The Best Boating Communities for 55+ Active Adults

As many adults remain active in their older years, there has been a growing effort to organize communities around shared hobbies and lifestyles. Sailing is one of the most exciting hobbies for 55+ active adults because it balances socializing, travel, and maritime adventure. 

Go Sail Virgin Islands is one of the best sailing schools for older adults, offering sailors a chance to explore some of the most beautiful islands in the Caribbean. However, the Virgin Islands are one of many sailing communities that our students, captains, and crew stay connected with.

In fact, you might find you want to live in a sailing-specific community after reviewing this list of destinations for active adults who share a connection to the water.

Why Are Boating Communities Ideal for Active Adults 55+?

For many adults aged 55 and older, choosing a seasonal or year-round seaside community is a great way to stay in shape. These areas typically have plenty of outdoor recreational spaces where people can take a stroll along the boardwalk, paddle a kayak, or go sailing.

Making boating part of your routine is a way to bond with other community members, share an adventure with family and friends, or attend fun sailing events.

Sailing communities also create opportunities such as:

• Enjoying a built-in routine, which helps older adults stay active while supporting physical and cognitive health.

• Developing new skills, from sailing techniques to navigation.

• Networking with other boating community members and sailors.

• Getting better sleep, thanks to action-packed days and quiet evenings on the coast.

Best Sailing Communities for Older Adults

After discovering sailing as one of the best hobbies for 55+ active adults, many Go Sail VI students end up having a lifelong passion for the sport. From the Virgin Islands to the mainland United States, these are some of our favorite sailing-specific communities. 

St. Thomas, US Virgin Islands 

The US Virgin Islands offer a perfect mix of Caribbean adventure and US convenience. There is access to good healthcare, local businesses all use US currency, and it’s an ideal starting point for sailing the US and British Virgin Islands. Sailing communities like Red Hook and Charlotte Amalie have walkable marina areas with restaurants, grocery stores, and small businesses. They are both active boating areas where you’re likely to bond with other sailors. 

Annapolis, Maryland

Home to the Annapolis Boat Show, which has been drawing thousands of boaters to the historic town for over 50 years, Annapolis is a thriving sailing community year-round. Located on the Chesapeake Bay, the area is excellent for fishing, boating, and paddle sports. Even in the chillier months when sailboats are docked for the winter, residents will find plenty to do and can catch up with other sailors at the many nautical-themed restaurants and pubs throughout the village.

Flathead Lake, Montana

When you think about sailing communities, Montana may not be the first place that comes to mind, but the Rocky Mountains are home to some excellent sailing spots! Active adults who want to settle down in a sailing community where they can sail in the summer and stay active in the winter will love Flathead Lake. The freshwater sailing appeals to sailors who prefer quiet, mountainous scenery with long days of uncrowded sailing in the summer and excellent skiing nearby in the winter at Blacktail Mountain Ski Area.

Charlotte Harbor, Florida

The Charlotte Harbor area has a thriving sailing scene, as one of the largest estuaries in Florida provides easy access to the Gulf of Mexico. The warm winter temperatures and active boating community make it an excellent place for sailing year-round. Punta Gorda and Port Charlotte are where many older sailors call home, as they are near the marinas, yacht clubs, and Charlotte Harbor Community Sailing Center.

Sailing, Community, and Staying Active After 55

When you live in the right place, sailing becomes part of your daily routine. If you’re looking to stay active after retirement, you might want to try your hand at a new type of boating and learn to sail!