Gloucester, MA to Kittery Point, ME

Monday, July 6, 2026

Departure: Ocean Alliance Docks (Gloucester, MA) 7:30AM

Special Comments:

Gray skies and cool temperatures as we departed.
Ocean looks smooth but has a seesaw punch.
I found this interesting…Thacher Island Twin Lighthouses (aka: Cape Ann Light Station) (Rockport, MA) are the only operating twin lighthouses in the USA. Measuring 124′ tall these granite towers are exactly 300 yards apart. Aligned precisely on a north-south axis, when mariners see them perfectly in line, one could easily determine true north to navigate Cape Ann’s dangerous ledges. Built in 1771, and rebuilt in 1861. First station in the USA to mark a navigational hazard rather than a harbor entrance.
Conditions are smooth and favorable. But, where is everyone?
While underway, Jacques called ahead, no mooring balls available so we’ll be swingin’ on the hook.
On starboard, we passed Isles of Shoals which is a strand of islands that separate the border of Rye, NH and Kittery, ME.
We observed a C/V iKati struggling to anchor, tried along our port, stern, and starboard for over a hour. Eventually, they gave up and hailed the Harbormaster for a mooring ball.
Apparently, on July 4th the was a Humpback Whale sighting here at Pepperrell Cove. WOW, hoping I can be so lucky!

About Kittery, ME:

Approximately 1,007 residents (2025), functioning as a stable, tight-knit, year-round community.
Attractions: Fort Foster Park, Fort McClary State Historic Site, Kittery Historical & Naval Museum, Rachel Carson National Wildlife Refuge, and Spruce Creek.
Average annual household income is $149,058 (2025).
Average residental purchase price, $663,500 (2025) with a suggested premium Kittery Point neighborhood average between $830,000 - $850,000.
Bistro 1828 at Pepperrell Cove Restaurant (Kittery Point, ME) is a local hub for boaters. A multi-level waterfront destination, the Ski Club Bar on the 3rd floor offers panoramic vistas of the cove and Ft McClary.
Chauncey Creek Lobster Pier (Kittery Point, ME) on Chauncey Creek, this considered an iconic waterfront lobster shack with its own private floating docks. Tender friendly for enjoying a waterfront meal.
First settled in 1623.
Fort McClary State Historic Site (Kittery Point, ME), an active defense from the Revolutionary War (1775 – 1783) – WWI (1914 – 1918), and the former military base Fort Foster Park (Kittery Point, ME).
Frisbee’s Wharf (Kittery Point, ME) is a casual outdoor summertime favorite place.
Home (1662) of late John Bray House is recognized as the state’s oldest standing property.
Newcomen Society (1920) built a cluster of Tudor cottages as summer retreat.
Popular for 17th Century (1601 – 1700) colonial architecture, coastal fortifications, and scenic ocean views.
Provisions at Pepperrell Cove open daily (8 AM – 6PM) offers essentials: beer, groceries, ice cream, homemade soups, made to order sandwiches, nautical gear, and wine.
Portsmouth Naval Shipyard (Kittery, ME), keeps the local economy active and stable through the winter, shielding it from being a total “ghost town“.
Safe Harbor Kittery Point (Kittery, ME) has a dedicated dinghy dock, complimentary for transient mooring ball guests.
Seapoint Beach (Cutts Island)is a beautiful curving stretch of sand bordered by a salt marsh.
State’s oldest town (1647).
William Pepperrell Sr arrived from Devonshire, England as a lowly fisherman’s apprentice at the Isles of Shoals, NH. Eestablishing fisheries to supply the London, England market, building a mercantile empire later inherited by his son. His landmark mansion at Pepperrell Cove is on the Piscataqua River.

Arrival: Pepperrell Cove Anchorage (Kittery Point, ME) 1:30PM (N43°04.800′ W70° 42.523′)

Next Stop: Unknown?

