Chesapeake cruising

rcmafgny

Active Member
Oct 10, 2009
1,245
Long Island, NY
Boat Info
2008 33 Sundancer; Kohler Gen set; Simrad electronics
Engines
Twin 8.1 Horizons w/ V Drives
New to area. Boat is in Indian River Delaware. Looking to make trip to Chesapeake - either loop around peninsula or via C&D or around Norfolk. Thoughts on places not to miss? probably 7 - 10 days. Thanks in advance
 
Annapolis, St Michael’s, Oxford.
Wont get wordy, look into these 3 for sure.
What boat?
I would go over top thru the canal. I am not a fan of the ocean (depending on boat). But Hellaware Bay can be treacherous; that is not a typo.
 
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Thanks...
Annapolis and St Michaels will be on the list. Don't know much about Oxford. Also heard of Kent Narrows? Solomons ? port charles [or st charles?], tighman>?
33' Sundancer - No choice but Ocean travel on this side of Delmarva - just have to watch winds and tides.......
 
Doesn't matter as the whole bay has something to offer. Are you looking to relocate or pass through? If looping can enter south or north but the c and d canal is the easiest so long as you time the Delaware Bay tides.
In general eastern side of bay has more rural beautiful anchoring, western side more development and restaurants...its all good.
My aunt used to have a place in Lewes del so I know you will find it very different. We boat the northern half from Annapolis up,both power and sail, but look forward in 2022 to exploring the southern part which I am told is much more rural nd sandy, which we love.
Goodluck.
 
Thanks...
Annapolis and St Michaels will be on the list. Don't know much about Oxford. Also heard of Kent Narrows? Solomons ? port charles [or st charles?], tighman>?
33' Sundancer - No choice but Ocean travel on this side of Delmarva - just have to watch winds and tides.......
Heard? Been to them all many times.
You be fine in a 33. I guess I meant thru the canal is less time in ocean.
Solomon’s is definitely a great destination. I have heard the James River at Norfolk is a fantastic cruise area to see the Navy ship (dont get close, they frown on it). Not been there, too far.
Oxford is an old town, like 1600’s old. Very quaint old Chesapeake.
Kent Narrows used to be a great destination but I just learned the main restaurant and bar closed so not much of a destination anymore.
Shanty Bar on weekends at Tolchester just north of Kent Narrows may be the best tiki bar on upper bay and free day slips.
 
Hellaware Bay is notorious for fog, strong tides, winds, bad shoaling out of channels. So when traversing in fog, with wind and shallow water close either side it can get scary. As Larry said, it takes careful planning on that water.
I recently read an article by a hubby and wife that did exactly what you planning on. If I can find I will post the link here.
 
What type of boating and cruising do you guys do out of Indian River? Any thoughts to relocating to the Chesapeake area? Indian River is great in the back bays for water sports and fishing but not the optimal place for a Sea Ray. Grew up there, ran charters, etc., but enjoy the Chesapeake so much fun for our type of boating and cruising.
 
What type of boating and cruising do you guys do out of Indian River? Any thoughts to relocating to the Chesapeake area? Indian River is great in the back bays for water sports and fishing but not the optimal place for a Sea Ray. Grew up there, ran charters, etc., but enjoy the Chesapeake so much fun for our type of boating and cruising.
We moved down Spring 21. Our boat is not conducive to Indian River bay.... Currently choices are heading out inlet, going north or south...Would give it year or so then think about relocating boat to Chesapeake, which is what we are most accustomed to coming from NY. What location in the Chesapeake would be a reasonable "commute" from Rehoboth area?
 
Doesn't matter as the whole bay has something to offer. Are you looking to relocate or pass through? If looping can enter south or north but the c and d canal is the easiest so long as you time the Delaware Bay tides.
In general eastern side of bay has more rural beautiful anchoring, western side more development and restaurants...its all good.
My aunt used to have a place in Lewes del so I know you will find it very different. We boat the northern half from Annapolis up,both power and sail, but look forward in 2022 to exploring the southern part which I am told is much more rural nd sandy, which we love.
Goodluck.
Thanks - for now touring. At some point may relocate boat as on coast with inboards, limited things to do... Maybe first trip is more of a "loop".. a search and figure our where to spend time. Have been to both St Michaels & Annapolis and love them. have not really ventured anywhere else as was on my Brother in laws center console. Would like to spend some time near Oceana when the Blue Angels do their thing.... if Covid allows.
 
We spent 6 weeks in the Bay in 2017 and 2 weeks in 2018 and I agree with what has been said as a visitor. I also felt that some trips up the rivers were worth the time if you can. While the marinas are great in all the popular places, the slip holders and Marina staff are friendlier off the beaten trail.
 
Sassafras River has some really nice marinas with a relatively short drive across the peninsula. That part of bay is really freshwater so you don’t have to worry about the saltwater thing.
Where are you planning to live?
Not clear, if you live in NY and looking to keep boat on the Chesapeake, you will find a lot company on the Sassafras. Many peeps from NY and Philly keep boats there.
 
