Cruising Maine with Friends and Family


Last Updated on November 18, 2019 by Amy

Our passage to Portland from Lunenburg was quick!

Sail Repair

One of our first orders of business was getting the spinnaker out. The spinnaker rip was fixed by Canadian Sail Makers, a Doyle rep, who had the sail the whole time we were in Canada. Unfortunately, they didn’t have the capability to furl the sail, so we took advantage of light winds from behind as we were leaving Lunenburg and got the sail up and properly furled.


Sailing Conditions

  From there, we started with moderate winds, keeping us sailing swiftly downwind along the Nova Scotia coast. The winds even shifted a bit to our beam, so we were able to roll out our screecher (our very large headsail) and fly along. In a 12-hour period, we sailed 94 nm – pretty dang good!

As we passed into US waters, however, the wind died down to almost nothing. We cranked our engine and motored in. We passed seals, a whale, had a hawk land on us, and dodged hundreds of traps!  My god, Maine is full of them!

oh hello human.  – Peregrine Falcon
fine, I won't eat my lunch here
fine, I won’t eat my lunch here – Peregrine Falcon

Formalities for the US

I had set up David’s Floridian SIM card before we left Lunenburg, so David was able to properly call the customs office and report our entrance. We were instructed to go to the customs dock and we caused quite a stir – apparently, the port security (the customs dock being by the ferry and cruise ship terminals) were not expecting us. But our customs agent quickly showed up, cleared us in, and confiscated my citrus fruits (yes, the Floridian citrus fruits that I bought in Canada were not allowed in).

Anchoring in Portland Maine

Once cleared in, we anchored on the edge of a channel and a mooring field. We’ve learned that this area is VERY difficult to stay in because the wakes from all the boats passing through cause us (and the boats in the mooring field next door) to bounce around a lot. Being a 3-day holiday weekend, traffic was extra rough. We were constantly observing tankers, ferries, lobstermen, sailboats, and small powerboats.

Kayaking in Portland

From our anchorage, I took our kayak out for a spin. In the morning, I kayaked to Pomroy Rock and the East End Beach. Nothing too terribly exciting.

the view from East End Beach

In the afternoon, I kayaked to Fort Gorges. Now that the holiday weekend was over, traffic was extremely reduced. I enjoyed spotting Harbour seals on my way to the island and then found that I had the island all to myself. Fort Gorges, built in 1865, is on the National Register of Historic Places. It is completely abandoned. No office, very much an enter-at-your-own-risk situation.

Having the fort all to myself was stunning. I love places like these where you get to see nature reclaiming our past. I walked through the fort and then spent some time shelling on the beach before kayaking back.

Dimillo’s Marina

On Monday, we dinghied over to Dimillo’s Marina. Our reservation doesn’t start until Wednesday, but they were nice enough to hold mail for us. David had ordered some supplies for a project, so we picked up our packages. David headed back to the boat, while I ran errands – AT&T (lost my Floridian SIM card), west marine (more parts for David) and Starbucks (internet).

Wednesday we left first thing in the morning and headed to Dimillo’s. A quick fueling up and we were tied to our dock and the real work began. David gave the boat a bath, and 2 loads of laundry later, our guest rooms were set up and ready to roll. It was great to have the marina laundry to use. Our washer/dryer machine is great for small loads and line drying. It would have probably taken me six loads in our machine to do all the sheets and towels.

While it was great to be right in the center of town, Dimillo’s is EXPENSIVE! We paid $200 a night to be there….our most expensive marina ever.

Dining in Portland

I managed to grab a very late lunch at Blue Rooster (excellent falafel) and bring back a treat for David (donuts from Holy Donuts). The donuts were so delicious!

Catching up with Galileo

Wednesday night, we had guests over for dinner – Sari and Eric. Sari had been in our Offshore Emergency Medicine class in Portland last year, and living nearby, she had a group of us over for dinner one night. Sari and Eric are also catamaran people, and they have a 52.5′ Balance cat named Galileo.

Sari and Eric were the perfect guests; after a long day of cleaning the boat – they brought dinner!  It was great to catch up with them.

