TOP 30 Best Unforgettable vacations in Portland, Maine

Sail Portland Maine, located at 1 Marina Way in Portland, Maine, offers the best boat charters in the city. Relax with friends and family aboard the Eleanor Hawkes or Calista Ann as you cruise through the tranquil waters of Portland Harbor and Casco Bay. Enjoy the sights of the Portland skyline, historic forts, and wildlife like seals swimming in the harbor. Experience the ultimate Flappy Hour celebration with a chartered cruise to Crown Jewel on Great Diamond Island. Choose from public or private charters, and bring your own food and beverages aboard. Private charters are perfect for special occasions, from romantic dinners to elopements.

New England EcoAdventures in Portland, ME offers unique and thrilling boat tours that blend adventure and education. Departing from the picturesque Portland Harbor, our small, intimate excursions take you to places other tour boats can't reach. From whale watching in the Gulf of Maine to exploring the Kennebunkport Coastline, our tours offer something for everyone. Our knowledgeable captains will tailor the tour to the weather and your preferences, ensuring a first-class experience. Whether you're a sightseer, thrill-seeker, or marine lover, our boat tours are the perfect way to explore the beauty of the Maine coastline. Don't miss out on the opportunity to see lighthouses, wildlife, and historic forts while enjoying a thrilling marine adventure with New England EcoAdventures. Book your tour today and create unforgettable memories on the Atlantic Ocean.

Portland Paddle is a travel agency located at 1 Cutter Street in Portland, Maine, United States. Glide across Casco Bay as the sun sets on a leisurely paddle along the waterfront or into the islands for a panoramic view of the city. Explore historic sites like Fort Gorges on a guided sea kayak tour or learn basic sea kayaking skills in a weekend workshop. Island-hop through Casco Bay or join a three-day journey on the Maine Island Trail. Experience Muscongus Bay on a three-day trip or explore the waters between Penobscot Bay and Acadia National Park on a four-day expedition. Learn kayak rescues or plan a winter paddling adventure with Portland Paddle. Clients rave about their experiences, praising the knowledgeable guides and unforgettable trips. Book your kayaking adventure with Portland Paddle today!

Portland Schooner Co. is a premier travel agency located at the Maine State Pier in Portland, Maine. Specializing in sailing adventures, they offer unique and unforgettable experiences aboard their historic schooners. Whether you're looking for a romantic sunset cruise or a fun-filled day trip with family and friends, Portland Schooner Co. has something for everyone. Set sail with them and explore the stunning coastline of Maine while enjoying top-notch service and hospitality. Book your next sailing excursion with Portland Schooner Co. for a truly memorable and exciting adventure on the water.

Longer Vacations is a premier travel agency located at 110 Marginal Way in the bustling city of Portland, Maine. With a commitment to providing exceptional service and unforgettable experiences, Longer Vacations specializes in creating dream vacations that cater to all preferences and budgets. Whether you're looking to relax on a tropical beach, explore historic landmarks, or embark on a thrilling adventure, our team of experienced travel experts will help you plan the perfect getaway. Contact us today to start planning your next unforgettable vacation with Longer Vacations.

Visit Portland Maine is a premier travel agency located at 1375 Congress Street in Portland, Maine, United States. Specializing in creating unforgettable experiences in one of New England's most charming cities, Visit Portland Maine offers a wide range of services including hotel bookings, guided tours, and personalized itineraries. Whether you're looking to explore the historic Old Port district, sample delicious seafood, or take in the natural beauty of the surrounding coastline, Visit Portland Maine is your go-to resource for all things Portland. Let us help you plan your next adventure in this vibrant and welcoming city.

DreamVista Vacations is a premier travel agency located at 443 Western Avenue in South Portland, Maine. Our team of experienced travel experts is dedicated to helping you plan your dream vacation. Whether you're looking to relax on a tropical beach, explore a new city, or embark on an adventure-packed getaway, we can make it happen. Let us take the stress out of travel planning and turn your vacation dreams into a reality. Contact us today to start planning your next unforgettable trip with DreamVista Vacations.

Casco Bay Custom Charters, located at 14 Ocean Street in South Portland, Maine, invites you to embark on an unforgettable journey through the splendor of Casco Bay. Our customizable private boat charters and tours offer a unique perspective of Maine's coastal beauty. For over a decade, we have been providing personalized experiences that showcase the region's landscapes, lighthouses, and culinary delights. Our experienced crews are passionate about sharing their knowledge and love for Maine, ensuring that each voyage is not only enjoyable but truly memorable. Whether you are looking for an intimate cruise for up to 6 guests on a vintage lobster boat or a larger gathering of up to 16, we offer exclusive charters tailored to your preferences.

