14 Activities
Island Hopper: Road Trip to Martha's Vineyard
Starts from
Boston
Transportation
By Car
Guidance
Self-Guided
Activities
14
Duration
2 days
Length
138 mi
Guide details
Starts from
Boston
Transportation
By Car
Guidance
Self-Guided
Duration
2 days
Length
138 mi
- Unusual Locations
- Family-Friendly
- Relaxation
Kelsey Perrett
Travel Expert
- Sunbathe on one of the island's best public beaches.
- Watch the sunset over Oak Bluffs Harbor with a cold drink in hand.
- Photograph the iconic Aquinnah Cliffs.
The island of Martha’s Vineyard, Massachusetts, located seven miles off the coast of Cape Cod, is a short and easy drive from Boston, but it’s best enjoyed as a multi-day experience. On this two-day road trip, you’ll take a ferry across Vineyard Sound to spend the night in the beach community of Oak Bluffs. Spend the next day touring the island — including the iconic Gay Head cliffs — before returning to the mainland.
This road trip visits the traditional lands of the Wampanoag and Pokanoket peoples. Because ferry reservations to the island book quickly in summer, we recommend traveling in spring or fall. It’s a good idea to book ferry reservations well in advance at steamshipauthority.com. Plan to arrive at least 30 minutes before your boat is scheduled to depart.
This road trip visits the traditional lands of the Wampanoag and Pokanoket peoples. Because ferry reservations to the island book quickly in summer, we recommend traveling in spring or fall. It’s a good idea to book ferry reservations well in advance at steamshipauthority.com. Plan to arrive at least 30 minutes before your boat is scheduled to depart.
Categories
- Unusual Locations
- Family-Friendly
- Relaxation
The island of Martha’s Vineyard, Massachusetts, located seven miles off the coast of Cape Cod, is a short and easy drive from Boston, but it’s best enjoyed as a multi-day experience. On this two-day road trip, you’ll take a ferry across Vineyard Sound to spend the night in the beach community of Oak Bluffs. Spend the next day touring the island — including the iconic Gay Head cliffs — before returning to the mainland.
This road trip visits the traditional lands of the Wampanoag and Pokanoket peoples. Because ferry reservations to the island book quickly in summer, we recommend traveling in spring or fall. It’s a good idea to book ferry reservations well in advance at steamshipauthority.com. Plan to arrive at least 30 minutes before your boat is scheduled to depart.
This road trip visits the traditional lands of the Wampanoag and Pokanoket peoples. Because ferry reservations to the island book quickly in summer, we recommend traveling in spring or fall. It’s a good idea to book ferry reservations well in advance at steamshipauthority.com. Plan to arrive at least 30 minutes before your boat is scheduled to depart.
Kelsey Perrett
Travel Expert
- Sunbathe on one of the island's best public beaches.
- Watch the sunset over Oak Bluffs Harbor with a cold drink in hand.
- Photograph the iconic Aquinnah Cliffs.
Travel itinerary
6 Activities
Day 1
17 mi0.2 mi
On Your Way to Oak Bluffs
Set out early to beat traffic on your way to Falmouth, Massachusetts. After touring the village of Woods Hole, hop the ferry to Martha’s Vineyard, where you’ll spend the night in Oak Bluffs.
8 Activities
Day 2
121 mi
Exploring Martha’s Vineyard
You’ll circle Martha’s Vineyard by car, visiting the island of Chappaquiddick, the fishing village of Menemsha, and the iconic cliffs of Gay Head before returning to Boston.