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Portland · the home-base city

🏙 Portland, on foot and on wheels

You're based at the Holiday Inn By the Bay Friday through Monday, which puts the whole peninsula inside a fifteen-minute walk and the whole harbor inside a half-hour ride. The hotel's e-bikes are free — that quietly changes what's reachable, so there's a full route section below. Everything the hosts specifically called out is badged host pick.

Host picksOld PortMuseumsViewsOn the waterBeerBy e-bikeBike notes
The host picks
Austin & Jeannette's own list
Tandem Coffee & Bakeryhost pick 4.6★ · from 7 AM — old gas station on Congress St, biscuits and the best coffee in the city. ~15 min walk, 5 min ride. Already on the Monday card at 9:00a.
Eventide Oyster Co.host pick 4.5★ · from 11 AM — the brown-butter lobster roll on a steamed bun that made Portland's name, plus a full raw bar. No reservations: go at open or wait.
Eastern Promenadehost pick 4.8★ — 68 acres of open hillside over Casco Bay behind Munjoy Hill. Best at golden hour, when the islands stack up in front of you. Connects straight to the Eastern Prom Trail (route 2 below).
Portland Museum of Arthost pick 4.6★ · daily 10–6, Fri to 8 — two blocks from the hotel. Homer, Wyeth, Monet, a deep Maine collection. Open every day in August, so it's a real rain plan. Two hours is plenty. 207-775-6148
The dinner listhost picks — Fore Street (wood-fired, the icon, reserve) · Central Provisions (small plates) · Street & Co. (seafood bistro) · Twelve (tasting menu, the splurge) · Mr. Tuna (hand rolls) · Luke's Lobster (on the pier). Monday's dinner comes off this list — detail on the food page.
The Old Port & waterfront
10 min walk from the hotel
Wharf St & Exchange St — the cobbled core. Brick warehouses, independent shops, no chain-store feel. Exchange for browsing, Wharf for the postcard.
Commercial St & Custom House Wharf — this is still a real fishing port, not a re-creation of one. Walk out on the wharf for lobster boats unloading, and step inside Harbor Fish Market 4.7★ — the red-doored fish house everybody photographs — even if you're buying nothing.
Museums & landmarks
All within a mile
Portland Observatory 4.6★ · Thu–Sat 10–7, Sun 10–3:30 — top of Munjoy Hill, the last surviving maritime signal tower in the country. Guided climbs every 30 min, capped at 10 people, ~45 min. The 360° view beats the lighthouse for orienting yourself. It's a stair climb, not accessible. 207-253-1800
Victoria Mansion 4.6★ · daily 10–4 — five minutes' walk. An 1860 Italianate house with nearly all of its original interiors intact, which is rare to the point of absurd. ~1 hr; guided mornings, self-guided afternoons. 207-772-4841
Wadsworth-Longfellow House 4.6★ — the poet's boyhood home, Maine Historical Society next door, quiet garden behind. Short and easy.
Maine Narrow Gauge Railroad 4.5★ · closed Mondays — a 40-min two-foot-gauge train along the Eastern Prom waterfront. Sunday only, for you. Charming rather than essential.
Views, parks & shore
Where the city earns it
Eastern Promenade & Fort Allen Parkhost pick — the best free hour in Portland. Bring coffee, sit on the hillside, watch the ferries work the bay.
Back Cove Trail — 3.6-mi flat gravel loop around the tidal cove with the skyline on the water the whole way. Sunset here is the local ritual.
AllTrails · Back Cove Trail ↗
Bug Light Park, South Portland 4.7★ · 6 AM–10 PM — the squat, oddly ornate breakwater lighthouse across the harbor, and the best skyline view of Portland there is. Big lawn, free parking, WWII shipyard memorial.
Spring Point Ledge Light 4.8★ — a mile past Bug Light on the SMCC campus. You walk out on a 900-ft granite breakwater with real gaps between the blocks: sturdy shoes, watch your feet. Fort Preble is right there — check its closure notice first.
Willard Beach 4.7★ — a proper neighborhood sand beach a few minutes on, looking back at both lighthouses. Natural turnaround for the South Portland ride.
On the water
Casco Bay Lines · Maine State Pier
The mailboat run — the cheapest good boat ride in Maine. The actual mail route stops at five islands over about three hours; you never get off, you just watch the bay work. Locals rate it over the paid harbor tours.
Peaks Island — 20 minutes out, $14 round trip. You'll know it from Friday's lobster bake, but the back shore is what most people miss: 4 mi of paved perimeter road past open ocean. Bikes need their own $7 round-trip ticket — see route 5.
Lucky Catch lobster cruise 4.9★ · ~1.5 hr — you haul actual traps on an actual working boat, and they'll sell you the catch at boat price. Book ahead in August.
Beer & the not-downtown side
Industrial Way · East Bayside · Thompson's Point
Allagash Brewing 4.8★ · Sun 11–7, Mon 12–7 — anchor of the best beer block in New England — Foundation, Austin Street and Battery Steele share the lot: four breweries, one stop. Shuttle or Lyft this one — it's 5 mi out on arterial road and it ends in a tasting flight.
East Bayside brewery row — Rising Tide, Oxbow and Maine Craft Distilling inside two blocks on Fox and Washington. Ten minutes' walk off the Eastern Prom, so it pairs with a prom evening.
Thompson's Point 4.5★ — converted rail yard on the Fore River: Bissell Brothers taproom, food trucks, an outdoor amphitheater, cider, a distillery. Check what's playing.
🚲 By e-bike
Free bikes · front desk, By the Bay

