Guided Tour Of Portland, Maines Largest City By The Sea

Beautiful Maine

Tour # 2272010

October 9, 2026 - October 19, 2026

(11 days/10 nights)

$1,998

Per person/Double Occupancy

Single Supplement: $545

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Daily Itinerary for this Tour

Day 1: Depart your group's location in a spacious, video and restroom equipped motorcoach and set off on your exciting trip! Tonight, settle into a comfortable en route hotel for a good night's rest.
Day 2: After enjoying a Continental Breakfast, you will depart for the Indiana State Museum in Indianapolis. Later in the day, enjoy Dinner and check into your en route hotel.
Day 3: Enjoy a Continental Breakfast before leaving for the National Civil War Museum in Harrisburg, PA. Later that day, after a relaxing Dinner, you'll check into your en route hotel.
Day 4: Today after enjoying a Continental Breakfast, depart for beautiful Maine! Later that day, enjoy a relaxing Dinner and check into your accommodations in Maine for a four-night stay.
Day 5: After a Continental Breakfast, take a Guided Tour of the seaside city of Portland. View Longfellow's boyhood home and sea captains' houses, and stop at Portland Head Lighthouse, the most photographed lighthouse in America. Enjoy free time at the historic Portland waterfront, home to unique shops and eateries. Next, tour Victoria Mansion, an elegant historic home featuring spectacular architecture, stunning interiors, and exquisite, original furnishings. This evening, enjoy Dinner with entertainment.
Day 6: Enjoy a Continental Breakfast before departing for a visit to the Maine Maritime Museum, located on a 20-acre campus on the banks of the Kennebec River in “The City of Ships,” Bath, Maine. The museum connects people to the past, present, and future of Maine's waterways and their global reach. Your visit also includes a tour of the Percy & Small Shipyard, America's only surviving shipyard site where large wooden sailing vessels were once built. Next, explore Boothbay Railway Village, featuring 28 historic structures. You can take a ride aboard the Narrow Gauge Steam Train, marvel at the antique auto exhibit, see an immense model railroad exhibit, authentic boxcars, and much more! Then continue on to Dinner.
Day 7: Today, after a Continental Breakfast, enjoy a Guided Tour of the Maine coastal villages of Kennebunk and Kennebunkport. See Dock Square in Kennebunkport, and follow Ocean Avenue along the Atlantic Ocean. Drive by the estate of President George H.W. Bush at Walker's Point, and see the coastline comparisons of Kennebunk beaches. Explore the gardens and shrines of the Franciscan Monastery. During free time, visit the quaint shops and eateries in downtown Kennebunkport. Next, visit the Seashore Trolley Museum, where you can enjoy a trolley ride on an authentically restored streetcar through the Maine countryside. Later, enjoy a Lobster Dinner, and then visit the L.L. Bean flagship store.
Day 8: Enjoy a Continental Breakfast before leaving for the Boott Cotton Mills Museum in Lowell, MA. Later that day, after a relaxing Dinner, you'll check into your en route hotel.
Day 9: Enjoy a Continental Breakfast at your hotel before leaving for the Hershey's Chocolate World in Hershey, PA! That night, enjoy Dinner and check into your en route hotel.
Day 10: Today you will have Continental Breakfast and then go to the National Museum of the United States Air Force in Dayton, OH. Tonight, rest in your en route hotel.
Day 11: Today, after enjoying a Continental Breakfast, you depart for home... a perfect time to chat with your friends about all the fun things you've done, the great sights you've seen and where your next group trip will take you!

Price Includes ALL of the Following

Top Quality Motorcoach Transportation - Video & Restroom Equipped - 54 Seats

At Diamond Tours, quality is a priority. We know how important it is that you have a comfortable journey. We guarantee each group receives a top quality, video and restroom equipped motorcoach with 54 seats or more.
All Lodging Including 10 Nights Lodging in Maine

Your group deserves a good night sleep each and every night. At Diamond Tours, we provide your group with quality lodging almost always with interior corridors. The lodging we provide is often times national franchise hotels. Sometimes, due to a unique geographic location, the property may not be called a hotel, but rest assured it will always be a quality property.
18 meals: 10 breakfasts and 8 dinners

Diamond Tours trips include All Breakfasts (except on the day of departure) and most Dinners.
LL Bean

It’s not just about the shopping either! The LL Bean Flagship Store also boasts plenty activities as...

