Sailing North:

Sadly the farthest south we’ve made it so far has been St. Augustine.  Now don’t get me wrong St. Augustine is indeed a great place to get “stuck” each winter.  There are kind people, and active cruising community, and just about any marine service you might need.

But then there is the task of heading north for the summer. We tend to favor going on the “outside” on our way north simply because we are often racing north for an arbitrary obligation.  Last year was Ryan needing to get to Casco Bay so he could take a course and this year we need to make it to Portland Maine so that Liam can participate in his High School Graduation then we’ll make our way to Newport RI so he can take his STCW courses, then after that, we’ll probably bounce around New England for a while.

So what is our plan of action heading north and once north what are the spots of interest?

Here we go!

Fernandina Beach/Cumberland Island:

North of St. Augustine is the St. Mary’s River.  This inlet is super easy and can easily be done in the dark in calm weather.  The key of course is don’t try to cut either of the breakwaters covering the entrance.  Head straight in and then turn North for Cumberland Island or South for Fernandina Beach.

Fernandina Beach:  Fernandina Beach offers first-come first-serve moorings, and a solid anchorage for free.  There is a dinghy dock at the city marina available to all.  If you pick up a mooring you’ll need to visit the city marina office to register and pay.  At last visit, a full month was only $500 and well worth the price.  Fernandina Beach offers great restaurants, a place to get fuel, and to pick up packages.  The grocery store is a walk you won’t want to do without a wheeled cart, preferably a bike and a bike cart.  There is propane at the UHaul and diesel/pumpout at the city marina.  Overall a great place that we have stayed for weeks on a mooring.

Random Fernandina Beach Points:

• Salty Pelican Bar & Grill serves Alligator Bites.
• Island Time Ice Cream & Frozen Yogurt can be dangerously addictive.
• Propane at UHaul is too far to walk.
• Groceries can be delivered to the dinghy dock.

Cumberland Island: Cumberland Island is a child’s playground.  We anchor off the southern dingy dock and spend our days exploring the endless hiking trails, visiting with wild horses, and exploring the ruins of a Carnegie Mansion.  There is also an “endless beach” that is essentially deserted.  The last time we stayed at this anchorage we stayed for Three Weeks!  The island is primitive and has no services but the kids love it.

Cumberland Island Points:

• The southern dinghy dock is less crowded and is closer to the cool stuff.
• The dingy dock at the mansion ruins is super tempting but not realistic.
• The beach really is endless.

Charleston SC:

After leaving St. Mary’s River we head north to Cape Fear.  We have tried to stop at Beaufort SC and Georgetown SC BUT honestly found their endless inlets to be too much of a bother.  Instead, we head directly to Charleston SC.

Our dingy only has a 1hp engine so we stay at the Charleston Maritime Center.  The cheapest place in town with UNLIMITED FREE LAUNDRY which makes up for just about everything.  It’s also in the heart of downtown making everything cultural within walking distance.  Propane is a bit of a walk but the grocery store is essentially next door as are all of the historical sites.

Charleston SC Points:

• Second State Coffee is the best spot to get work done while hiding from the children on the boat.
• There are too many museums in the city to get to them all.
• The King Street shops are too tempting.

Cape Fear and Carolina Beach:

From Charleston we sail directly to Cape Fear, enter in the morning, and then make our way to Carolina Beach.  There are inexpensive moorings but honestly, the holding is good and once we anchored I’m not sure I would pay for the moorings unless there was some wind predicted.

Carolina Beach is a classic seaside resort town, right down to the boardwalk and the Ferris wheel and arcade.  The area is also super well protected and has easy access to two hardware stores and solid grocery stores.  Laundry is less than convenient but also available.  There are two dinghy docks, a well-populated beach, and adequate restaurants.  We often stay here for several weeks as we work on the boat and get job-related work done in the local cafes.  There is ample room to anchor north of the mooring field and on the north side of the small island in the cove but moorings are cheap and we often pick one up for convenience.

Carolina Beach NC Points:

• The boardwalk is worth the time.
• Island Burgers & Bites, the “gas station” just off the southern dingy dock may look like crap but it is AMAZING and worth the visit.
• Malama Cafe is my preferred cafe to get work done during the day.
• Latella Gelato on the boardwalk sells Gelato that is laced with wine.. While it’s good DON’T get it mindlessly. It’s stronger than you realize.
• UBER Eats, Pizza Hut, and other Delivery places will deliver to the upper dinghy dock if you give them the neighbors’ address and wait for them.

