A sailing monohull

The “How To’s” Of Planning A Charter

Sailing catamarans and monohulls docked at a pier

It’s never too early to plan a spring vacation! Right now, we’re offering a savings of 20% when you schedule a charter between 4/1/19-5/15/19*. Share these helpful “how to’s” for chartering and help your vacation buddies make the most of the Chesapeake Bay:

  • How to Pick the Perfect Yacht to Charter: Picking the perfect charter for your group starts with a headcount and a desired length of your trip. Once you know how many people will be chartering you can browse our fleet page for a yacht that will accommodate everyone. It is also important to know if you will need to hire a captain. In order to book a bareboat charter, there must be an experienced sailor onboard.
  • How to Decide When to Charter: Our current special offer is perfect for taking advantage of all the bustling spring activities in the Annapolis and the Chesapeake Bay area! The spring and summer both offer lovely weather for chartering. Our schedule is filling up fast, so be sure to contact us now to book.
  • How to Prepare for Your Charter: So your charter is booked, now what? The Cruise Annapolis team strives to go above and beyond when it comes to helping charter guests prepare for their trip. Whether you’re a local or are coming into Annapolis from out of town, here is some advice on how to prep.
  • How to Take Advantage of Annapolis History: Originally settled in the 1600s, America’s Sailing Capital is home to centuries worth of history. Before or after charters, our guests love soaking in all the city has to offer from local landmarks to tours of the U.S. Naval Academy.
  • How to Pick the Best Anchoring Spots: Repeat charter guests will be the first to tell you they have favorite spots to anchor throughout the Chesapeake. From the Severn River to St. Michaels, it’s really up to you to decide what looks like a good spot! Want some suggestions? Just ask your personal concierges, Susan and Amanda!
  • How to Share Your Experience: We adore being sent photos and videos from your charter! Future guests want to see what it’s like too. Be sure to follow us on Facebook, Instagram, and Twitter. Tag us in your social media posts and use #CruiseAnnapolis!

If you need help planning your trip, please reach out to our Charter Sales team. Susan and Amanda are more than happy to help you craft a personalized itinerary. Happy sailing!

  • New and direct bookings only. Not combinable with any other specials. See Charter Specialist for more details and availability. Must book by 1/31/19.