{"id":39312,"date":"2023-11-29T17:03:05","date_gmt":"2023-11-29T22:03:05","guid":{"rendered":"https:\/\/www.boatsetter.com\/boating-resources\/?p=39312"},"modified":"2023-11-29T17:05:05","modified_gmt":"2023-11-29T22:05:05","slug":"chesapeake-bay-boating-guide","status":"publish","type":"post","link":"https:\/\/www.boatsetter.com\/boating-resources\/chesapeake-bay-boating-guide","title":{"rendered":"Chesapeake Bay Boating Guide: Cruising America\u2019s Largest Estuary"},"content":{"rendered":"<p><a href=\"https:\/\/www.boatsetter.com\/boat-rentals\/chesapeake--va--united-states\"><span style=\"font-weight: 400;\">Cruising the Chesapeake Bay<\/span><\/a><span style=\"font-weight: 400;\"> by boat can be a lifetime endeavor since there is so much to see and do in America\u2019s largest estuary. The bay is nearly 200 miles long and anywhere from 3 to 30 miles wide. Its shoreline is over 11,000 miles, and about half of the bay\u2019s 8,100 square miles of watery surface is in Maryland and half in Virginia.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">The Bay spills from the Susquehanna River source in the north down to the Atlantic near Norfolk, Virginia leaving thousands of anchorages and 150 rivers to explore! In our <\/span><b>Chesapeake Bay Boating Guide<\/b><span style=\"font-weight: 400;\">, we\u2019ll explore:<\/span><\/p>\n<ul>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">Things to do\u00a0\u00a0<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">Best time of year to boat on Chesapeake Bay\u00a0\u00a0<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">What to look out for\u00a0<\/span><\/li>\n<li style=\"font-weight: 400;\" aria-level=\"1\"><span style=\"font-weight: 400;\">Pro tip!<\/span><span style=\"font-weight: 400;\"><br \/>\n<\/span><\/li>\n<\/ul>\n<p><a href=\"https:\/\/www.boatsetter.com\/boat-rentals\/chesapeake--va--united-states\"><b>Explore boats &amp; on-water experiences in Chesapeake, VA<\/b><\/a><\/p>\n<p>&nbsp;<\/p>\n<h2><b>Things to do at Chesapeake Bay<\/b><\/h2>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"size-full wp-image-39314 alignnone\" src=\"https:\/\/www.boatsetter.com\/boating-resources\/wp-content\/uploads\/2023\/11\/St.-Michaels-1.jpeg\" alt=\"St. Michaels\" width=\"720\" height=\"480\" srcset=\"https:\/\/www.boatsetter.com\/boating-resources\/wp-content\/uploads\/2023\/11\/St.-Michaels-1.jpeg 720w, https:\/\/www.boatsetter.com\/boating-resources\/wp-content\/uploads\/2023\/11\/St.-Michaels-1-300x200.jpeg 300w\" sizes=\"auto, (max-width: 720px) 100vw, 720px\" \/><\/p>\n<p><span style=\"font-weight: 400;\">Perhaps the best-known town on the Bay is Annapolis with its <\/span><a href=\"https:\/\/boatsetter.com\/boating-resources\/annapolis-sailboat-show-2022\"><span style=\"font-weight: 400;\">renowned sailboat show<\/span><\/a><span style=\"font-weight: 400;\">, the prestigious Naval Academy, countless museums, and dozens of quaint eateries. It makes a great place from which to launch an exploration.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Approximately 25 miles southeast of Annapolis lies St. Michaels, a seaside resort on Maryland\u2019s eastern shore. St. Michaels is a must-see for history buffs, crab lovers, and amateur photographers looking for inspiration because this place never takes a bad picture.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">In the summer, the population of St. Michaels swells beyond its 1,500 permanent residents, and getting a guest dock is like winning the lottery so you won\u2019t be alone anchoring out on the Miles River in 15-30 feet of water. Visit the outstanding Chesapeake Bay Maritime Museum with its 18 acres of exhibits and restored boats on display.\u00a0\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Farther south around Tilghman Island and up the Tred Avon River is Oxford, one of Maryland\u2019s oldest towns. There are lots of wonderful bistros and restaurants like Schooners and The Masthead but save room for dessert because if you leave Oxford without stopping at Scottish Highland Creamery, you\u2019d have missed possibly the entire reason to be here. This ice cream shop is hardly more than a window front but serves homemade frozen treats to die fo<\/span><span style=\"font-weight: 400;\">r.