Explore the Atlantic Coast & Caribbean

Cruise Annapolis offers the best bareboat and crewed yacht charter options along the Atlantic Coast and the Caribbean. From New England, along the mid-Atlantic, around Florida into Key West and the Gulf Coast – even the Bahamas and Virgin Islands – we have charter options available in the Atlantic’s finest sailing waters.

We provide a world-class charter experience, planning out a customized route for your personal sailing adventure. In addition to the Chesapeake, we can provide the same charter experience from a host of destinations, including the Bahamas, Newport, Rhode Island, Ft. Lauderdale, Florida, St. Petersburg, Florida, Key West, Florida and the Virgin Islands.

Annapolis Maryland

Annapolis Maryland

  • Gentle and predictable winds
  • Protected harbors
  • Historic and scenic ports
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Newport Rhode Island

Newport Rhode Island

  • Consistent breeze
  • Beautiful beaches
  • Incredible islands
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Fort Lauderdale Florida

Fort Lauderdale Florida

  • Vibrant cities
  • Quiet hideways
  • Premier cultural destinations
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St. Petersburg Florida

St. Petersburg Florida

  • Beautiful seaside towns
  • Secluded anchorages
  • Fine marinas
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Key West Florida

Key West Florida

  • One-of-a-kind paradise
  • Pristine waters
  • Epic sunsets
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Bahamas

Bahamas

  • Crystal waters by day
  • Snorkeling
  • Beautiful beaches
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US & British Virgin Islands

US & British Virgin Islands

  • Best sailing destination in the Caribbean
  • Year-round warm weather
  • Bountiful marine life
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Newport, RI offers consistent breeze, gorgeous beaches, incredible islands, great yachts and first-class charter service.

Annapolis, MD and the Chesapeake Bay offer over 5,000 miles of navigable, protected coastline with an incredible diversity of cruising potential.

St. Petersburg, FL is home to beautiful seaside towns, secluded anchorages, fine marinas, white sandy beaches, sparkling blue waters, and an array of wildlife.

Ft. Lauderdale, FL is an ideal port for exploring South Florida’s vibrant cities, quiet hideaways, and exotic locales.

Key West, FL is like no other destination in the world, combining history, natural beauty, and culture for a one-of-a-kind paradise.

The Bahamas deliver an amazing island-hopping adventure, from Guana Cay to snorkeling at Foul Cay Underwater Park.

US & British Virgin Islands offer consistent trade winds, year-round warm weather, and line of sight sailing – ideal for your cruising adventure.

Map of destinations