“Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” – Mark Twain

The First Week

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Admittedly, we have been a bit slow in updating the blog since leaving.  We have been enjoying the transition to full-time cruisers and always mean to get back to the blog but it keeps slipping from the days to-do list.  Now that we are secured in a marina on Staten Island waiting to see if hurricane Joaquin is going to turn towards us or out to see we have some time to get back to the blog. 

On September 9, 2015 at 3:20 AM we “cut the lines”.  Not literally but it’s a common expression used by cruisers for cutting ties to your land based life and moving to the nomadic life on the sea.

We left so early due to the currents in the Cape Cod Canal. The transit of the Canal is something we have done several times before and with a sailboat most be done with the current.  Going against the current with a boat that can only do 6-7 knots doesn’t work when the current is against you at as much as 6 knots.  We have done it once by accident (or mistake by me in reading the tide tables).  So, unfortunately, our first day as cruisers was dominated by a schedule, something we are trying desperately to avoid. 

So up we were before dawn, making a pot of coffee, walking Summer and getting ready for departure.  We left the dock under the cover of darkness and headed out the channel towards Cape Cod Bay.  The forecast was for 10-15 kts of wind out of the southeast.  Not a great direction for our course of travel.  We couldn’t sail without missing our window for the Canal so we were motoring south with a goal of hitting the Canal entrance by noon to make the last of the favorable current.

Since it was still dark, my Bride had to go to the bow to spot for lobster pots as we went.  She  stood out there with our trusty spot-light illuminating the way whenever she spotted a lobster pot buoy.  Around 5:30 AM we started to get a very picturesque predawn and with it enough light to see the buoys from the cockpit. 

First Week Cruising 2015

The wind was a little heavier than forecasted at 15-20 kts.  But the angled stayed just too close to our course to let us sail.  If we weren’t on the time crunch to get to the Canal we could have just taken more time to cover the miles and got to the anchorage a little later.  But in this case that would mean missing the favorable current and having to wait until 7:30 PM for the next turn of the current and setting our anchor in the dark.  So we just kept powering into the wind.

As we neared the canal the winds picked up.  We were now seeing 25 knots consistently and gusts up to 30 knots.  I had thought that once we entered the Canal we would be more sheltered from the wind.  I was wrong.  We continued to see 25-30 knots as we transited the Canal.  What was worse is the wind was opposed to the current and this was causing steep, narrowly spaced chop.  We were getting 3-4 foot waves in the Canal.  We had never seen these conditions in the Canal.

Eventually, we made it through and made the turn to enter Onset Harbor.  I am really familiar with this area from sailing in my youth but had only been on power boats in this area.  The channel was narrow and winding but well marked.  We made it to the anchorage area off of Wickets Island.  A few boats were already anchored in the choice spots in the 10-15 foot deep hole near the island.  So we move over to the second hole that was about a quarter mile from the island.  It took 3 attempts and one small domestic to get the anchor set.  The anchorage had the kryptonite for our Manson Supreme, eel grass.  On the first two attempts it came up covered in large clumps of the stuff.  We had to clean it off and try again.  We had some communication issues that lead to our disagreement. My Bride couldn’t hear me at the helm and my hand signals were not clear enough.  But eventually we got it set and back downed hard at 2,500 rpm.  We were set hard and set Drag Queen, the anchor drag alarm program from Active Captain. 

Once we were set we got a call from my Dad.  He had gone out in his fishing boat to see us come in but had missed us coming down the Canal.  He came over and rafted up.  We had a few beers and took a dingy ride over to Wickets Island to let Summer run.

First Week Cruising 20151

Later he left to head home and my Mom came by after she got off work.  We walked around Onset Harbor with her, said good bye and then headed back to boat for early dinner and bed. 

The next day the forecasts were confirmed and it was not a good day for travel.  The winds were still up around 30 knots and seas in Buzzard’s Bay were a bit snotty.  So we decided to stay put and do some work around the boat.  That was actually a good thing.  We didn’t actually have time to store a lot of our last minute provisions and gear.  We had just shoved it below and the settees were filled with stuff making the boat feel a little cramped.  We spent the day finding places to store food and gear.  We made dinner on the boat and started to feel the concept of Cruiser’s Midnight hit us [cruisers tend to be up early and be active most of the day, as a result by 9 PM you’re tired and ready for bed].

The next morning the weather had cleared a bit.  The winds were down to 15-20 knots and seas were forecasted to 2-4 feet.  So we hauled up the anchor and headed over to the Onset fuel dock to pump out and fill up on water and fuel.  Once that was done we headed out for Cutty Hunk, one of our favorite stops south of the Canal. 

We had an excellent down wind sail.  We had the head sail out but no mainsail. With 10-15 knots of wind with gusts up to 25 knots pushing us and following seas we made great time.  The seas built throughout the day and eventually we had sets of 6 foot waves on a short, 5-6 second periods.  Surfing these waves down wind we hit 9-10 knots of speed at times.  We were able to sail on a single tack all the way to the entrance to Cutty Hunk Harbor.