Nautilus Sailing Company is a premier travel agency located at 1 Marina Way in Portland, Maine, United States. Specializing in sailing adventures, our experienced team of experts can help you plan the perfect sailing excursion. Whether you're a seasoned sailor or a beginner looking to learn the ropes, Nautilus Sailing Company offers a range of services to meet your needs. From private charters to group sailing trips, we are dedicated to providing unforgettable experiences on the open water. Contact us today to start planning your next sailing adventure with Nautilus Sailing Company.

Reel Action Charters is a premier charter service located at 1 Portland Street Pier in South Portland, Maine. Our goal is to provide our customers with an unforgettable fishing experience, whether you're looking for that "once in a lifetime catch" or a leisurely cruise along the coast. Our courteous and knowledgeable crew, top-notch equipment, and attention to detail ensure that every trip with Reel Action is enjoyable and productive. Our captains have Master licenses issued by the United States Coast Guard and over 20 years of experience, guaranteeing your safety while on the water. We pride ourselves on using the best tackle available and encourage you to bring your "lucky" rod to land a trophy fish. With a focus on customer satisfaction, Reel Action Charters goes above and beyond to exceed your expectations and keep you coming back for more.

Kristin K Charters is a renowned institution located at 231 Front Street in South Portland, Maine, United States. As a leading school and travel agency, we specialize in providing unforgettable deep sea fishing experiences in Portland Maine. Our skilled Captain Ben offers a variety of fishing trips, including inshore saltwater fishing for Sea Bass, Cod, Bluefish, and Mackerel, as well as ground fishing for Cod, Haddock, Pollock, and more. Additionally, we offer ocean cruises and tours, such as seal and whale watching, dinner and sunset cruises, and scenic island tours. With a high rate of returning customers, we take pride in ensuring that every trip with Kristin K Charters is a memorable one. Captain Ben is dedicated to providing a fun and active experience for all guests, including families with children and beginners. Whether you're looking for a short family fun trip or a full-day deep-sea fishing adventure, we have options to suit every preference.

LiveLiner Charters-Maine Deep Sea Fishing Charters is a premier fishing charter located at 257 Front Street in South Portland, Maine. We offer unforgettable deep sea fishing experiences for anglers of all skill levels. Our experienced captains and crew will guide you to the best fishing spots in the area, ensuring a successful and thrilling day on the water. Whether you are looking to catch trophy fish or simply enjoy a relaxing day on the ocean, LiveLiner Charters is the perfect choice for your next fishing adventure. Book your trip with us today and create memories that will last a lifetime.

Lucky Catch Cruises is a premier travel agency located at 170 Commercial Street in Portland, Maine, United States. Specializing in unique and unforgettable cruise experiences, Lucky Catch Cruises offers a variety of excursions for travelers looking to explore the beautiful coast of Maine. Whether you're interested in whale watching, lobster fishing, or simply enjoying a leisurely boat ride, Lucky Catch Cruises has something for everyone. With expert guides, top-of-the-line vessels, and a commitment to customer satisfaction, Lucky Catch Cruises ensures that every journey is a memorable one. Book your next adventure with Lucky Catch Cruises and discover the beauty of Maine's coastline like never before.

Maine Brews Cruise, located at 320 Fore Street in Portland, Maine, is the ultimate destination for craft beer and beverage enthusiasts. Founded as The Maine Brew Bus in 2012 by Zach and Allison Poole, this institution offers all-inclusive tours and experiences that give guests a unique behind-the-scenes look at Maine's top craft breweries, distilleries, wineries, and more. With expert guides and dedicated drivers leading the way, guests have the opportunity to explore both established and up-and-coming producers, gaining valuable insights into the craft alcohol industry. Since its inception, Maine Brews Cruise has connected over 35,000 people to the vibrant world of Maine's craft alcohol producers.

Whiptail Adventures Fishing Charters offers exciting and memorable fishing experiences in the beautiful waters of South Portland, Maine. Our experienced captains will take you on a thrilling journey to catch a variety of fish species, including striped bass, bluefish, and more. Whether you are a novice angler or a seasoned pro, our charters cater to all skill levels. Our state-of-the-art boats are equipped with top-of-the-line fishing gear and safety equipment to ensure a safe and enjoyable trip. Join us at 1 Spring Point Drive for an unforgettable day on the water with Whiptail Adventures Fishing Charters.