From Carolina Beach, we move to anchor in Wrightsville Beach and then wait for a weather window to head to Beaufort NC where we enter the ICW between Cape Hatteras and Norfolk VA.

ICW between Cape Hatteras and Norfolk VA:

Beaufort NC:

Beaufort NC is a pleasant town with adequate services, it has the benefit of also having an array of wild horses on the nearby islands and a good balance of hiking trails and a small town.

Anchoring can be tight and there is shoaling.  We try to anchor as close to directly across from the town Dinghy Dock as possible off the channel in between G9 and G7 (favoring the G7 side).  If the area is overly crowded we will often move directly to Oriental NC.

Beaufort NC Points:

• Groceries are a hike but a reasonable biking distance
• Watch your feet on the House Island there are pickies.

Oriental NC:

Just north of Beaufort is the small town of Oriental.  The town is exceptionally cruiser friendly with spots to pick up mail via a UPS Access Point, a small chandlery that seems to have everything, and marinas that offer exceptional service.

We try to anchor inside of the breakwater just off the Oriental Harbor Village Marina.  I always feel like we are too close to the marina and too close to the channel but always seem to make it work.  If it is too crowded inside there is plenty of room to anchor on the outside of the breakwater.  With only 1hp on the dinghy, we prefer to be closer.

Oriental NC Points:

• Inland Waterway Provision Co is just off the dingy dock and has everything you don’t even know you want.
• The Bean Cafe is awesome and is right off the dock.
• You’ll want to take time to walk the town, you will meet other cruisers.

Bellhaven NC:

The next stop we make on the ICW is in Bellhaven.  For the “Birthplace of the ICW” there is little there but it is an excellent and convenient stop.  We anchor as far in the harbor as we can go close to the bridge.  The primary reason is that there are three places to take the dinghy, the official town dinghy dock in the “downtown” area where there is not much at all.  The “free dock” is a fixed dock and can be difficult to climb. And the town’s boat launch near the bridge all the way inside the harbor.  We tend to prefer to beach just next to the boat launch since it offers the shortest walk to the grocery store.  We also tend to top up the diesel jerry cans here so that we can pay shoreside prices and avoid needing to visit the fuel dock.

Bellhaven NC Points:

• The town center is tiny with only a handful of shops but it’s still worth a walk.
• The Food Lion grocery store is an excellent provisioning spot and just a short walk up the road.

The Alligator River:

Depending on the weather the base of the Alligator River just off “Deep Point” is an excellent spot to anchor that is well protected.  There is nothing here and the darkness, lack of cell phone coverage, and isolation can offer some great views of the night sky.  It is important to note that the Alligator River Bridge does not open if the winds pick up near 30MPH.  We have used this anchorage in a wind storm with 40+MPH winds.  You’ll want to be sure you are out of the channel since barges go through at night.

Alligator River Points:

• If you’re lucky enough to not have StarLink then after the children calm down from being disconnected.  You’ll have a chance for an amazing sky.

The North River:

Another isolated anchorage that we stop at is off the channel in the North River.  After crossing the Albermarle Sound you will enter the North river.  Once in the river pull off to the east and enjoy a MASSIVE area of open water that could easily fit 1,000 boats at anchor.  We tend to try and anchor East of Green Marker 161 aiming for the radio tower.  Rumor has it (and exploring the chart seems to confirm) that there is a dinghy-accessible small canal that leads to a town with groceries within a mile or so.  This would be a 1mile dinghy ride and then a 1-mile walk.  I’ve yet to do this but am excited to try and see if it’s true.

North River Points:

• I’m still just 1 HP so who’s going to check this rumored canal out!

Great Bridge Lock Free Docks:

We push North of the North River all the way to the Great Bridge in Chesapeake VA.  On the southern side of the bridge is a marina that has fuel and a pump out (They do not take American Express).  There is a free dock on the southern side of the bridge and you can tie up to the western wall north of the bridge.  We’ve stayed at both and have no preference

This is one of our favorite stops on the ICW for provisioning.  There is a large grocery store within walking distance, a hardware store nearby, Propane, Kerosene, and Diesel are all steps from the boat.  And since you are tied to a free dock getting everything back on the boat is that much easier.

