Getting there

The easiest and most convenient way to arrive is by plane; fly into the local airport in West Tisbury (relatively central point to touch down!) *Jet Blue has plenty direct flights in the summer from JFK!

Another common way to arrive is by car and ferry; you can drive from wherever you hail, and book a car ferry to the island out of Woods Hole or Hyannis (great option if you would like to do some exploring and have your own car!). You can also drive to any of the ferry docks on the mainland (Woods Hole, Hyannis, Providence) and ride a ferry as a passenger! I love the ferry rides - go up on the top deck to take in the fresh air and waterline views, read a book and grab a coffee on board!

Get checked in!

Find your house rental or hotel and get settled. Highly recommend the Harbor View Hotel in Edgartown.

Dinner in town

Make your way to Bettini for dinner - waterfront views, relaxed, warm environment with a chef inspired menu featuring the season’s freshest offerings from local farms, fishing boats, foragers and markets.

Start your day by walking over to your breakfast spot of choice...Espresso Love for fresh baked pastries, bagels, breakfast sandwiches and of course coffees and lattes, Among the Flowers for smoothies and lighter morning fare, or Toccopuro Coffee for the best coffee on the island in my opinion - strong and lots of flavors/options!

Rent bikes in Edgartown and hop on The Chappy ferry across to Chappaquiddick. Ride down the island roads to the Royal and Ancient Par 3 course for activity! You can rent clubs or bring your own, as well as bring your own drinks or buy a bucket of beers. Such a fun, walkable course for family and friends.

Post golf, ride around Chappy and return to Edgartown. Head back to your hotel, shower and change!

Do some shopping in town; wonderful boutiques line the streets of Edgartown. Then head to dinner at The Covington or The Atlantic.

Enjoy a slow morning and grab breakfast + lunch to go at one of the spots I mentioned for Day 1 that you did not try yesterday, and load up for the beach...there are so many wonderful options for beaches that you can explore during your time on the island. State Beach (home of the Jaws Bridge!), Inkwell Beach, Menemsha (wonderful for sunset + don't forget to grab a fresh lobster roll on your way to set up!), South Beach (probably the best "classic beach day" option! has parking along the water, and the option to deflate tires to do some sand driving!).

Post beach day, head to Nomans for a casual dinner! This spot has lawn games and open air dining - perfect for winding down after a day in the sun.

Up and at 'em today! Get an early start and head to Grey Barn - such an ethereal, bucolic start to your day! Chickens and bunnies roam free, with horses and cows in the distance. Willow trees and gardens line the walk up to the farmhouse, where you can get your hands on some of the best croissants and honey buns known to man - they go quick, so must get there early! They also have fresh cheeses, meats, spreads, and produce for a killer charcuterie board.

Once you have your morning fuel, head to Oak Bluffs - explore the historic Gingerbread houses, Main St (Fat Ronnie's are fabulous burgers if you are looking for a classic fix!), and Ocean Park.

Head to Vineyard Haven and pick up sandwiches at Waterside Market for a day on the water. You can rent a boat for the day and be picked up at the Vineyard Haven Marina. Such a great day to see more of the island and enjoy the great outdoors!

For dinner, highly suggest Lambert's Cove. A wonderful hidden gem tucked in the woods up island. They have a beautiful outdoor set up with twinkly lights and fresh island menus during the summer. Very romantic!

Drive out to view the Cliffs at Aquinnah + Lighthouse - a classic vineyard view! Then head to the Katama Airfield for lunch and a bi-plane ride; you can hear more island history while getting a sky-high lay of the land, whilst also spotting wales, seals and sharks...do the tricks tour to do some loop-de-loops in the sky!