Established in 1633 as a fishing village, Portland became New England’s largest port. With its narrow cobblestone streets, it’s one of America’s most vibrant small towns. (Listen to music pour onto the water.) Into the woods, and cross the White Mountains to New Hampshire. Hundreds of bubbling streams and rivers and towering trees seen from the deluxe upper dome of a historic train car.
Explore the wilds of Maine on your way to the coast, and stop at small roadside stands. When the trees fall back, you’re in Booth Bay. The coastal capital of America, indulge in sunsets on a schooner and fine dining, overlooking the ocean. Imagine white, blue, and calico lobsters. From here, Acadia calls you. The natural beauty of the highest headlands along the Atlantic coast also has a rich cultural heritage. There are still 45 miles of carriage roads. Take a walk.
This 3 hour leisurely walking tour carves a path through the streets of the charming Old Port educating you on local food, drinks and history. Friendly and engaging tour guides take you to several Old Port artisanal shops, restaurants and pubs where you’ll sample a delectable mix of classic Maine and cultural foods and beverages. Meet with culinary artisans along the way, learn what inspires them and how they got their start. Along the way we’ll dish about the colorful, social and culinary history unique to the “Port City” we call home with lots of additional recommendations on how to dine and imbibe.
Examples of servings your tour MAY include: Fresh picked lobster From-scratch confections from a hip local bakery Cold-pressed nut mylk smoothie Locally-sourced temaki/hand roll Farmer’s market sourced soups or a Maine seafood “chowdah” Iconic Maine craft beer Dark chocolate truffles made with Aroostook County potatoes Variations regularly occur as this is our Flagship walking food tour. This experience showcases the culinary culture comprised of talented food and beverage artisans, from bakers and brewers to confectioners, chefs and more…the spots we locals enjoy visiting on a daily basis.
Arrive at
Arrive at Portland International Jetport (PWM), Maine
Today you will arrive at Portland International Jetport (PWM) in Maine.
Overnight Location
Portland, Maine
Established in 1633 as a fishing village, Portland became New England’s largest port. With its narrow cobblestone streets, artistic and outdoor adventures, it’s one of the most vibrant small towns in America. A place where grey flannel and plaid flannel coexist companionably. And underlying the latest tech, fashion, and culinary scene is a deep sense of continuity. Experience the character of a region that blends the present with a very special past.
Day 2
Daily Itinerary
Drive to North Conway, New Hampshire
The drive from Portland, Maine to North Conway, New Hampshire takes 1 hour and 30 minutes. Check into the finest resort in North Conway in the heart of the White Mountains. Relax by the heated indoor and outdoor pool and lounge on the sun deck with jaw-dropping scenery.
Suggested Sightseeing
Diana's Baths, North Conway, New Hampshire
Diana’s Baths are a must-see any time of the year when you are in the North Conway area and want to experience nature at its finest. Diana's Baths is a series of small waterfalls located in the southeastern corner of the town of Bartlett, New Hampshire, near the village of North Conway in the White Mountains of New Hampshire, United States. This historic site is within the White Mountain National Forest. The hike to Diana’s Baths is a fairly easy 6/10ths of a mile on a relatively flat, wide gravel path. Being part of the US National Forest System, there is a large parking lot at the entrance to the hiking path and a self service pay station which requires visitors to purchase and display a daily pass on the dashboard of your vehicle.
Overnight Location
North Conway, New Hampshire
A village set amid mountains and forest, North Conway is a jumping-off point for hiking excursions on Mt. Washington and fall leaf-viewing tours on vintage trains, as well as ski trips and visits to Diana’s Baths cascades.
Day 3
Included Unique Activities
Conway Scenic Railroad
North Conway, New Hampshire
Take the scenic Conway Railroad through dramatic natural scenery in the East as you travel through spectacular Crawford Notch – past sheer bluffs cliffs, steep ravines, cascading brooks and streams, panoramic mountain vistas, across Frankenstein Trestle and Willey Brook Bridge – en route to Crawford Depot.
Suggested Sightseeing
Zeb’s General Store, North Conway, New Hampshire
On the Map: 2675 White Mountain Hwy, North Conway, NH 03860
One of the essential North Conway things to do is to pay a visit to Zeb’s. This general store is smack in the middle of downtown North Conway and it is an iconic spot.
You could spend an hour or more wandering around this shop and looking at all the goods they have to buy. They offer the largest collection of New England-made products in an old-fashioned ‘mercantile’ style setting. Be sure to check it out and grab a souvenir or two.
