According to forum posts, popular outdoor activities in Portland include taking a walk along the Eastern Promenade Trail, visiting Fort William Park to see the Portland Head Light, and hiking around local trails such as those at the Fore River Sanctuary. Travelers have also enjoyed exploring Peaks Island and the Greenbelt in South Portland for ocean views and lighthouse sightings.

Some travelers suggested visiting museums like the Portland Museum of Art, which has a strong permanent collection and special exhibitions. The Wadsworth-Longfellow House and the adjacent Maine Historical Society Museum offer insights into local history with original furnishings and exhibits.

For those looking for unique experiences, forum users recommended activities such as taking an oyster shucking class, participating in a Brews Cruise, or enjoying a painting party at Muse Paintbar. These activities provide a mix of fun and learning and are suitable for groups looking for something different to do.

Portland is noted for its vibrant food scene. Travelers have called out spots like DiMillo’s, Back Bay Grill, and various lobster shacks for memorable dining experiences. For casual dining, places like Gilbert’s Chowder House and Portland Lobster Co. are popular for seafood lovers.

According to forum posts, the Portland Regency and the Press Hotel are popular choices in the Old Port area, appreciated for their unique charm and central location. The Portland Regency is built in an old armory and offers some rooms with fireplaces, whereas the Press Hotel is established in a former newspaper building. Neither hotel provides significant views but is well-liked for its distinctive character and proximity to local amenities.

For travelers seeking picturesque views or a beachfront location, the Inn by the Sea in Cape Elizabeth is highly recommended by some users. It offers a more scenic and tranquil setting compared to downtown Portland options, though it requires a short drive into the city. This hotel is particularly favored for its romantic setting and proximity to the beach.

For families or those needing more spacious accommodations, the Residence Inn in Portland offers suites, and the Holiday Inn by the Bay was mentioned for potentially meeting similar needs. These options are suitable for those traveling with children or needing extra space during their stay.

According to forum posts, travelers can take the Amtrak train or Concord Coach buses from Boston to Portland. The train departs from Boston North Station and the bus service operates from Boston South Station, adjacent to the main Boston bus terminal. The train journey is noted to be about half an hour slower than the nonstop bus service.

Some travelers stated that the Portland Transportation Center, where both the train and bus services arrive, is approximately 2.3 miles from the central attractions in Old Port, Portland. This distance might require additional transportation such as a taxi or Uber to reach downtown areas.

For those considering alternative transport options, the Portland MetroBus system is available with specific routes like the #1 bus linking the Portland Transportation Center to the Old Port and Munjoy Hill. This provides a convenient option for local travel within Portland.

According to forum posts, travelers seeking parking options in downtown Portland have various choices, including street parking and parking garages.

Some travelers mentioned that city-owned and private parking garages are available, with daily rates around $28 at city garages and higher rates at private garages. Notably, the Fore Street Garage and Temple Street Garage are central to many downtown attractions.

For many users, on-street parking is an alternative, free from 6 pm to 9 am from Monday to Saturday and all day on Sundays and holidays. However, it's essential to read parking signs carefully to avoid fines.

Travelers with disabilities can utilize parking meters at no charge and park for twice the normal allowed time with a disability placard. This information is particularly beneficial for those needing closer access to destinations within downtown Portland.

According to forum posts, some high-end hotels recommended in the Old Port area include The Press Hotel, the Portland Regency Hotel & Spa, and the Portland Harbor Hotel. These hotels are noted for their proximity to local attractions, shops, and restaurants.

Travelers have called out that accommodations in the Old Port can be expensive, particularly during peak seasons. One user mentioned that even less expensive options like the Holiday Inn in the Old Port area were higher priced than expected.

For many users, staying in the Old Port is worth the price due to the walkability to major attractions and dining options. The Portland Museum of Art and various local businesses are easily accessible from this area, making it a favorable choice for visitors focused on exploring downtown Portland.

According to forum posts, popular places to eat lobster in Portland include Portland Lobster Company, DiMillos, and Lukes Lobster. DiMillos is noted for its variety in lobster preparations and the ability to take reservations, making it a convenient option for visitors.

For those interested in different culinary approaches to lobster, Eventide offers a unique take on the lobster roll, providing options with warm butter. Additionally, the Lobster Shack at Two Lights is recommended for its classic Maine lobster rolls and scenic location.

Some travelers have suggested exploring local food trucks for a more casual lobster experience, such as Bite Into Maine, which offers lobster rolls at various locations including Fort Williams Park. This spot allows diners to enjoy their food in a picturesque outdoor setting.

At Portlands airport, travelers have mentioned car rental options such as Hertz and Enterprise. The cost of renting a car directly at the airport can be around $90 per day.

Some users have discussed renting cars through Turo for approximately $70 per day, with pickup and drop-off outside the airport, necessitating additional transportation costs to reach these off-airport locations.

When renting a car through airport facilities like Hertz or Enterprise, travelers can use credit card benefits such as those from Chase Sapphire for rental insurance coverage. However, the insurance scenario might differ with services like Turo, where personal insurance policies and Turo’s terms need to be reviewed.