A note on following seas in wide, open transom modern hulls.  I have often heard or read the ol’’ salts talking about their fear of modern hulls.  The transoms were too wide and the open transom would allow following seas to just flood right into the cockpit.  This fear fails to take into account all of the buoyancy in the wide, flat stern.  With this buoyancy the waves just lift up the stern and push you along.  Our first step on the walkthrough transom would get a little wet, but never more than an inch of water.  Instead the stern would lift with the power of the wave and we would surf down the face. Give me a boat with a wide stern any day over a narrow hulled boat. 

When we got into Cutty Hunk Harbor we decided to get a mooring rather than anchor.  The anchorage here is small and notorious for really thick soft mud and tons of eel grass that prevent a good setting of the anchor.  The moorings are great and we don’t mind supporting towns that come up with creative ways to make the most of their anchorages.  The anchorage was almost empty and so was the little town.  We walked around but little was open and not many people were around.  There weren’t even enough boats in the anchorage to justify running the raw bar boat.  So I had a half dozen oysters at the dock and we walked around before heading back to Smitty for dinner.  We ate dinner in the cockpit and a cocktail or two.  Eventually we were treated to a spectacular sunset poking below the line of clouds.

Cutty Hunk

First Week Cruising 20152

The next morning was my Bride’s birthday.  She was hoping to spend it on Block Island.  The forecast was for 5 knots of wind and 2 foot ocean swells.  So we left early and headed for the island.  With no wind we were a power boat again. I let the autopilot do most of the work while I read a little, took a shower in the cockpit and tinkered around the boat. As we approached Block Island the winds and seas picked up.  But at this point it was too late for the sailing to really be much, less than an hour.  So we just kept powering into the Great Salt Pond.  All my Bride wanted for her birthday was a good nights sleep so we grabbed a town mooring.  We called the local harbor master but he never came over to charge us. 

We took the dingy to shore and went and toured Old Harbor walking back to New Harbor with several stops along the way. We looked at the beautiful beaches at Ballard’s with their great beach bars. I got a Block Island Cigar from the Block Island Cigar Store.  Great little shop with a guy playing an acoustic guitar and leather couches to sit and enjoy your smoke.  They also have a wooden female pirate out front to advertise the store.  We stopped at the Poor People’s Pub for a relaxing beer on their patio.  We stopped at Dead Eye Dicks for some mojitos and a light dinner.  We got back to the boat after dark and right before some light rain started. We looked at the weather and decided our best bet would be to make a break for Connecticut in the morning.


Got up the next morning, made coffee, walked Summer and slipped our mooring by 8:30 AM. The weather window for the day was a bit unclear.  We thought we had enough time to make it to Mystic but didn’t know if the conditions would be ok to get all the way to Niantic Bay.  We left Block Island with 5-10 knots of wind with gusts to 25 knots on a down wind run heading for Fisher Island Sound at the Watch Hill Passage.  The seas were very confused with 5 foot ocean swell coming from port and 2-4 foot steep chop coming from our starboard quarter. It was very active sailing for about two hours to get through the Watch Hill Passage (preferred entrance from Block Island Sound into Fisher Island Sound).  We motor sailed our way towards Connecticut.

As we approached this passage we could see why it was recommended. The confused seas began to unify and build as we approached the channel markers.  But they also began to turn so that we had them as following seas. But to our port there was a reef.  You could enter Fisher Island Sound by going over deeper sections of the reef but the seas were really steep and rough in those areas.  We watched on sailboat head out over the reef and we saw that boat’s keel on several occasions as it broached. 

Once in the lee of Fisher’s Island winds calmed to a steady 10 knots and the seas were about 2 feet.  We checked the weather and it looked like we were good to continue on to Niantic Bay.  We continued on and texted our friends Chris and Liz and let them know that we would be into Niantic Bay by 2 PM. 

We passed some great light houses and a tall ship but the rest of the trip to Niantic Bay was uneventful.  Eventually the winds died and we furled in the headsail and just motored on.  We pulled into Niantic Bay Yacht Club and got a mooring. 

The Yacht Club was interesting.  We had never been to a YC before that didn’t have a bar.  This one was setup more for a kids sailing program.  In fact, we came in right during a big event and there were about twenty Optis out there sailing.  Later on, we watched some teenagers launch some 420s to head out for some racing.  But the club had showers with hot water and even a little work shop that I could put to use.  The down side is that nothing was close to this marina and we were completely exposed to the west wind and swell.  We bounced all night while trying to sleep and it was some of the most exposed moorings we have ever been on.

