In the morning, head to Anderson's Bike Rentals in Oak Bluffs to pick up your rental bikes for the day. If you spent the night closer to Vineyard Haven, there are bike rental options there as well.
The first ride is 6 miles to Edgartown, where you can pick up some sandwiches for lunch. Ride along Seaview Ave the whole way, which offers breathtaking views of the coastline, and several soft sand beaches if you want to take a break. 3.5 miles into the ride you'll come across Jaws Bridge, made famous by the movie Jaws, which was filmed here. You'll often see kids jumping off the bridge into the water below.
Edgartown
Follow the curvy road as it turns to Beach Rd, then Main Street as you arrive into quaint Edgartown, much quieter than Oak Bluffs. Spend some time exploring the various shops and art galleries, or head over to Lighthouse Beach for a short walk to the Edgartown harbor light.
Before crossing over to Chappaquiddick, stop at the Rosewater Market to pick up a picnic of fresh sandwiches, salads, or other delicious sides, then hop on the Chappy Ferry with your bike for an extremely quick ride over the Chappaquiddick.
Chappaquiddick
Once on Chappy, you have 3 miles to go before you arrive at East Beach (stay on Chappaquiddick Road, which turns into Dike Rd). The last bit is unpaved before you arrive at the infamous Dike Bridge, where Ted Kennedy crashed his car into the water in 1969.
Once on East Beach, find a spot to call home for the next couple hours as you enjoy the warm, fine sand and the sound of the waves. Stay as long as you like on the beach, you can walk for miles in either direction if you like.
More things to do
Back in Oak Bluffs, you can explore the Gingerbread Cottages, a small village of brightly-colored, cookie-cutter cottages. Or, relax on the grass in Ocean Park, you'll often hear music played from the Gazebo.
Treat yourself to a much-deserved (jumbo) ice cream cone from one of the many shops, such as Mad Martha's Homemade Icecream. Or enjoy a heartier meal at one of the many restaurants in town.