I grew up just outside of Portland, so I’ve spent more weekends in Portland than I could ever count. I’ve watched it grow into one of New England’s best food destinations, I have my go-to coffee shops and favorite restaurants, and I never visit without walking home with more than my fair share of Holy Donuts.
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Because of that, I honestly thought I’d experienced just about everything Portland had to offer. But on my most recent trip home, I found something that completely changed the way I see the city — a private boat charter with Legacy Charters.
As someone who’s spent years exploring Portland, I can’t believe it took me this long to experience it the right way — from the water, in a luxury private boat, of course. Now, I genuinely think it’s one of the best things you can do in Portland, Maine.
Why Seeing Portland from the Water Is So Special
As beautiful as Portland is, I think you’re only seeing half of it from land. Within minutes of leaving the harbor, everything slows down. The city skyline fades into the background, the air gets noticeably cooler, and suddenly you’re cruising through Casco Bay surrounded by rocky islands, working lobster boats, historic forts, and some of Maine’s most iconic lighthouses.
It’s peaceful in a way that’s hard to explain until you’re actually out there.
My favorite part wasn’t even one specific stop—it was simply being on the water. Watching lobster boats pull traps, waving to passing sailboats, and taking in the coastline from a completely different perspective reminded me why I love coming back to Maine every summer.
If you’ve only explored Portland by walking the Old Port, hopping between restaurants and breweries, or catching the ferry to Peaks Island, I genuinely think this is the experience you’re missing.
Why I Loved Legacy Charters
One of the things that stood out most to me was how personal the entire experience felt. It’s a small, family-owned, local business, and the captains are genuinely interested in their guests and how to make sure they have the best experience.
Every charter is private, so it’s just your group and your captain. The experience is completely customized, whether you’re hoping to explore the islands, chase the sunset, celebrate something special, or simply spend a few hours soaking up the Maine coast. It also doesn’t hurt that the boat is extremely spacious and luxurious, for the same price as some other options I explored that were… not.
There’s no rushing from one landmark to the next or listening to a scripted tour. Instead, you get to slow down, enjoy the scenery, and appreciate everything that makes Casco Bay so special. It felt less like checking another activity off my itinerary and more like spending an afternoon with friends on the water—which, if you ask me, is exactly what vacation should feel like, especially in Vacationland.
My Perfect Summer Day in Portland
If I were planning the perfect summer day in Portland, this is exactly what I’d recommend:
- Start the morning with breakfast and an iced latte from Forage Market (still my favorite breakfast spot in the city).
- Wander the Old Port, browsing the local shops along Exchange and Commercial Streets.
- Spend the afternoon cruising Casco Bay with Legacy Charters.
- Freshen up before dinner at Scales, Street & Co., or Via Vecchia.
- End the night with cocktails at Blyth & Burrows or live music on the waterfront at The Porthole.
Honestly, I don’t think it gets much better than that.
Is a Private Boat Charter Worth It?
Absolutely. If you’re visiting Portland for the first time, I think it’s one of the best ways to experience the city beyond the restaurants and the Old Port. And if you’ve been to Portland before, it’s such a fun way to see a side of the city you probably haven’t experienced yet.
I’ll always recommend grabbing a lobster roll, walking the Eastern Prom, or watching the sunset at Bug Light Park. But after this trip, if someone asked me for the one experience I’d splurge on, this would be my answer every single time.
Final Thoughts
One of the reasons I keep coming back to Portland is because every trip feels a little different. There’s always a new restaurant to try, a new neighborhood to wander, or a new corner of the Maine coast to explore. This time, it was Casco Bay.
I’ve spent years recommending my favorite restaurants, coffee shops, beaches, and neighborhoods around Portland. This is the first time I’ve felt like I needed to add an entirely new experience to that list.
If you’re planning a trip to Portland, make time to get out on Casco Bay. Whether it’s your first visit or your fifteenth, seeing the city from the water gives you a whole new appreciation for this little corner of Maine.
For someone who grew up here, that’s saying a lot. Here’s hoping you enjoy your next trip to Vacationland. ☼