Chesapeake VA Points:

• The laundromat down the street takes credit cards on the machines themselves.
• The Marina doesn’t take American Express (yes that’s bitten me more than once).
• The Great Bridge Service Center sells Gas, Diesel, Propane, and Kerosene.. Everything fuel wise you may need which may or may not be cheaper than that Marina.

Hampton VA:

After stocking up and fueling up we then move north to Hampton VA skipping Norfolk entirely. We’re typically in a rush at this point and position ourselves near the mouth of the river by Fort Monroe National Monument.  We pull in and anchor off the channel.  The primary concern is being sufficiently out of the channel for the large fishing vessels that dock all the way in.

There is shore access via a dinghy dock found by going under the fixed bridge.  The town is cute but following the convenience of Chesapeake VA for provisioning we try to focus on watching for a weather window.

Exiting the ICW and Moving Back Offshore:

Lewes DE:

Weather permitting we prefer to head all the way from VA to Sandy Hook NJ but if weather or exhaustion dictate we duck into Lewes DE on the southern side of the Delaware River entrance.  There is ample room to anchor behind the breakwaters and if shore access is required or desired it is possible to anchor close to the beach west of the ferry landing site.  Shore access is beaching on a very sandy beach.  There is limited resources on shore other than restaurants.

Lewes DE Points:

• There is no easy land access. Beaching there is a pain.

Atlantic Highlands NJ:

One of our favorite stops on the way north is hands down Atlantic Highlands NJ.  One fall we ended up needing to stay for three weeks due to illness and waiting for repair parts to arrive.  We worked in the local cafe each day, saw a show in the tiny movie theatre, and had New York Style Pizza far too many times at the local pizzeria.  The entrance is pretty straightforward, turn around Sandy Hook and aim for the tip of the breakwater protecting the mooring field.  During the day watch for absent-minded local fishermen and at night keep a clear watch for large barges that may be anchored in the middle of the harbor.  It’s no joke I almost hit them and would have if they didn’t have AIS.  The lights from shore can obstruct navigation lights.

Mooring balls are expensive but come with a launch.  There is however ample room to anchor and we more often than not are able to anchor within the breakwater near the eastern side of the mooring field.  If there isn’t room inside the breakwater there is plenty of room outside.  Inside is preferred since the breakwater will protect you from the ferry’s wake.

Speaking of the ferry, there is a ferry from Atlantic Highlands to Manhattan for $45 a person.

There are multiple marine stores nearby but they are a hike and you may find yourself wanting to UBER back if you walk there.  There is an excellent hardware store, automotive store, and grocery store all within walking distance.  We have our mail delivered the UPS Access Point at CVS.

Atlantic Highlands Points:

• The walk long the trail, up the stairs, up the road to West Marine (or CVS for UPS Access Point Mail Delivery) is 100% worth the walk once. But you may want to UBER back.
• Super Foodtown of Atlantic Highlands isn’t too far, you can go grocery shopping every day.
• 1st Cup Coffee is the place to hide from your children and get work done.Smodcastle Cinemas is adorable and worth taking the whole family to.Jaspan Brothers Hardware has most you’ll need and also sells propane.
• Julio’s Pizza Co. is addictive! Avoid or you’ll be visiting there for lunch every day for the duration of your stay.

Long Island Sound:

We’ve only done long island sound and so have only #1 Slept under the Statue of Liberty just off the ferry channel.  We did however get woken up after dark because there were fireworks over Manhattan so .. Worth it.

The East River MUST be done with the current.  We made that mistake and it was VERY unpleasant.  Also double-check to make sure the UN isn’t in session or else the river might be closed.

North of the city on the “inside” is Port Washington.

Port Washington:

If sailing inside Long Island Sound with school-aged children then a mandatory stop is Port Washington specifically if the children are near High School age and will be subjected to “The Lost Generation” or specifically “The Great Gatsby” by F. Scott Fitzgerald.

The Great Gatsby is set in “East and West Egg” these are the very real “Kings Point” and “Port Washington” NY.  We had the luck to be assigned The Great Gatsby at the very time we were sailing through Long Island Sound.  We were able to listen to the book while sailing and then enter the harbor.

For those who have forgotten, Gatsby is obsessed with an old love Daisy who lives in “East Egg” (Port Washington). He lives in a mansion with a massive pool overlooking the water.  And between his mansion and her house is a “Green Light” that messes with his head.

Think Green Navigation Beacons. The character Gatsby was a sailor as was the author.

