Boston to Kennebunkport Day Trip & Ogunquit Walk with Pickup

Summary

York lighthouses, Ogunquit cliff walks & Kennebunkport charm

You’ll ride from Boston up through Maine’s coast—see Cape Neddick Nubble Lighthouse up close, walk Ogunquit’s Marginal Way above crashing waves, then explore Kennebunkport with plenty of time for lunch or shopping. Expect salty breezes, local stories from your guide, and small moments that stick with you long after heading home.

What’s the experience like?

I’ll be honest—the day started with me nearly missing the pickup spot in Boston because I got distracted by a bakery window (the smell of cinnamon rolls at 7am is no joke). Our guide, Mark, just grinned and waved me over like he’d seen it all before. The drive north was easy—just enough chatter from Mark about Maine’s coastline to keep us awake, but not so much that you couldn’t stare out the window. The trees were still damp from last night’s rain, and somewhere around Portsmouth I realized my shoes were squeaking every time I shifted. No one seemed to mind.

First real stop: York’s Cape Neddick Nubble Lighthouse. It’s kind of wild how many people have photographed it—I tried for the classic shot but ended up more interested in the way seaweed clings to the rocks below. There was this briny breeze coming off the water that made my eyes sting a little. Mark told us a story about a keeper who once rowed supplies across in winter ice; I half-listened while watching gulls fight over something shiny. We didn’t linger too long—just enough for a few photos and some awkward attempts at group selfies.

Ogunquit came next. Walking Marginal Way felt like being inside one of those old postcards—jagged rocks, Atlantic waves smashing below, couples holding hands (and one guy jogging backwards for his fitness tracker). The path’s only about a mile or so but I kept stopping to watch boats or just breathe that salty air. Someone nearby was eating fried clams and honestly, that’s all I could smell for ten minutes. My legs were sore by Perkins Cove but in a good way—you know?

Kennebunkport was busier than I expected—shops with lobster rolls everywhere and locals chatting on benches like they had nowhere else to be. I skipped the trolley tour (some folks loved it though) and wandered instead, eavesdropping on two older women debating who made better blueberry pie. Had lunch at a café where the waitress called everyone “hon” without blinking. There was this moment sitting outside with my sandwich where everything felt slow and easy—like maybe you could just stay here for the rest of summer.

Step-by-step itinerary

Day 1 — Boston to Kennebunkport day trip

• Pickup at Downtown Boston hotel
• Drive to York, Maine
• View Cape Neddick Nubble Lighthouse
• Walk 1.25 mile Marginal Way path
• Wander Perkins Cove, optional lobster boat tour
• Explore Kennebunkport town sights
• Optional narrated trolley tour of Kennebunkport

Top questions

How long is the Boston to Kennebunkport day trip?

The guided day trip lasts approximately 11 hours including travel time.

Is hotel pickup included for this tour?

Pickup is available from five central locations in downtown Boston.

Do I need to book the Kennebunkport trolley tour in advance?

The trolley tour is optional and can be purchased separately if desired.

How much free time do we get in Kennebunkport?

You’ll have around 2.5 hours of free time for lunch or exploring on your own.

Is food included on this day trip?

Bottled water and snacks are provided; meals are not included but there are many options during free time.

Are infants or small children allowed on this tour?

Yes, infants and small children can join using a pram or stroller.

What’s special about Marginal Way in Ogunquit?

Marginal Way is a scenic 1¼ mile coastal path overlooking the Atlantic Ocean’s rocky shoreline.

Can service animals join this tour?

Yes, service animals are allowed on this day trip.

What’s included

Your day includes pickup from central Boston locations, air-conditioned transport with snacks and bottled water along the way, stops at Cape Neddick Nubble Lighthouse and Ogunquit's Marginal Way walk, plus about 2.5 hours of free time in Kennebunkport for lunch or shopping—with an optional narrated trolley tour if you want even more local color before heading back.