Make hotel reservations for your visit. Marblehead and neighboring Swampscott have some nice bed and breakfasts and quaint inns. If you are looking for a more traditional hotel, try looking in the nearby cities of Salem, Lynn or Danvers.
Decide what time of year you would like to make the trip. If you are unsure then visit: www.marblehead.org and look at the many different festivals and events that are going on throughout the year.
Visit historic Marblehead Harbor. Some of the best views can be seen from Chandler Hovey Park which is located on Marblehead Neck. Another great place to view the Harbor is in Crocker Park on Front Street.
Continue down Front Street and visit Fort Sewall. Fort Sewall was formerly a United States army fort. The Fort protected the USS Constitution from the British Navy in 1814. Today, you can see the Fort and visit a beautiful park that has views of Marblehead Harbor and the Atlantic Ocean.
Visit Old Town, Marblehead, where you will see many buildings still standing from the 17th century and the Colonial Era. You can also visit some modern boutiques that carry high end merchandise.
On the way back to your hotel, make a stop at Deveraux Beach. It is one of the most popular places to swim and to build a sandcastle in Marblehead. It's worth a look even if you visit during the cold winter months.