IPW Sample Itinerary

Exploring Lighthouses, Working Waterfront, and Culinary Delights

Just a short 1 to 4 hours (respectfully) from other East Coast hubs like: Boston (Logan International Airport (BOS) or Manchester-Boston Regional Airport (MHT)) and New York City (John F. Kennedy International Airport (JFK) LaGuardia Airport (LGA)), Greater Portland is ready to welcome you with open arms.

For international travelers seeking to explore Maine from Boston, the Amtrak Downeaster is a convenient and scenic alternative to renting a car. This comfortable passenger train connects Boston’s North Station to several destinations in Southern Maine, including Portland, offering a stress-free travel experience without the need to navigate unfamiliar roads or deal with parking. With spacious seating, free Wi-Fi, and onboard refreshments, the Downeaster allows visitors to relax and enjoy the quintessential New England landscape, from salt marshes and coastal villages to forested stretches. Arriving right in the heart of walkable downtowns, it’s also a more sustainable and accessible option—ideal for those seeking a smooth, car-free adventure through the Northeast.

Day 1 : Maine Beaches – Old Orchard Beach

Morning: Exploring Old Orchard Beach offers a nostalgic blend of seaside fun and classic New England charm. Stroll along the iconic seven-mile stretch of sandy beach, wander the bustling pier lined with shops and snack stands, or take a spin on the rides at Palace Playland, New England’s only beachfront amusement park. Just a short drive or bike ride from downtown, Funtown Splashtown USA delivers even more excitement with roller coasters, water slides, and family-friendly attractions. Whether you’re craving sun, thrills, or a bit of both, OOB delivers a timeless, playful escape perfect for all ages

Afternoon: Arrive for check in at the Alouette Beach Resort which is a warm welcome to the laid-back charm of Old Orchard Beach. Just steps from the sand, this oceanfront resort offers a mix of cozy rooms and beachfront suites, perfect for unwinding after a day of seaside adventure. Guests can wake up to the sound of waves, enjoy a morning walk along the shore, or explore the nearby pier and local shops. Conveniently, the Amtrak Downeaster station is just a short walk away, making it easy for travelers arriving from Boston or other coastal towns to settle in without hassle. Whether you’re here for a weekend escape or a longer stay, Alouette offers a comfortable and scenic home base by the sea.

Day 2 : Up to Portland

Morning: On your way up to Portland Dive into the captivating landscapes of Cape Elizabeth. Join a guided tour to the lighthouses or arrange transportation for the ten minute trip. Explore the iconic Portland Head Light and its rocky coast surroundings at Fort Williams Park. Capture this magic through your camera lens or simply breathe in the invigorating sea breeze.

Afternoon: Check into the Longfellow in Portland. This centrally located boutique hotel serves as an excellent base to explore the city’s attractions and waterfront before continuing your coastal adventure. The design-forward hotel with a focus on wellness provides a unique and captivating backdrop to your stay, enhancing the overall travel experience. The comfortable, elegantly appointed rooms as well a visit to the Astraea Spa ensure complete relaxation. Other hotel amenities include the Twinflower Café, and the Five of Clubs lobby bar. Additionally, The Longfellow Hotel’s staff can provide valuable local insights, helping you make the most of your coastal journey with recommendations and guidance.

Make your way down to the wharf to catch a Wine Sail. Sailing with Wine Wise Events is one of the most unforgettable—and delicious—ways to spend an afternoon in Portland, Maine. Set aboard a classic windjammer, this unique experience combines the beauty of Casco Bay with expertly curated wine and culinary pairings led by your guide and sommelier Erica Archer. As you glide past lighthouses, islands, and lobster boats, you’ll savor thoughtfully selected wines alongside locally inspired small plates, all while soaking up the fresh sea air and scenic views. It’s not just a tasting—it’s a moving feast of your senses on the water, offering a true taste of Maine in the most picturesque setting imaginable.

Evening: Savor the delectable flavors of locally-caught seafood, including succulent Maine lobster, as you dine by the ocean’s edge. Try an outdoor dining experience where you can watch the fishing boats go in and out on the Working Waterfront. It just might be the perfect way to cap off your coastal welcome to Maine.

We recommend Boone’s Fish House & Oyster Room. Dinner at Boone’s means stepping into a piece of history—and a feast of local flavor. Established in 1898 by Alexander Boone, this classic seafood landmark sits on Custom House Wharf, offering waterfront views and timeless New England charm. Its menu shines with fresh, locally sourced seafood: think wood-grilled fish, whole Maine lobster steamed over rockweed, and its legendary Baked Stuffed Lobster, a signature dish invented right here over a century ago. With two outdoor decks perfect for watching lobster boats and harbor sunsets, plus welcoming indoor spaces complete with a cozy fireplace, Boone’s delivers both atmosphere and exceptional fare. Whether sharing oysters at the raw bar or digging into fish & chips, Boone’s offers a memorable blend of historic legacy, quality ingredients, and scenic ambiance—making it a top choice for an authentic Portland dining experience.

