3-night Maine Itinerary

Check out this 3-night trip itinerary to Portland, Maine (and iconic surrounding cities!).

Highly recommend renting a car from the Portland airport. 

Maine's MUST Experiences!

• Lobster rolls
• Oysters
• Whoopie pies
• Blueberry anything in the summertime

Friday, Portland, Maine

• Arrive in Portland
• Pickup rental car
• Drive to Hyatt Downtown Portland, Maine. Valet park.

Saturday, Northern Road trip to Camden

• Coffee at Tandem Coffee and Bakery (Anderson Street) - Best cinnamon rolls + coffee, get there early, there’ll be a line and they sell out!
• Drive to Freeport and visit the L.L. Bean Flagship store.
  • Monogram your boat totes and pick them up on the way back...
    
• Optional
  • Grab a beer along the water at Sea Dogs Brewing in Topsham
• Lunch in Camden at Peter Ott's on the Water
• Explore downtown Camden
• Drive back to Portland
  • Stop in Freeport to pickup your monogrammed totes!
• Park car at Hyatt Downtown Valet
• Walk to Dinner in Downtown Portland at Sur Lie (rez required)
• Optional
  • Catch a show at the State Theater downtown
  • Ice Cream at Beals Ice Cream (classic Maine ice cream) or Gelato Fiasco (artisan gelato)

Sunday, Portland Sailing Adventure 

• Drive to morning breakfast at Scratch Bakery (line moves fast!)
• Drive to Aspacia Marina for the Portland Maine Sailboat Adventure (10-12pm)
  • Tell Alex and Thor we sent you! Bring a light jacket and water bottle. Light snacks provided on the boat.
• Drive to The Lobster Shack at Two Lights (authentic Lobster roll by the water, easy parking, bring a raincoat in case it rains, limited inside seating, lots of outdoor picnic tables)
• Optional: Cliff walk hike starting at Blackpoint Inn
• Drive to Portland Head Light at Fort Williams Park (picturesque!) in Cape Elizabeth
• Optional: Then visit C Salt Market, The Cookie Jar, Kettle Cove ice cream
  
• Drive back to Portland
• Dinner downtown by the water at Scales (rez required) 
• Optional Portland activities:
  • Stroll around Old Port and souvenir shop. Cute shops on Exchange Street and Fore Street, Commercial Street
  • Breakfast at Bread & Friends Maine (elevated bakery & café-style brunch), Bayside Cafe, Becky’s Dinner, Holy Donut (famous potato donuts)
  • Lunch/snack at Bite Into Maine (food truck-style lobster rolls), The High Roller Lobster Company (trendy, creative lobster dishes, fun indoor vibe), Portland Lobster Company (traditional, casual lobster rolls & seafood), Duck Fat (highly recommended)
  • Dinner at Scales, Fore Street, or Street & Co.

  • Blyth and Burrows speakeasy for cocktails

Monday, Kennebunkport and travel home

• Checkout of hotel
• Hit up the other Tandem Coffee location (Congress Street) on the way out of town (the Kimchi Cheddar Scone is amazing)
• Drive to Kennebunkport (The Blowing Rock of Maine!)
• Walk around downtown for window shopping
• Drive by Walker's Point (See the Bush's house!)
• Drive back to Portland airport (50 minutes)
• Fill up the rental car
• Fly home

Ayuh!!!!