Domestic Sailing Adventures

Ready for a getaway on the water? No need to go far—there are some great bareboat charter sailing destinations throughout the US.

June 18, 2020
bareboat charter
Ready for a getaway on the water? No need to go far—there are some great bareboat charter sailing destinations throughout the US. Marianne Lee

Let’s face it, we could all use a vacation, and what could be better (or more socially distant) than escaping on a sailboat with your family or a few close friends? If a charter vacation is calling your name, but travel restrictions are keeping you close to home, fear not—there are plenty of vacation sailing opportunities that are just a drive (or short domestic flight) away. 

We checked in with charter companies in the Great Lakes, Chesapeake Bay and Southwest Florida to see how summer 2020 is shaping up for them, and what charter guests can expect in this new normal.

“This year is such a head-spinner,” said Cindy Kalow, owner of Superior Charters in Bayfield, Wisconsin. “Wisconsin opened up boat rentals early in May, so we’ve been able to open on schedule. We usually have 60 percent of our season booked up by our season start, in mid-May. This year, we experienced a 54 percent reduction in where we would have been by season launch! On a brighter note, in the last few weeks we’ve seen a significant increase in calls, emails and bookings on our website. We are getting a lot of new customers—many who had trips overseas cancelled or even trips domestically, but didn’t want to fly—who want to drive to a vacation destination. We have families looking for an alternative to more crowded vacation options. People are also not planning very far in advance. We’re experiencing more bookings for the same week or a few weeks out. People are uncertain about the future, but feel they need to get out of the house and do something fun and outdoors.”


Barb Hansen, owner of Southwest Florida Yachts, which offers both sail and power charters from the company’s base in Cape Coral, Florida, agrees: “I talk to a lot of people who say they don’t want to get on a plane. They want to be able to get to their destinations by car. With our location being easily accessible by car or plane and with our miles of beautiful barrier islands, Southwest Florida is a perfect choice for those looking to get away from it all.”

Dream Yacht Charter, which has bases all over the world, has reopened two locations that are both accessible to US sailors. “For the first bases that opened, St. Thomas, in the US Virgin Islands, and Annapolis, Maryland, we were overwhelmed with the demand and bookings are strong. Most of our Caribbean bases are opening in June, if people can get there. We have customers wanting to sail in the British Virgin Islands now, but the borders are opening in September,” said Emily Turner, Dream Yacht Charter’s global marketing and communications manager. 

So what can charter guests expect? Similar restrictions to what you’re already likely getting used to at home. At Superior Charters, in addition to handling all paperwork remotely ahead of time, orientations will be held outside, and all boats will have a minimum of 24 hours of down time between each trip for additional cleaning and sanitizing. 


At Dream Yacht Charters, “guests will notice a difference when they arrive at our bases, when they will be asked to observe our COVID-19 measures,” said Turner. “Only one guest is allowed in the office area and only the skipper will take part in the technical briefing and on the pontoon for check in. Check-in and check-out procedures will be conducted outside where possible. Guests will be asked to wear masks and sanitize hands before any face-to-face interaction. Once on board, guests do not need to take any additional precautions than you would going about your daily business at home right now. Keep washing hands, keep to social distancing when not with members of your immediate household, and respect the local restrictions. We can help with ideas for provisioning and itinerary tips to avoid crowds.”

Hansen adds, “We want to let all of our customers know that we are as committed to offering you a beautiful, clean vessel as we have been for the last 36 years! Our office and our boats are receiving an even higher level of cleaning at this time. So, come and enjoy the sunshine and fresh air!”

Adventures Close to Home

We asked the experts: What makes these sailing destinations spectacular?


Great Lakes

Superior Charters’ location in Bayfield, Wisconsin, is right on Lake Superior and is the gateway to the beautiful Apostle Islands. “Sailing the Apostle Islands has always been a pristine wilderness sailing experience,” Kalow said. “This is THE year for people to experience it as we are always naturally social distancing here. The anchorages are not crowded. The beaches are nearly deserted. The scenery is breathtaking. We call this the ‘Caribbean of the North’ as you’re always sailing within sight of land, in the protection of islands, and the islands are within five to 10 miles of each other. The water is crystal clear and the beaches are rippled sand.”

Chesapeake Bay

The Dream Yacht Charter base is located in beautiful, historic Annapolis. “Chesapeake Bay offers 11,600 miles of coastline, so it is ideal for finding a remote creek or anchorage where you watch wildlife in a truly stunning landscape,” Turner said. “The area is renowned for its welcoming atmosphere, scenery, vibrant history, crabs and bird species. Soak up the local history at Oxford, one of Maryland’s oldest towns with a rich maritime history. Immerse yourself in the beauty of St. Leonard’s Creek on the Patuxent River, or head to the nearby Perigeaux Vineyards. Enjoy peace and quiet at Herrington Harbour, explore the six miles of trails on Wye Island and watch the birds at the Eastern Neck National Wildlife Refuge on the Chester River.”

Southwest Florida

Florida’s southwest coast, on the Gulf of Mexico, is a world away (yet a very reasonable drive) from the busy east coast metro areas of Miami and Fort Lauderdale. “For people who have never cruised in Southwest Florida I would say that they don’t know what they are missing!” Hansen said. “They will definitely be pleasantly surprised by the variety of cruising in our area. There are quiet anchorages, private islands, resorts with all the amenities including pools and beaches, fabulous restaurants, great fishing and more. We customize our clients’ float plans to meet the style of cruising they want. We can book you into a marina every night or you can anchor out your whole charter and never go ashore. Most people do a combination of staying ashore and staying on the hook during their charter whether it is for three days or three weeks!”


Domestic Charter Resources

For domestic and international charter provider listings, visit Cruising World’s Charter Directory

Great Lakes

Superior Charters

Great Lakes Sailing Co.


Dream Yacht Charters/ Annapolis Bay Charters

Waypoints/ Cruise Annapolis

New England

Bareboat Sailing Charters


Southwest Florida Yachts

Florida Yachts and Charters

Pacific Northwest

San Juan Sailing

Anacortes Yacht Charters

San Francisco Bay

Club Nautique


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