Cape Cod, Nantucket & Martha's Vineyard: Your Complete Luxury Travel Guide
Three coastlines. One classic American summer. Here is how to experience New England's most iconic islands the way they deserve to be experienced.
I get asked about the Cape and Islands constantly — which island, which hotel, which season, whether it's worth it if you've only got a long weekend. The honest answer is that all three destinations reward the traveler who shows up knowing what they want. And knowing the difference between them is where it starts.
Cape Cod is accessible and varied — a destination for everyone, which is both its strength and its limitation. Martha's Vineyard has a personality all its own, relaxed and rooted in local culture, the kind of place that regular visitors come back to the same week every August for twenty years. And Nantucket is the most polished of the three — cobblestone streets, upscale boutiques, a certain quiet confidence that feels entirely earned.
What to Know Before You Go
Summer is peak season, and these destinations fill up fast. Book accommodations and activities at least three to six months in advance, particularly for summer weekends and holiday weeks. A few things worth knowing before you start planning:
Ferry car spots book months ahead. Arrive on foot for flexibility, or plan well in advance if you need a car on the islands.
Beach access varies. Most Cape Cod beaches are public. Martha's Vineyard has more private, sticker-only options. Nantucket is a mix — check before you go.
Most businesses run May through October. Year-round offerings are strongest on Nantucket and Martha's Vineyard.
Traffic on the Cape gets heavy on summer weekends. Arrive midweek or early morning when you can.
"The sweet spot is September through early November — warm water, fewer crowds, and that golden late-summer light that makes everything look like a painting."
The Case for Nantucket
Nantucket is the island people mean when they say they want to feel like they've stepped out of their real life entirely. It is small enough to feel contained and beautiful enough to fill every corner of a week without effort. The cobblestone streets of Nantucket Town give way to historic inns, boutiques that feel considered rather than curated, and restaurants that take their oysters seriously.
Head out to Sconset and the pace drops another register entirely. Rose-covered shingled cottages line quiet lanes. The beach at the end of the path is largely empty. You begin to understand why people come back here the same week every year.
Brant Point Lighthouse — one of the oldest in the United States — sits at the harbor entrance where the ferry comes in, and photographing it when you arrive has become something of a Nantucket ritual. The Whaling Museum tells the island's complex, extraordinary story: Nantucket was once the whaling capital of the world, and its cobblestones and sea captains' houses carry that history in every detail.
Where to stay in Nantucket
White Elephant Nantucket — a Nantucket institution, right on the harbor. Rooms, suites, and cottages spread across a harborfront property with a full spa, a lively brunch scene, and blue lounge chairs lined along the lawn facing the water. This is Nantucket at its most classic — and most indulgent. Sirena Collective clients: complimentary perks available.
The Brant — a more playful, design-forward option just outside downtown. Lawn games, complimentary bikes, a beach shuttle, and an atmosphere that's social without being loud. Sirena Collective perks include a welcome amenity, complimentary bottle of rosé, room upgrade whenever possible, and guaranteed late check-out.
Blue Iris — 12 rooms in the heart of town. Intimate, design-led, and entirely walkable. Beach bags and Turkish towels at the ready, a courtyard for morning coffee. The kind of stay that feels effortless.
Nantucket is for
The traveler who wants polish without pretension. The couple who wants to feel like regulars somewhere beautiful. Anyone who has been meaning to go for years and keeps putting it off — go now.
The Case for Martha's Vineyard
Martha's Vineyard has a personality that Nantucket does not. It is bigger, more varied, and more rooted in the community that actually lives there year-round. Each town feels distinct: Oak Bluffs is lively and colorful, with gingerbread Victorian cottages painted in shades that look like they belong in a children's book. Edgartown is quieter and more refined, with white clapboard houses and a harbor that looks exactly as you imagined it would.
The Aquinnah Cliffs — dramatic bands of red and grey clay rising above the white sand beach — are unlike anything else on the East Coast. They are also sacred land of the Aquinnah Wampanoag Tribe, who have lived here for centuries, and should be visited with the respect that deserves.
Menemsha is the fishing village worth building an evening around. Grab a lobster roll from the counter at Larson's Fish Market, find a spot on the dock, and watch the sun go down over the water. It is one of those evenings that costs almost nothing and stays with you for years.
Where to stay on Martha's Vineyard
Harbor View Hotel, Edgartown — a timeless property above Edgartown Harbor, with wraparound porches designed for sunset cocktails and rooms that balance classic New England charm with modern ease. Steps from the lighthouse, boutique shops, and the sailing scene. Sirena Collective perks include a $100 food & beverage credit, daily breakfast, upgrade, and extended check-in/out.
Winnetu Oceanside Resort — a short walk from South Beach, ideal for families and groups. Spacious suites, private homes, firepits, lawn games, and Jeep rentals. The kind of place where everyone finds what they need without the day feeling scheduled.
