1 | plan around event or spectator sport

A cornerstone of any great trip can be a event that ties everything together. Portland is packed with year-round events, festivals, and fairs, making it easy to anchor your trip around something special. Whether you’re into art, food, music, or outdoor celebrations, Portland’s events are filled with seasonal highlights that can give your visit focus. A major performance, exhibit, or activity can offer a central theme to your itinerary, providing both a reason to visit and a way to organize the rest of your stay.

Portland, Maine, offers a variety of sports activities year-round, attracting fans of all types of games and competitions. From minor league hockey to baseball, the city boasts a strong sports culture that keeps both locals and visitors engaged. One of the city’s standout teams is the Maine Mariners, a professional ice hockey team that competes in the ECHL. Playing their home games at the Cross Insurance Arena.

2 | Find a Deal or Package

Maximizing your budget is a smart way to make the most of your trip to Portland, Maine. Our partners offer a variety of deals and packages that allow visitors to enjoy luxury stays, exciting tours, and dining experiences at a fraction of the cost. Seasonal offers often bundle hotel stays with local tours or dining vouchers, adding to the value of your stay. Whether you’re eyeing a romantic getaway, a family trip, or an adventure with friends, you can find packages tailored to suit your needs. Keep an eye on local sites to discover the latest promotions and special offers during your stay.

For those planning special events like meetings or weddings, our site also offers exclusive group deals and discounts. Many of the city’s services provide group packages to help you organize large gatherings while staying within budget. Whether you need to book a block of rooms for a wedding deal or secure space for a conference, Portland’s venues offer plenty of options to ensure your event is seamless and affordable.

3 | use trip planner for personalized itinerary

Creating a personalized itinerary is key to making the most of your visit to Portland. With so many attractions, restaurants, and activities to choose from, the Portland Trip Planner tool helps you customize your trip based on your interests. All you have to do is explore Visit Portland’s website to find aspects of the potential trip you want to save for later. You’ll see a “Save Your Trip Plan” button on almost every content page.

By using the trip planner, you bookmark your favorite activities and events and design a detailed itinerary that covers everything from future dining reservations to hotel bookings. It also allows you to map out distances between stops, so you can maximize your time and avoid the hassle of last-minute decisions. With this trip plan in hand, you’ll stay organized and ensure your trip goes smoothly, start to finish​.

4 | book THE BEST hotelS IN PORTLAND early

Booking your Portland, Maine hotel early is one of the most important steps in planning your trip to Portland. With a wide range of options, from boutique inns to modern waterfront hotels, there’s something to suit every traveler’s taste. However, Portland is a popular year-round destination, and accommodations fill up quickly, especially during peak seasons and major events. By reserving your room in advance, you’ll ensure that you get the perfect location, whether it’s in the heart of the Old Port or with stunning coastal views across the region.

Early booking also allows you to find packages that save money on vacation that may include breakfast, spa services, or even discounted tours. By planning ahead, you can secure these special offers and enjoy added perks during your stay.

5 | reserve table at top restaurants in portland

Portland’s dining scene is renowned for its creativity, quality, and focus on local ingredients. Whether you’re craving fresh seafood, farm-to-table meals, or a unique culinary experience, the city offers some of the best restaurants in the US. Planning ahead by booking your restaurants not only guarantees you a spot at your top dining choices, but also allows you to time your meals around activities and events.

By booking your restaurant reservations early, you can create the perfect place to start when booking your trip. Best restaurants in Portland are especially popular during peak seasons like summer and fall, so securing a table in advance ensures you get to experience every spot on your must-do list. If you’re visiting during the vibrant winter season, you’ll find a different side of Portland’s dining scene—quaint, cozy restaurants loved by locals. Cooler weather means fewer crowds and a more relaxed experience, allowing you to skip the lines at your favorite spots while soaking in the intimate, laid-back atmosphere.

6 | Secure Tickets to CONCERTS + Touring Performances

Portland’s entertainment scene is diverse and inclusive, with everything from headlining music acts and theatre to art shows and historic exhibits. If you’re planning a trip to Greater Portland, exploring the variety of performances and events available can be a great starting point. Whether you’re interested in catching a local performance or a larger production/touring act, there’s always something happening. This wide range of entertainment options makes it easy to shape your visit around unique experiences that match your interests.

7 | organize a guided tour IN gREATER pORTLAND

Exploring Portland’s attractions through guided tours and activities is a great way to dive deeper into the city’s history, culture, and natural beauty. Whether you’re interested in walking tours, boat cruises, brewery visits, or outdoor adventures, there’s something for every type of traveler. Starting your trip planning with a look at available tours can help shape your itinerary, giving you the opportunity to explore Portland’s hidden gems with expert guidance.

From scenic lighthouse tours along the coast to food and drink experiences downtown, you can find a variety of activities that fit your interests. Browse Portland’s tour options and experiences to discover the best ways to see the city up close, ensuring your visit is filled with memorable moments and unique adventures

8 | plot YOUR Maine day trips

When planning a trip to Portland, figuring out how much ground you want to cover is key to shaping your itinerary. Portland is perfectly positioned for easy day trips to nearby attractions, whether you’re interested in coastal towns, beaches, scenic parks + trails, or local lighthouses. A day trip is a great way to expand your experience without straying too far from the city.

To make the most of your trip planning stage, start by checking out our Visitor’s Guide to explore maps and discover the best places to visit within 30 minutes of Portland. With a variety of nearby destinations, you’ll find plenty of options for day trips that fit into your schedule.

9 | pICK + pack for the season

One of the best parts of visiting Portland is that every season offers something special. Deciding when to visit can shape your entire experience, whether you’re exploring during the vibrant fall colors or taking in the cozy winter atmosphere. Winter into the Spring you’ll enjoy cooler, refreshing weather perfect for strolling through the city cobblestones and twinkling lights. Summer brings warm sunshine, ideal for coastal adventure and outdoor dining, while fall delivers vibrant hues and seasonal harvests. Once you’ve chosen the season that excites you most, it’s time to pack accordingly.

For all seasons, think about layers. Cozy sweaters, jackets, and boots are perfect for staying warm as you explore the waterfront in the late Fall through the start of Spring. In the warmer months, pack light clothing, sunscreen, and comfortable shoes for walking. With the right gear, you’ll be ready to fully enjoy all the seasonal activities Greater Portland has to offer. Knowing when you plan to visit is a great way to start figuring out how to plan the rest of the trip.

10 | Follow VISIT PORTLAND for Inspiration + Insider Info

Want to stay updated with the latest events, deals, and insider tips? One of the easiest ways to keep your Portland trip planning on track is by subscribing to our Insider Newsletter. By signing up, you’ll receive exclusive offers, travel inspiration, and up-to-the-minute information on Portland’s best-kept secrets, all delivered straight to your inbox.

Our social media channels are another great way to stay connected and inspired. Follow us to get real-time updates on local happenings, seasonal highlights, and hidden gems. Whether you’re in the early stages of planning or just looking for the final touches, staying connected ensures you have all the tools you need to create the perfect Portland getaway.