The hotel lends e-bikes free to guests, checked out at the front desk and subject to availability — so ask on arrival and again the night before rather than assuming three are free at 9am on an August Sunday. Portland is small, hilly exactly where you don't want it, and ringed by flat waterfront trail: a near-perfect e-bike city. All routes start and end at 88 Spring St.

1 · Back Cove loop
≈6 mi round trip · ~45 min · flat · easiest
Out the Bayside Trail to Back Cove, once around the 3.6-mi gravel loop, home. Flat, separated from traffic, skyline over the water the whole northern half. Do this first to learn the bikes — and it's the right length if anyone's ambivalent about the whole idea.
Route ↗
2 · Eastern Prom & the waterfront
≈6 mi round trip · ~1 hr with stops · the classic
Down to Commercial St, east past the ferry terminal, onto the Eastern Promenade Trail — 2.1 paved waterfront miles on the old rail bed to East End Beach. Climb the prom to Fort Allen Park, coast down through Munjoy Hill, home past the Old Port. Add the Back Cove loop at Tukey's Bridge and it becomes a 9-mi figure-eight around the whole peninsula. Best ride here at golden hour, and it delivers the hosts' Eastern Prom pick on wheels.
Route ↗
3 · South Portland Greenbelt — two lighthouses and a beach
≈11 mi round trip · ~2.5 hrs with stops · the standout
Cross the Casco Bay Bridge on its protected bike-and-pedestrian path — genuinely great view mid-span — then pick up the South Portland Greenbelt to Bug Light Park. Continue a mile to Spring Point Ledge Light and walk the breakwater, then a few minutes more to Willard Beach. Mostly separated path, one short stretch of road. If you do one ride, do this one — the whole harbor from the other side.
Route ↗
4 · Cape Elizabeth & Portland Head Light
≈16 mi round trip · ~3 hrs · the ambitious one
Same bridge crossing, then Broadway to Cottage Rd to Shore Rd — a quiet, leafy, rolling coastal road into Cape Elizabeth ending at Fort Williams and Portland Head Light. Committing on an acoustic bike; a pleasant morning on an e-bike. You see the lighthouse Friday at 10:30 anyway — treat this as the ride, not the sightseeing.
Route ↗
5 · Peaks Island perimeter
≈4 mi loop + ferry · half a day · confirm first
Ten minutes to the Maine State Pier, ferry across, loop the back shore — open Atlantic, cliffs, almost no cars. $14 round trip per person plus $7 per bike, bought at the terminal that day. Two things to check: that the hotel is fine with its bikes leaving the mainland, and that Casco Bay Lines takes e-bikes specifically — their published bike policy predates them. Brad's, three minutes from the landing, rents by the hour including e-bikes if either answer is no — the cleaner plan regardless.
Route to the pier ↗
Bike notes worth reading once
Small things that ruin rides
Ask early, twice. Hotel e-bike fleets are small and first-come. Three at once on an August weekend morning is not guaranteed — raise it at the front desk and confirm the night before.
Ask what comes with them: helmets, locks, and the battery's actual remaining range. Maine doesn't require adult helmets; the Casco Bay Bridge and Commercial St make a case for them anyway.
Avoid the cobbles. Wharf St and parts of the Old Port are laid cobblestone — slow, jarring, no fun on a heavy bike. Ride Commercial St and walk the last block.
Lock them, always. Portland is safe, and bike theft is still its most common property crime. Never leave one unlocked outside a taproom.
The free bikes may make Sunday's rental unnecessary. Sunday's Option B books paid e-bikes at Gorham Bike & Ski in Portland for a South Portland Greenbelt ride — which is route 3 above, on bikes you already have for nothing. Worth checking before you pay. Monday's Option B is different: those are in Saco, 25 min south, and the hotel's won't get there.
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