Emma & Kevin

Emma & Kevin

September 27, 2025 • Portland, ME
139 Days To Go!
Emma & Kevin

Emma & Kevin

September 27, 2025 • Portland, ME
139 Days To Go!

Where to Stay

There are many hotels to stay at in The Old Port. Prices vary widely, but early autumn is busy tourist season for Southern Maine, which will drive up the prices for many of these hotels. A few (ranging from most beautiful to more cost efficient) are listed below for your convenience, but there are many more options that cost much less.


- The Portland Harbor Hotel

- Hyatt Place Portland-Old Port

- Portland Regency Hotel and Spa

- The Press Hotel

- Hampton Inn Portland Downtown - Waterfront

- Holiday Inn Express & Suites South Portland (15min Uber ride)

-DoubleTree by Hilton Hotel Portland

- Airbnb

- **If looking for a more cost-effective option, there are plenty of places to stay in the greater Portland area outside of The Old Port. Most places in the surrounding area will still be Uber accessible. Surrounding towns could include South Portland, Scarborough, Westbrook, Falmouth and more.

Where to Eat

Breakfast (there are also so many excellent bakeries – a quick Google will give you a slew of them)

- The Holy Donut: Donuts made from Maine potatoes. A real fan favorite. These sell out fast, so we’d suggest going early in the morning.

- The Friendly Toast

- Forage

- Blake Orchard

- The Front Room

- Bread & Friends

- Becky’s Diner


Lunch

- Duckfat

- Flatbread Company

- Highroller Lobster Co

- Yosaku

- Pai Men Miyake

- Red’s Eats: Honestly, there are so many lobster rolls in Portland that you needn’t leave. If you’re craving adventure (and the #1 lobster roll in all of NE), however, this is what we would suggest. The drive is just under an hour and the line can get pretty long, but it’s worth it. Personally, we try to get there as close to its opening hour as we can. https://www.redseatsmaine.com/


Dinner

- Via Vecchia

- Eventide Oyster Co

- Scales

- Street & Company

- Luke’s Lobster Portland Pier

Activities Nearby

The Old Port: If you aren’t staying in the Old Port, I strongly suggest an afternoon/evening walking around and exploring the shops, restaurants, and renowned breweries.


Scarborough/Pine Point/Old Orchard Beach:

- Rent kayaks and paddle through one of the local marshes at the Scarborough Marsh Audubon Center.

- Grab some of OOB’s popular Pier Fries and Pizza, then walk from the pier down to Pine Point in the sand.

- Pine Point area is smaller and has a good handful of delicious seafood shacks. Grab some of Maine’s most famous soft-serve at The Dairy Corner!


Freeport: Quaint downtown Freeport is home to shops, outlets, restaurants, and breweries. Most of these can be found along the main drag, although some of our favorites require a short drive. You can’t go wrong with any choice; below are our go-to places every time we visit.

- L. L. Bean Flagship Store

- The British Goods Store

- Wolfe’s Neck State Park

- Tuscan Bistro

- Maine Beer Company

- Harraseeket Lunch and Lobster


Local Lighthouses:

- Portland Head Light

- Cape Elizabeth Lighthouse

- Portland Breakwater Light


Kennebunk/Kennebunkport/Ogunquit: Beautiful enough for President Bush to own a home here, Kennebunkport is a small, resort, ocean town that is a popular destination in the summer.

Make it a Maine Trip!

Camden/Rockport: Enjoy beautiful midcoast Maine and the gorgeous drive along Route 1!


Bar Harbor:

- So many beautiful places to stay; there is no wrong choice. Some of our personal favs include the Bar Harbor Inn, Harborside Hotel, Spa & Marina, and Ivy Manor Inn.

- Acadia National Park

- Schedule a boat ride on a Schooner!

- You can really bee-bop all around the little town. Quaint restaurants, shops, and art line the charming streets of this ocean-side gem.


Rangeley: A hidden and unlikely gem. An extremely rural but beautiful place in the mountains relatively close to the Canadian border. If you drive up here, don’t forget to stop at the Height of the Land. Although not easy to get to, this is one of our favorite places in the entire world!