times and accommodations to securing dining reservations and hotel upgrades, a travel advisor handles the details so you can focus on the experience.
Advisors often have access to VIP benefits at top hotels—think daily breakfast credits, resort amenities, room upgrades, and flexible check-in/out. Plus, if anything changes during your trip, you have an expert in your corner ready to help. Whether it’s your first visit or a return to your favorite island, I’ll create a custom itinerary tailored to your travel style.
Cape Cod, Martha’s Vineyard, and Nantucket aren’t just destinations—they’re experiences steeped in history, charm, and coastal beauty. Whether you're savoring a lobster roll with your toes in the sand or pedaling past lighthouses and hydrangea-lined lanes, this corner of New England has something unforgettable for every traveler.
Ready to plan your dream trip to the Cape and Islands? Reach out today and let’s build your perfect coastal escape—from ferry bookings and boutique hotels to seafood stops and sunset sails. Your unforgettable summer getaway starts here.
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