<\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"size-full wp-image-39317 alignnone\" src=\"https:\/\/www.boatsetter.com\/boating-resources\/wp-content\/uploads\/2023\/11\/Solomons-Island.jpeg\" alt=\"Solomons Island\" width=\"720\" height=\"480\" srcset=\"https:\/\/www.boatsetter.com\/boating-resources\/wp-content\/uploads\/2023\/11\/Solomons-Island.jpeg 720w, https:\/\/www.boatsetter.com\/boating-resources\/wp-content\/uploads\/2023\/11\/Solomons-Island-300x200.jpeg 300w\" sizes=\"auto, (max-width: 720px) 100vw, 720px\" \/><\/p>\n<p><span style=\"font-weight: 400;\">Cross the bay and head down to Solomons Island, another former boatbuilding and seafood packing town that today is a tourist magnet. Jutting out between Back Creek and the Patuxent River, Solomons is connected to the mainland by a long causeway.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Less than 1 \u00bd miles long and in parts just the width of a two-lane road, the island has a long wooden boardwalk that takes you up to the Calvert Marine Museum with its Drum Point screwpile lighthouse and narrated tours on an 1899 bugeye boat. In the 1880s, more than 500 locally built boats made up the Solomons fishing fleet and by the 1930s, the town specialized in building wooden pleasure yachts.<\/span><span style=\"font-weight: 400;\">\u00a0\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">At the bottom of the Bay, you\u2019ll find Norfolk, which is part of the largest shipping port on the East Coast. Naval vessels, commercial ships, and recreational boats all share the same waters, and Mile Marker Zero, the official beginning of the Intercoastal Waterway (ICW), marks the beginning of the 1,200-mile <\/span><a href=\"https:\/\/boatsetter.com\/boating-resources\/best-boating-destinations-in-florida\"><span style=\"font-weight: 400;\">journey to Florida<\/span><\/a><span style=\"font-weight: 400;\"> and beyond.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">For more than two centuries, Norfolk has been a Navy town, and today, you can still tour the naval base. A must-visit is the Nauticus, a multi-level maritime museum designed to educate as well as entertain. The <\/span><i><span style=\"font-weight: 400;\">USS Wisconsin<\/span><\/i><span style=\"font-weight: 400;\"> is berthed next door and dwarfs the surrounding buildings. It was a veteran of three wars and the last battleship built for the U.S. Navy.\u00a0<\/span><\/p>\n<p>&nbsp;<\/p>\n<h2><b>Best time of year to boat on Chesapeake Bay<\/b><\/h2>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"size-full wp-image-39316 alignnone\" src=\"https:\/\/www.boatsetter.com\/boating-resources\/wp-content\/uploads\/2023\/11\/Chesapeake-Bay-best-time-to-visit.jpeg\" alt=\"Chesapeake Bay best time to visit\" width=\"720\" height=\"480\" srcset=\"https:\/\/www.boatsetter.com\/boating-resources\/wp-content\/uploads\/2023\/11\/Chesapeake-Bay-best-time-to-visit.jpeg 720w, https:\/\/www.boatsetter.com\/boating-resources\/wp-content\/uploads\/2023\/11\/Chesapeake-Bay-best-time-to-visit-300x200.jpeg 300w\" sizes=\"auto, (max-width: 720px) 100vw, 720px\" \/><\/p>\n<p><span style=\"font-weight: 400;\">Summers can be sweltering and winters freezing but the shoulder seasons of spring and fall are phenomenal. In April to May and September to October, the crowds are small, and the weather is usually perfect for boating.\u00a0<\/span><\/p>\n<p>&nbsp;<\/p>\n<h2><b>What to look out for<\/b><\/h2>\n<p><span style=\"font-weight: 400;\">The Chesapeake is a fairly protected body of water, but it can get boisterous. Northerly winter storms kick up large square waves that build the entire length of the shallow Bay and become quite serious in the southern parts. Also, it\u2019s very easy to wrap a prop on one of the ubiquitous crab pots or ground in the shallows. Keep a good lookout and rest easy knowing that the Bay is nearly all soft mud which shouldn\u2019t cause too much damage to your keel.<\/span><span style=\"font-weight: 400;\"><br \/>\n<\/span><span style=\"font-weight: 400;\"><br \/>\n<\/span><b>Pro tip:<\/b><span style=\"font-weight: 400;\"> If this is your first time on a boat or have little experience, we strongly recommend <\/span><a href=\"https:\/\/www.boatsetter.com\/boat-rentals\/chesapeake--va--united-states\"><span style=\"font-weight: 400;\">booking a boat with a USCG-certified captain<\/span><\/a><span style=\"font-weight: 400;\">.\u00a0<\/span><\/p>\n<p>&nbsp;<\/p>\n<h2><b>Pro tip: Rent a boat for your Chesapeake Bay boat trip!