In the morning, head to the Tabor Academy Sailing Center for a two-hour sailing lesson in Sippican Harbor. Enjoy the scenic views of the harbor and learn the basics of sailing. For lunch, head to the nearby Wave Pizza Café for delicious wood-fired pizzas and salads. Spend the afternoon at the Silvershell Beach, swimming or sunbathing. In the evening, have a seafood dinner at The Atlantic Bistro overlooking the harbor.
Start the day at Marion Natural History Museum which displays the wildlife and habitats of the area. The museum also has a beautiful butterfly garden. For lunch, head to Uncle Jon's Coffee & Café for some coffee and sandwiches. In the afternoon, explore the Washburn Park, a 17-acre park with walking trails and picnic areas. In the evening, head to The Kittansett Club, a historic golf club with ocean views, for a sunset cocktail.
If you have extra time, visit the Hamlin Preserve for a beautiful hiking trail or the Spring House Farm for fresh produce. You can also take a day trip to Cape Cod to explore the beaches and lighthouses. If you are looking to maximize your fun, rent a bike and explore the town on two wheels. For more ideas, check out https://booking.tp.st/VhZsadPo.