Overnight Location
North Conway, New Hampshire
A village set amid mountains and forest, North Conway is a jumping-off point for hiking excursions on Mt. Washington and fall leaf-viewing tours on vintage trains, as well as ski trips and visits to Diana’s Baths cascades.
Day 4
Daily Itinerary
Drive to Boothbay Harbor, Maine
Depart from New Hampshire and drive to Booth Bay Harbor, Maine. This drive takes 2 hours and 30 minutes. Check in to your historic Victorian inn located on the waterfront in the heart of the scenic coastal town of Boothbay Harbor. Enjoy the convenient, quiet location, right on the harbor, and just steps to downtown Boothbay Harbor's art galleries, shops, restaurants, and boating excursions.
Included Unique Activities
Coastal Maine Botanical Gardens
Boothbay Harbor, Maine
Coastal Maine Botanical Gardens began as a casual conversation between friends and evolved into the largest botanical garden in New England. Located along the MidCoast, the Gardens is a true Maine experience with woodland trails, plants, ornaments, waterfalls, and scenic views. Here you'll see sculptures of fine artists from Maine. Be sure to stop by the cafe for organic produce and the gift shop filled with local handmade goods.
Suggested Sightseeing
Boothbay Harbor, Maine
The Boothbay Harbor Region is perfectly situated to provide visitors with the very best Maine has to offer. Whether charging forward or kicking back there are limitless options. Take a hike, and watch for wildlife and birds, along trails preserved by the Boothbay Region Land Trust, with scenic views of rocky shores, coastal islands, and river corridors. Visit Coastal Maine Botanical Gardens, open year-round, and ranked one of the top 10 public gardens in the USA. Boothbay Harbor’s downtown is filled with shops and restaurants that pack in as much history as they do souvenirs and seafood. Pick up a beach read at Sherman’s Maine Coast Book Shop, known as Maine’s oldest bookstore, and something sweet at Orne’s Candy Store, a Boothbay Harbor staple since 1885. Don’t miss Gimbel & Sons Country Store for everything from knickknacks and toys to sauces and jams; at Seawicks Candle Company, you can take home the scents of the coast.
Overnight Location
Boothbay Harbor, Maine
The Boothbay Harbor Region is perfectly situated to provide visitors with the very best Maine has to offer. Whether charging forward or kicking back there are limitless options. Take a hike, and watch for wildlife and birds, along trails preserved by the Boothbay Region Land Trust, with scenic views of rocky shores, coastal islands, and river corridors. Visit Coastal Maine Botanical Gardens, open year-round, and ranked one of the top 10 public gardens in the USA. Boothbay Harbor’s downtown is filled with shops and restaurants that pack in as much history as they do souvenirs and seafood. Pick up a beach read at Sherman’s Maine Coast Book Shop, known as Maine’s oldest bookstore, and something sweet at Orne’s Candy Store, a Boothbay Harbor staple since 1885. Don’t miss Gimbel & Sons Country Store for everything from knickknacks and toys to sauces and jams; at Seawicks Candle Company, you can take home the scents of the coast.
Day 5
Included Unique Activities
Traditional Clambake on the Island
Boothbay Harbor, Maine
Enjoy a Clambake on an Island (June to Sept) Board a boat at Pier 6 in Boothbay Harbor and set off on a narrated scenic cruise while you take in Maine's breathtaking coastline. As you step off the boat, you will be greeted and welcomed onto the island. With indoor and outdoor dining options, you will have ample choices on where to sit. Whilst on the island enjoy a traditional Downeast clambake including fish chowder, two lobsters, clams, golden corn on the cob, potato, onion, a hard steamed egg and Maine's finest blueberry cake. Clambakes are cooked in traditional fashion - steamed over open fires between thick layers of seaweed and covered with tarpaulins to seal in all the great flavor and natural sweetness. After you enjoy your meal, take time to explore the natural beauty of Cabbage Island.
Suggested Sightseeing
Footbridge Brewery, Boothbay Harbor, Maine
Footbridge Brewery is small batch brewery tucked away in Boothbay Harbor, Maine. Focused on making craft beer with as many Maine sourced ingredients as possible while conserving Maine's natural resources. With a broad array of styles, they will very likely have the beer for your palate and also a few beers that you may not have known you were looking for. Their family friendly tasting room is the perfect place to bring some food from the local eateries and enjoy some time with family and friends.
Hours: 12 pm- 8 pm daily.
Rackliff Island, Maine
Rackliff Island is part of the Tenants Harbor and St. George Peninsula, accessed by a breathtaking causeway drive from the mainland. Rackliff Island is perfect for walking, running and biking – plus, it is equidistant to the villages of Port Clyde and Tenants Harbor and the larger cities of Rockland and Camden/Rockport. The communities have vibrant centers with restaurants, museums, shops and cultural events.
