There are always decisions to be made when planning a cruise and it’s never too early to start. I already found marinas sold out for dates we wanted. Should we go east or west for a rendezvous? Last week our west-favoring bunch looked at Mystic and Long Island. Now our east-leaning crew was considering leaving from Warwick, heading over to the East Passage and going east to Cuttyhunk. This would be a real change from busy ports we had done before. First of all, no cars on Cuttyhunk, no grocery stores, no malls. There is a once-a-day ferry to New Bedford where islanders go to shop. The quiet of the island is its charm. You can do an easy walk up a hill for spectacular views, or investigate the old church or schoolhouse. You can swim, hike, or do some photography. The people are friendly and love to socialize. Even on this remote island there is pizza, or you can order lobster rolls and chowder and take them back to your boat or park on the lawn for some utter relaxation.

After you have shed some of the stress of the mainland, it is time to move on to Martha’s Vineyard. It is easy to see why this lovely island has been the vacation choice of presidents and celebrities for years. In fact, Ulysses S Grant stayed here in 1874. Celebrities who lived here or regularly visit here include Bill Murray, Ted Danson, David Letterman, Dan Aykroyd and many more. John Belushi is buried here. 

Oak Bluffs is the town where you will find streets of colorful gingerbread houses and the tabernacle where most events like concerts and art shows are held. A carousel runs for most of the day next to little shops filled with unique treasures by local artisans. Restaurants abound from fine dining to a quick burger. The vineyard is bigger than it looks and in order to really see it, you may want to rent a car for a day. Otherwise, there is the Martha’s Vineyard Transit Authority to take you from town to town all day for an $8 pass ($5 for seniors). You can Google the schedule. Top of the list is magnificent Gay Head, or Aquinnah, at the west end of the island. This is a center for Wampanoag Native Americans. There are shops and places to eat before you climb up the lighthouse to get incredible views. On a clear day, you can see Newport. Go near sunset and watch the changing colors of the cliffs.

Edgartown is the site of many old homes of sea captains. Again, great shops and restaurants. Make sure to visit The Newes for great pub fare. Ask waitress Ashley about all the celebrities she has waited on there. A tiny ferry takes you on the 5-minute ride to Chappaquiddick Island for a swim at the really fine beach, and some exploration. When selecting a town for dinner, be aware that some of them are dry and no alcoholic beverages will be served there. Edgartown and Oak Bluffs are not dry. The boating group plans to stay at least a couple of days in Martha’s Vineyard. There is plenty to see and do.

There are so many options for wonderful cruises this summer. Going with friends makes it even more enjoyable. A little planning now will make sure you have the best experience. Make sure your captain and crew are ready to take on the navigation, boat handling, etc. for a safe trip. Enroll in a safe boating course. Google Northstarflotilla.com and sign up for a Coast Guard Auxiliary course right away.