1. Where to Stay
Climb under crisp Frette sheets at the Captain Fairfield Inn (from $225; from $185 after November 1), whose young owners have created a rarity in these parts: a contemporary, luxe bed-and-breakfast with flat-screen TVs and a 24-hour guest pantry. Take the five-minute walk to Dock Square (the center of Kennebunkport) or the ten-minute stroll to the ocean, or just laze away on the private porch of the Library Room.
Choose from either the couple’s suites or the family-ready cottages at the Maine Stay Inn (from $229; from $129 after October 16). If you’re staying in the latter, avoid awkward communal-table conversations by having your breakfast—a warm apple-cranberry crisp; almond-crusted French toast with Maine maple syrup—delivered to your door.
In what could be an industry first, the quirky Colony Hotel (from $99) gives its main-house guests wireless Internet access but no TVs. Not that you really need either. The Georgian-style inn is right on the Atlantic and looks over a private beach. With ocean temps dipping, take a midnight plunge in the heated saltwater pool.
2. Where to Eat
Soak in the salty atmosphere at Big Fish (17 Western Ave., Kennebunk; 207-967-1198), decked out with raw beams and a driftwood chandelier and lit almost entirely by candles. Native-born siblings Sara and Chris Rundlett excel at high-low dishes like fish-and-chips with tempura-fried ahi tuna, and macaroni and cheese with porcini mushrooms and shaved white Italian truffles.
Take matters into your own hands by pairing meats or veggies and sauces (servers can guide you toward the best combos) at Bandaloop, a casual Dock Square spot named after the tribe of immortal beings in Tom Robbins’s novel Jitterbug Perfume.
Get a little rowdy at Bentley’s Saloon, a biker bar in Arundel built out of rough-hewn pine. After ripping into St. Louis–style barbecued ribs (pig roasts are held on an outdoor rotisserie), test your sobriety with a game of horseshoes or volleyball out back.
3. What to Do
Gorgeous, culinarily blessed Cape Porpoise has somehow remained the least known and most down-to-earth of the Kennebunks (which also include the villages Kennebunk, Kennebunkport, and Arundel). Get brunch at the Wayfarer (2 Pier Rd.; 207-967-8961), a down-home, cash-only diner where chef-owner Brandy Hynes makes the biscuits, pancakes, and corned-beef hash from scratch.
Stroll the pier overlooking the Goat Island lighthouse, which offers a perfect vantage point for watching fishing boats chug in and out of the harbor. Nunan’s Lobster Hut (9 Mills Rd.; 207-967-4362) has the most highly sought-after lobster roll in Cape Porpoise (open 5 p.m. nightly through October 13). If it’s later in the season (or earlier in the day), try the roll at the Cape Pier Chowder House, which opens at 11 a.m.
For a more intimate experience with the waters of Cape Porpoise, book a guided kayak tour with Port Paddle (arrange through Cape-Able Bike Shop). A four-hour trek ($59 per person) drifts past ghostly, wind-torn pine and hemlock forests on Bumpkin, Goat, and Cape Islands; the pebbled beach on Trott Island is the best place to stop for a snack. Afterward pull up to the Ramp Bar and Grille for fish-and-chips, a burger, or a North Carolina–style pulled-pig sandwich with tidewater slaw.
4. Insider’s Tip
One thing the Bushes definitely don’t do at their Kennebunkport compound: surf. With the right gear, you can ride Kennebunk Beach’s waves straight through the fall. Take surfing lessons (or just rent a wetsuit and a board) from Aquaholics, a surf shop owned by a former pro volleyball player, Nanci Grenier Boutet, whose mission is to get more people (especially women) into surfing. Sign up for weekend surf camps ($105) or a private lesson ($100 for one person; $150 for two people), or just rent a wetsuit, booties, and gloves ($25) and a board ($30 to $50) and hit the waves. Check NESurf.com for the forecast for Kennebunk Beach.
5. An Oddball Day
Combine a bunch of Lithuanian monks, grounds designed by Frederick Law Olmsted, and a neo-Tudor mansion and you get St. Anthony’s Franciscan Monastery, an impossibly serene estate set on 66 acres alongside the Kennebunk River. Take a self-guided walking tour (open 9 a.m. until 4 p.m. daily), stopping to admire the stunning views and the Lithuanian-style shrines and grottoes. After a calming morning among the monks, make your way back down Beach Avenue and take a right onto Route 9 to get to the Clam Shack, a tiny stand perched on the bridge linking Lower Village with Kennebunkport. If you haven’t overdosed on lobster rolls yet, try these: They come on round buns from a local bakery, rather than the traditional top-split hot-dog rolls.
6. Related Links
The owners of the Maine Stay Inn also happen to write a useful (if overly enthusiastic) blog about Kennebunkport.
For tips on walks, tours, and attractions, check out the Kennebunks’ chamber-of-commerce site.
Orient yourself with this interactive map of Cape Porpoise.