SO. The learning Activity is to figure out which mansion the author visited and which navigation beacon pointed at which dock to inspire the story.  (Hint Daisy’s dock is no more but it’s on the chart as “ruins”) 

In the novel, there were trips to the city via car and train.  You can take the same train from “East Egg” for a tiny fee and have your boat secured on an inexpensive site mooring where you will enjoy launch services.

I’m purposely not sharing charts to aid in the school effort.

In practical terms, there are multiple dinghy docks in town, if you pick up a mooring there is a launch service that will take you to any of the docks and all offer great convenience and provisioning ease.

Newport RI:

We prefer to go outside once again from Atlantic Highlands to Newport RI, it’s an easy overnight from Atlantic Highlands on the outside or from “East Egg” on the “Inside”.

Newport is often referred to as the Sailing Capital of New England.  Not without merit as you will see every type of sailboat there.  We prefer to anchor on the southern side of the harbor just east of the Ida Lewis Yacht Club’s mooring field.  Specifically, we try to get as close as we can to “Kings Park Boat Ramp and Dinghy Dock”.  The primary concern with anchoring is to be sure to anchor south of the underwater electrical line, it is well-marked and impossible to miss.

We almost exclusively use the Kings Park Dinghy Dock since our dingy only has 1hp but there are many city-run free dinghy docks in town including one at the Maritime Center.  The Maritime Center offers coin showers, and coin laundry, and hosts the harbor master’s office making it an excellent resource.

Overall Newport has every possible resource related to boating and is overflowing with expertise.  There is a 14-day anchoring limit, although we have stayed longer outside of the season after the maritime center had closed.

Newport RI Points:

• Gourmet Exotic Jerky is worth the visit even just for the photo opportunity but the jerky is good.
• Be sure to visit The City of Newport Maritime Center and introduce yourself even if you don’t think you’ll need to use the services.
• Find the “Rubber Ducky Store” it’s a scavenger hunt.
• This town may just have the largest West Marine I’ve ever seen. 
• Rent a Scooter, or a three-wheeled silly scooter, or a Fancy Three Wheeled Slingshot! 
• Empire Tea & Coffee may be the best place to get your work done, especially the Bellevue Ave location..
• Bellevue Plaza has all you need, Stop & Shop for groceries, the UPS store for Mail (last time they charged $20 to pick up mail so coordinate your mail), Ace Hardware, BIG Laundry, and Mama Leone’s which may or may not be the best Pizza in Town.
• There is a pumpout Boat and a Water Boat and a launch all for a price. VHF 68 If memory servers.

The Cape Cod Canal:

In order to make it through the Cape Cod Canal you MUST go with the current.  And for a pleasant ride you’ll hopefully have the wind on your back as well since exiting the canal into an opposing wind can cause significant chop (think 3-4 foot standing waves).  You’ll also want to go through with daylight.  It is possible to leave Newport RI go through the canal and then slow down and arrive at either Boston or Provincetown Mass the next morning.  We often stop at Hadley Harbor south of the canal to better time our way through.

Hadley Harbor:

Hadley Harbor is a well protected and often forgotten spot just outside of Wood’s Hole MA, there is essentially nothing there and if your boat is small enough to go inside the inner harbor you may find one of several free moorings that you can pick up.  The rule is that if the owner shows up you have to vacate but in all of the times we’ve gone that has never happened.  If there are no moorings available there may be room to anchor inside but there is almost always plenty or room to anchor in the outer harbor which is still very well protected.

There is only shore access permitted on the private islands on “Bull Island” so that folks can walk their dogs.  There are ticks on the island but overall a cute spot to stretch your legs.

Provincetown Mass:

Provincetown is one of our hands down favorite spots to stop and spend an extended period of time.  Easy to enter and exit with excellent holding.

We find the town prohibitively expensive for even a transient mooring ball and so we anchor, sometimes for over a month at a time.

The anchorage we prefer is all the way to the west near the shallows just past the town’s mooring field.  Alternatively, there is anchoring available on the north east side of the harbor just outside of the breakwater.

There are two dinghy docks, the town dinghy dock is located in the center of the “action” and close to the hardware store but with our limited dinghy engine we almost never use that one.  West of the coast guard pier is “Captain Jack’s Wharf” which is a private wharf cut up into condos that can be rented as short term rentals which can be excellent for guests.  The wharf also has a deeded dinghy dock that almost no one uses.  The caveat is that you have to walk down a private wharf with random visitors and, the big one, is that for 2-3 hours before and after low tide the dinghy dock is too shallow to get to via dinghy and at low tide it sits on the sand.  There is no dragging the dinghy to the water either it’s just too far.  Still we prefer this dingy dock because of the people and its convenience walking to the grocery store.