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Guided Tour of Portland

Your first glimpse of Portland’s blend of seaport history and the city’s modern flair is the Ocean...

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Historic Portland Waterfront

The renewed interest in preservation and merging Portland’s history with contemporary aspirations...

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Guided Tour of Kennebunkport

This narrated tour will lead you around Portland, Maine’s largest city by the sea, where you can see the town’s amazing beaches, scenic lighthouses, museums, historic neighborhoods, and Walker's Point Estate (or the Bush compound), the summer retreat of the Bush family.

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Victoria Mansion

Morse hired Gustave Herter, a German trained cabinetmaker and interior designer, to decorate his...

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Maine Maritime Museum in Bath, ME

From the moment you arrive, the museum invites you to step into the world of shipbuilders,...

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Boothbay Railway Village

Take a journey through the exhibits of cars, starting in the early 1800’s with carriages and...

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Seashore Trolley Museum

The Seashore Trolley Museum’s campus currently occupies over 330 acres and offers a living history...

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Frequently Asked Questions

For over 38 years, over two million people across America have traveled with Diamond Tours. We are the largest bus tour operator in America dealing exclusively in motorcoach group travel.

Yes! Diamond Tours offers special accommodations for seniors with mobility issues or handicaps. We ensure that all our tours are accessible and enjoyable for everyone.

Yes, adults under the age of 55 can take our trips. We also offer special deals for children.

Our incredible prices include: Top Quality Motorcoach Transportation, most of your meals, all attractions listed, and and all shows listed, all tours, all guided tours, on-site support, and more. You mainly only need extra money for lunch each day and gifts, etc. If the motorcoach vacation you choose is six days in length or more, you will have to pay for two dinners, after that all the others are included in the price.

After you choose the vacation you want to join, click the "Request Information" button and fill out the short contact information form. You will INSTANTLY be sent the group leader's contact information, pick up location, and much more. Then go ahead and contact the group leader to ask any questions and sign up!

A $75 per person deposit is required to secure your reservation and is also applied toward your amount due. Both payments are made directly to the leader of the group for the trip you want to join. If you are joining a trip that is leaving within 9 Weeks of signing up, payment in full would be due. Each group leader has their own methods of accepting payments securely from their passengers. They will discuss methods of payment they accept when you contact them about signing up.

Each group has their own designated departure location and car parking for their bus tours. It is usually a Community Center parking lot, Church parking lot, or something of that nature. That is where you can park your vehicle and also where the passengers get onto the motorcoach to begin their vacation. When you choose the tour you want to join and instantly receive that group leader's contact information, you will be provided with the exact starting location details for that tour.

We have one of the most liberal cancellation policies in the travel industry. Reimbursements for all individual cancellations will be made and honored up to 30 days prior to departure.

For further peace of mind, we suggest purchasing Travel Protection. The group leader for the tour you would like to join can provide you with information on how to purchase it at a low cost.

YES! Diamond Tours' Destination Managers are on-location at the destination to assist you!!! They are there to make sure the trip goes exactly as planned and help with any needs that arise.

Diamond Tours deals with 55+ senior citizen groups. For example, Senior Citizen Centers, Community Centers, Church Groups, AARP Chapters, and Travel Agents that resell our tours to Seniors, etc. The designated "Group Leader" for each trip is the person you pay directly and sign up with. They are also trained to answer all of the common questions passengers typically have.

Diamond Tours is a Wholesale Group Tour Operator, specializing in Motorcoach Travel. Most Groups we work with have been using Diamond Tours for their Motorcoach Vacation needs for many years! We sell our group motorcoach vacation packages to these groups who then offer them to their group's members and the 55+ community in their surrounding area.

We only use top quality, video and restroom equipped touring motorcoaches with at least 54 reclining, comfortable seats. If the bus is not already equipped with WiFi, you can always use the data connection from your mobile phone.

Diamond Tours books major franchise hotels. Our on-site representatives regularly inspect hotels for sanitation, hospitality and safety. Common hotels chains we use are: Fairfield Inn & Suites, Courtyard by Marriot, Sheraton Hotel, Springhill Suites, Comfort Suites, and other similar properties in quality and type.

Yes. We supply you with all of tour documents and itineraries you need. They are the most detailed itineraries than any other tour company in America.