Hob Knob, Edgartown — a beautifully restored 19th-century home-turned-boutique-hotel. Individually styled rooms, slow mornings with house-made pastries, a spa, and genuinely attentive service. Sirena Collective perks include a $100 hotel credit, welcome amenity, upgrade, and guaranteed late check-out.
Martha's Vineyard is for
The traveler who wants a sense of place alongside the beauty. Families who want space and variety. Anyone who has dreamed about a classic American island summer — the real version, not the Instagram version.
The Case for Cape Cod
Cape Cod is the entry point and, for many travelers, the most satisfying destination of the three. It is varied enough to suit almost any travel style — from the family-friendly calm of Chatham to the bold, artistic energy of Provincetown at the very tip of the Cape. The beaches are public, the seafood is extraordinary, and the pace is exactly what the word "summer" is supposed to mean.
Chatham Bars Inn has been the definitive Cape Cod resort since 1914. Atlantic views, a private beach, and the kind of evening where oysters and rosé on the veranda feel like the only logical conclusion to the day. If you have never been, it is worth building a trip around.
Where to stay on Cape Cod
Chatham Bars Inn — a Cape Cod landmark since 1914. Atlantic views, a private beach, and refined New England elegance without stiffness. Sirena Collective perks include a $100 hotel credit, daily breakfast, room upgrade, and extended check-in/out.
Wequassett Resort and Golf Club — set on Pleasant Bay with manicured grounds, multiple pools, a golf course next door, and waterfront dining. Refined but genuinely family-friendly. Sirena Collective clients access Preferred Platinum perks: $100 credit, welcome amenity, daily breakfast, upgrade, and extended check-in/out.
Salt House Inn, Provincetown — adults-only and minimalist, with whitewashed walls, vintage coastal touches, and a sun-drenched patio that feels like the best beach house you've ever been invited to.
Cape Cod is for
First-timers to New England. Families who want options. Anyone who wants to move around — Provincetown one day, Chatham the next, whale watching in between — without committing to a single island pace.
The Honest Answer
You want polish, quiet glamour, and the feeling of being somewhere that takes itself seriously without taking itself too seriously. You'd rather linger than cover ground.
You want variety, character, and a sense of place that goes deeper than a beautiful backdrop. Families, groups, and travelers who want to feel like they've actually been somewhere.
You want options — different towns, different beaches, different energies — all within reach. And if you want the most iconic New England resort experience, Chatham Bars Inn is the answer.
You have a week or more. The Cape and Islands ferry-hop beautifully, and each destination adds something the others don't. We can build that itinerary for you. Start here →
New England doesn't ask you to pick a side. It just asks you to show up — ideally in September, with no agenda and a very good appetite.
If a luxury sailing along the New England coast is more your style, American Cruise Lines offers intimate small-ship itineraries that actually dock in Cape Cod, Nantucket, and Martha's Vineyard — one of the few cruise lines that does. We can help you choose the right itinerary and handle everything from there.
Looking for something further afield? Read The South Caucasus with Kids — Armenia, Georgia, and Azerbaijan with three children and no rigid itinerary.
Planning a Cape & Islands Trip?
Whether it's one island or all three — Sirena Collective builds New England itineraries that get the details right, with exclusive hotel perks you can't book on your own. Always complimentary.
Start Planning →Frequently Asked Questions
Do I need a car on Nantucket or Martha's Vineyard?
Not necessarily. Both islands are very bikeable, and ferries from the Cape make it easy to explore on foot or by local transport. That said, a car gives you more flexibility, especially on Martha's Vineyard. If you're bringing a car on the ferry, book your spot months in advance — they go fast.
What is the difference between Cape Cod, Nantucket, and Martha's Vineyard?
Cape Cod is the most accessible and varied, great for families and first-timers. Martha's Vineyard is relaxed and community-oriented with a strong local culture. Nantucket is the most polished — upscale boutiques, cobblestone streets, and a distinctly refined atmosphere. All three are worth experiencing, and they ferry-hop beautifully together.
When is the best time to visit Cape Cod, Nantucket, and Martha's Vineyard?
September and early October are the sweet spot — warm water, fewer crowds, and that golden late-summer light. May through August is peak season with packed beaches and buzzy towns. Book well in advance for summer visits, especially for the islands.
Can I visit all three in one trip?
Absolutely — and we love building this itinerary. A week gives you time to sample all three. Two weeks lets you really settle in. Contact Sirena Collective and we'll map it out based on your travel style and group.
What are the Fora Perks you mention for hotels?
As Fora-affiliated advisors, Sirena Collective clients receive exclusive benefits at select properties that you can't book online — including hotel credits, complimentary breakfast, room upgrades, and guaranteed late check-out. It costs you nothing extra; we simply book on your behalf.
What is the best luxury hotel in Nantucket?
White Elephant Nantucket is the classic choice — right on the harbor with a full spa and the most iconic lawn chairs in New England. The Brant is our pick for a more social, design-forward stay with exclusive Sirena Collective perks including a complimentary bottle of rosé and guaranteed late check-out.