Things To Do
Casco Bay Islands and Ferries
Each island of Casco Bay off the coast of Portland, Maine are full of classic New England charm with history, character, and style. Casco Bay Lines offer year-round ferrys or private charter/sea taxi. Once across the water, enjoy biking and/or golf carting across the islands.
Acadia National Park
~2hr drive north of Portland, Acadia is one of the flagship national parks on the east coast with 47,000-acres covering woodland, granite peaks & rocky shores, offering camping, hiking & more. Plenty of accessible trails, lookouts, and activities for all ages. It is highly recommend you make your Acadia day plans, reservations, and parking routes well in advance before you arrive at Mt. Desert Island due to limited cell service and availability in the beginning of the season.
Maine Oyster Trail
Interested in partaking in oysters while in Maine? This interactive customizable trip planner helps you discover and plan the best oyster experiences Maine has to offer. Filter by regions, experiences (ie farm tours, buy oysters, raw bars, boat/kayak tours, ect), select your locations, and build a custom Oyster Trail Itinerary & Map. Plus, lots of information and history about oysters in Maine!
Rocky Bottom Fisheries
Get out on the water and learn more about the environmental and sustainability efforts surrounding your favorite crustaceans on a lobster boat tour. We recommend booking with Rocky Bottom Fisheries (family-owned and operated), but Lucky Catch Cruises also operates out of Portland.
Puffin and Whale Watching Cruises
Bring binoculars to watch the puffins and whale watch only six miles off the Portland coast! If you're interested, please book early. Peak puffin season is June, but you should get some cute critters no matter which 2.5-4 hour cruise you select from multiple competing companies.
Boat Rentals
There's many places to rent boats for pleasure, fishing and island hopping! This is one recommendation that should be fun and available before, during and after our weekend together. Another is Casco Bay Boat Rentals (North Portland).
Kennebunkport-area Lighthouses
Maine is famous for its lighthouses, and Kennebunkport and Cape Porpoise are no exception. From the Kennebunks, you can tour more Maine lighthouses by driving the scenic coastline. The most iconic lighthouses are Portland Headlight (oldest in Maine, 1791) and Nubble Lighthouse in York, Maine.
Riverside Golf Course
If you're interested in golfing during your stay, we recommend Riverside Golf Course. It has operated since 1932 and boasts a classic layout, rolling hills and tree-line fairways. Bordered by the beautiful Presumpscot River, there are 18-hole and 9-hole courses along with a 3-hole practice course.
Portland Hiking and Nature Walks
Embrace the natural beauty surrounding Portland with an abundance of hiking and nature walk opportunities. From coastal paths with stunning ocean vistas to serene woodland trails, there's a route for every preference. Explore scenic outlooks within the city limits or venture just a short drive to discover hidden gems and breathtaking landscapes.
Vintage & Antique Shopping
Downtown and the Old Port are treasure troves for vintage and antique enthusiasts. Explore a delightful array of shops brimming with one-of-a-kind finds, from quirky collectibles to timeless furniture.
Art Galleries
Explore Portland's vibrant Arts District, a hub of creativity featuring numerous galleries showcasing diverse works. Don't miss the renowned Portland Museum of Art, home to an impressive collection spanning American, European, and contemporary art, including iconic pieces with Maine connections. It's a fantastic opportunity to immerse yourselves in the city's rich cultural scene.
The Portland Encyclepedia
The Portland Encyclepedia is a local bike shop located on the waterfront in Old Port. Gorham Bike & Ski is another local bike shop located on top of the Hill on the Portland Peninsula for those looking for a bike rental in the West End neighborhood.
Maine Surfers Union
Not your average coffee shop, as it's also a full surf shop for all your surf craft and ocean enthusiastic apparel.
Rosemont Market & Bakery
Situated on a quaint corner in Portland’s West End neighborhood, this sunlit store is a local favorite for morning coffee, lunch, and evening cooking provisions. Inspired by a European-style grocer, this locally sourced markets has plenty of fun delights for all. Browse and pick up a fun cooking/baking treasure to take home, as we'll be doing this too!