**Ten Pound Island Light**
Ten Pound Island
Gloucester, MA

**Hammond Castle Museum**
Gloucester, MA

**Thacher Island Twin Lighthouses**
(AKA: Cape Ann Light Station)
Rockport, MA

**Isles of Shoals**
Rye, NH & Kittery, ME

Tuesday, July 7, 2026

Anchored: Pepperrell Cove Anchorage (Kittery Point, ME) (N43°04.800′ W70° 42.523′)

Special Comments:

Took me awhile to fall asleep with the rolliness and thought that our anchor would lift. Regardless, to the three different anchor alarms set. Doesn’t mean everyone else around us does the same.
Rainy morning.
My Belgian hubby celebrating the Belgium’s World Cup victory. Meanwhile I’m giving him the stink eye.
YIKES, just read about the Kadey Krogen Yachts LLC bankruptcy filing in DE. When we were shopping, one of the brands we considered.
Even though it’s drizzling outside, we’re dropping the tender for lunch in town. Yesterday, we were just both too tired to do so, certain cruising motions are so fatiguing.
Our tender outbound tender stroll was a drizzle. The inbound return was a torrential downpour.
Approaching our vessel in the tender, we hear lots of screaming and yelling from M/V Utopia on a mooring ball. Apparently, this charter/cruise vessel out of Newington, NH just moors for a few hours for their guests to fish/trap. Overheard the deck hand advising them to do so anytime somebody approaches. One would think they would find a better location than a anchorage/mooring field.
Hot lobster roll lunch at Frisbee’s Wharf at Pepperrell Cove (Kittery Point, ME).
Browsed the Provisions Cafe & Coffee (Kittery Point, ME). Like any good bakery, most baked goods were sold out for the day. That said, we managed to find apple danish (Jacques) and blueberry scones (Janet) for tomorrow morning.
Nice to toss our wet clothes into our new dryer with far less electricity power and without even needing to turn on the generator, pure solar.
Gosh, barely any boat traffic or even wind but, it is so rolly here. Often having us feel like we were on a overnight in 1′ – 2′ swells. Our core muscles are getting a workout (LOL). For the first time in all of years of owning the vessel, we actually used the flopper stopper. A gentle sway we don’t mind but a beam to beam roll is not pleasant for a continuous 24 hours.

Next Stop: Casco Bay, ME (Thursday, 7/9/26?)

Wednesday, July 8, 2026

Anchored: Pepperrell Cove Anchorage (Kittery Point, ME) (N43°04.800′ W70° 42.523′)

Special Comments:

YAH, sunny skies. Cool morning, 66°F.
Local waterman has infested the area with pot lines. All in front of the mooring and anchorage field.
Observed C/V iKati depart from the mooring ball to reattempt anchoring after our sailboat neighbor departed. Painful to watch, but after a hour they finally got hooked. However, less than 2′ from traps though. So, when they swing as they will they’ll be right on top of it. We suspect they must be new because during yesterday’s tender stroll, they were placing a stern anchor while on a mooring ball which is a big, no, no as you’ll no longer swing in the choreographed direction of others around you. As I’m typing this, they realized how close they were to the trap line and lifted anchor again.
Went for a nice long tender ride.
We tried to have lunch at Warren’s Seafood & More (Kittery, ME) and the Buoy Shack (Kittery, ME) however, while both had docks neither offered a public dock or even a tender dock for dining. So, we throttled forward to Morrison’s Lobsters (Kittery, ME). For lobster rolls, of course.
We received a text notification for a $360.54 transaction from Bahia Mar Yachting Center (Ft Lauderdale, FL) which was a surprise given we were paid in full and haven’t been there since early March. Apparently, Annie, charged our card because of another vessel named Soulmates reservation. UGH, seems as though they need to do better. In accordance, to the global Payment Card Industry Data Security Standards (PCI DSS) (which all Florida businesses must comply with to accept card payments) and Florida Statute 501.0118 they can not keep your credit card information on file, once payment in full has been rendered. Now, they may keep ledger records and sales receipts for 3 – 7 years. Consumers have the right to request that their payment profile be deleted, to which we exercised. We both previously worked for a corporation that had to follow strict guidelines.
With the alarm clock set for 6AM, we stowed away the flopper stopper and tender. Gosh, did we immediately notice the difference regarding the flopper stopper thereafter.