How to Spend a Week on Southport Island (7 Day Itinerary)
A Relaxing 7-Day Itinerary for Southport Island, Maine
Whether you’re booking a full week or just daydreaming about a quick coastal escape, Southport Island is the kind of place where a few days is enough to reset your brain and slow your pace. Whether it’s your first visit or your fifteenth, a week is the perfect amount of time to exhale, explore, and settle into the rhythm of summer.
This 7-day itinerary gives you a taste of what a laid-back week at Camelot Cottage might look like — from deck coffee and coastal trails to ice cream runs and low-key lobster dinners.
No packed agendas. No tight timelines. Just suggestions for how to enjoy the island, one relaxed day at a time.
Day 1 (Saturday): Arrive + Settle In
Afternoon:
Arrive, unload, breathe.
Swing by the Southport General Store to grab a pizza, snacks, and the essentials you forgot.
Do a slow walk-through of the cottage and pick your favorite chair.
Evening:
Dinner on the porch, even if it’s just cheese and crackers.
Sunset at the Southport Town Dock.
Cook a simple dinner at the cottage or pick up takeout from Robinson’s Wharf (but be aware that peak dinner hours are busy).
Pour a drink, sit on the deck (or screened porch for golden light), and watch the light fade through the trees.
Sleep like a log.
Day 2 (Sunday): Get Your Bearings
Morning:
Coffee on the deck (yes, this will be a recurring theme).
Drive to Oak Point Farm for an easy trail walk with views over Hodgdon Cove.
Afternoon:
Head to Hendricks Head Beach with a towel and a picnic (don’t forget sunscreen and a hat!).
Evening:
Make dinner at the cottage or go out for a lobster roll at Cozy’s Eatery (right by the yacht club).
End the day with a board game or puzzle from the cottage shelf.
Southport’s General Store & Gift Shop
Day 3 (Monday): Explore the Island Perimeter
Morning:
Breakfast on the porch, then a slow drive around the island loop.
Afternoon:
Visit Coastal Maine Botanical Gardens in Boothbay (you’ll be glad you did).
Ice cream stop on the way back. (It’s vacation.)
Stop at Robinson’s Wharf fish market if you’re feeling ‘fresh caught’ for dinner.
Evening:
Pour a glass of wine and toss the fish you got earlier in the day onto the stove.
Firefly-gazing from the porch if they’re out.
Day 4 (Tuesday): Rest, Read, Repeat
Morning:
Stay in your pajamas. Make breakfast slow: eggs, toast, blueberry jam from the general store.
Pick a book from the shelf or one you brought, and read until you forget what time it is.
Afternoon:
Walk a nearby trail again — or don’t. Sit on the deck and let the breeze do its thing.
Sketch, knit, journal, or nap. Whatever feels quiet and grounding.
Evening:
Dinner at home — maybe leftovers, maybe something new.
End the day with a long sit outside. Let the fireflies (or fog) be the main event.
Day 5 (Wednesday): Go Off-Island (Just a Little)
Morning:
Quick breakfast, then head into Boothbay Harbor.
Browse shops, visit a gallery, maybe catch a harbor cruise if that’s your thing (we recommend Balmy Days Cruises).
Afternoon:
Grab lunch at Boothbay Lobster Wharf or Shannon’s Unshelled.
Stock up on groceries at Hannaford on the way back.
Evening:
Easy dinner at the cottage, maybe something you picked up in town.
A movie night… but make it a book, a blanket, and a window cracked open.
Day 6 (Thursday): Unplug Day
Morning:
Coffee, deck, book, repeat.
Leave your phone on airplane mode. We dare you.
Afternoon:
Revisit your favorite spot — maybe the beach, maybe just the porch Adirondacks.
Nap optional but encouraged.
Evening:
Cook a full meal, just because.
Share stories, play cards, linger longer.
Day 7 (Friday): Local Life + Little Joys
Morning:
Pop down to Cape Newagen Alpaca Farm to get your furry animal fix in (if you want to get your steps in, it’s only 0.9 miles from the cottage).
Afternoon:
Attend a local event if one’s happening (Yacht Club craft fair? Clambake?).
Pick blueberries if you spot any on the roadside (in season in August).
Evening:
One last “dinner out” if you’re feeling it — or a porch picnic spread (you’ll rarely find us eating inside).
Sit out late and soak in the summer air.
See that red house on the left? It belonged to Margaret Hamilton (who played the Wicked Witch of the West in The Wizard of Oz) for 25 years before she died in 1985. See it for yourself from Southport Island’s town dock.
Day 8 (Saturday): Pack Up, Slowly
Morning:
One more slow breakfast, one more round of porch coffee.
Walk around the neighborhood one more time. Let the fog or sun hit your face.
Pack up, load the car. Maybe even plan your return before you’ve left the driveway?
A week on Southport isn’t about checking off activities. It’s about letting the island do its thing while you remember how to slow down. Whether you do everything or almost nothing, we hope this guide helps you settle into the joy of just being here.
Looking for more trip tips? Explore our blog or check availability here to plan your own summer stay at Camelot Cottage.