Southern Maine, first stop: Portland
Where to stay: Check into the trendy Press Hotel, an Autograph Collection Hotel, in the Old Port.
Where to eat: Cruise through the Old Port waterfront and stop at DiMillo's for to-the-point dining with the best view of the bay. The staff isn't friendly but forward, and with a motto that says, "We don't cook complicated masterpieces, just good food from fresh ingredients," you'll understand. Get the fried scallops, you'll thank us later.
What to do: Walk the cobblestone streets of the Old Port, take a brewery tour (Portland is considered a leader in the microbrew movement), and take a ferry to the Casco Bay Islands, a group of islands located off the coast of Portland, with each island having its own vibe, attractions and activities. Make sure you have these road trip planner apps before hitting the road.
Southern Maine, second stop: Kennebunkport, Maine
Where to stay: Cape Arundel Inn & Resort is by far the most gorgeous resort in Kennebunkport, and perhaps all of Southern Maine. It has old-timey charm but with subtly nuanced luxury throughout. Gazing at the ocean from the Adirondack chairs on the lawn or from the wrap-around porch will give you that simple Maine flair. Champagne and warm cookies on arrival, and decadent design features in the rooms, like marble bathroom floors and French doors that open out to a delicious view of the Atlantic, will make you feel special, to say the least.
Where to eat: Hands down, Ocean Restaurant. Located at the Cape Arundel Inn & Resort, the warm atmosphere isn't overbearingly chic, while the food is unbearably good. The inventive ocean-inspired cuisine is brought to you by the superbly talented and friendly Chef Pierre Gignac. The Rock Crab Velouté, featuring peekytoe crab, lemongrass scented bisque, beech mushroom, snow peas, and sweet corn purée is mind-blowing.
What to do: Check out a beach cruiser for free at the inn, and ride it into the bustling town. The cruise itself is enough to take your breath away with ocean views to your left and old colonial mansions to your right. Lock it up and step aboard the Spirit of Massachusetts, an enormous sailboat docked in the river right in the center of town. Keep it simple and order a pound of steamers (that's Maine speak for steamed clams, just in case you're confused by the ambiguous word on the menu).
Did you know about all of these amazing free tourist attractions in each state?
Southern Maine, third stop: Ogunquit
Where to stay: The Cliff House is a coastal dream come true. Situated on the edge of the Atlantic on the rocky coast of Southern Maine, it boasts panoramic views from just about everywhere, including your swanky, nautical-themed hotel room. The resort is located in Cape Neddick, which is just a few minutes from Ogunquit. The infinity pool and spacious hot tub overlook nothing but vast ocean, with the occasional lobster boat cruising close to shore.
Where to eat: The Front Porch, located in the heart of downtown Ogunquit village has excellent food and an inviting atmosphere. The sing-along piano bar will surely keep you entertained long after you've filled yourself to the brim with scrumptious bites like the blue cheese mussels, lobster flatbread, and the shrimp and scallop carbonara.
What to do: In the morning, stroll Marginal Way, a cliff walk with coastal views, benches, and a lighthouse. You must spend the day on Ogunquit Beach. It's a long, sandy peninsula with grassy dunes that resides between the Atlantic Ocean and the Ogunquit River. Plop your stuff down on the riverside, jump in the water, and let the river's fast current whip you out to the ocean side. Then, take a walk along the beach and catch one of the volleyball games. Be sure to catch a show at the Ogunquit Playhouse—one of the town's cultural icons.
Portsmouth, New Hampshire
Where to stay: Settle in at the Great Island Inn. It's located in New Castle, which is a scenic five-minute drive from Portsmouth. New Castle is composed entirely of islands, making up a mere 0.8 square miles. Great Island Inn is a newly-renovated historic home offering apartment-style rooms. The nautical theme pairs perfectly with the view outside your window: the Piscataqua River, where colorful lobster boats sway on their moorings, people are kayaking in the glassy water, and birds are constantly flying about.
Where to eat: Downtown Portsmouth has so many incredible restaurants it's hard to call out just one. Check out Row 34, for oysters and seafood dishes in a sleek space with a hip vibe, or head to "The Decks," a row of restaurants and bars on the Piscataqua River. Sip back a "Jimmy Juice" at The Old Ferry Landing while you watch tugboats pull in and help dock massive vessels carrying precious cargo. But for the very best view in town? Cross the bridge back into Kittery, Maine, and take a left onto Badger's Island West where you'll park it at Morrison's. It's a quintessential lobster shack where you get to watch the hustle and bustle of Portsmouth but from what feels like your own private dock. Scattered with plastic red chairs and rickety tables, this place is BYOB. Order a pound and a half lobster for yourself, put on your cute lobster bib, and pig out while the sun sets and the sky ignites to a pastel hue you'll have to drop a lobster claw and pick up your camera for.
What to do: Portsmouth is best explored on foot, so ditch the car and walk along Market Square, Congress, Daniel, Pleasant, Bow and Penhallow Streets where eclectic shops and restaurants line the streets. If you're looking for some high-end shopping, you can drop a pretty penny on Deer Street. It wouldn't be a trip to Portsmouth without sauntering through Prescott Park, where more than 500 flower varieties fill the riverside common. Check out a food or beer festival here, and catch a play or concert put on by Prescott Park Arts Festival. Mosey over to the park's pier and catch a view of the Portsmouth Naval Shipyard across the harbor. This historic landmark has been here since 1800, where the Navy's submarines have continued to get repaired. Don't forget to pack these essentials on your next road trip.
