Top Portland Wine, Beer & Spirits

Food lovers can explore Portland's historic Old Port independently, but to uncover the best places serving traditional local fare, you really need a guide to lead the way. Taste the best that Portland has to offer on this guided foodie walking tour, complete with stops at up to seven different eateries—and enough tastings to replace a meal. Along the way, your guide offers some stories about Portland's food scene, so you can get familiar with the local culinary stalwarts.

Board your boat, the Elizabeth Grace, near the Portland ferry terminal and cruise around Portland Harbor at sunset, when Casco Bay and the coast of southern Maine are the most romantic. See lighthouses, historic forts, and stray groups of swimming seals and enjoy local craft beer from the boat. As the sun sets, turn toward Portland to see the town light up before returning to harbor.

Embark on a boat to a private island historic fort that’s only accessible with this tour. Leave from Portland and for a boat ride on Casco Bay, landing at the privately owned Fort Scammel on House Island. There, explore the architecture and preserved ruins of the stone fort—the only fort in the Portland harbor to see battle. Discover underground passages and learn the history of this previously inaccessible site.

What sets this experience apart is that it is designed around your group and brought directly to you. Choose a private sensory wine tasting or begin with an all-levels yoga practice before gathering around the table. I come to your Airbnb, vacation rental, private home, waterfront deck, or another Portland-area location. The tasting is relaxed, engaging, and approachable. I guide your group through the aromas, flavors, stories, and sense of place behind each bottle. No wine knowledge is needed. With WSET certification, I bring expertise without making the experience feel formal or intimidating. For groups adding yoga, the movement portion is tailored to your energy, experience, and occasion. First-time participants and regular practitioners are equally welcome. Ideal for bachelorette weekends, birthdays, girls’ trips, anniversaries, family gatherings, and corporate retreats, this private experience helps your group slow down, connect, and enjoy something memorable together.

All of our tours are done in a comfortable vehicle with a local driver guide and can be done at your pace. Tours can always be customized to your interests. This particular tour will show you all the main sites of Portland proper and then all of the South Portland lighthouses, including admission to the Portland Headlight at Fort Williams Park. After Portland, you will head on down the highway to Kennebunkport to visit this popular coastal village that former President George W. Bush and family called their summer home. We have a standard routing but being a private tour, we can tailor your experience to you interests.