Rockland today is a different place than some cruisers may remember. What once felt like a hard-working commercial port on Penobscot Bay is now more upscale, with a renovated downtown, good facilities for recreational boats (the Maine Boats, Homes & Harbors Show is held here annually), and plenty to do ashore. There are museums (the Farnsworth is a good place to start, for the Wyeth collection alone), good restaurants, and shops. No one comes to Maine with formalwear in their sea bag, but even so, it’s always fun for a crew to explore a port with boutiques carrying preppy brands like Lilly Pulitzer and Vineyard Vines. Rockland is also a good stop for families, with festivals scheduled throughout the summer and kid-friendly places like the Project Puffin Visitor Center, where the staff makes it fun to learn about Maine seabirds. Rockland Harbor offers an easy entrance, with a breakwater on the northern side and an Instagram-worthy lighthouse at its end. Anchorages are available and the harbor has several mooring fields. If you want a marina, there are a few good ones here, including Trident Marine, which has hosted the Cruising Club of America. North of the breakwater is Samoset Resort. You can put up guests there, or play a few holes on a course that’s one of the top 10 golf resorts in the Northern U.S. by Conde Nast Traveler’s Reader’s Poll.