Maine (Portland, Kennebunkport) 7-Day Trip Itinerary

Arrive & Hotel Check-in

Arrive in Portland, Maine, pick up your rented van, and check into your accommodation.

Take some time to settle in and refresh after your journey.

Ensure your rental van is large enough for 7 adults and luggage. Pre-booking parking at your hotel is recommended if available.

Explore Historic Old Port

Wander through the cobblestone streets of Portland's Old Port district.

Discover unique boutiques, art galleries, and historic brick buildings. Enjoy the harbor views and browse the local shops.

Many shops close by 5:00 PM or 6:00 PM on Saturdays. Perfect for souvenirs and local crafts.

Welcome Dinner in Old Port

Enjoy a delicious welcome dinner featuring fresh local seafood or other Maine specialties at one of Old Port's acclaimed restaurants.

Reservations are highly recommended for a group of 7, especially on a Saturday night in October. Consider options like Eventide Oyster Co. or Fore Street Restaurant (if available and within budget).

Local Breakfast Spot

Start your day with a classic New England breakfast at a local diner or cafe in Portland.

Try Holy Donut for unique potato donuts, or Standard Baking Co. for pastries and coffee.

Visit Portland Head Light

Explore Maine's oldest lighthouse, Portland Head Light, located in Fort Williams Park.

Enjoy stunning coastal views and browse the museum and gift shop.

Parking is available at Fort Williams Park. There is a small entrance fee to the park (per car) and for the museum. Beautiful photo opportunities, especially with fall foliage.

Explore Bug Light Park

Visit the charming Portland Breakwater Light, affectionately known as 'Bug Light,' a replica of a Greek temple.

Enjoy the peaceful park and views of Portland Harbor.

Free parking available. Easy walk to the lighthouse, great for photos.

Lunch in South Portland

Grab a casual lunch in South Portland, perhaps some local clam chowder or a lobster roll.

Numerous casual eateries and cafes are available. You can also pick up provisions for a picnic at a scenic spot.

Stroll Eastern Promenade

Take a leisurely walk or scenic drive along the Eastern Promenade, enjoying panoramic views of Casco Bay, the islands, and the city skyline.

This is a great spot to see the fall colors.

Consider walking the paved path for stunning views. There's also a public beach if weather permits a quick stroll.

Brewery Dinner Experience

Portland is known for its craft beer scene.

Enjoy dinner and local brews at one of the city's popular breweries.

Many breweries offer full food menus. Try Allagash, Maine Beer Company, or Rising Tide Brewing Co. for a good selection. Designate a sober driver for the van!

Drive to Kennebunkport

Begin your scenic drive south to the charming coastal town of Kennebunkport (approx.

45-60 min drive).

Visit Franciscan Monastery

Explore the beautiful grounds of the Franciscan Monastery, a serene and historic site with lovely gardens and ocean views.

Known for its peaceful atmosphere and stunning architecture. Great for a quiet stroll and reflection. Respectful attire is encouraged.

Kennebunkport Historic District

Walk through the Kennebunkport Historic District, admiring the well-preserved architecture and learning about the town's rich past.

Many historic homes and buildings. Consider a self-guided walking tour to appreciate the history. Close proximity to Dock Square.

Lunch in Kennebunkport

Enjoy lunch in Kennebunkport, perhaps a casual meal at one of the waterfront restaurants in Dock Square.

Numerous options from casual seafood shacks to more upscale dining. Consider grabbing a lobster roll or fresh fish sandwich.

Intown Trolley Tour

Take a narrated tour with Oli's Trolley to get an overview of Kennebunkport's sights and history, including famous landmarks and coastal views.

A great way to see the town without driving and get historical context. Check schedules as October might have limited operations.

Shopping & Photo Ops

Spend some time browsing the charming shops and art galleries in Dock Square and around Kennebunkport.

Don't forget to get a photo with the 'Kennebunkport City Sign'!

Unique boutiques, souvenir shops, and local artisan crafts. The Kennebunkport City Sign is at Mathew J. Lanigan Bridge, 2 Western Avenue.

Return to Portland

Drive back to Portland after a lovely day exploring Kennebunkport.

Casual Dinner in Portland

Enjoy a relaxed dinner in Portland, perhaps trying a different neighborhood or type of cuisine.

Portland offers a wide variety of dining, from pizza to ethnic cuisine. Take advantage of your van for ease of access.

Breakfast at a Cafe

Enjoy a relaxed breakfast at a charming cafe in Portland.

Numerous options available, from quick pastries to full breakfast menus.

Explore Arts District

Discover Portland's vibrant Arts District.

Visit galleries, admire street art, and explore local craft shops.

The Portland Museum of Art is a central feature if your group is interested in a museum visit (check for Monday closures, though this is a Tuesday). Also home to unique boutiques and shops.

Lunch from Food Trucks

Experience Portland's diverse culinary scene with lunch from one of its popular food trucks.

Check local listings for locations.

Food trucks often gather at specific spots, especially around the Arts District or breweries. A great casual option for variety.

Walk the Back Cove Trail

Enjoy a scenic walk along the Back Cove Trail, offering beautiful views of the Portland skyline and surrounding nature, perfect for autumn colors.

A paved 3.5-mile loop, great for a leisurely stroll or enjoying the fresh air. You can do a portion of the loop if you prefer a shorter walk.

Happy Hour & Local Spirits

Relax with happy hour drinks at a local bar or try a tasting at a craft distillery or winery in the area.

