Boating is a big part of Maryland living and Maryland summer’s are one of my favorite things ever. From the beaches, to boating and water sports, to some of the fishing in the world, there’s no shortage of water activities to keep you entertained all summer long. Take a cruise around the Chesapeake Bay or head to and explore Annapolis. If sportsfishing is more your thing than OCMD and the Eastern Shore is the place for you. I’m rounding up some of the best places to boat in Maryland and some tips and tricks for first-time buyers (and renters!) to help you make the most of your summer on the water!
OCMD/DE
Ocean City and The Delaware shores are where I spend most of my time in the summer. From OC you can reach points as far south as VA Beach (if you have the time) and as far north as Cape May, NJ, but we love to stay closer and explore around Assateague Island and The Wedge (in West OC) and Little Assawoman Bay in Fenwick! Here are some of my favorite spots in Ocean City,Maryland to check out by boat or jets:
SANDBARS
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Hoopers Sanbar
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“the wedge” sandbar by the inlet across from west oc/north assateague
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the beaches by the route 90 bridge
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RESTURAUNTS
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Tailchasers
West oc ( Check out micky fins, teasers/sunset grille, Harborside, Pier 23, etc)
Catch 54, Harpoon Hannahs + cruising around Little Assawoman Bay (stay in the channel, it gets shallow!)
Paradise Grill (Millsboro, De)
If you don’t have your own boat, there’s several options here in OCMD!
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Odyssey watersports
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Free Cruise w/ Dinner from the Angler
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Sail Alyosha (sailboat cruise)
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If you don’t feel comfortable, or would rather leave the driving to someone else so you can enjoy yourself..
There are a couple options for chartered boats around here.I typically use Boatsetter or Get My Boat to find options but there aren’t many around the OC area so I’ve put together my fave list of charted services!
Sea Quenched charters are my go to’s whenever I want to go out – the couple that runs it is so fun and goes above and beyond to make sure we always have the best day!
If you’re looking to boat with larger groups try:
A recent addition to OC is the floating tiki bars, tipsy tiki’s or Cruising Tikis (comes with a captain and bartender!), which you rent (with a captain) for an exploration or a fun bar hopping day. Exploring the water and pulling up to sandbars to hang out and drink is one of my favorite ways to spend the summer.
& if fishing is more your speed,check out
Head out on a deep sea fishing charters
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The Angler Charters (also offers a great sunset cruise + it’s discounted with dinner if you eat at the Angler)
Check out more info about Ocean City’s White Marlin Open, the largest billfish tournament in the world, Here!
KENT ISLAND/Annapolis
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Nicks Fish House (Port Covington)
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Take a cruise on the 6 mile Severn River
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Tidewater Grill on the Susquehanna
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Watermark Cruises dinner cruise
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Explore Annapolis Harbor
BALTIMORE/INNER HARBOR
OTHER FUN SPOTS:
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Crisfield is a good place to check out (bonus: it is the “Seafood Capital of the World”),
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Jellyfish Joels tiki bar (chestertown,md)
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Explore the rivers and waterways around Cambridge and Easton
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Explore the historic waterways + restaurants of St.Michaels
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Sail on one of the last commercial sail fleets in the country, the H.M. Krentz, based at the Chesapeake Bay maritime Museum. (sailing April-October only)
tips for buying:
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One of the First things you should do is Find out what boat you like! Charter a few boats, or ask your boat owner friends if you can look at theirs so you can get a feel of what you like and what you don’t so you know when you go to start looking for yours! This includes deciding whether you want to purchase a new or used boat!
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Most first time boat owners wish they would have gone a bit bigger in size. So make sure you’re not limiting yourself or holding back. Really, the key takeaway is to don’t buy smaller just because it is cheaper. Don’t sacrifice your happiness in the long run to save a little money, but at the same time don’t go crazy and only spend what you can afford.
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Take your time! You do not want to rush into anything. A boat is a big purchase, and you want to make sure that you are absolutely certain that you found the right boat for all of your needs (especially years to come). Do all your research, and be sure that you are getting the boat that you want. The worst thing you can do is rush into a purchase and then regret it later on. Good things come to those who wait!
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I definitely recommend attending a Boat Show or working with a Broker as there is so much insight and knowledge to be gained (Even if you’re not in the market, and just want to browse). The Baltimore Boat Show is a great local place to start! From virtual simulators, to the kid-friendly interactive activities, to seminars with industry and local pro’s, to their Discover Boating experience offering hands-on learning about boat care, conservation and productinnovation, dynamic demos and one-on-one advice to help you discover which boat is right for you! Make sure to stop by the Progressive Insurance booth for education and inspiration to help you get the most of your boating lifestyle, or take a spin at one of their interactive VR boat experiences!
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Once you decide on the boat for you, make sure you conduct a thorough walk-around and test out the boat in a sea trial and a survey if possible, so you know what you’re getting into BEFORE you commit yourself to buying!
tips for renting:
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For affordable boat rental’s (with or without a caption), just about anywhere in the world, I recommend Boatsetter! They make it easy to browse options + book the best fit for you!
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If you’re operating your own boat or jet ski, remember Safety First, Always! All boating regulations should be carefully followed and alcohol should never be consumed by anyone operating a boat.
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Take a water & boating safety course The US Coast Guard provides safety courses in boating areas across the country and many are free. This is a great way to make sure all safety issues are covered and ensure a positive boat rental experience.
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Some of my fave OCMD Rentals:
