Travel Itinerary:
Boothbay Harbor

At a glance

Welcome to Maine — “The Way Life Should Be,” or “Vacationland,” as the license plates say. Once you arrive in Boothbay Harbor, check into your cozy bed & breakfast and soak in the view from your room. Head into town — walking distance — and grab a late lunch or early dinner at one of the various restaurants. For the rest of your stay, explore downtown Boothbay, visit the Botanical Gardens, set sail on a whale watch, or just breathe in the ocean air while you window shop.

Logistics

We live a mere two hours from Boothbay Harbor, so we drove. If you’re flying, the Portland airport (PWM) is only 37 miles away — rent a car for the 1 hour 15 minute drive. Portland itself is another fun city to explore if you have extra time, especially if you enjoy craft beer and great food.

Where to stay

Book a room at the lovely bed and breakfast, Bayside Inn. The innkeepers, Kathryn and Peter, have been running it since 2001 — the Inn was Kathryn’s childhood home and has been in her family since the 1950s. We highly recommend staying here. It’s welcoming, cozy, right on the water, with beautiful views from the rooms and walking distance to everything in Boothbay. We stayed in the Johns Bay room, which was a perfect set-up with kids.

Day 2 — Explore downtown

Wake up early and enjoy a pot of coffee brewed by the innkeepers — or sleep in and avoid the caffeine overload (we don’t normally get the option with two young children). Mama D’s is across the street and gets very busy at breakfast; we grabbed their scones and muffins as a quick bite instead. Note: cash only.

Walk towards the water and stop at the Red Cup Coffee House for breakfast to go. We ordered two panini breakfast sandwiches, coffees, and a blueberry muffin for Selima, then ate at the picnic tables across the street along the water in front of the town dock. The sandwiches, the weather and the location made an incredible way to start the day.

Next to those picnic tables is the entrance for Cap’n Fish’s Cruises, which came highly recommended by a lot of people. If the girls had been older, or if it had been warmer, we absolutely would have done the whale watch. It was mid-October and very chilly and windy, so we explored downtown instead.

In the late afternoon, eat at Boathouse Bistro for tapas or PORTS Pizzeria for Italian. We took the outside deck at Boathouse Bistro with views over the bay, and PORTS pizza-to-go for our own view back at the B&B. Stop at Coastal Maine Popcorn Co. on the way — friendly people, and flavours that are both unique (Frog Farts and Unicorn Toots) and genuinely good.

Questions, answered

How long should you stay?

A long weekend — three to four nights. That gives you a full day downtown, a day at the Botanical Gardens, and an arrival evening that isn’t rushed.

What’s the closest airport?

Portland International Jetport (PWM), 37 miles and about 1 hour 15 minutes away. Portland is worth a night of its own if you have time.

Is it good with young kids?

Yes. Downtown is walkable, the harbour itself is the entertainment, and the restaurants are genuinely kid-friendly. We did it with a toddler and a baby and never touched the car once we arrived.