We are on the very upper part of the Chesapeake on the C&D Canal. Easy access from home (38 min) and about 1.5hrs from Rehoboth, DE.

Can't even begin to compare the difference in boating between Indian River and the Chesapeake. The Chesapeake is offers some of the best boating and cruising on the entire east coast.

If you keep your boat at Summit North Marina it's literally 3 left hand turns from Rehoboth....straight north on Rt. 1 for 1.25hrs, left off the Delaware City exit, go 2 miles, left at the Wawa and the marina is 3 minutes down the road. Not to mention you'll be going the opposite direction of the beach traffic which is a huge bonus.

Being at Summit North the boating is protected, relatively immune to weather, the Chesapeake Inn is a nice 10 min ride down the canal and then from there the Bay is at there in front of you. Quick 30 min ride to the Bohemia river which is a fantastic place to anchor, spend the night, raft up, swim, etc. Next river south is the Sassafras then slightly to the south is Still Pond. Another incredible place to anchor up and enjoy the weekend.

I spent a ton of time in the area of Indian River and it's awesome if that is what you want. But it's crowded, salt water and essentially zero places to cruise to. You've got the inlet and then head north or south. Much better suited for a center console and fishing.

Not saying the year or so down there will be a waste, but you'll soon be bored and want the Chesapeake!! Where are you keeping your boat? Another major bonus for Summit North and the Upper Bay is it's fresh water and the marina is a designated hurricane hole should any storms head our way.

Bite the bullet and come to Summit North and you'll have a very fun boating experience. The cruising destinations are endless on the bay.
 
Sassafras River has some really nice marinas with a relatively short drive across the peninsula. That part of bay is really freshwater so you don’t have to worry about the saltwater thing.
Where are you planning to live?
Not clear, if you live in NY and looking to keep boat on the Chesapeake, you will find a lot company on the Sassafras. Many peeps from NY and Philly keep boats there.
 
We moved from Long Island to the Rehoboth area in early 21
 
We are on the very upper part of the Chesapeake on the C&D Canal. Easy access from home (38 min) and about 1.5hrs from Rehoboth, DE.

Can't even begin to compare the difference in boating between Indian River and the Chesapeake. The Chesapeake is offers some of the best boating and cruising on the entire east coast.

If you keep your boat at Summit North Marina it's literally 3 left hand turns from Rehoboth....straight north on Rt. 1 for 1.25hrs, left off the Delaware City exit, go 2 miles, left at the Wawa and the marina is 3 minutes down the road. Not to mention you'll be going the opposite direction of the beach traffic which is a huge bonus.

Being at Summit North the boating is protected, relatively immune to weather, the Chesapeake Inn is a nice 10 min ride down the canal and then from there the Bay is at there in front of you. Quick 30 min ride to the Bohemia river which is a fantastic place to anchor, spend the night, raft up, swim, etc. Next river south is the Sassafras then slightly to the south is Still Pond. Another incredible place to anchor up and enjoy the weekend.

I spent a ton of time in the area of Indian River and it's awesome if that is what you want. But it's crowded, salt water and essentially zero places to cruise to. You've got the inlet and then head north or south. Much better suited for a center console and fishing.

Not saying the year or so down there will be a waste, but you'll soon be bored and want the Chesapeake!! Where are you keeping your boat? Another major bonus for Summit North and the Upper Bay is it's fresh water and the marina is a designated hurricane hole should any storms head our way.

Bite the bullet and come to Summit North and you'll have a very fun boating experience. The cruising destinations are endless on the bay.
Currently boat is at Indian River Marina. Certainly a consideration. Will check it out!
 
My old stomping grounds. Those days it was getting up at 2am, heading anywhere from 30-100miles offshore, fishing for the day and then heading back to IR.

Now it's rafting up, grilling, spending the the night on the hook and swimming all day with family and friends.
 
Well if you circumnavigate the DelMarVa, you are a Boss in my book. That is the trip that I want to make.

Our boat is 100 miles up the Potomac River near Washington, so when we go to the Bay it is generally for a week long trip. Some of our favorites are:

Solomons Island: We are partial to Spring Cove Marina. However any Marina down by the Tiki Bar would be fine, too. Lots to do. Very walkable.

Herrington Harbor South: Disney Land for Boaters!!! A country club type destination. Great restaurant and pool on premises.

Anapolis: A great place to see!! I haven't found the marina that suits me just yet but I'm sure it's out there. I'm glad that we've been there.....once.

St. Michael's: We stayed at the Resort, which was very nice and fun. Next time, I want to stay at the Marina across the canal by the bar....I think it is St. Michael's Marina.

Chesapeake Inn & Marina on the C&D Canal: I real surprise for me. A one night stop over on our way to Cape May, NJ. I wasn't expecting a lot and was absolutely blown away. It was a weekend, we were on B dock, the band was less than 100' away, a young lady brought us drinks and ice. Plus it was cool bringing the boat in with a ton of people watching.

