Things to Do in Annapolis, MD on a Sailboat Charter

Incredible experiences aboard a boat rental in America’s sailing capital

Home to the US Naval Academy is one of the best places to jump on board your own sailboat charter in Annapolis, MD and feel the ocean spray! Sailo offers a great selection of monohull, motorboats and catamarans.


Anchored deep in the Chesapeake Bay, Annapolis is the perfect place to jump aboard a sailboat and spend some time on the water. Although this isn’t the open sea, there is lots of opportunity to let the wind fill the sails and experience the thrill of sailing. In fact, Chesapeake Bay is a huge expanse of water that easily warrants multiple visits for keen sailors, cruisers or fishing enthusiasts.


Annapolis itself is a city with a small town atmosphere and many historic sites to entertain visitors. Some of the best things to do in Annapolis include a visit to the Naval Museum and the Maritime Museum. If museums aren’t your thing, you’ll also find the colorful historic district and some great parks to visit.


But, probably the main thing to do by Annapolis boat rental in Maryland is enjoy sailing on the Bay. Chesapeake Bay is blessed with countless islands and nature reserves that can be discovered by boat, as well as sleepy towns calling out for you to moor and explore. Being just a stone's throw from Washington DC and Baltimore, Chesapeake Bay is a world away from the urban hustle and bustle, making some time on a Sailo boat rental a great way to recharge those batteries.

Port Annapolis Marina

Zahniser's Yachting Center


W&P Nautical

Inner Harbor Marina

White Rock Marina

Island hopping in Chesapeake Bay


With so many creeks, islets and rivers, the Chesapeake Bay offers limitless options when it comes to finding your own corner of serenity. With a private boat charter from Sailo you can explore the many islands to your hearts delight, and find a place you want to moor for a few hours or overnight. Head to places like Eastern Neck reserve, or Beverly Beach just south of Annapolis. Chesapeake Bay is packed full of hidden beaches and coves to find, making it perfect for a long weekend, or longer, exploring by sailboat.

Annapolis Boat Shows


With its great location and maritime history, Annapolis is home to several boat shows throughout the year. October and April see the main events, with opportunities to view some of the best boats in class. In fact the Spring show is one of the biggest sailboat shows in the world. And of course, one of the best things to do in Annapolis during the boat shows is get out on the water! Sailo has a great selection of some of the best sailboats, so if you want to experience it yourself, take a look at our inventory.

Oxford day trip by sailboat


The sleepy village of Oxford is found down the Tred Avon river, and although there isn’t much to do, it’s the journey that matters. The approach takes you past rural retreats and tranquil backwaters. The town is home to the Oxford Museum which offers some of the history of the Chesapeake Bay. There’s also some great places to grab a bite including the Scottish Highland Creamery ice cream parlor, perfect after a hot and sultry sailing trip from Annapolis.

Go boat spotting on Ego Alley


Maybe the name gives it away, but Ego Alley is actually a waterway where some of the most luxurious boats line up. You can either view these beauties from your own boat rental, or sit on the docks and marvel at the specimens on display. Dock Street in the city is where you’ll find ‘Ego Alley’, and as one of the best things to do in Annapolis, you’ll also find many other people casting admiring glances at some of these behemoths. They don’t call it Ego Alley for nothin’!

Hart Miller Island day trip


In the northern end of the bay, near Baltimore, Hart Miller island is a popular draw for weekend boating enthusiasts. With a sailboat charter from Annapolis, MD you can come up, moor your boat and enjoy the fantastic beaches and family friendly atmosphere. The island is a state park and has moorings for yacht arrivals, and camping is also available. There is little in the way of cover though, so bring plenty of sunscreen as well as water and refreshments. But, don’t forget to take your litter home with you!

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