Casco Bay: Private Afternoon Charter on Heart’s Desire
Experience Portland’s stunning Casco Bay on a private 2-hour yacht cruise aboard Heart’s Desire, with iconic lighthouse views and personalized service.

Experience Portland’s stunning Casco Bay on a private 2-hour yacht cruise aboard Heart’s Desire, with iconic lighthouse views and personalized service.

Experience a relaxing 2-hour morning sail on Casco Bay with historic schooners, scenic views, and friendly crew—perfect for all ages and interests.

Discover Portland’s top sights with a small-group tour, visiting parks, neighborhoods, and landmarks in just half a day with a knowledgeable guide.

Experience the scenic beauty of Casco Bay on a 2-hour Maine windjammer cruise. Relax, bring your own food and drinks, and enjoy stunning coastal views.

Explore Portland Maine’s stunning coast on a 1.5-hour lighthouse cruise, with wildlife sightings, scenic views, and opportunities to bring your own food and drinks.

Discover Portland’s Black history through a 2-hour guided walking tour showcasing landmarks, stories, and local heroes, with expert insights and authentic experiences.

Explore Maine and New Hampshire’s coastal charm on a private tour through Kennebunkport, York, and Portsmouth, with personalized experiences and expert insights.

Discover Portland’s vibrant neighborhoods, iconic sights, and hidden gems on this 4-hour guided tour led by local experts. Perfect for urban explorers.

Experience Portland’s skyline from a tropical-themed tiki boat with drinks, music, and city views on a 2-hour happy hour cruise with Island Style Charters.

Discover the Columbia River Gorge on a half-day small-group hike. Enjoy waterfalls, scenic views, and expert guides for an authentic outdoor experience.

Explore Portland, Maine’s East End Bakery Crawl with a knowledgeable guide, sampling 6-8 treats from women-owned bakeries—perfect for a girls’ day out.

Explore stunning waterfalls and boutique wineries on this all-inclusive 6-hour guided tour from Portland, combining natural beauty with local wine tasting.

Discover Portland’s dark past on this engaging evening walking tour through Old Port, revealing true crime stories, hidden secrets, and local legends.

Discover Portland’s Alberta Arts District on this 3-hour food tour featuring tastings, street art insights, and Oregon wine, all with a small-group setting.

Explore Portland’s vibrant wine scene with this curated urban tasting tour. Enjoy 10+ wines, local bites, and neighborhood sights—all in 2.5 hours.

Discover Portland’s spooky side with this 2-hour ghost walking tour through Old Port, featuring haunted landmarks, ghost stories, and eerie legends.

Discover Portland’s top lobster rolls on this 2.5-hour walking tour featuring fresh tastings, waterfront sights, and local Maine craft beer.

Discover Portland’s craft beer scene on a guided bus tour featuring exclusive brewery visits, tastings, and a relaxed small-group experience for beer lovers.

Discover Oregon’s renowned Pinot Noir on a guided tour in Willamette Valley, paired with delicious wood-fired pizza in stunning vineyard settings.

Discover Oregon’s stunning coastline on this guided day trip from Portland, featuring iconic sights, nature walks, and coastal charm in one immersive tour.

Discover the charm of New Hampshire’s White Mountains on this small-group day tour, visiting scenic spots, historic bridges, and charming towns with expert guides.

Experience Portland’s coastline on a scenic 90-minute lighthouse cruise, with expert guides, wildlife sightings, and stunning historic views.

Discover Portland’s vibrant food scene with this small-group walking tour featuring tastings of local seafood, wine, desserts, and seasonal delights.

Discover Oregon’s stunning landscapes on a private tour from Portland to Mount Hood, Columbia River Gorge, waterfalls, orchards, and charming towns.