10-Day Island Hopping In New England

Come Monday It’ll be alright

Jimmy Buffett

Last year I took an ‘East Coast Road Trip’ so I decided to shake things up a little bit and tag along on a 10-day boat vacation ‘Island Hopping’ with Paul! Many of the places I had never been before, so it was quite the adventure.

Day 1

Onset

Onset is a quiet town with nice beaches. We only stopped for the day before our trip to Cuttyhunk. We had a lobster dinner on the boat and beautiful weather. The water was calm and made for comfortable paddle-boarding! 

Day 2

Cuttyhunk

Cuttyhunk is an adorable little island with a quiet way of living. There are homes used for residence in the summer, but less than 100 people live there all year round. A very cute ice cream shop rests right off the dock and there are quiet trails to walk. 

Days 3 – 6

Block Island

Sites to See:

  • Southeast Lighthouse
  • Mohegan Bluffs
  • Block Island North Light 

Days 7 + 8

Oak Bluffs

Sites to See:

  • Ocean Park
  • East Chop Light
  • Farm Neck Golf Club
  • Circuit Avenue

Days 9 + 10

Provincetown

Sites to See:

  • Commercial Street
  • Pilgrim Monument
  • The Lobster Pot

Look out for my upcoming blog ‘Essentials for Summer’ and check out photos from the trip on Twitter and Instagram.

Have a trip suggestion? Message me or comment below!