A long weekend in Portland, ME

This quaint New England seaside city has converted numerous pre-war maritime warehouses to art galleries, restaurants and bars. This among many other New England state capitals brings a thriving restaurant scene to walkable historic cities that are easily manageable on a weekend. This is a great long weekend from Boston, MA, and is only a two hour drive. 

For those interested in literature I would recommend reading Olive Kitteridge by Elizabeth Strout, Empire Falls by Richard Russo, or Maine by Courtney Sullivan, all of which are set in Maine.

Friday:

Arrive and get settled in your hotel. I stayed at Courtyard Portland Downtown/Waterfront (321 Commercial St, Portland, ME 04101) which was an easy location to walk to everything downtown.

Get some grub at Fore Street (288 Fore St, Portland, ME 04101) then enjoy a rooftop drink at Top of the East (157 High St, Portland, ME 04101) on the top of the Westin Hotel to get oriented on with the city and if possible watch the sunset.

Saturday

Start your morning off with breakfast at LB Kitchen (249 Congress St), you order at the counter and get the food served to your table. 

Portland is great for a seaside bike ride. We rented bikes from Portland Encyclopedia ( 6 Commercial St). On your ride don’t miss both Bug Light and Portland Head Lighthouse (12 Captain Sprout Cir, Cape Elizabeth, ME 04107) Take a break and grab a lobster roll from the Bite of Maine food truck, right outside the Portland Head Lighthouse. They will NOT disappoint!

After biking, relaxing over an IPA from Shipyard brewing company.  We spent some time at the brewery. After getting your hops on, window shop down the Old Port section of the city. This is quintessentially New England with the cobblestone street and colonial brick buildings. I did not miss out on tasting Portland’s favorite donut shop, Holy Donut (7 Exchange St), which is a great afternoon snack.

Get dinner at Eventide Oyster Company (86 Middle St, Portland, ME 04101). This sleek and busy restaurant is great for any seafood lover. We ordered some oysters for the table and then continued to sample most of the menu!

Sunday

Get breakfast at Tandem Coffee and bakery or the standard baking company before heading for a last walk downtown and head home. 

If you are interested in other ideas for weekend getaways from Boston, check out my article 5 Seaside Getaways from Boston.

5 Seaside Getaways from San Francisco, CA

  1. Sausalito, CA

This artists’ village is just off the Golden Gate Bridge in upscale Marin County. Most of the small city offers a spectacular view of the Golden Gate Bridge, Richardson Bay, and many houseboats in the bay. It’s a popular day-trip destination, with sheer cliffs and a rugged shoreline dotted with trails and villages. Personally, Sausalito reminds me of the Pacific version of the Amalfi Coast! You can use this as a jumping-off point for many of the nearby hikes such as Mount Tamalpais (“Mt. Tam”), the leisurely Tennessee Valley Trail, and Alamere Falls. Spend some time checking out the many galleries, stores and restaurants. Any trip to Sausalito, I love perusing handmade dinnerware at Heath Ceramics (400 Gate 5 Rd, Sausalito, CA 94965)

  1. Carmel, CA

Carmel-by-the-Sea is a small beach city on the Monterey Peninsula, two hours south of San Francisco. Historically a Bohemian artists’ village, Carmel-by-the-Sea has been home to many famous people such as Doris Day, John Madden, Ansel Adams, and John Steinbeck. Clint Eastwood was not only a resident, he was elected Mayor of Carmel. This picturesque city of less than 4,000 residents features unique homes including many cottages with minute detailing valued in the millions because of the location. One house which we viewed was decorated with heart-shaped cut-outs decorating the picket fence, the shingles, and gracefully furbishing the interior decorative trim. The lush gardens roll into each other in ever flowing bloom. This is worth a day-trip for a coastal walk and a stroll around the interesting shops, restaurants, and homes.  For a more in depth itinerary check out A Day in… Carmel, Ca!

  1. Santa Cruz Mountains and Capitola, CA

The Santa Cruz Mountains are dappled with houses among wooded forest and many trails to hike. Skip the honky tonk in Santa Cruz proper, and instead head to Capitola Village. Capitola Village developed as a seaside resort when the Soquel Mountains were a thriving location of the lumber industry.  The small downtown area is worth a stroll to look at the Soquel Canal, and iconic Capitola Venetian with it’s brightly colored guest suites. There is a beautiful and brief (10 minute) pedestrian walk along the Soquel Creek. One hour south of San Francisco, the Santa Cruz Mountains are great to slow down and enjoy the serene nature that California has to offer. For a more in depth itinerary check out A Day… in the Santa Cruz Mountains & Soquel Cove!

  1. Half Moon Bay
Part of the walk Coastal Walk near Moss Beach, CA

Half Moon Bay is a charming seaside town approximately 45 minutes south of San Francisco. I enjoy the beautiful Coastal Trail, which is about 11 miles of leisurely coast side walking roads with beautiful waterfront views. The Ritz Carlton in Half Moon Bay offers free parking for the public who would like to visit the beach. Walk all the way north to Cypress Ave on Moss Beach and back. I enjoy grabbing a beer from Half Moon Bay Brewing company in Princeton Harbor. When the pandemic ends, watch the sunset with a glass of wine and dinner over the fire pit at Moss Beach Distillery, situated on the cliffs overlooking the Pacific Ocean. Beware: Moss Beach Distillery is supposed to be haunted by the ghost of the “Blue Lady”. 

Please note: On the coastal trail, Princeton Harbor does not have a trail and you will have to walk on the streets.

  1. Tomales Bay
Outdoor seating at Hog Island Oyster in Marshall, CA

Road trip along east coast of Tomales Bay. From San Francisco our first stop on Route 1 was Point Reyes Station, the small town which developed around a (now) bygone railroad station. The whole town reminds me of the “Wild West”, with mostly country roads surrounding it. The town prides itself on local produce, agriculture, and organic food. We bought lunch at Cowgirl Creamery in the picturesque Tomales Bay Foods, which has been renovated from an old hay barn. The tiny town has Bovine Bakery, which is worth a delicious pastry! The area has a Farmers Market on Saturday Mornings. Second stop on our coastal road trip is Hog Island Oyster (Marshall, Ca), to relax and shuck your own oysters. It is surprisingly a lot harder than I thought! We brought our CowGirl Creamery picnic here. We spent quite a bit of time relaxing and enjoying the views. Last stop on our road trip was: Nick’s Cove, with renovated historic seaside cottages and restaurant. We ended our road trip here for a glass of wine and a little snack. The beautiful Point Reyes National Seashore is a great day getaway that is often overlooked. The natural landscape also provides many options for hikers, bikers and beach side day trippers. Next time I make it up there, I am going to try to bike!

Cheers to your summer getaways!