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Where to stay: The newly-renovated Four Seasons Boston overlooks the city's historic Public Garden, where your walk beneath canopied trees is complete with swans waddling at the water's edge. The Four Seasons is elegant, sure, but in a New England way that is not overwhelming. It's historic and simple. Somehow, despite being one of the most sought-after worldwide luxury hotels, the Boston location pays homage to that classic old charm that feels humbly sophisticated. The overly accommodating staff will make you feel like a movie star.
Where to eat: Start with a martini and the mussels at The Bristol, the dimly-lit restaurant at The Four Seasons. For that coastal view, go to Legal Harborside and head up to the rooftop.
What to do: Walk, walk, walk. If you drive around, you're bound to get frustrated by the traffic and the constant horns as people cut each other off. Start your city tour on the Freedom Trail, where you'll get to see landmarks like the Paul Revere House and Boston Common. For the high-end clientele, get your shopping on Newbury Street. It's just a street over from your stay at the Four Seasons. Baseball fan? Catching a game at Fenway, or "The Green Monster," is a must. The stadium is intimate, the hecklers are hilarious, and the surrounding bars on game night are packed to the brim with diehards. Go to Fanueil Hall Marketplace. It's touristy, but it's worth it. Speaking of touristy, do the Boston Duck tour. It's a boat, it's a car, it's your guide to Boston trivia.
Southern California, first stop: San Diego
Where to stay: The Catamaran Resort and Spa is a beachfront beauty. Residing in the Pacific Beach community on the gorgeous shores of Mission Bay, it's a Polynesian-themed resort that's equal parts casual and elegant.
Where to eat: If you want the best Mexican food north of the border, surely San Diego is a must. People love their breakfast burritos here. Get the El Jefe breakfast burrito at Lucha Libre, which comes with steak, eggs, cheese, Pico de Gallo, avocado slices, special chipotle sauce, and fries. The Cottage in La Jolla has to-die-for French toast. Little Italy has, of course, your classic Italian fare, but my favorite is by far Ironside. It's a creative space inspired by the ocean, from the seafaring decor, like the plastic-cast piranha heads and live fish tanks, to the creative cocktails and fresh, local seafood and raw bar.
What to do: Where to start? It's San Diego, so you're bound to spend the majority of your time outdoors. Hike the sandstone cliffs of Torrey Pines State Reserve, spend a day at Balboa Park, hit up the various museums, theaters, and gardens, rent a board and surf, then eat, drink, eat, drink, repeat!
Southern California, second stop: Newport Beach
Where to stay: Pelican Hill is the bougie of all bougie places. Go if you're willing to spend your Benjamins. Located in Newport's Crystal Cove, its view of the ocean is obscenely mesmerizing—never mind its Coloseium Pool, which was designed with more than one million glass mosaic tiles, laid by hand to form the pool's perfect circle, 136 feet in diameter. If you want that laid-back vibe, check out Balboa Bay Resort. It's the only AAA Four-Diamond, waterfront resort in Newport Beach.
Where to eat: Bear Flag. This is a no-frills fish market and restaurant known for its salmon poke so much so that if you come too late in the day, you'll miss out. In that case, get the ahi poke—it's incredible.
What to do: Rent a duffy boat and cruise through the Newport Harbor. Dock at one of the restaurants to grab a bite and drink. Even better? Do the whole thing on paddleboards! Hop on a bike and ride along the peninsula's boardwalk for people watching, plenty of shops and restaurants to stop at, and ocean views galore. Take your bike to the harbor side and check out the peninsula's new Lido Marina Village for al fresco dining on the water and charming boutiques.
Southern California, third stop: Rancho Palos Verdes
Where to stay: Terranea Resort & Spa is a playground for adults and children alike. Walk about the grounds of the 102-acre private peninsula paradise, and you'll quickly understand why. There are four oceanview pools, eight restaurants, bars, cafes, and lounges, an award-winning nine-hole, par-three golf course, an oceanfront spa, and so much more. With Mediterranean touches throughout, outdoor fireplaces, gorgeous courtyards and gardens, and Pacific views on three sides of the resort, you'll feel like you're in a faraway oasis meant for very important people—all with a very laid-back vibe only California has to offer.
Where to eat: Mar'sel, of course. Offering ocean views, this is the crème de la crème of the resort and Rancho Palos Verdes as a whole. The fine dining menu features locally-sourced ingredients that pay homage to the California coast. The environment, the people, and the food offer approachable luxury that's not overwhelming, but simply Californian through and through. Get the diver scallops and perfectly grilled calamari for an appetizer, and the branzino for an entree. A side of the melt-in-your mouth mushrooms never hurt anybody. In the morning, go to Catalina Kitchen for an insane buffet brunch and bottomless mimosas. Crab legs, sushi, cioppino, French toast, omelets, quinoa salad, slabs of brie cheese, jam and fresh bread all await. (Make sure you read our tips on how to navigate a buffet before you go!)
What to do: When you're not getting a revitalizing marine massage at Terranea's spa, or sipping cocktails poolside, check out the Point San Vicente Lighthouse. Tour the light station. Only open once or twice a month, a tour will have you climbing the stairs to the top to look out. Then, check out Point Vicente Interpretive Center, where 10,000 square feet of exhibits on the history of the peninsula resides.
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