After a shower, Chris and Liz came and picked us up via Chris’s power boat High Life.  They gave us a great tour of the Niantic River.  We could have gone under the two draw bridges and headed up the river to anchor or to a marina. But the charts all looked very shallow and all of the Active Captain reviews said that you need local knowledge to go in the river with anything over a two foot draft.  Of course now that we had people with local knowledge with us they showed us how to get to a very protected anchorage.  The river was really great with some interesting bars and restaurants that you could boat to and a really nice marina.  We continued up the river to what felt like the end.  There was Liz’s house, with a nice floating dock right in front.  Most of the houses on the water in this area had a floating dock, including Chris’ s dad’s house just a few houses down. Some of the docks looked way over designed and you could dock Smitty there during a hurricane if it wasn’t for the shallow water.  We enjoyed a great night with our friends with a fire by the river and eating some great grilled food on the outside patio.  After dinner we got a car ride back to the YC and got a tour of different areas we hadn’t been able to see from the river.  Liz’s parting gift to us was the Good Luck Mermaid that watches over Smitty and crew’s safe travels – to be returned when we meet up again in the tbd future.

The next morning I tried to put that shop at the YC to use.  Our exhaust elbow had started to leak. I had made this exhaust elbow out of galvanized pipe 4 years ago when the original one broke into pieces.  The shop had a nice big vise and I knew from past experience I would have to crank on the elbow to get it apart. So I took the dingy over to the YC, asked to use the shop, put the elbow in the vise and started to crank it apart.  The vise came right off the bench! The cast iron base was cracked and fell apart as soon as I started putting pressure on it.  So now what? I was cranking on it using two wrenches but I just couldn’t get enough torque to get it apart. I tried for several hours. I was eventually ready to give-up and pay someone to get it apart. Just then one of the club members (who is a retired shop teacher) showed up. Working together we were able to get it apart. Unfortunately, all of the cranking on the elbow got the one piece I was trying to salvage out of true. The retired teacher showed me a couple of old school tricks and we were able to get the elbow back to true enough to put the new exhaust system together. I’ll take a rolling nights sleep for help like this any time. 

The next morning we again got up early and headed for Milford, Connecticut.  This is my Bride’s hometown and we were pushing to see some relatives before they left the area.  Unfortunately ,they left earlier than we thought they were going to and we didn’t make it to see them.  Because we were pushing we went to make a 42 nautical mile day under less than ideal conditions. We had a 20 knot head wind, when the current was with us we had 4-5 foot chop and when the current was against us that laid down to 3 foot chop.  It was a long day of motoring with seas too rough for the autopilot.  We were in Block Island Sound for the first time and it reminded me of a bad day on Buzzards Bay.  The chop can be really steep and aggressive. It feels much higher than it is because of the steep nature of the chop and the short periods in between waves, sometimes as short as 2 seconds.  So while sounds like this can be considered protected waters, I find they can be more uncomfortable that open ocean.  Ocean swell is more spaced apart and less steep.  So I would take a 10 foot ocean swell over a 5 foot Buzzards Bay chop any day. 

On our way into The Gulf (opening to Milford Harbor) we started seeing these wooden sticks with flags sticking up everywhere. My Bride had read a comment on the charts a few minutes before we began seeing this that said “numerous oyster stakes present” but we had no clue what an oyster stake was. All we could see is these bamboo looking sticks with colored flags on them.  We didn’t know what the sub-surface structure around these stakes were.  We didn’t know if there were lines or nets connected between these stakes. At one point we found ourselves completely surrounded by them.  We tried hailing the harbor master and other boaters to find out what they were but had no luck.  Eventually we decided to just motor between them and chance it.  Turns out these are just wooden stakes to mark territories for the different oyster fisherman.  We eventually pulled into Milford Harbor, which is really just a dredged creek.  We were headed for the Milford Landing which is all the way down at the end. We pulled up to an empty dock with only two commercial boats on a dock that could hold 30 boats.

We stayed in Milford for 5 days.  We visited with family, spent time working on some maintenance tasks. We did some hardcore provisioning with stops at Costco and Walmart.  I topped off fuel. 

As we stayed in the harbor, more and more boats came in as the weekend approached.  The Friday through Saturday of our stay was the Milford Irish Festival.  A lot of the boats coming in were there for the festival and many were local boats that just wanted to move to a closer stop to enjoy the partying.  We met some nice boaters on m/v Sea Surveyor that very graciously offered there  mooring in Lloyds Harbor, NY for our use.


The first week of cruising is strange to explain. In many ways it just feels like being on vacation. We didn’t have a big break between working and starting this cruise. Plus we still had a bit of schedule to meet family and friends. We weren’t free to change plans like we hope to be a cruisers and we pushed on days like we did on vacation sails.

We covered just under 200 nautical miles in the first week (190.7 nm to be exact). Of those only 50 of those nautical miles were under sail. Of the 5 ports we had visited, 4 of them were new to us. Well sort of. We had been to most of them, just not by boat.  But we are used to exploring new ports on a vacation schedule.  Many mornings I still wake up thinking about work. I think we need more of a time separation from our working life to really know how cruising feels. 


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