The town has an excellent grocery store, multiple hardware stores, and amazing restaurants.  The restaurants however can be pricy.  It’s also important to note that this is one of the LGBT havens so it should be avoided by anyone who has issues with that community since you are likely to be one of only five or six straight people in the entire town.  Okay that’s an exaggeration but straight people will be in the extreme minority in town.  On the flip side any parent with a child who fits the LGBT group should make an extended visit a priority.

Provincetown Mass Points:

• You’ll find us at the Wired Puppy even though it’s a crazy walk from our preferred dingy dock.  Simply because it’s the best cafe to actually get work done.
• The grocery store doesn’t sell alcohol so you’ll need to visit another store.
• The Pilgrim Monument is insane but 1,000% worth the walk up the million steps.
• Lands End Marine Supply has a ton of stuff but they’re not super knowledgeable on the marine side. They stock what they can to be helpful but this is not a super popular sailing destination.  Well worth multiple visits while you’re there.
• Mailspot Express is the place to have your mail sent.  They charge $10 but it’s 1,000% worth the convenience.
• The town itself needs to pay for water so get water where you can.  There is a pay for water dock you can take your dinghy to.  It sometimes gives free water. If it does keep your mouth shut.
• The Harbormaster has a pumpout Boat for FREE.  CALL them on VHF 12 and they will put you on the schedule.  100% free even if you’re on anchor.
• The people at Capt. Jack’s Wharf really do make the tidal issue worth the sacrifice.  You’ll feel more a part of the community in no time.
• At least one Drag Show is a requirement.  You won’t forgive yourself if you don’t go.

Portland VS Boston:

Boston is about 10 hours from PTown and Portland Maine is about 20 hours.  Both make for excellent sails out of PTown depending on the time you have.

Boston:

There is limited anchoring in Boston Harbor and limited shore access via dinghy.  Boston is one of the cities where a marina stay is strongly advised.  We always stay at Constitution Marina which is all the way in the harbor.  Steps from North Station and a short Water Taxi ride to Logan Airport this makes Boston an excellent place to receive guests.  And a hotel next door to the marina make it an excellent place to host guests who don’t want to stay on the boat.

Boston is an amazingly walkable city and the there are bike share bikes available just across the street from the marina through Boston’s Blue Bike service which is highly subsidized by the local hospital to promote health.  Everything in the city is essentially at your fingertips.

Boston Points:

• There is a MASSIVE grocery store under North Station .  Star Market I swear I almost thought it was a tiny corner store until I saw the escalator.  They have Everything you need.
• North is Whole Foods and Ace Hardware they have everything else you need.
• Up the street is Tatte Bakery & Cafe which may or may not be the best cafe to get work done at.
• The Freedom Trail is at your doorstep you really want to take advantage
• Across the bridge is the North End which is Boston’s Little Italy. Regina Pizzeria is the best Pizza and Bova’s Bakery (open 24 hrs) has the best everything else from cookies to Arancini to cannoli.  Going in the middle of the night is an adventure.
• Do all the classic Boston things.  Faneuil Hall, Haymarket, a broadway show, Etc.

Salem MA:

Just north of Boston is Salem Mass.  There is limited space to anchor so either a dock stay or a mooring ball is advised.  The Hawthorn Cove marina offers a launch service for boats at mooring.  Historic Salem is rich with maritime history and has the infamous history related to the Witch Trials of the 1600s.  There is plenty to do in town.  There is less than convenient provisioning in town but small grocery stores are near by.

Salem MA Points:

• The city is cheesy. Sorry but it’s true.
• Nautical History wise: The House of Seven Gables, Salem Maritime National Historic Site, Friendship of Salem, and the city as a whole.
• Witch and Cult Wise.. Salem Witch Trials Memorial, and a few ocult shops.
• Peabody Essex Museum really shows off the nautical history.
• Local Ethnic Grocery Stores are limited but adequate.  The larger supermarket is essentially out of walking/biking distance.

Gloucester MA:

A practical stop north of Salem is Gloucester.  A major fishing port the city has ample marine services.  There is room to anchor but mooring balls from the Harbormaster are quite inexpensive and come with a launch, showers, and rumor has it the harbormaster’s office will let you have mail sent there.

