Colorful town with shops and dining. This is the main destination in Oak Bluffs.

Casual indoor and outdoor dining and drinks. Be sure to check out Donovan's Reef for a festive frozen cocktail. Steve highly reccomends the Bahama Mama or the Dirty Banana from Donovan's Reef.

Arriving late in the evening? Park Corner is open late and serves food till close. They often have a DJ and lively bar scene after 10PM.

Love a dark and stormy? Steve thinks they make the best on the island.

Pop into this hot spot for craft beer, whiskey and local food right in town. If you're lucky you can snag a seat on their outdoor patio.

Located in the heart of Oak Bluffs, this restaurant is a short walk from the Summercamp. Check it out for drinks, lunch and dinner.

Grab a sandwich, sunscreen and snacks before you head to the beach at this local deli/market.

Grab a drink and some fried seafood overlooking the ocean watching the ferries come in. This is a great place to stop in for lunch, post-beach snack and for one last oyster before you board your ferry home. Lookout tavern is a short walk from the center of Oak Bluffs and the Steamship Authority boat dock.

Want to dine under the stars? Make a reservation at Sweet Life and request a table outdoors. This romantic restaurant is right on Circuit Ave but feels far away from the hustle and bustle.

Get there early to grab a table at this popular diner. Those staying in Oak Bluffs or Vineyard Haven can take a quick bike or jog over to the Art Cliff for a special breakfast.

Walk down Main Street to discover various shops, restaurants, and ice cream stores.

Grab a drink or daytime meal here and come back in the evening for a lively party. There is often a band or DJ and lots of dancing. This is a go-to spot for many seeking a fun night.The Atlantic is conveniently located for those of you staying in Edgartown however it's an easy and worthwhile cab ride for those in other towns.

Grab lunch and a drink at this popular restaurant/bar with a large outdoor space and a harbor view. Come back after dark for dancing till last call.

Make a reservation at this popular upscale restaurant or pop into their more casual Brick Cellar Bar downstairs for a drink, burger and fun cocktails.

Make a reservation for dinner or grab a late night drink at the upstairs bar right on Main Street in Edgartown.

Enjoy a special dinner in this cozy upscale restaurant highlighting the best of local produce and fish.This is a convenient option for those staying in Edgartown and looking for a nice dinner.

Visit L'Etoile for a casually elegant contemporary dining experience and a vibrant bar scene in the heart of downtown Edgartown

Staying in Oak Bluffs? Make sure you check out the historic Inkwell beach. This smaller beach is right in town and a short walk from the "main drag", Circuit Ave, and hotels in town. With calm surf, similar to State Beach, the Inkwell is a great family friendly beach.

Jump off of the iconic bridge from the movie Jaws…Just make sure it is high tide. The bridge is located at State Beach

State Beach is conveniently located between Oak Bluffs and Edgartown. Those staying in either town who have rented bikes can take a short ride to this popular beach. State Beach is adjacent to the Inkwell, has gentle surf and is another great beach for families. A lifeguard is located on the Edgartown side of the beach.

This is one of Dana's favorite beaches. The sand quality is ideal yet the surf can be rough at times. It is not always the best for young children and those who are not strong swimmers.

A fairy tale-like land awaits in Oak Bluffs. More than 300 easter egg-colored houses complete with dainty trimmings and names such as "Angel Cottage," "Wooden Valentine," and "The Pink House," make up the cottage colony, a major tourist draw.

Flying Hores is the nation's oldest platform carousel and has been designated by the U.S. Department of the Interior as a national landmark.

This is a great activity for families with children.

This grassy public park is a relaxing retreat for a stroll or picnic. It is conveniently located between the Inkwell beach and Circuit Ave.

Golf like Barack Obama and Bill Clinton. There are many other courses to explore in the area.

They also have tennis and brunch.

Check out the restaurants, bakeries and clothing stores at this island classic. They also carry high quality accessories for all of the dog lovers. They can be found in most towns.

Locations can be found here: https://www.theblackdog.com/Black-Dog-Locations.ht...

Check out this small up-island beach. This is Steve's favorite! The sand is a little rocky but it has some of the freshest seafood on the island. Be sure to walk to Larsen's Fish Market for a lobster roll, chowder or fresh oysters. They also have the best sunset on the island. Dinners can be pre ordered from Larsen's. Steve proposed to Dana at sunset on Menemsha beach!

Stop by The Bite on the way in or out for a fried food snack. Steve loves the fried clam bellies.

Catch the sunset at this popular up-island tourist destination known for it's breathtaking scenery.