Boothbay Sailing Trips Aboard the Bay Lady
A Friendship Sloop
Looking for Boothbay Harbor sailing trips in Boothbay Harbor? The Bay Lady is a 31′ Friendship Sloop, and this 90-minute sail is the longest continuously operating sailing excursion in the harbor. The moment the sails go up, everything changes. Feel the wind, hear the water, and experience Boothbay Harbor the way it was meant to be — under sail aboard the Bay Lady.
A Real Sail, Not a Boat Ride
This is a real sailing experience. Watch the crew expertly hoist the sails right in the harbor, then listen as the engine goes quiet and the Bay Lady leans into the breeze. From that moment on, it is wind, water and canvas — no motor, no noise, no soundtrack but the harbor itself.
Trade engine noise for the whisper of the wind in the sails. With just twelve passengers aboard, there is no crowd between you and the water. Bench-style seating gives everyone something to lean back against and a clear view of the harbor as the Bay Lady glides across it.
Boothbay Harbor sailing trips are never quite the same twice. Wind direction and speed decide where we go, which is exactly how sailing is supposed to work.
| Duration | 90 minutes |
| Departure times | 10:30 am, 12:30 pm, 2:30 pm, 4:30 pm daily |
| Departs from | Pier 8, 42 Commercial Street, Boothbay Harbor, Maine 04538 |
| Capacity | Up to 12 passengers, bench-style seating |
| The Boat | 31′ Newman/Lanning fiberglass Friendship Sloop, Maine built, launched 1979 |
| Booking | Online, at the Pier 8 ticket booth, or by phone at 207-633-2284 |
What You’ll See on the Water
Because the wind writes the route, every sail is a little different. Depending on the breeze, you may find yourself cruising past spruce-topped islands, rocky Maine shoreline and working lighthouses, with Boothbay Harbor opening up behind you.
The water is busy in the best way. Harbor seals haul out on the ledges, porpoise surface alongside the hull, and osprey work the shallows overhead along with terns, cormorants and gulls. Bring a camera — the light off the water in the late afternoon is the reason people come back.
Catch the afternoon breeze on the 2:30 or 4:30 departure, or sail in the calmer morning air at 10:30. Both are good. They are just different days on the same harbor.
Boothbay Sailing Since 1979
The Bay Lady launched in 1979 and has been carrying passengers on sightseeing sails ever since — the longest continuously operating sailing excursion in Boothbay Harbor. Nearly five decades of the same harbor, the same wind, the same eleven-and-a-half tons of Maine-built sloop leaning into it.
She is a Friendship Sloop, a design born in Friendship, Maine in the 1880s as a working lobster boat: gaff-rigged, sweet-lined and built to handle whatever the Gulf of Maine sent at it. Fishermen chose them because they were fast, forgiving and could be sailed by one person. That heritage is why the Bay Lady handles the way she does, and why a 31-foot sloop still turns heads next to boats twice her size.
If you want to know what sailing this coast actually felt like a hundred and forty years ago, this is as close as you are going to get with a ticket.
Before You Board
- Dress for the water, not the parking lot. It runs 10 to 15 degrees cooler under sail than it does on Commercial Street. Bring a layer even in August.
- Soft-soled shoes. Sneakers or boat shoes, no heels.
- Sunglasses and sunscreen. The glare off the harbor is real, and there is no shade under a sail.
- Arrive 15 minutes early at the Pier 8 ticket booth so we can leave on time.
- Boats fill up in July and August. Reserving ahead is the difference between sailing at 2:30 and watching the 2:30 leave without you.
Parking fills fast downtown in peak season — see our parking information before you head down to the pier.
Who’s at the Helm
Balmy Days Cruises is family owned and operated, and has been since 1981.
Capt. Bill Campbell has worked the water off Boothbay Harbor for more than fifty years. He earned his captain’s license at twenty, running the Squirrel Island ferry under Capt. Bob Fish, then spent years on deep sea fishing boats before coming back to the harbor for good. In 1981 he and his father, Capt. Bob Campbell, bought the Maranbo II and the Balmy Days from Capt. Fish and started the company.
He oversaw the building of the Balmy Days II in 1988 and the Novelty in 1996, and brought the Bay Lady into the fleet to keep Boothbay Harbor’s longest continuously operating sailing excursion running.
Every vessel in the fleet holds a current USCG Certificate of Inspection. The crew is local and experienced, and Bill will tell you himself they’re the heart of the business.
Bay Lady Sailing Trip FAQs
How long are the Bay Lady Boothbay Harbor sailing trips?
The sail lasts 90 minutes from the time we leave Pier 8 to the time we tie back up. Plan to arrive about 15 minutes before your departure time.
Where does the Bay Lady depart from?
Pier 8, at 42 Commercial Street in Boothbay Harbor, Maine. The ticket booth is right on the pier.
What time does the Bay Lady sail?
Four times daily: 10:30 am, 12:30 pm, 2:30 pm and 4:30 pm, weather permitting.
How many people can go on the boat?
Up to 12 passengers per trip, with bench-style seating. Groups larger than 12 should ask about a private charter.
Is this an actual sailing trip, or a motorboat tour?
It is an actual sail. The sails go up soon after we leave the dock and the engine is shut off. The route is determined by wind direction and speed.
What will we see on a Boothbay Harbor sailing trip?
Islands, rocky shoreline and lighthouses, with a good chance of seals, porpoise, osprey and other sea birds along the way. The exact route depends on the day’s wind.
How do I book a Bay Lady sail?
Reserve online at balmydayscruises.com, stop by the ticket booth at Pier 8, or call 207-633-2284. Reservations are strongly recommended in July and August.
Photo Gallery
From the moment the sails are raised, every trip is a true sailing adventure. Experience sailing the way it was meant to be.
Reserve online, stop by the ticket booth at Pier 8, or call 207-633-2284.