Rock Hall: Great restaurant next door. Basic, nice marina. We've been there twice. Walkable to a very cool town. The transient docks can be a bit rolly if a storm comes in from the south.

Cape Charles Town Marina: Not an especially "nice" marina but the town is cool. Walkable or golf carts available for rental. Cell service can be sketchy. Nice distilleries, bars, and restuarants.

Norfolk/Portsmouth: GO NAVY!!! THE MOST EXCITING PLACE TO RUN YOUR BOAT!!! We are partial to Tidewater Marina in Portsmouth, directly across the Elizabeth River from downtown Norfolk. We love the USS Wisconsin tour and the boat tour of the Naval base. Our next favorite marina down there is Hampton Bluewater Yacht Center. Not the greatest "area" but for a COOL marina to just hang out in, nice pool, and great restaurant it can't be beat. Plus, the boats that come in there for fuel are incredible!!! Take a deck chair and hang out at the fuel dock and watch the 100+foot yachts come in one after another. It really is a sight!

Yorktown: A nice quiet marina, great ship's store, pool and bar/restuarant. You can take a care over to the Yorktown Memorial.

Cape May: We stayed at South Jersey Marina. It was a blast. That would be an easy trip for you if you haven't already done it. I enter Cape May from the Ocean Side.

Places we haven't been yet: Cambridge, Kent Island, Herrington Harbor North. There are a ton of small marinas around the West River on what I call the Western Shore of the Bay. Towns are Shady Side and Galesville. A friend keeps his boat at Hartge Marina. Very quiet vibe. And there are restaurants/Tiki Bars near most of the marinas.

Hope this helps. You'll get a lot of good advice.

Jaybeaux
 
My old stomping grounds. Those days it was getting up at 2am, heading anywhere from 30-100miles offshore, fishing for the day and then heading back to IR.

Now it's rafting up, grilling, spending the the night on the hook and swimming all day with family and friends.
Thats what we did before coming here!
 
Well if you circumnavigate the DelMarVa, you are a Boss in my book. That is the trip that I want to make.

Our boat is 100 miles up the Potomac River near Washington, so when we go to the Bay it is generally for a week long trip. Some of our favorites are:

Solomons Island: We are partial to Spring Cove Marina. However any Marina down by the Tiki Bar would be fine, too. Lots to do. Very walkable.

Herrington Harbor South: Disney Land for Boaters!!! A country club type destination. Great restaurant and pool on premises.

Anapolis: A great place to see!! I haven't found the marina that suits me just yet but I'm sure it's out there. I'm glad that we've been there.....once.

St. Michael's: We stayed at the Resort, which was very nice and fun. Next time, I want to stay at the Marina across the canal by the bar....I think it is St. Michael's Marina.

Chesapeake Inn & Marina on the C&D Canal: I real surprise for me. A one night stop over on our way to Cape May, NJ. I wasn't expecting a lot and was absolutely blown away. It was a weekend, we were on B dock, the band was less than 100' away, a young lady brought us drinks and ice. Plus it was cool bringing the boat in with a ton of people watching.

Rock Hall: Great restaurant next door. Basic, nice marina. We've been there twice. Walkable to a very cool town. The transient docks can be a bit rolly if a storm comes in from the south.

Cape Charles Town Marina: Not an especially "nice" marina but the town is cool. Walkable or golf carts available for rental. Cell service can be sketchy. Nice distilleries, bars, and restuarants.

Norfolk/Portsmouth: GO NAVY!!! THE MOST EXCITING PLACE TO RUN YOUR BOAT!!! We are partial to Tidewater Marina in Portsmouth, directly across the Elizabeth River from downtown Norfolk. We love the USS Wisconsin tour and the boat tour of the Naval base. Our next favorite marina down there is Hampton Bluewater Yacht Center. Not the greatest "area" but for a COOL marina to just hang out in, nice pool, and great restaurant it can't be beat. Plus, the boats that come in there for fuel are incredible!!! Take a deck chair and hang out at the fuel dock and watch the 100+foot yachts come in one after another. It really is a sight!

Yorktown: A nice quiet marina, great ship's store, pool and bar/restuarant. You can take a care over to the Yorktown Memorial.

Cape May: We stayed at South Jersey Marina. It was a blast. That would be an easy trip for you if you haven't already done it. I enter Cape May from the Ocean Side.

Places we haven't been yet: Cambridge, Kent Island, Herrington Harbor North. There are a ton of small marinas around the West River on what I call the Western Shore of the Bay. Towns are Shady Side and Galesville. A friend keeps his boat at Hartge Marina. Very quiet vibe. And there are restaurants/Tiki Bars near most of the marinas.

Hope this helps. You'll get a lot of good advice.

Jaybeaux
Great information. Thanks! We've been to cape may a bunch of times. Like Utsch marina. Super people
 

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