<\/b><\/h2>\n<p><span style=\"font-weight: 400;\">The Chesapeake Bay is a unique place begging to be explored by boat. It\u2019s also great for a corporate event, a birthday party, a sailing regatta or a romantic sunset outing. Book a boat with a USCG-certified captain for a local guide, or take the helm on a bareboat\u2014Find all options on the <\/span><a href=\"https:\/\/boatsetter.com\/boating-resources\/\"><span style=\"font-weight: 400;\">peer-to-peer (P2P) boat rental marketplace.<\/span><\/a><span style=\"font-weight: 400;\">\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">There are dozens of boat rentals in the <\/span><a href=\"https:\/\/www.boatsetter.com\/\"><span style=\"font-weight: 400;\">Boatsetter<\/span><\/a><span style=\"font-weight: 400;\"> fleet with locations from Baltimore, to Annapolis and Deltaville to Norfolk. And if you\u2019re in town for the boat show, staying on a boat will save you a bundle due to skyrocketing hotel prices.<\/span><\/p>\n<p>&nbsp;<\/p>\n<h2><b>You\u2019ll be back<\/b><\/h2>\n<p><span style=\"font-weight: 400;\">The vast Chesapeake Bay can\u2019t be seen in a day, a week, or even a month. You\u2019ll want to come back again and again to stay in the towns, <\/span><a href=\"https:\/\/www.boatsetter.com\/fishing-charters\"><span style=\"font-weight: 400;\">fish the rich waters<\/span><\/a><span style=\"font-weight: 400;\">, and watch sunsets from secluded anchorages. Once is definitely not enough.\u00a0<\/span><\/p>\n<p>&nbsp;<\/p>\n<h3><b>About us\u00a0<\/b><\/h3>\n<p><span style=\"font-weight: 400;\">Boatsetter is the go-to app for boat rentals and on-water experiences. Whatever the adventure, we\u2019ve got a boat for that\u2014Set <\/span><a href=\"https:\/\/www.boatsetter.com\/sailboat-rentals\"><span style=\"font-weight: 400;\">sail<\/span><\/a><span style=\"font-weight: 400;\">, start the <\/span><a href=\"https:\/\/www.boatsetter.com\/party-boat-rentals\"><span style=\"font-weight: 400;\">party<\/span><\/a><span style=\"font-weight: 400;\">, go <\/span><a href=\"https:\/\/www.boatsetter.com\/yacht-rentals\"><span style=\"font-weight: 400;\">yachting<\/span><\/a><span style=\"font-weight: 400;\">, make your <\/span><a href=\"https:\/\/www.boatsetter.com\/fishing-boat-rentals\"><span style=\"font-weight: 400;\">trophy catch<\/span><\/a><span style=\"font-weight: 400;\">, and hone your <\/span><a href=\"https:\/\/www.boatsetter.com\/wakeboard-boat-rentals\"><span style=\"font-weight: 400;\">watersports<\/span><\/a><span style=\"font-weight: 400;\"> skills! Download the Boatsetter app (<\/span><a href=\"https:\/\/apps.apple.com\/us\/app\/boatsetter-boat-rentals\/id1449873080\"><span style=\"font-weight: 400;\">App Store<\/span><\/a><span style=\"font-weight: 400;\"> | <\/span><a href=\"https:\/\/play.google.com\/store\/apps\/details?id=com.boatsetterrenters&amp;hl=en_US&amp;gl=US\"><span style=\"font-weight: 400;\">Google Play<\/span><\/a><span style=\"font-weight: 400;\">). Make sure to follow <\/span><a href=\"https:\/\/www.instagram.com\/boatsetter\/?hl=en\"><span style=\"font-weight: 400;\">@boatsetter<\/span><\/a><span style=\"font-weight: 400;\"> on Instagram, and tag us in all your boat day pictures for the chance to be featured.\u00a0<\/span><\/p>\n<p>&nbsp;<\/p>\n<p><a href=\"https:\/\/www.boatsetter.com\/\"><b>Rent. List. Share\u2014Only at Boatsetter<\/b><\/a><b>\u00a0<\/b><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Cruising the Chesapeake Bay by boat can be a lifetime endeavor since there is so much to see and do in America\u2019s largest estuary. The bay is nearly 200 miles <a href=\"https:\/\/www.boatsetter.com\/boating-resources\/chesapeake-bay-boating-guide\" style=\"text-decoration: none\">[&#8230;]<\/a><\/p>\n","protected":false},"author":24,"featured_media":39318,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[94],"tags":[],"class_list":["post-39312","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-destination-travel"],"acf":{"key_insights_html":"","faq_html":""},"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.4 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Chesapeake Bay Boating Guide: America\u2019s Largest Estuary<\/title>\n<meta name=\"description\" content=\"Explore the Chesapeake Bay (America\u2019s largest estuary) by boat with our easy to follow guide.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, 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