My Weekend in Boston

And then I got kicked off the boat! David hosted a bachelor party for his friend Jared on Starry Horizons. That’s right, our girl hosted seven perfectly well-behaved gentlemen for two nights of esoteric debates and early bedtimes. Or something like that.

The guys coming in were very nice about it and offered to put me up in a hotel, but instead, I decided to take the train down to Boston and stay the weekend with some family.

The bachelor party was spending their first night in Boston, so I was able to take the early train down with David. We arrived in Boston around 10:30, dropped our bags off at the hotel and went off for lunch. One of our favorite foods is one you can’t find in small towns – dim sum. Boston has a fascinating Chinatown, so we easily found Winsor Dim Sum and had a great (and cheap) meal.

David and I parted ways and I headed to Copley Square, where my Great Uncle Jim and Great Aunt Lois live. They are in a great location and are always very welcoming to have me stay with them. My first night with them, they had another guest. Let’s see if you can get this connection – their daughter-in-law’s father. He was in town to pick up a Norwegian cruise to Canada. Jim & Lois also had their son Doug and his wife Ann for dinner. Doug & Ann (my first cousins once removed) live in Wellesley, so I have also spent a lot of time in the area visiting them.

L to R: Jim, Lois, Me, Ann and Doug

Friday we walked to Boston Common and back for a bit of execise (Jim & Lois walk ALOT, which is I’m sure the primary reason for their excellent health).  I split with them to run and visit the farmers market.

If only I could stock Starry Horizons up with these veggies!

After lunch,  we walked (2.5 miles!) to the Spirit of Boston.  I met Bob Lawler from the Passenger Vessel Association, many years ago. Every time I’ve been in Boston, Bob has been so generous to allow me to come and cruise. This time I was thrilled to actually get to have him join us on the cruise. Bob gave us a tour of the newly renovated Spirit of Boston, and told us all about the new cruise type that we were attending; Boathouse Fridays. The Spirit of Boston’s new renovations included lounges, bar seating and games, making it much more conducive to a party atmosphere. The boat goes out every other hour, and you can get one ticket for $23.90 and cruise all the way until 9 pm. The drinks and food were excellent, and I was so impressed with the new interior. It was great to catch up with Bob, who caught me up on what was going on in the PVA.

L to R: Jim, Lois, me and Bob

On the way back from the cruise I split with Jim & Lois and walked along the Harborwalk, checking out the waterfront of Boston. There was a Lagoon catamaran named Anomaly out on a mooring, but no other cats. Starry Horizons would have looked good in the harbor.

Saturday I was picked up by my big sister from my sorority, Lexie. I don’t think I had seen her since her own wedding 5 years ago, so it was great to see her and meet her baby Gabe for lunch at Bon Me. Afterward, we went to the Children’s Museum and let Gabe play with the exhibits while we chatted.

 Friday evening, I went up to the Top of the Hub, a restaurant on the 52nd floor of the Prudential Building. I met up with my sorority twin Jan for drinks and then were later joined by another sister Amanda, and her boyfriend Steve. Amanda, Steve and I went out to dinner (Back Bay Social Club – very good).

L to R: Jan, me and Amanda

Finally, on Sunday, Jim, Lois and I went to the New England Aquarium, which was an excellent attraction. They have large tanks and lots of special presentations. We got to watch the pufferfish in the large round tank being hand-fed, and saw penguins, seals, and a ton of aquatic life. My highlight was the shark and ray touch tank. It’s the largest touch tank in the Northeast, and you can put your hand in while all kinds of rays and sharks swim by for you to touch. Very cool!  Of course it’s not quite the same as when they swim up to you in the wild like Honeymoon Harbor, but still neat!

He looks so blissful…

Jim and Lois took me for one last dim sum fix, and then it was time to head back home to Starry Horizons and see what kind of shape she was in after a weekend of debauchery. (The boys took good care of her!)

