How Long to Stay in Martha’s Vineyard and Nantucket?

Deciding how many days to spend in Massachusetts' most prestigious islands, Martha’s Vineyard and Nantucket, is a crucial question for any traveler planning a visit.

Martha’s Vineyard and Nantucket are renowned summer destinations, drawing crowds from Memorial Day to Labor Day (June to September). While these islands offer breathtaking scenery, several factors should be considered before planning your trip.

Budget: Both islands are known for their high costs, covering accommodation, dining, bars, and activities.

Flight: Personally flying from New York City's JFK airport, the roundtrip ticket to Martha’s Vineyard and back from Nantucket cost around $350, even during early summer (June). While the flight is short, it can be relatively expensive.

Transportation: One advantage of these islands is their walkability. While many locals drive Jeep Wranglers, renting a car might not be necessary, especially for a three-day trip. We found ourselves using Uber within the islands only a few times.

Now, let's dive into exploring these two islands over three days!

Martha’s Vineyard:

I explored two different towns in Martha’s Vineyard, each just 10 minutes apart yet offering distinct atmospheres, crowds, and beaches.

Edgartown:

Edgartown is a classic New England seaside village and Martha’s Vineyard's most charming location. It boasts beautiful historic streets, top-notch restaurants, excellent shopping, and vibrant nightlife. During my stay, I lodged at the Vineyard Square Hotel & Suites, perfectly situated next to the beach and in the heart of town.

Restaurants: The Seafood Shanty and Atlantic Restaurant are must-visits. With their delicious food and fantastic ambiance right by the beach, they're ideal spots for long conversations over drinks.

Afternoon: We wandered around the town, taking a break at a cool coffee/bookstore.

Nightlife: Evening drinks at The Wharf, a local hotspot in the village, rounded off our day.

The following morning, we embarked on an adventure, obtaining a trail map from the hotel and exploring Sheriff’s Meadow Sanctuary before cooling off with a swim at Fuller Street Beach.

Oak Bluffs:

Oak Bluffs, also known as OB, offers a different vibe compared to Edgartown. We stayed at the SummerCamp hotel, which felt oddly reminiscent of Disneyland. We enjoyed happy hour at Nancy’s restaurant, among several other dining options on the deck.

While Edgartown has a more laid-back atmosphere, Oak Bluffs is famous for its gingerbread cottage architecture and lively nightlife. Both towns offer unique experiences, making our exploration of Martha’s Vineyard unforgettable.

Nantucket, Massachusetts:

Nantucket stole the show during our trip. Taking a one-hour ferry from Oak Bluffs directly to Nantucket, we arrived at the heart of the island. We spent a night at the Martin House Inn, a pleasant stay despite the relatively high price.

Upon arrival, we indulged in a delectable lunch at Cru, which quickly became our favorite restaurant on the island. In the afternoon, we explored the town, shopped at charming stores, and enjoyed sunset drinks at Sandbar at Jettie’s beach bar. For dinner, Bar Yoshi's delicious food and outdoor garden seating created a perfect summer evening ambiance.

On our final day, we savored lunch and lobster rolls at Galley Beach, spending the entire day swimming and sunbathing. In the afternoon, we caught our flight back to JFK from Nantucket. After three days exploring these quaint Massachusetts islands, I'm delighted to say we experienced every aspect of their charm.

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