For many sailors, the dream goes beyond a day or two on the water. It’s about waking up at anchor, exploring new harbors, and spending a string of days fully immersed in the sailing lifestyle.
That’s exactly what the SailTime Voyager Charter Membership is designed to deliver.
Launching this season in Annapolis, Chicago, and Boston this new program gives qualified members access to extended, charter-style sailing experiences aboard fully equipped cruising yachts, without the limitations of a traditional bareboat charter.
A New Way to Experience Sailing
Traditional sailing memberships are perfect for day sails and short overnight outings. Voyager builds on that foundation by offering something more: time and freedom.
With Voyager, members can book half-week and full-week sailing experiences, allowing for true destination cruising. Whether it’s a long weekend getaway or a full week on the water, the program makes it easier to plan meaningful trips with family and friends.
Instead of rushing back to the dock, you can slow down, explore, and enjoy sailing the way it was meant to be experienced.
Designed for Real Sailing Adventures
Voyager isn’t just about more time—it’s about greater, better experiences.
Members have access to premium cruising yachts equipped for extended trips, giving you the comfort and capability to travel farther and stay out longer. The program is structured around seasonal access, with flexible scheduling that includes both weekday and weekend sailing periods.
Two membership levels allow sailors to choose how much time they want on the water throughout the season:
- Silver Membership: Two full weeks of sailing
- Gold Membership: Four full weeks of sailing
This structure gives members the ability to plan multiple trips across the season, from spontaneous getaways to well-planned sailing vacations.
Explore the Chesapeake Bay Like a Boat Owner
In Annapolis, Voyager opens up one of the most iconic cruising grounds in the United States: the Chesapeake Bay.
Imagine setting out for a full week of sailing, stopping in charming waterfront towns like St. Michaels, Solomons, or Rock Hall. Drop anchor in quiet coves, enjoy waterfront dining, or spend the evening aboard under the stars.
With extended time on the water, destinations that once felt “too far” for a sailing day trip on the Chesapeake suddenly become part of your regular sailing routine.
From the protected waters of the South River to the peaceful anchorages of the Magothy, Voyager allows you to experience the Chesapeake the way seasoned cruisers do; unhurried and immersive.
Your Gateway to Sailing New England
In Boston, Voyager opens up an iconic sailing playground along the Northeast coast, from the bustling Boston Harbor to the scenic islands of Cape Ann.
Picture setting sail for a day—or a full week—exploring historic harbors like Salem, Marblehead, or Provincetown. Drop anchor in quiet coves, enjoy seaside dining, or unwind aboard under a star-filled sky.
Extended time on the water transforms what once felt like a far-off destination into a regular part of your sailing routine. Navigate protected bays, wind along the rocky coastline, or venture to the open Atlantic for a true cruising adventure.
Voyager in Boston allows you to experience the Northeast like a seasoned cruiser: unhurried, immersive, and entirely at your own pace. From tranquil island anchorages to charming coastal towns, the region becomes your personal playground on the water.
Discover the Freedom of the Great Lakes
In Chicago, your Voyager Membership offers a completely different but equally rewarding sailing experience.
Picture leaving the Chicago skyline behind as you head out across Lake Michigan. With favorable summer winds, sailors can enjoy long, smooth passages before arriving at destinations like New Buffalo or continuing north along the Michigan coastline.
Harbor-hopping becomes part of the journey, with each stop offering something new, whether it’s a quiet marina, a beachside town, or a scenic overnight anchorage.
For sailors looking to expand their skills and confidence, the Great Lakes provide a unique opportunity to experience open-water cruising in a dynamic and rewarding fresh water environment.
Built for the Next Step in Your Sailing Journey
The Voyager Membership is ideal for sailors who are ready to move beyond day tripping and into true cruising.
Whether you’ve been building your skills through lessons, local sailing, or previous charters, this program offers a natural next step. It provides the time, access, and flexibility needed to grow as a sailor while creating unforgettable experiences along the way.
It also removes many of the common barriers associated with extended sailing; no need to manage maintenance, logistics, or ownership responsibilities.
Part of the SailTime Community
One of the key advantages of the Voyager Membership is that it’s built on the trusted SailTime model.
Members still benefit from professional fleet management, well-maintained yachts, and a structured scheduling system, all backed by a global network of sailing locations.
And this is just the beginning.
SailTime plans to expand the Voyager program into additional destinations, giving members even more opportunities to explore new waters in the future.
Start Planning Your Next Sailing Adventure
If you’ve ever imagined spending a full week on the water, exploring new destinations, relaxing at anchor, and truly disconnecting, the Voyager Membership makes it possible.
From the historic waters of Annapolis to the open horizons of Lake Michigan, this new membership program is designed to help you sail farther, stay longer, and experience more.
To learn more about SailTime Voyager Charter Membership or to reserve your sailing time, contact your local SailTime base in Annapolis or Chicago.