Return to Portland

After the bachelor weekend, we stayed one more night at Dimillo’s in Portland.  David was able to get oil changes done for our engines and generator (200 hours for the generator, the engines weren’t really in need of a change but we did it anyway) and we were able to see my cousin Ed and his friend Kathleen.  They live in Bowdoinham Maine, and Ed is a pretty amazing guy!  In addition to being a helicopter pilot and avid kayaker, he brought us gifts of his homemade Peruvian Pepper Pate and raw Honeycomb (yum!!).  After drinks aboard SH, we went out to dinner at 555.

Ed, Kathleen, and us!
Ed, Kathleen, and us!

Boothbay Harbor

Tuesday we left Portland and sailed most of the day up to Boothbay Harbor.  We anchored in Boothbay and spent two nights there – but we didn’t even go ashore.  

Billings Cove

Thursday we sailed to Billings Cove, which was a lovely anchorage until the sun went down and we were blinded by the dock light at one of the waterfront houses.  Although it was awful, we could still sit on the bow and see the stars and Milky Way for at least half of the sky…

Atlantic Boat Co in Brooklin

Friday we motored over to Atlantic Boat Co, in Brooklin.  This was a short drive from my Uncle Jim and Aunt Melinda’s new home, a cozy little cottage.  We picked up a mooring at ABC, and in a few hours, Uncle Jim motored past and picked up the mooring next to us.  SH got to meet Requiscere – a Hinkley Bermuda 40, that Uncle Jim has had since 1986.  Onboard were Jim and Melinda, in addition to their daughter Courtney, her husband Peter, and their kiddos Graham & Camden.  We got to have the whole family over for dinner on SH.  Graham is an avid crawler, and it was amazing to have him in the cockpit.  We zipped everything up so it was fully enclosed and he just motored around under our feet!


In the cockpit of Req in 1987.
In the cockpit of Req in 1987.
In the main salon of Req in 1987.
In the main salon of Req in 1987.
Me and Graham.
Me and Graham.
Camden, Peter and Courtney.
Camden, Peter and Courtney.

Shellback International Regatta

The REAL reason we were all here was the 7th Annual Shellback International Regatta.  Last year, Uncle Jim built a shellback named Frolic, just for his granddaughter, Camden.  Camden is four, but she is the actual owner of the boat…and isn’t she just the cutest boat owner you’ve ever seen?  (A shellback is a wooden dinghy, designed by Joel White.)

Camden and her very proud Cappy.
Camden and her very proud Cappy.

Uncle Jim entered Frolic in the regatta and sailed the seven races on Saturday.  Camden even crewed the first two!  The rest of us hung out on Starry Horizons and watched the race from our lounge deck.  We had a picnic and cheered every time Frolic rounded the race buoy.  The fog threatened every once and a while, but we enjoyed watching it roll in and out, playing hide and seek with the island across the bay.

Watching from the lounge deck.
Watching from the lounge deck.
Shellbacks everywhere!
Shellbacks everywhere!
Frolic, with Jim at the helm.
Frolic, with Jim at the helm.
Fog rolled in and out all day.
Fog rolled in and out all day.
Me and Camden.
Me and Camden.

Saturday night was dinner at a local inn, and the awards ceremony included a very special one – the “Littlest Sailor” award.

Camden and Cappy

Sunday we enjoyed a leisurely day on the boat and caught up with the family for one last dinner.  We had SUCH a good time with the family.

Ebenecock Harbor

Monday morning we (and by that I mean David) got up at 6 am to slip our mooring and head out.  We sailed 12 hours to Ebenecook Harbor, on the Sheepscot River, where we anchored for the night.  It was a beautiful anchorage, and plenty of room, even with a few marinas and mooring fields around.  We spotted a lot of seals, and the sunset was fabulous!

Ebenecook sunset
Ebenecook sunset

Robinhood Marine Center

Tuesday morning we motored to Robinhood Marine Center, just across the Sheepscot River, where we picked up a mooring.  David and I were very productive and prepped the boat for our departure.

Robinhood Sunset

SH is safely tucked in at Robinhood, and David and I are in Texas for a 2-ish week visit.  Our plans are to spend time with friends and family, attend a wedding on the 3rd, and then start to look at the weather to identify a window to make the jump to Bermuda!

Watch the Video:  Meandering Around Maine

Watch the Video:  2015 Shellback National Championships

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