Day Two : Mid-Coast

Morning: Start your day bright and early with a hearty breakfast to fuel your Maine adventure. Whether you’re staying in town or hitting the road, Portland offers plenty of great spots to grab a morning bite—but for a true local favorite, Becky’s Diner is a must. Located right on the working waterfront, Becky’s has been a beloved institution for decades, serving up classic diner fare with a side of authentic Portland charm. From fluffy pancakes and perfectly cooked eggs to fresh Maine lobster omelets, it’s the kind of place where fishermen, tourists, and locals all rub elbows over bottomless coffee and comfort food. It’s the perfect way to kick off the day before heading out to explore more of what Maine has to offer.

As you continue your journey up the coast, a morning stop in Freeport is a must for anyone looking to blend retail therapy with small-town charm. Home to the world-famous L.L.Bean flagship store, Freeport offers a uniquely Maine shopping experience—open 24/7 and filled with everything from iconic boots to outdoor gear perfect for your next adventure. Just steps away, Toad&Co delivers sustainable, adventure-ready clothing with a focus on comfort and eco-conscious style. Don’t miss a visit to Fiore Artisan Olive Oils & Vinegars, where you can sample an impressive variety of small-batch, globally sourced oils and balsamic vinegars—perfect for bringing a taste of Maine home with you. After a morning of browsing, enjoy lunch at Linda Bean’s Maine Kitchen, where you can indulge in lobster rolls, chowder, and other coastal classics in a casual, locally inspired setting. With its mix of local flavor, flagship shopping, and walkable village feel, Freeport is a convenient and rewarding stop that truly captures the essence of Maine.

Afternoon: Brunswick is an absolute must on a coastal road trip through Maine. Check in at The Federal, a stylish boutique hotel that blends historic charm with modern sophistication. Housed in a beautifully reimagined 19th-century building, it offers a refined, contemporary stay just steps from Bowdoin College and Brunswick’s vibrant downtown. Thoughtfully designed rooms feature upscale amenities and sleek finishes, while the hotel’s on-site restaurant, 555 North, serves inventive coastal cuisine in a relaxed yet elegant setting. The Federal offers a polished, comfortable retreat in the heart of midcoast Maine.

Day Three: Up to Bar Harbor/Acadia

Morning: After soaking in the charm of Brunswick, it’s time to get back on the road and head north for a scenic journey into Maine’s western mountains. A stop at Sunday River offers the perfect midday break—take a relaxing ride on their scenic chairlift, which glides up the slopes for sweeping views of the Mahoosuc Range and lush summer landscapes. Enjoy a casual lunch at the summit or base lodge, soaking in the crisp mountain air before continuing east toward the coast.

Afternoon – As the afternoon fades, the drive to Acadia National Park and Bar Harbor winds through classic Maine countryside and ends at the ocean’s edge, where charming inns, coastal dining, and the rugged beauty of Acadia await for a memorable overnight.

Evening: check into the Acadia Wilderness Lodge for an immersive and memorable experience. Nestled in the heart of nature, this lodge offers unparalleled access to the breathtaking Acadia National Park, renowned for its rugged coastlines, pristine lakes, and lush forests. Guests can enjoy the tranquility of wilderness while still being within reach of Bar Harbor’s vibrant dining and cultural offerings. The lodge’s rustic charm and cozy accommodations provide a true escape from the ordinary, allowing visitors to unwind in harmony with the natural beauty that defines the Maine coast. It’s the perfect base for outdoor enthusiasts and those seeking a serene retreat in an enchanting wilderness setting.

Last Day: Before heading south, we recommend making the most out of your last few hours in Bar Harbor by taking the Maine Day Venture’s Lunchtime Tasting Tour. This experience is an exceptional way to savor the local flavors and culture. The guided tour provides an insider’s perspective on Maine’s culinary scene, introducing visitors to hidden gems and iconic eateries. It’s a convenient, organized way to sample the freshest seafood, artisanal cheeses, and other regional specialties, enhancing the road trip experience. Guests can indulge in a variety of delectable dishes while learning about the area’s history and culinary traditions. It’s a delightful, hassle-free opportunity to immerse yourself in Maine’s culinary heritage and make the most of your coastal journey.

As your afternoon begins you can make your way back down south, reflecting on an unforgettable exploration of Maine’s coastal beauty, from quaint coastal towns to the rugged Acadia National Park.

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