The city is stereotypical in its modern “New England Fishing Town” persona but offers convenient provisioning and is a pleasant and if you are lucky enough to be in the inner harbor amazing all around protection.  This is one of the places that we go to hide from hurricanes.

Glouster Ma Notes:

• Grocery Store within walking distance
• Shops for Foul Weather Gear

Rockport MA:

On the very tip of Cape Ann is Rockport.  It’s largely exposed to the East but in the right wind conditions it’s well worth the stop.  The town has an abundance of little shops, art galleries, restaurants and the like.  Anchor close to Front Beach and there is dinghy access inside of the tiny man made harbor.  The “official” dinghy dock is at the entrance where you tie up and then climb up the ladder which can be 10-12 feet straight up the rock wall.  Alternatively if you go inside the mini-harbor there is a small dock for local boats, we have tied up to the “inside” of that where it is too shallow for the local boats and then used the ramp to walk up more safely.

However it is important to note there is a tiny grocery store, hardware store with not that much, but essentially it’s all art galleries and restaurants.

Newburyport MA:

Another historical stop is Newburyport MA.  The birthplace of the US Coast Guard the city is full of history, and a ton of restaurants.  There are moorings available, limited if any anchoring opportunities, and no launch offered.  With high current it may be necessary to wait for slack tide to use the dinghy effectively but you may prefer a mooring unless you want to make conversation with the MANY tourists and who walk by the boardwalk and look down onto the boats tied to the face dock.

Newburyport MA Notes:

• Grocery store is one heck of a walk from the docks.
• The town is full of art galleries and little shops.

Isles of Shoals ME/NH:

An excellent stop is the Isles of Shoals.  Located just a few miles off the coast near the boarder of Maine and New Hampshire the islands host just a few things.  One of them is the Star Island Hotel which hosts a variety of retreats throughout the year.  There is no room to anchor leaving the only option to pick up a mooring.  The standard New England rules apply of if you take a private mooring and the owner shows up you are expected to move.  That said there are a number of moorings sponsored by local Yacht Clubs which minimizes the risk that a large contingent of yacht club members will all show up at the same time.

The island is worth a good walk through and the harbor is quite pleasant to stay in.  Essentially there is nothing on shore.

Portland Maine and Casco Bay:

Overall the shore along Maine’s southern most coast is often crowded and less than accessible.  Kennybunk, Biddeford/Saco involve long trips up rivers that we just don’t bother with.  Especially when Portland Maine and Casco Bay is just 10 hours or so up from the Isles of Shoals.

Portland Maine:

Portland is an excellent city to stop in with some great services.  These days there is primarily only one good anchorage with solid access to the city.  On the eastern side of the city just outside of the “Back Cove” you’ll find an anchorage outside of the channel by Red #6.

There is an “Official” dinghy dock in Portland along the southern shore on the Maine State Pier.  The dock has a two hour limit and given its proximity to the custom and immigration offices is seems clear it is intended for the large commercial ships to check into the country.

There is a dinghy dock in South Portland just under the Casco Bay Bridge.  While the South Portland Dock offers convenient access to a grocery store we tend to not use it simply because of how far it is from the anchorage.

Instead we use the much closer boat launch off the East End Beach.  It’s important to note that you are not permitted to tie up to the boat launch for anything other than loading or unloading.  But it makes it possible to offload your crew and then to beach the dinghy just to the right of the boat launch where you will often see kayaks launching and other dinghies beached.

From this landing the entire city is at your disposal.  Within a one mile walk along a paved trail and road you will find a UHaul with propane, a Whole Foods with Amazon Lockers, a West Marine, a UPS Store to receive mail and packages, a Trader Joes, a regional grocery store, along with all of the other things you’d expect in a small city from medical services to marine services and with the added benefit of being an award winning culinary destination you’ll find some of the highest concentrations of restaurants, and even breweries per capita in the nation.

Marina wise when we stay in the city we either stay at Four Points Marina for walking the city convenience or Spring Point Marina in South Portland for a bit less expensive and closer to parks where children and dogs can both run “off leash”.

Casco Bay Highlights:

You can spend an entire summer just inside of Casco Bay and not run out of places to explore and since you can sail from one end to the other in just a few hours in well protected waters it’s always easy sailing.  Rather than list everything here are a few of our favorite spots that we try to hit every year.