Overnight Location
Boothbay Harbor, Maine
The Boothbay Harbor Region is perfectly situated to provide visitors with the very best Maine has to offer. Whether charging forward or kicking back there are limitless options. Take a hike, and watch for wildlife and birds, along trails preserved by the Boothbay Region Land Trust, with scenic views of rocky shores, coastal islands, and river corridors. Visit Coastal Maine Botanical Gardens, open year-round, and ranked one of the top 10 public gardens in the USA. Boothbay Harbor’s downtown is filled with shops and restaurants that pack in as much history as they do souvenirs and seafood. Pick up a beach read at Sherman’s Maine Coast Book Shop, known as Maine’s oldest bookstore, and something sweet at Orne’s Candy Store, a Boothbay Harbor staple since 1885. Don’t miss Gimbel & Sons Country Store for everything from knickknacks and toys to sauces and jams; at Seawicks Candle Company, you can take home the scents of the coast.
Day 6
Daily Itinerary
Drive to Acadia National Park
Drive from Boothbay Harbor, Maine 2 hours and 30 minutes to Acadia National Park. Your hotel borders Acadia National Park and the charming coastal village of Bar Harbor.
Included Unique Activities
Lobstering Boat Ride
Bar Harbor, Maine
Take a Lobster Boat Ride with the experts. Set off from Bar Harbor on a traditional Downeast-style lobster boat with your experienced lobster boat captain, prepare for a personal and unique adventure. Learn all about Maine lobsters and watch them being caught right in front of you and be on the lookout for seals and bald eagles. See beautiful summer cottages, privately-owned islands, and picturesque lighthouses on this exciting Maine experience.
Suggested Sightseeing
Agamont Park, Bar Harbor, Maine
Agamont Park is truly one of the most breathtaking parts of Bar Harbor. This park is located right along the water and is near the downtown area, so you couldn’t miss it if you tried. It’s right next to the town’s Main Street. Because it overlooks the water, one of the best activities here is to pack a picnic (or grab lunch from a local restaurant) and then sit at one of the benches. From there, you can watch all of the great boats on the water. This is also an incredibly epic spot to watch the sunrise or the sunset, especially in the summer!
Overnight Location
Acadia National Park, Maine
Acadia National Park is a stunning national treasure on the coast of Maine covering 47,000-acre primarily on Maine's Mount Desert Island, it is one of the most visited National Parks in North America. Its landscape is marked by woodland, rocky beaches, and glacier-scoured granite peaks such as Cadillac Mountain, the highest point on the United States’ East Coast. Among the wildlife are moose, bear, whales, and seabirds. The bayside town of Bar Harbor, with restaurants and shops, is a popular gateway.
Vehicle reservations for Cadillac Summit Road are required mid-May through mid- October. Vehicle reservations must be paid directly. Visitors must have a park entrance pass to enter the park in addition to purchasing a vehicle reservation for Cadillac Summit Road. Park entrance passes are available at the park or online at Recreation.gov. Vehicle reservations are not required for any other areas of the park, or for visitors who enter the area by foot, bike, or taxi. Cadillac is not served by the Island Explorer bus system. https://www.nps.gov/acad/planyourvisit/vehicle_reservations.htm
Day 7
Daily Itinerary
Explore Acadia National Park
Today you are free to explore the beautiful Acadia National Park. Set off along the iconic Park Loop and explore highlights such as Cadillac Mountain, Sand Beach, and Thunder Hole. Cadillac Mountain is the highest point along the North Atlantic seaboard and a spectacular sunrise or sunset viewing point! Drive or hit the trail up to the top. There are so many trails to choose from in Acadia. If you are looking for a short moderate hike we recommend Flying Mountain. This loop offers a steep hike to the top of a small mountain with spectacular views of Somes Sound and descends to a quiet ocean cove with a rocky beach.
Suggested Sightseeing
Egg Rock Lighthouse, Bar Harbor, Maine
The Egg Rock Lighthouse is one of the most picturesque attractions in the area and overlooks Frenchman Bay. The lighthouse was built in the nineteenth century on 12.5 acre Egg Rock in 1875, is still active today, and is owned and managed by the U.S. Fish and Wildlife Service. The 1.5 story wood keeper's house, also built in 1875, is actually an integral part of the tower. The fog signal house, oil house, boathouse, and generator house were built later in 1904. It is considered one of the most interesting lighthouses in the whole state due to its square tower, which is incredibly unique and unlike any other lighthouses in the area! It was named because of all of the eggs that were commonly found in the area.
