Depart Boston at 4 p.m., arrive Portland by 5:45 p.m. Check into your Airbnb in the Munjoy Hill neighborhood (see WHERE TO STAY below). Walk 10 minutes downhill to dinner at The Bard Coffee & Co. for their wood-fired focaccia sandwiches ($8–12)—a local institution that doubles as a wellness hub with house-made kombucha on tap. Grab a street pastry from Holy Donut (potato donuts, $3–5) as an evening snack while walking the Eastern Promenade waterfront trail at sunset—free, meditative, stunning views.

Start at Fore Street Farmers Market (8 a.m.–1 p.m., open-air in Congress Square Park) for fresh berries, coffee from local roasters, and energy. Grab breakfast tacos from food vendors ($6–8). Fuel up for a 6-mile coastal drive north to Cape Elizabeth Lighthouse Park (free)—hike the rocky coastal trail for 90 minutes; wellness through nature immersion.

Drive back to downtown (15 mins). Spend 2 hours at Portland Museum of Art ($15 admission with student discount, or free community hours 4–8 p.m. on Fridays—but you're here Saturday, so budget the entry). Alternatively, walk to Willard Beach (20-minute walk from downtown, free, pristine) for saltwater swimming and beach meditation.

Dinner at Eventide Oyster Co.'s walk-up counter window ($12–16 for fried fish sandwiches and raw oysters)—high-energy, local, zero pretense. Post-dinner: catch live music at Portland City Hall's outdoor courtyard (free concerts, weather permitting) or walk the Old Port'snarrow cobblestone streets until 11 p.m., popping into vintage shops and galleries (all free to browse).

Sunrise yoga at Yoga Loft Studio (drop-in class ~$12) or free: walk to Back Cove Park for a 3.3-mile loop walk meditation at 7 a.m.—locals only, peaceful. Brunch at Tangled Up Cafe ($10–12 for acai bowls and avocado toast) or grab lobster rolls from Red's Eats takeout window ($14–16, worth it once).

Leave by 1 p.m. to arrive Boston by 3 p.m. Scenic route back: take Route 1 north through Yarmouth and Freeport (20 mins out of the way) to browse L.L. Bean's outlet and grab coffee at a roadside café. Or skip it and take I-295 south directly—90 minutes flat. WHERE TO STAY 1. Munjoy Hill Airbnb (shared room, $60–75/night)—residential hilltop neighborhood with local bakeries, quieter than Old Port, 10-min walk to downtown and Eastern Promenade. Look for listings near Congress Street. 2. Bayside/Parkside shared apartment ($50–70/night)—quieter pocket with direct access to Back Cove walking trail, 15-minute walk to downtown, populated by locals not tourists. 3. East End house share ($55–80/night)—bohemian neighborhood with the most street food vendors, vintage shops, and yoga studios; closest to the farmers market. GETTING THERE Drive from Boston via I-95 North to I-295 North → Portland exit. 100 minutes, straightforward highway. Parking: street parking is free on residential Munjoy Hill (where your Airbnb will be); downtown has metered lots ($1.50/hour). Keep coins handy or use the ParkPortland app. Gas cost ~$12–15 round trip. INSIDER TIPS - Timing: Farmers Market opens 8 a.m. Saturday—arrive by 8:15 to catch the best vendors and avoid crowds. Cape Elizabeth Lighthouse is most stunning 1–2 hours before sunset. - Local secret: Skip the crowded Old Port tourist trap; instead, eat breakfast at Tangled Up Cafe on Free Street (where locals actually go), and walk through the Congress Street Arts District on Saturday evening—galleries, street art, and zero tour groups. - Book in advance: Check your Airbnb host's cancellation policy immediately, as May is peak season. Fore Street Farmers Market doesn't require booking, but arrive early. Yoga Loft's drop-in classes fill up Saturday mornings—text ahead to confirm availability.