Collect luggage and check into your Charlottetown Airbnb; give yourself time to settle after the flight. Most Airbnbs have 3:00pm check-in but confirm with host.
Pleasant pedestrian area with shops, galleries and restaurants; a great first-walk to get a feel for downtown Charlottetown. Public spaces are open year-round but some shops are seasonal—check specific shop hours.
Well-regarded seafood restaurant on the Charlottetown waterfront; try local oysters or seafood chowder. Restaurant hours typically 5:00pm–10:00pm; reserve a table if possible.
Walk past the Confederation Centre of the Arts and plan any shows for later; gallery hours vary (often 9:00/10:00–5:00), so check performance schedules in advance if you want to see live theatre.
Guided or self-guided tour of where Canadian Confederation began; interesting for history buffs. Visitor centre hours often 9:30–5:00; check for seasonal tour availability.
Short drive to Brackley Beach in PEI National Park for dunes, boardwalks and a beach walk; park access and trails are open year-round though visitor centres may have reduced hours in fall.
Visit the house, trails and interpretive centre that inspired L.M. Montgomery; popular in fall—note Parks Canada seasonal hours (often until October but confirm exact closing dates and times).
Famous white-sand beach with unique 'singing' sand; beach and trails are open, but facilities hours are seasonal—plan for limited services in late October.
Scenic coastal drive to the North Cape area to see wind dunes and interpretive displays; the outdoor areas are open year-round, visitor centre hours vary in shoulder season.
The Confederation Trail is an island-wide rail-trail ideal for cycling; many rental shops in Charlottetown or Cavendish rent bikes by the day—confirm rental/return locations and seasonal availability.
Unique dune system and boardwalks at Greenwich—excellent coastal scenery; trail is open year-round but the Greenwich visitor centre may have limited hours in October.
If a market is open this season, it's a great place for local produce and souvenirs; otherwise a cafe works fine. Market schedules are seasonal—check what's open in October.
If the Confederation Centre has an evening performance, book ahead. If not, enjoy a final seafood meal at a favourite spot—check show and restaurant availability.
Morning flight from Charlottetown to Boston Logan; arrive at least 90 minutes before departure for domestic flights—flight durations about 1.5 hours. Airline hours and schedules vary—confirm your exact flight time and terminal.
C&J runs shuttles between Logan and Portsmouth; check current schedules (frequency varies by season). Allow extra time for baggage claim and terminal transfer.
Historic downtown and waterfront are great for an afternoon stroll; Strawbery Banke Museum has seasonal hours (often 10:00–4:00) so verify if you want to go inside.
Odiorne Point offers coastal trails and tide pools; Kittery has outlet shopping if you prefer shopping to hiking—both are short drives from Portsmouth. Park and trail access are open year-round; visitor centre hours vary.
Short harbor cruises run seasonally—check availability; Strawbery Banke (open-season dependent) offers historic house tours if you prefer a museum visit.
Nubble Light at Cape Neddick (York) is a classic New England lighthouse — viewing area open year-round; sunset occurs earlier in October so plan timing accordingly.
Scenic coastal drive into southern Maine; Marginal Way in Ogunquit is an easy coastal walk with great views and photo ops. Roads and parks are open year-round, but some seasonal businesses may be closed—check ahead.