Boating and Water Access on the Other Casco Bay Islands: Ferries, a Second Ferry Line, and Two Real Marinas
Long Island, Chebeague Island, Great Diamond Island, Little Diamond Island, and Cliff Island are five genuinely distinct communities that share one thing every reader needs to understand before anything else: none of them connect to the mainland by bridge or road. Every trip on or off any of these islands -- for a resident, a visitor, a delivery truck's worth of groceries, or a contractor's truck -- moves by boat. That makes "boating and water access" a bigger, more load-bearing topic here than it would be almost anywhere else on this site. This page is about the five islands' own ferry connections, Chebeague's genuinely unusual second ferry operator, the handful of real marinas and mooring fields actually documented on these islands, and the working lobstering heritage that runs alongside all of it. Peaks Island -- the largest, most populous, and most frequently served of the Casco Bay islands -- is covered in its own depth on this site's separate peaks-island-me pages and is mentioned here only as context, not as part of this page's subject.
Casco Bay Lines: One Ferry Operator, Five Very Different Crossings
Casco Bay Lines, the Portland-based ferry operator, is the connective tissue linking all five of these islands (plus Peaks Island) to downtown Portland, but the actual crossing looks nothing alike from one island to the next. Long Island's passenger run is commonly described as taking anywhere from 30 minutes to a full hour, depending on the specific route and how many stops the boat makes along the way. Great Diamond Island is served at a Diamond Cove stop on the island's northeastern side. Little Diamond Island is also a Casco Bay Lines stop, consistent with its tiny, largely private, seasonal-retreat character. Chebeague Island's Casco Bay Lines route is its slower option -- a roughly 60 to 90 minute mail-boat run from downtown Portland out to the island's Chandler's Cove wharf.
Cliff Island gets the longest ride of the group by a wide margin: commonly cited at roughly 60 to 120 minutes one-way depending on the route and how many freight stops the boat makes, with five daily round trips operating year-round (with seasonal schedule variation). A barge ramp added in 2008 supports freight delivery to Cliff Island, a genuinely practical detail for an island with no bridge and entirely unpaved roads. Because fares and schedules are a live, currently-disputed topic -- Casco Bay Lines proposed a passenger fare increase in 2026 that drew enough resident pushback that the Maine Public Utilities Commission voted in June 2026 to open a full investigation into both the increase and the rate-setting process -- this page won't quote a single fare figure as fixed. Verify current schedules and fares directly with Casco Bay Lines before planning a trip or a move around them.
The Vehicle Ferry: A Real, Reservation-Only Way to Bring a Car
Beyond passenger service, Casco Bay Lines also runs a dedicated vehicle and freight ferry -- checking the carrier's own current site turned up a genuinely useful, more current detail than most general guides carry: the vessel is the Maquoit II, and as of this research it serves four of these islands directly -- Long Island, Chebeague Island, Cliff Island, and Great Diamond Island. This isn't a fixed-schedule service. Reservations are taken first-come, first-served, by text message, by email, or through an online form on the carrier's own site, and the carrier is explicit that a requested date and time "cannot be guaranteed," so booking as far ahead as possible matters.
Current one-way fees, per Casco Bay Lines' own site, run from roughly $88.65 for a car, van, or pickup in the October-through-April off-peak season up to roughly $122.65 in the April-through-October peak season, with separate, lower rates for trailers under 20 feet. Vehicles face real logistics on both ends: arrival at the Portland terminal at least 90 minutes before departure, 30 minutes' advance arrival when leaving from an island, a 5,500-pound weight cap, a 6-foot-6-inch height cap, and no same-day round trip. Anyone planning to bring a car to any of these islands should treat this as a service to book well in advance, not a walk-up option -- and should re-verify current fees directly, since they're tied to the same seasonal schedule and rate structure currently under state review.
Chebeague's Second Ferry Line: A Genuinely Unusual Two-Operator Setup
Chebeague Island is the one island in this group with its own dedicated, independent ferry company in addition to Casco Bay Lines, and that's a real structural difference worth understanding on its own terms. The Chebeague Transportation Company (CTC) runs a much shorter passenger route than Casco Bay Lines' Portland run -- roughly 15 minutes -- connecting Cousins Island in the mainland town of Yarmouth to Chebeague's own Stone Wharf. Checking the CTC's own current site found a peak-season schedule effective May 22, 2026, along with a clear rule for riders: tickets must be purchased in advance, whether as single tickets, monthly ticket books, annual passes, or resident ticket packages. Riders with bulky items are directed to a satellite parking lot on Cousins Island rather than trying to bring everything aboard, and the CTC's office can be reached directly for current timing.
Separately from its passenger boats, the CTC also operates a 43-foot vehicle and freight barge from April through November, by reservation -- Chebeague's own answer to the car-ferry problem, running alongside (not instead of) the Casco Bay Lines vehicle ferry described above. Having two independent ferry operators serving one small island, each with its own dock, schedule, and fare structure, is genuinely unique among these five islands and reflects how central water access is to daily life on Chebeague specifically.
The Real Marinas: Diamond's Edge and Chebeague Island Boat Yard
Two of these five islands have a genuine, currently operating marina -- and it's worth naming them specifically rather than gesturing vaguely at "boating facilities," since so much of this market is otherwise thin on documented private-boating infrastructure. At Diamond Cove on Great Diamond Island, Diamond's Edge Restaurant & Marina is a real, named facility -- checking the marina's own current site found it described as a 43-slip deep-water marina handling vessels up to 109-plus feet, with a 20-foot approach depth and 12 feet of depth at the dock. Transient boaters reserve through Dockwa (a widely used boater-reservation platform) and are asked to hail the marina on VHF channel 09 while entering the harbor. The marina does not offer fuel or pump-out service, but does offer complimentary water and Wi-Fi, shore power, restrooms, showers, ice, and dinghy dockage alongside its on-site restaurant.
