From Silver Screens to White Sails:Inside the most exclusive summer experiences of Cape Cod and Martha’s Vineyard

John F. Kennedy and Jackie Kennedy stroll across the lawn in Hyannis Port after announcing their engagement. Credit: Bettmann/Getty

There are places where summer means beach crowds and beach clubs. And then there is Cape Cod and Martha’s Vineyard, along the coast of Massachusetts, it becomes a carefully anticipated season.

For generations, both destinations have attracted political families, artists, filmmakers and affluent summer residents. Cape Cod is closely associated with the Kennedys, whose Hyannis Port compound became an informal centre of American political life. President John F. Kennedy sailed these waters and helped establish the Cape Cod National Seashore in 1961, protecting much of the coastline from unrestricted development.

Martha’s Vineyard developed its own mythology of privacy and prestige. Former presidents, actors and writers have holidayed there, but the island’s appeal extends beyond celebrity. Its real distinction lies in the culture of summering: returning to the same house, harbour and traditions year after year.

The summer calendar begins with gatherings that reveal the island’s deeper history. Juneteenth, celebrated on 19 June, commemorates the end of slavery in the United States and is marked in Oak Bluffs through music, food, cultural events and community celebrations. The occasion reflects Martha’s Vineyard’s longstanding importance as a summer meeting place for generations of African American families.

Soon afterwards, film screenings, Independence Day celebrations, sailing and garden openings reveal the region at its most compelling.

Cinema on the island

Martha’s Vineyard already occupies an important place in film history. Steven Spielberg filmed Jaws across the island, transforming its beaches, streets and harbours into the fictional Amity Island.

Edgartown Town Hall is located at 70 Main Street. It was turned into Amity Town Hall for the filming of Jaws. Source: CapeCod Times

Today, its relationship with cinema continues through the Martha’s Vineyard Film Society. From 25 to 28 June, FILMUSIC explores the intersection of music, documentary and cultural history.

The festival’s intimate scale is part of its appeal. Rather than competing premieres and large industry crowds, audiences gather at the Martha’s Vineyard Film Center in Vineyard Haven for screenings, conversations and live performances.

The 2026 programme opens with We Want the Funk!, tracing the genre from its African, jazz and soul roots through James Brown, Parliament-Funkadelic, Fela Kuti and hip-hop. A discussion with the directors follows the screening, offering the kind of direct access that distinguishes a small island festival.

Another highlight is Questlove’s documentary about Earth, Wind & Fire. Drawing on previously unseen footage, it examines the vision of founder Maurice White and the band’s fusion of music, costume, spirituality and performance.

Here, culture becomes part of the holiday itself: a day by the harbour can end with a film, a conversation with its director and dinner nearby.

The Fourth of July by the harbour

By Independence Day, the summer season is fully underway.

Across Cape Cod and Martha’s Vineyard, flags appear above historic houses and crowds gather for parades, concerts and fireworks. In Edgartown, the celebration unfolds against white-painted homes, church towers and a harbour filled with boats.

The parade moves through the town in the late afternoon. Later, fireworks rise above Edgartown Harbor, reflected across the water. It is a public celebration, but one that can be experienced from very different vantage points. Some watch from the waterfront; others from hotel lawns, verandas, private gardens or boats anchored in the harbour.

The same display feels entirely different when accompanied by dinner, and the excellent tradition of seafood of the region, seen from a waterfront room or observed from the deck of a sailing boat. The exclusivity lies not in escaping the celebration, but in finding an exceptional way to participate in it.

When the white sails return

Only a few days later, Martha’s Vineyard turns towards the water for the Vineyard Cup Regatta. The event brings together racing, seafood, maritime craftsmanship and island social life. From the shore, white sails scattered across Vineyard Sound create an almost painterly scene. Up close, however, sailing is demanding: it requires knowledge of tides, weather, equipment and crew.

This combination of elegance and expertise explains sailing’s enduring association with luxury. A yacht may be a valuable object, but genuine participation also requires time, confidence and familiarity with the water.

The Vineyard Cup supports Sail Martha’s Vineyard and its maritime education programmes, helping preserve the island’s sailing traditions for another generation. For spectators, the most memorable vantage point may be from the water itself, where the sound of sails, the movement of the crews and the scale of the fleet can be fully experienced.

Behind Cape Cod’s garden gates

As the regatta fills the waters around Martha’s Vineyard, Cape Cod enters hydrangea season. From 10 to 19 July, the Cape Cod Hydrangea Festival opens more than 80 private gardens from Falmouth to Provincetown. Blue, white, pink and violet blooms surround historic houses, coastal estates and cedar-shingled cottages.

These are not simply public flower displays. Many of the gardens normally remain hidden behind hedges and gates, making temporary access the festival’s greatest attraction.

The programme extends beyond garden tours to include workshops, expert talks, artistic events and hospitality experiences. Highlights include a garden luncheon at the historic Dan’l Webster Inn & Spa and a specialist hydrangea session at Chatham Bars Inn, one of Cape Cod’s best-known resorts.

Each garden tour also supports a local charitable organisation, connecting private beauty with community philanthropy. For a few summer days, visitors are invited into landscapes shaped over decades. The luxury lies in entering spaces that are usually seen only from the road—or not seen at all.

Source: Cape Cod Hydrangea Society– Hydrangea Festival

The privilege of arriving at the right moment

Cape Cod and Martha’s Vineyard offer different experiences. Cape Cod invites movement between villages, beaches, inns and gardens. Martha’s Vineyard feels more self-contained, with the ferry crossing creating the atmosphere of a retreat.

Together, they share a culture of seasonal return.

Their exclusivity is partly material: waterfront property is scarce, accommodation is difficult to secure and some experiences depend upon access to private houses, boats or gardens. But their deeper appeal lies in a calendar that briefly appears and then disappears. The privilege is not simply visiting Cape Cod and Martha’s Vineyard. It is understanding when they are most fully themselves - and arriving at precisely the right moment.