Longtime Cruisers’ Favorite East Coast Summer Destinations

Longtime cruisers Mary Drake and her photographer husband, Bob, have spent more than 25 years exploring summertime destinations up and down the U.S. East Coast. Their journeys focus on marinas, waterfront communities and small towns that celebrate maritime tradition and welcome boats and boaters. Over the decades the couple has profiled 150 destinations for Soundings, from Maine to the Keys, along the Gulf Coast and across New York’s lakes, rivers and canals.

How Mary and Bob Choose a Destination

Mary and Bob approach every port and anchorage with curiosity and a simple routine: first they walk the docks and talk with boaters, then they walk the streets to get a feel for the local scene. For them, one of the clearest signs of a friendly community is whether strangers greet you with a wave. That immediate courtesy—on docks, sidewalks and waterfront promenades—often reveals more about a place than a guidebook ever could.

The Drakes prefer destinations that combine peace and tradition. They are drawn to tree-lined streets, comfortable marinas and historic waterfronts where maritime heritage is visible in boatyards, old wharves and local museums. At the same time, they recognize and accept change: in many towns they’ve watched dilapidated waterfronts transformed into lively harborside districts. Those changes usually reflect broader shifts in boating culture and demographics.

What They’ve Observed Over 25+ Years Cruising

Mary notes a clear evolution in the cruising community. Where once long-term cruisers often lived frugally and traveled with children or pets on modest budgets, today many cruisers are retirees enjoying comfortable nest eggs and well-equipped vessels. The boats themselves have changed, too—modern systems, electronics and amenities make extended cruising more accessible and comfortable for a wider range of people.

Despite these changes, Mary and Bob still seek out places that retain character and community. They look for waterfronts where restaurants, small shops and marina services cater to visiting boaters, and where local residents value their maritime roots. Those qualities, combined with calm anchorages and good dockage, make for lasting favorite haunts.

Personal Background and Why History Matters

Mary’s personal history with traditional wooden boats helps explain her affinity for historic ports. In a previous chapter of her life she and her then-husband, George Maynard, built a faithful reproduction of Joshua Slocum’s wooden sailboat Spray in the backyard of their Noank, Connecticut home and then completed a five-year circumnavigation with their dog and three children—without the aid of an engine. Bob’s earlier cruising experience included time in the Caribbean aboard a 43-foot William Atkin ketch named Kismet, also a wooden boat. Those formative experiences anchor their sensibilities and draw them toward destinations with a strong sense of maritime continuity.

Practical Tips for Boaters and Cruisers

From their years on the water, Mary and Bob offer practical, experience-based advice for others exploring the East Coast:

• Walk the docks and introduce yourself—local boaters and marina staff are an invaluable source of information about local conditions, facilities and hidden gems.
• Stroll the town—shore-side culture, shops and restaurants often shape the cruising experience as much as the harbor does.
• Observe how people interact—friendly greetings and waves are good indicators that a community genuinely welcomes visitors.
• Embrace both tradition and change—historic charm often sits beside thoughtful redevelopment, and the best destinations balance both.
• Plan for amenities—check for fuel, provisioning, waste pump-out and local repair services when choosing marinas or anchorages.

Examples of Places They’ve Covered

The Drakes have written about many favorite ports and towns over the years. A sample of destinations they have profiled includes:

• Block Island, R.I.
• Stonington, Conn.
• Key West, Fla.
• St. Marys, Ga.
• Rockland, Maine

Each of these places offers its own blend of maritime history, welcoming waterfront communities and amenities that appeal to cruising sailors and powerboaters alike. Readers can look for the Drakes’ destination features to learn more about what makes each harbor special.

This article originally appeared in the August 2012 issue.