Overnight Location
Acadia National Park, Maine
Acadia National Park is a stunning national treasure on the coast of Maine covering 47,000-acre primarily on Maine's Mount Desert Island, it is one of the most visited National Parks in North America. Its landscape is marked by woodland, rocky beaches, and glacier-scoured granite peaks such as Cadillac Mountain, the highest point on the United States’ East Coast. Among the wildlife are moose, bear, whales, and seabirds. The bayside town of Bar Harbor, with restaurants and shops, is a popular gateway.
Vehicle reservations for Cadillac Summit Road are required mid-May through mid- October. Vehicle reservations must be paid directly. Visitors must have a park entrance pass to enter the park in addition to purchasing a vehicle reservation for Cadillac Summit Road. Park entrance passes are available at the park or online at Recreation.gov. Vehicle reservations are not required for any other areas of the park, or for visitors who enter the area by foot, bike, or taxi. Cadillac is not served by the Island Explorer bus system. https://www.nps.gov/acad/planyourvisit/vehicle_reservations.htm
Day 8
Daily Itinerary
Depart from Portland, Maine
Check out of your Bar Harbor Inn and drive 3 hours to the Portland International Jetport in Maine to depart for home.
Depart From
Depart from Portland International Jetport (PWM), Maine
Today you will depart from Portland International Jetport (PWM) in Maine.
2025
Available Dates
Jan, Feb, Mar, Apr, May, Jun, Jul, Aug, Sep, Oct, Nov, Dec
From $2,591 per person
Based on 2 people traveling, customizable to your group size
Your Price Includes:
ACCOMMODATION
1 night Portland's Old Port District
2 nights 3 Star Hotel overlooking the White Mountains
2 nights Historic Victorian B&B on the Waterfront
2 nights Bar Harbor Inn bordering Acadia National Park
DINING OPTIONS INCLUDED
4 Breakfasts at your B&B's
Culinary Walking Tour in Portland
Traditional Clambake in Boothbay
Lunch Aboard Scenic Train
UNIQUE EXPERIENCES
Portland Culinary Walking Tour
First Class Scenic Train Ride with Lunch
Traditional Clambake Experience (June-August)
Enjoy Sailing and Lobstering with Experts
Coastal Maine Botanical Gardens
1. Click the “GET QUOTE” Button Above.
Complete our inquiry form by selecting your departure date, and all other relevant fields. Be sure to let us know if you're traveling for a special occasion! We can adjust most of our vacation packages to suit your needs, based on the details you provide.
2. Online Account & Quote Created
Your request will be forwarded to our team of Destination Experts, and a price quote will be prepared, based on your submitted preferences and criteria. A free Authentic Vacations online account will also be created, allowing you to view and request changes to your quote at any time. Log into your account via “LOGIN” at the top of any of our webpages.
3. Fine-Tune Your Tour Quote
Work with your assigned Destination Expert to tweak your quote in any way you wish. Our customers continually tell us that our flexibility in this regard is exceptional – your Destination Expert’s sole brief is to create the perfect tour for you!
4. Reserve & Pay Online
Once your quote is 100% to your liking, you can pay for your package with your credit card via your Authentic Vacations online account. We also accept payment by personal check and wire transfer. We only require a 20% deposit to secure your vacation, and our Risk-Free Cancellation Policy provides you with complete peace of mind.
5. Print Your Travel Documents & Go!
Once your vacation has been paid in full, you will be able to print your travel documents directly from your online account. You’re ready to embark on your ideal, authentic vacation!!
Questions?
If you would prefer to discuss your perfect vacation on the phone, we would be delighted to hear from you! Our Destination Experts are standing-by and looking forward to speaking with you at any time during our business hours listed below. We also operate a very responsive and efficient Live Chat service on our website…instant gratification awaits!
Toll-free from the US and Canada: 1-888-443-5259 Rest of World: +1-707-687-0191
Hours of Business:
Monday – Thursday: 7:00am – 5:00pm PST
Friday: 7:00am – 4:00pm PST
Saturday: 6:00am – 3:00pm PST
Sunday: 6:00am – 3:00pm PST
With offices in Scottsdale, San Francisco, London, Dublin, Copenhagen and Edinburgh, we can offer you unrivaled support while you are abroad. We truly believe all our clients deserve an extraordinary, authentic experience!
Day 1
Day 2
Day 3
Day 4
Day 5
Day 6
Day 7
Day 8