Munjoyous is a tranquil health and spa institution located at 83 Vesper Street in Portland, Maine. Offering a wide range of rejuvenating services, Munjoyous is dedicated to providing a holistic approach to wellness and relaxation. From soothing massages to invigorating facials, guests can indulge in luxurious treatments that promote both physical and mental well-being. The expert staff at Munjoyous are committed to creating a peaceful and rejuvenating environment for all visitors, ensuring a truly unforgettable spa experience. Visit Munjoyous and discover a sanctuary where relaxation and rejuvenation are the top priorities.

Maine Island Kayak Co is a premier store and travel agency located at 88 Island Avenue in Portland, Maine. We offer a wide range of high-quality kayaks and gear for all your paddling adventures. Our experienced staff is dedicated to providing expert advice and guidance to help you make the most of your time on the water. Whether you're a beginner looking to rent a kayak for a leisurely paddle or an experienced paddler seeking a guided tour of the beautiful Maine coastline, Maine Island Kayak Co has everything you need for an unforgettable experience. Visit us today and start planning your next kayaking adventure!

Summer Feet Cycling is a premier cycling institution located at 6 Commercial Street in the vibrant city of Portland, Maine, United States. We offer a variety of guided cycling tours that allow you to explore the beautiful landscapes and charming towns of Maine on two wheels. Whether you're a beginner or an experienced rider, our knowledgeable guides will lead you on unforgettable adventures, showcasing the best of what this picturesque region has to offer. From coastal rides to mountain excursions, Summer Feet Cycling has something for everyone. Join us for a unique and active way to experience the beauty of Maine.

Located at 9 Main Street in Waterville, Maine, the Lockwood Hotel has been voted as the #1 lodging in the 2023 Morning Sentinel Reader's Choice Awards. This unique destination blends the classic beauty of New England with modern hospitality, offering guests a one-of-a-kind experience. Centrally located between Portland, the Sugarloaf ski area, Acadia National Park, and the Mid-Coast, the Lockwood Hotel is the perfect basecamp for exploring Maine's natural beauty. The hotel's restaurant, Front & Main, serves creative and nourishing cuisine made with locally sourced ingredients, showcasing Waterville's community-focused dining scene. Each room at the Lockwood Hotel features elegant modern touches, museum-quality artwork, and thoughtful amenities that cater to guests who appreciate the finer things in life.

The Maine State Visitor Information Center in Kittery, located on U.S. 1, is the perfect starting point for anyone looking to explore all that Maine has to offer. From iconic lighthouses to award-winning restaurants, Maine has unique experiences year-round for every traveler. Whether you're seeking a peaceful retreat or a fun-filled family adventure, the Maine Tourism Association can provide you with the information and resources needed to plan an unforgettable trip. Maine is a state of vast natural beauty, with 90 percent of its land covered in forests and a coastline that stretches as far as California. With diverse wildlife, rich history, and deep cultural roots, Maine offers something for every history buff, art enthusiast, and foodie. From exploring historical landmarks to indulging in local cuisine at lobster shacks and fine dining restaurants, Maine has it all.

The Maine State Visitor Information Center in Yarmouth, located at 1100 U.S. 1, is a hub for travelers looking to explore the beauty and wonders of Maine. From iconic lighthouses to award-winning restaurants in Portland, Maine offers unique experiences year-round. Whether you're seeking a peaceful retreat or a fun-filled family adventure, the Maine Tourism Association provides all the information and resources you need to plan an unforgettable trip. With 90 percent of the state covered in forest and a coastline that stretches for miles, there is no shortage of things to see and do in Maine. Explore the rich history, cultural attractions, and diverse wildlife that make Maine a truly special destination. Indulge in Maine cuisine, shop for unique souvenirs, and experience the outdoor adventures that the state has to offer. Whether you're interested in hiking, fishing, sailing, or dog-sledding, Maine has something for everyone. Plan your trip with the Maine Tourism Association and discover all that this beautiful state has to offer.

Funtown Splashtown USA is a premier amusement and water park located at 774 Portland Road, Saco, Maine 04072, United States. As one of New England's top family destinations, this vibrant park offers a thrilling array of rides, slides, and attractions designed to entertain visitors of all ages. Funtown Splashtown USA boasts a wide variety of amusement rides, from heart-pounding roller coasters to classic carousels, ensuring fun for both adrenaline seekers and those looking for a more relaxed experience. The water park section, Splashtown, features an exciting selection of water slides, wave pools, and lazy rivers, providing the perfect way to cool off on a hot summer day. In addition to its rides and attractions, the park offers numerous dining options, games, and live entertainment, making it a complete family-friendly destination.