Check out Liquid Riot Bottling Company or Maine Craft Distilling for local spirits. Always ensure a designated driver.

Upscale Dinner in Portland

Indulge in a higher-end dining experience in Portland, known for its innovative cuisine and fresh, local ingredients.

Consider restaurants like Central Provisions, Miyake, or Scales. Reservations essential for a group of 7. Dress code may be smart casual.

Deli Breakfast & Coffee

Grab a quick and hearty breakfast at a local deli or cafe, perfect before a day of scenic drives.

Great for getting sandwiches or snacks for later in the day.

Scenic Drive to Cape Neddick

Enjoy a beautiful drive down the scenic coastal Route 1 to Cape Neddick, visiting 'Nubble Lighthouse' (Cape Neddick Light).

Approx. 1 hour drive one way from Portland. Nubble Lighthouse is one of Maine's most iconic and photographed lighthouses. There's a park for viewing but no direct access to the island.

Lunch in York or Ogunquit

Have lunch in one of the charming towns along Maine's southern coast, such as York or Ogunquit, known for their beaches and coastal beauty.

These towns offer great dining options and picturesque views. Perkins Cove in Ogunquit is a very scenic spot.

Ogunquit Beach Walk

Take a refreshing walk on Ogunquit Beach, enjoying the crisp autumn air and expansive sandy shores.

Even in October, the beach is beautiful for a stroll. Marginal Way walking path (if open and accessible) also offers stunning ocean views.

Return to Portland & Prepare for Next Leg

Drive back to Portland.

Use the late afternoon to relax, perhaps do some light souvenir shopping, and prepare for your onward journey to the Acadia region tomorrow. Ensure your van is fueled.

This is a good time to buy any snacks or essentials for the longer drive to Acadia National Park on Day 6. Check hotel for checkout procedures.

Farewell Portland Dinner

Enjoy a final dinner in Portland, perhaps revisiting a favorite spot or trying a new one that caught your eye.

Keep it moderate and relaxed before a travel day. Consider a classic pub or a cozy bistro.

Sunrise/Morning on Cadillac Mountain

Drive up to the summit of Cadillac Mountain, the highest peak on the East Coast, for panoramic views of the park and coastline. A reservation for timed entry is often required during peak season, so check in advance.

Dress in layers, as it can be windy and cooler at the summit. Check for sunrise/sunset times if you wish to experience them. Booking: https://www.tripadvisor.com/Attraction_Review-g143010-d108269-Reviews-Cadillac_Mountain-Acadia_National_Park_Mount_Desert_Island_Maine.html?m=66827

Scenic Drive on Park Loop Road

Explore the iconic 20-mile Park Loop Road, stopping at scenic overlooks like Thunder Hole, Otter Cliff, and Sand Beach.

Enjoy the stunning coastal and forest views.

Allow time for stops at popular viewpoints. Your rental van will provide easy access to all stops. Booking: https://www.tripadvisor.com/Attraction_Review-g143010-d208151-Reviews-Park_Loop_Road-Acadia_National_Park_Mount_Desert_Island_Maine.html?m=66827

Lunch in Bar Harbor

Head into Bar Harbor for a casual lunch at one of its many restaurants.

Enjoy fresh seafood or other local delights.

Many options available, from quick bites to sit-down meals. Consider trying a lobster roll!

Oli's Trolley Park Tour

Take a fully narrated tour of Bar Harbor and Acadia National Park with Oli’s Trolley.

It's a great way to learn about the area's history and highlights without the stress of driving.

This tour offers a comprehensive overview and comfortable seating for your group. Book tickets in advance, especially for a group of 7. Booking: https://www.tripadvisor.com/Attraction_Review-g60709-d1093485-Reviews-Oli_s_Trolley_Acadia_National_Park_Tour-Bar_Harbor_Mount_Desert_Island_Maine.html?m=66827

Dinner in Bar Harbor

Enjoy a delicious dinner in Bar Harbor, selecting from a variety of restaurants offering local Maine cuisine.

Reservations are recommended for groups, especially during the busy fall foliage season.

Walk around Eagle Lake

Enjoy a leisurely walk or bike ride along the carriage roads surrounding Eagle Lake, offering beautiful reflections of the surrounding foliage and mountains.

The carriage roads are relatively flat and easy, perfect for a relaxing morning stroll. Parking available. Booking: https://www.tripadvisor.com/Attraction_Review-g60709-d9784376-Reviews-Eagle_Lake_Acadia_National_Park-Bar_Harbor_Mount_Desert_Island_Maine.html?m=66827

Jordan Pond House & Bubbles

Visit Jordan Pond and enjoy the scenic views of the 'Bubbles' mountains.

You can walk part of the Jordan Pond Path or simply relax at the Jordan Pond House, famous for its popovers (check seasonal opening).

The full path around Jordan Pond is a moderate hike. You can do a shorter section or just enjoy the views from the visitor area. The Jordan Pond House usually closes for the season in late October.

Lunch and Last-Minute Shopping in Bar Harbor

Return to Bar Harbor for lunch and some free time to explore the unique shops, pick up souvenirs, or grab a final taste of Maine seafood.

Many shops offer local crafts, art, and Maine-themed gifts.

Leisure Time & Departure Preparations

Enjoy some leisure time, gather your belongings, and prepare for your departure from Bar Harbor.

Depending on your flight schedule or onward journey, you may begin your drive back towards Portland or Bangor.

Ensure your rental van is ready for the journey. A drive back to Portland typically takes 3-4 hours.