Jewell Island:

Jewell Island is just seven or so miles from the Portland Anchorage and yet feels completely remote.  The island hosts one resident, a summer caretaker who cares for the campsites and grooms the trails.

Anchor in the center of Cocktail Cove careful not to go in too deep.  Shore access is by beaching as deep in the cove as you are able to reach.  Many will go on the left hand side of the cove and climb up the rocks, some will go all the way in or all the way in and to the right and walk.  Nowhere is better but be aware of the ten foot tidal range.

The island has a variety of hiking trials and is home to an abandoned naval observation station from WWII.  There are two towers one of which is six stories high and allows you to see over the trees and look out to sea to look for German U-boats.  There are a variety of land buildings that can still be seen and there is an underground bunker that can be explored.  I recommend taking the highest power torch you have for the underground bunker since you will be able to shine light much farther in some areas than you are able to explore.

Cliff Island:

Swimming distance from Jewell Island is Cliff Island. There are several areas to anchor around cliff.  Primary focused on the large coves on the southern side of the island.  The large cove on the south east of the island is divided by a rocky outcropping that bisects the cove.  You can anchor on either side but if you choose the norther side of this cove you will find a variety of “Destination Moorings” which are privately owned moorings that the owners will visit on occasion.  Standard New England Private Mooring rules apply, you are free to pick up any mooring but need to be willing to move if the owner arrives.  We have spent as long as a week without ever seeing the owner of the mooring we stayed at only to discover that the owner DID show up but chose to pick up another random free mooring.

There is however plenty of room to anchor for those uncomfortable with the idea of picking up a private mooring.

Shore accesses beaching and we tend to beach on the large sandy beach that stretches the western side of this cove.  There is a house on the rocks to the northeast and a house in the middle of the beach.  In between them is some mowed grassy areas.  At first glance from the water side it looks like private property but it’s actually the islands park.  You can walk through the grassy path to a dirt road on the other side of this spit.  Turn North on the road and then west and you’ll find yourself walking to the “downtown” of the island.

Cliff Island has a post office, a public library, and a small store.  On your walk to the “downtown” area you are likely to pass the small church and the one room schoolhouse still in use.  This is an excellent place to see “Island Life”

Cliff Island Notes:

• Most folks will hang out on the library’s front porch and use their electricity and internet.  For keys to the library for books or printing visit the post office and ask for the keys.
• The island store is great and all BUT the last time I was there we purchased enough for a simple pasta salad and ended up spending over $50 so it’s best to purchase food in Portland.

Eagle Island:

Eagle Island has three day moorings.  You are not allowed to stay overnight but this island is still worth a visit.  Pick up a mooring and dinghy to shore to explore the private island and the retirement home of the polar explorer Admiral Robert Peary (1856-1920). The island and home are preserved as the Eagle Island State Historic Site. Peary bought the island in 1881 and retired there in 1911, after he had achieved fame and glory with his (sometimes disputed) expedition to the North Pole. His family continued to live in the house until the property was donated to the people of Maine in 1967.

Harpswell ME:

Another spot to “get away from it all” that sill has shore access and access to a small town is a little cove in Harpswell Maine off Stover’s Point.  The spot in Harpswell Harbor is well protected from all directions and rarely has more than one other boat at anchor.  The trick is to pull in as close to the moored boats in the harbor as you feel comfortable.  Shore access to the beach on the point is simple and there is good walking through country streets to stretch your legs on the shore.

A one mile dinghy ride across the sound brings you to the “Bailey Island Bridge” which is quite unique but in our case serves more as a landmark.  Enter the mooring field and point the dinghy to the unique bridge.  Just north of the bridge is the “Salt Cod Cafe” and their free dingy dock.  Tie up, if the cafe is open go in and order a tea, then feel free to explore Bailey and Orr’s Islands.

Orr’s Island is the Northern Island.  While there isn’t much on the island other than houses a walk up the road is worth the danger of being run over for the Island Candy Company which is only a short walk up from the Cafe and their dinghy dock.

Bailey Island is the island to the south and has a bit more in terms of services.. There are a number of restaurants, there is a post office, and a small general store with provisions.

An experience for sure is to dingy over to Cook’s Lobster & Ale House where you will tie up to a commercial and very questionable dock and then walk up past all of the fish guts covered commercial fishing attributes to the restaurant which I honestly think is mediocre and overpriced BUT for the experience it may be worth it.