Martha's Vineyard is a charming destination, perfect for a group of friends looking to relax, explore, and enjoy some quality time together. Here’s a delightful 4-day itinerary tailored for your group of ten fabulous women over 50. Let’s dive in!

Getting There from New York

To get to Martha's Vineyard from New York, you have a couple of options:

1. By Train and Ferry: Take the Amtrak from Penn Station to Boston (around 4 hours). From Boston, you can take a bus or taxi to the ferry terminal (about 15-20 minutes) and then catch a ferry to Martha's Vineyard (1 hour).

2. By Car: If you prefer driving, it’s about a 4-5 hour drive to Woods Hole, where you can catch the ferry to Martha's Vineyard.

3. Direct Flights: There are also seasonal flights from NYC to Martha's Vineyard, which can be a quick option.

Hotel Suggestions

Here are a couple of lovely hotel options that cater to groups:

1. The Harbor View Hotel (Edgartown)

   • Price: Approximately $300-$500 per night, depending on the season.
   • Features: Beautiful waterfront views, a pool, and a lovely restaurant.

2. Mansion House Inn (Vineyard Haven)

   • Price: Around $200-$400 per night.
   • Features: A spa, rooftop hot tub, and close to shops and restaurants.

3. The Kelley House (Edgartown)

   • Price: Approximately $250-$450 per night.
   • Features: Historic charm, a pool, and a great location.

Day 1: Arrival and Edgartown Exploration

• Morning: Arrive at Martha's Vineyard and check into your hotel. Take a moment to freshen up and relax.
• Lunch: Head to The Seafood Shanty for a casual lunch with a view. Try their lobster rolls!
• Afternoon: Explore Edgartown. Visit the Edgartown Lighthouse and stroll along the charming streets filled with boutiques and galleries.
• Evening: Dinner at The Port Hunter. Enjoy their fresh seafood and lively atmosphere. Don’t forget to try their signature cocktails!
• Night: Wind down with a nightcap at the hotel bar or a cozy gathering in your room.

Day 2: Vineyard Tour and Beach Day

• Morning: After breakfast at the hotel, embark on a Vineyard Tour. Consider booking a private van tour that can take you to Oak Bluffs, Vineyard Haven, and other scenic spots.
• Lunch: Stop at The Red Cat Kitchen in Oak Bluffs for a delicious farm-to-table meal.
• Afternoon: Spend some time at Inkwell Beach in Oak Bluffs. Relax, sunbathe, or take a dip in the ocean.
• Evening: Dinner at L’etoile in Edgartown, known for its upscale dining and seasonal menu. Reservations are recommended!
• Night: Enjoy a sunset walk along the beach or gather for games and laughter back at the hotel.

Day 3: Adventure and Culture

• Morning: After breakfast, take a biking tour around the island. Rent bikes from Vineyard Bicycles and explore the scenic paths.
• Lunch: Pack a picnic or stop at The Beach Plum Inn for a light lunch.
• Afternoon: Visit the Martha's Vineyard Museum to learn about the island's history and culture.
• Evening: Dinner at The Grill on Main in Edgartown, where you can enjoy a relaxed atmosphere and great food.
• Night: Check out a local event or live music if available, or enjoy a movie night at the hotel.

Day 4: Relaxation and Departure

• Morning: Enjoy a leisurely breakfast at The Black Dog Tavern. Their breakfast is a must-try!
• Late Morning: Spend your last few hours shopping for souvenirs in Edgartown or take a final stroll along the beach.
• Lunch: Grab a light lunch at The Grey Barn & Farm before heading back.
• Afternoon: Check out of your hotel and make your way back to the ferry or airport for your return trip to New York.

Tips for Your Trip

• Reservations: Make dining reservations in advance, especially for dinner spots.
• Group Activities: Consider booking group activities or tours to ensure everyone can participate.
• Transportation: Renting a van or using ride-sharing services can be convenient for your group.

I hope this itinerary helps you plan an unforgettable trip to Martha's Vineyard! Enjoy the beautiful scenery, delicious food, and wonderful company! 🌊🍷✨