On Chebeague Island, the Chebeague Island Boat Yard is a genuinely long-running working marina, not a recent add-on -- it traces back to a boatyard founded in the 1930s by Roy Hill, was sold to the Brewer family in 1960, and was incorporated under its current name in 1971. Checking current sources turned up a detail more recent than this site's underlying research: a 2025 ownership transition, with longtime co-owner Scott Searway transferring his majority stake to Paul and Jen Belesca, and longtime employee Justin Doughty set to join the ownership and management team -- with the new owners indicating plans for waterfront upgrades and shoreline stabilization work. The yard's own site describes transient rental moorings available by the night in season (no launch service, but restroom and shower access included), a fuel dock selling gasoline and diesel, and substantial boat storage -- roughly 15,000 square feet of indoor heated space plus outdoor wrapped storage, with a 30-ton hydraulic trailer capable of handling boats up to about 50 feet. No comparable marina, fuel dock, or organized mooring field was found for Long Island, Little Diamond Island, or Cliff Island in this research -- consistent with how small and thin these particular markets are, and worth stating honestly rather than papering over.
Lobstering: A Working-Waterfront Identity Alongside the Ferries
Boats around these islands aren't only ferries and pleasure craft -- lobstering is a real, if unevenly documented, part of the working waterfront here. Chebeague Island has the clearest documented lobstering identity of the five: Calendar Islands Lobster, launched in September 2009 by Dropping Springs LLC with support from the Island Institute, was built as a fishermen-owned, vertically integrated cooperative aimed at branding lobster caught by conservation-minded Casco Bay lobstermen. It grew to 29 participating fishermen, was led by John Jordan, and invested in lobster-holding tanks, a Portland wharf lease, and a smack boat for distribution -- a real, documented founding effort, though its current operating status wasn't confirmed in this research and shouldn't be assumed still active. A separately named business, Chebeague Island Lobster Co., also turns up as a real, findable entity, again with current operating status unconfirmed.
Long Island's own history leaned on farming, fishing, and lobster catching before tourism became the dominant industry after World War II. On Cliff Island, lobstering remains part of the current mix of how year-round residents make a living, alongside local island businesses and commuting to the mainland for work. No current lobster-license counts, boat counts, or named individual lobstermen for Great Diamond Island, Little Diamond Island, or Long Island turned up in this research -- a real gap, not a claim this page will paper over. Separately, Maine's statewide lobster landings were reported down again in 2025, and a 2026 report of a lobster "baby boom" in young-of-year counts applies to a different part of the Maine coast (the Stonington/Vinalhaven/Beals area), not Casco Bay -- so neither statewide trend should be read as a specific claim about these five islands' catch.
What This Means Before You Decide
Put together honestly: water access on these five islands ranges from a 15-minute hop on Chebeague's own ferry to a two-hour Casco Bay Lines crossing to Cliff Island, and bringing a car anywhere in this group means booking a reservation-only vehicle ferry well ahead of time, at a real cost, rather than driving on and off at will. Only two of the five islands -- Great Diamond (via Diamond's Edge) and Chebeague (via Chebeague Island Boat Yard) -- have a documented marina, fuel dock, or organized transient mooring field; Long Island, Little Diamond, and Cliff Island simply don't show up with comparable infrastructure in current research, and that thinness is itself a useful fact for anyone weighing a private boat as part of life here. Lobstering remains a real thread in the local economy, most clearly on Chebeague and Cliff Island, even where a specific business's current status couldn't be confirmed.
None of this should be read as either a reason to assume boating here is easy or a reason to assume it's impractical -- it's the honest, sourced picture available without inventing a fee, a slip count, or a schedule that wasn't confirmed. Before making any decision that depends on ferry reliability, vehicle-ferry reservations, mooring or slip availability, or current fares, confirm directly with Casco Bay Lines, the Chebeague Transportation Company, Diamond's Edge Marina, or Chebeague Island Boat Yard. Nothing on this page is legal, financial, or relocation advice.
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Get a Free Agent Referral →Independent research. No ads. No sponsored listings. Ferry crossing times, the 2008 Cliff Island barge ramp, and the Casco Bay Lines fare-increase dispute and Maine Public Utilities Commission investigation reflect this site's own competitive-market research. The Maquoit II vehicle-ferry service area, current one-way vehicle fares, reservation method, and vehicle limits; the Chebeague Transportation Company's May 22, 2026 peak-season schedule and advance-ticketing rules; Diamond's Edge Restaurant & Marina's 43-slip capacity, depth, and Dockwa reservation process; and Chebeague Island Boat Yard's 2025 ownership transition, mooring and storage services, and founding history were independently checked directly against Casco Bay Lines' own site, the Chebeague Transportation Company's own site, Diamond's Edge Marina's own site, Chebeague Island Boat Yard's own site, and a Mainebiz report during this page's research and were not found stated this specifically in this site's underlying research document. The Calendar Islands Lobster and Chebeague Island Lobster Co. founding details are stated as historical/founding facts; their current operating status was not confirmed. No lobster-license counts, boat counts, or marina details were invented for Long Island, Little Diamond Island, or Cliff Island -- none were found. Nothing on this page is legal, financial, or relocation advice.