The quaint seaside town is filled with locals welcoming you to the island (and it’s got some fantastic seafood… bonus!)

Almost everywhere you look is a scene right out of a postcard.  Like this sailboat near a lighthouse with a billowing American flag behind it.  Just gorgeous!

Martha’s Vineyard = white picket fences, flowers, flowers, flowers, and cedar shake siding.  Uniquely beautiful properties, all blending together into a picture-perfect New England atmosphere.

One of the things on my bucket list was to ‘experience bliss.’  At the time I wrote that down I had no idea what it meant, but I knew I wanted to know what it felt like.  Fast forward to a sunny afternoon sipping Miraval (my new favorite wine) on the beach with two ladies I’m inspired by, look up to, and love dearly.  As I gazed out over the shimmering light dancing on the waves, with the sun warm on my face, a wave of happiness and gratitude washed over me.  I didn’t rush it, I let it envelop me and soak into every pore of my being.  It was beyond simply being happy.  It was a feeling that was so deep and permeating that I had no other way to describe it than ‘bliss.’  And just like that, I checked it off my list.

Drinking wine on the beach (because Vineyard is in the name so you kinda have to, right?)

A perfect way to end the day is with a sunset cruise around the harbor.  People wave at you from the shoreline as you sip, you guessed it, more wine!  Ahhhh… perfection.

The main harbor has a number of beautiful statues (like the whale tail shown here.)  And just beyond the gift shop to the left is the most amazing little fast food joint with fried clams that will make you glad you’re on vacation and can eat whatever you want.  After all, that’s the beauty of vacation, right?!?  No calorie counting and savoring every last morsel?  Go ahead.  You deserve it.

Sunset behind the lighthouse.  Nuff said.

There are a number of bike rental shops, which I’d highly suggest using.  There’s no better way to see the island than riding around (in fact, I ran into Meg Ryan doing just that!  It was like a real-life scene from one of her romantic comedies!)

One thing that didn’t make it on my bucket list but should have?  Driving on a beach!  Affectionately referred to as “Chappy Safari,” driving along the sandy road and across the far beach offers some of the best spots to camp out for the day with a bottle of wine and some good tunes.  Don’t forget to deflate your tires before you cross the bridge though, or you’ll get stuck!

The small island of Chappaquiddick can only be accessed by boat (so tickets must be purchased to cross on the Chappy Ferry.)  Chappaquiddick was made infamous in 1969 when Ted Kennedy and Mary Jo Kopechne’s car drove off the one-lane bridge across the tidal channel, resulting in Mary Jo’s drowning.  Ted Kennedy fled the scene and didn’t report the incident until 10 hours later.  It was a scandal of epic proportions, and most likely influenced his decision not to run for president in 1972.

Sipping champagne at sunset while sailing around the harbor.  Just another Martha’s Vineyard ‘pinch me’ moment.