Located at 88 Grandview Avenue in Boothbay Harbor, Maine, Spruce Point Inn Resort & Spa is a Conde Nast Top Resort that offers the epitome of a Maine retreat. Nestled "down east" from Portland, this historic gem provides an iconic coastal experience with its oceanfront setting, mature woodlands, and thoughtful amenities. Whether you're looking for a romantic escape or a family getaway, Spruce Point Inn has inviting lodge rooms and cozy cottages designed for your comfort. Indulge in dining excellence at the on-site restaurant, where Northeastern culinary mastery and coastal elegance come together. Relax and rejuvenate at The Spa, nestled in refreshing pines, offering massages, facials, and luxurious body rituals. Boothbay Harbor summer colonies have been a popular destination since the 1870s, embodying timeless coastal charm and maritime allure. Guests can also enjoy sailing on a fully restored classic Friendship sloop, the only wooden sailing lobster boat on the Maine coast, exclusively available from the Spruce Point Inn Dock. Additionally, Spruce Point Inn hosts events such as the Windjammer Days SPI Cup, a day of R/C sailboat racing, and offers a picturesque setting for weddings and meetings.

Hemlock Grove Campground is a cozy and picturesque retreat located at 1299 Portland Road in Arundel, Maine, United States. This charming institution offers a variety of accommodation options, including campsites, cabins, and RV hookups, perfect for a relaxing getaway in the serene surroundings of nature. The campground features lush greenery, towering hemlock trees, and a peaceful atmosphere, making it an ideal destination for outdoor enthusiasts and nature lovers. Whether you're looking to unwind by a crackling campfire, explore the nearby hiking trails, or simply enjoy the beauty of the surrounding park, Hemlock Grove Campground provides a tranquil and unforgettable experience for visitors of all ages.

House Island is the ultimate private island retreat located in Portland, Maine, United States. This exclusive lodging destination offers complete privacy, safety, and security on its northern 12 acres, featuring 5 beaches and 3 luxurious homes. The rentals at House Island are weekly and include access to the entire northern half of the island. Guests can choose from 2 waterfront villas and 1 waterfront cottage, accommodating up to 20 guests in total. The accommodations are beautifully designed, with spacious bedrooms, modern amenities, and stunning views of the surrounding landscape.

Maine Tourism Associates is a travel agency located at 97 Main Street in Fryeburg, Maine, United States. From the iconic lighthouses to the cobblestone streets of Portland, Maine offers unique year-round experiences for everyone. Whether you're interested in world-class art museums, famous lobster shacks, fine dining, ski lodges, or spotting moose in the wilderness, the Maine Tourism Association has the information and resources to help you plan an unforgettable trip. Maine is 90% forest with a coastline that could stretch to California, offering endless opportunities for exploration. In addition to moose, the state is home to black bears, bobcats, and loons, making it a wildlife enthusiast's paradise. With a rich history and deep cultural roots, Maine also has plenty to offer history buffs and art enthusiasts alike.

The Maine Tour Connection is a premier tour operator located at 96 Ocean Street in South Portland, Maine. We specialize in providing unforgettable and unique tours throughout the beautiful state of Maine. Whether you're interested in exploring the rugged coastline, quaint coastal towns, or vibrant cities, we have a tour that will suit your interests. Our experienced guides are passionate about showcasing the best of what Maine has to offer, ensuring that you have a truly memorable experience. Join us on a journey through the stunning landscapes and rich culture of Maine with The Maine Tour Connection.

Maine Sailing Adventures offers unforgettable sailing experiences along the beautiful coast of Maine. Located at 56 Commercial Street in Portland, our experienced captains and crew are dedicated to providing guests with a safe and enjoyable journey on the water. Whether you're looking for a relaxing sunset cruise, a hands-on sailing lesson, or a multi-day sailing expedition, we have a variety of options to suit your needs. Come aboard and discover the magic of sailing in Maine with Maine Sailing Adventures.

Angie Johnson Travel Coordinator is an American Express Representative located in Portland, Maine, United States. As a travel agency, we specialize in creating unforgettable travel experiences for our clients. With a focus on exceptional customer service and attention to detail, we strive to make every trip seamless and stress-free. Whether you're planning a family vacation, romantic getaway, or business trip, our team of experienced travel coordinators is here to help you every step of the way. Contact us today to start planning your next adventure!

CGG Curated Travel is a premier travel agency located at 120 Clifton Street in the vibrant city of Portland, Maine, United States. Specializing in personalized and curated travel experiences, our team of expert travel advisors will work with you to create unforgettable journeys tailored to your unique preferences and interests. Whether you are looking for a luxury vacation, a cultural exploration, or an adventure off the beaten path, CGG Curated Travel will ensure that every detail of your trip is meticulously planned and executed. Let us take the stress out of travel planning and help you create memories that will last a lifetime.