TOP 30 Best Travel in Gloucester, Massachusetts

The Friki Tiki of Gloucester Harbor offers island-style vibes on enchanting Gloucester Harbor in Massachusetts, United States. Perfect for special occasions such as birthdays, bachelor and bachelorette parties, retirement celebrations, and company parties, this unique venue can accommodate up to 20 people. Guests are welcome to bring their favorite snacks and beverages, including alcohol, and can even bring their own playlist for the Bluetooth enabled speaker on board. Choose from a 90-minute Harbor Cruise or Annisquam River Cruise, where you can enjoy picturesque views of Gloucester Harbor, the fishing fleet, Ten Pound Island, Rocky Neck Art Colony, Annisquam River, Three Bridges, Annisquam Lighthouse, and more. The vessel, "The Friki Tiki," is equipped with an onboard bathroom, coolers with ice provided, and a capacity for 20 people. The locally owned and operated business is run by Captain Mark Sinkinson and Captain Forrest, both experienced and certified boat captains. Public cruises are available for booking up to 21 days prior to departure, with options for rescheduling or refunds in case of cancellations. Experience the beauty of Gloucester Harbor and Annisquam River with a fun and relaxing cruise on The Friki Tiki.

The Gloucester Fisherman's Memorial is a poignant tribute to the brave fishermen who have lost their lives at sea. Located in Gloucester, Massachusetts, this park serves as a place of remembrance and reflection for the sacrifices made by those who work in one of the most dangerous professions in the world. The memorial features a larger-than-life statue of a fisherman looking out to sea, symbolizing the strength and resilience of the Gloucester fishing community. Visitors can pay their respects to the fallen fishermen and learn about the rich maritime history of Gloucester. The Gloucester Fisherman's Memorial is a must-visit destination for anyone interested in the maritime heritage of New England.

Long Beach Gloucester is a charming lodging institution located at 44-30 Rockport Road in Gloucester, Massachusetts, United States. Nestled in a picturesque coastal town, this institution offers comfortable accommodations for visitors looking to relax and unwind by the sea. With its serene atmosphere and convenient location near Long Beach, guests can enjoy a peaceful getaway while still being close to local attractions and amenities. Whether you're seeking a weekend retreat or a longer vacation, Long Beach Gloucester provides a welcoming and cozy environment for all travelers.

Cape Ann Travel Services is a premier travel agency located in Gloucester, Massachusetts. With a convenient location at 20 Birch Grove Heights, our experienced team of travel experts is dedicated to providing personalized and tailored services to meet all of your travel needs. Whether you are planning a family vacation, a romantic getaway, or a business trip, we are here to help you every step of the way. From booking flights and accommodations to arranging tours and activities, Cape Ann Travel Services is your one-stop shop for all your travel planning needs. Contact us today to start planning your next adventure!

Connections Adventure Travel is a premier travel agency located at 17 Lincoln Street in Gloucester, Massachusetts. Specializing in unique and unforgettable adventure experiences, our team of expert travel agents are dedicated to creating one-of-a-kind trips for our clients. Whether you're seeking a thrilling outdoor expedition or a culturally immersive journey, we have the knowledge and resources to make your travel dreams a reality. From hiking the rugged mountains of Patagonia to exploring the ancient ruins of Machu Picchu, we offer a wide range of exciting destinations and activities to choose from. Let Connections Adventure Travel be your guide to the ultimate adventure vacation.

Taste Gloucester is a renowned travel agency located at Harbor Loop in Gloucester, Massachusetts, United States. Our most popular tour allows guests to explore downtown Gloucester on foot while sampling delicious food from local vendors. From chowder to cannoli, our tour exposes you to unique local treats that you may not discover on your own. Our knowledgeable tour guides provide interesting facts about the city's 400-year-old history, making sure you leave full of both food and knowledge. If you're looking for a more immersive experience, join our Ales and Tales tour where you can enjoy a drink while listening to thrilling stories from local fishing captains. From wild storms to encounters with the Coast Guard, these tales will give you a glimpse into the life of those who have made their living off the North Atlantic. Don't miss out on this unique opportunity to explore America's oldest working seaport in a fun and informative way.

Welcome to US Customs Services Gloucester Port of Entry, your dedicated partner in facilitating international trade and travel. Located at 100 Cummings Center in Beverly, Massachusetts, we serve as a vital gateway for goods and travelers entering the United States through the Gloucester area. Our team of experienced professionals is committed to ensuring efficient and secure customs processing, compliance with federal regulations, and safeguarding our nation’s borders. At US Customs Services Gloucester Port of Entry, we offer a comprehensive range of services to meet the needs of importers, exporters, and travelers. Our facilities are equipped to handle a variety of shipments, from commercial cargo to personal effects. We provide expert guidance on customs documentation, duties, and tariffs, ensuring a smooth and hassle-free experience for our clients.

Shells Dream Travel is a premier travel agency located at 18 Chestnut Street in Gloucester, Massachusetts, United States. With a team of experienced travel professionals, we specialize in creating unforgettable travel experiences for our clients. From luxurious beach getaways to adventurous mountain expeditions, we offer a wide range of travel packages tailored to suit every traveler's needs and preferences. Let us help you turn your travel dreams into reality at Shells Dream Travel.

Gloucester House Rental - Belle View is a charming lodging establishment located at 57 Grapevine Road in Gloucester, Massachusetts, United States. As a real estate and travel agency, we specialize in providing luxurious house rentals with breathtaking views of the surrounding area. Our properties are meticulously maintained and offer all the amenities needed for a comfortable and relaxing stay. Whether you are looking for a weekend getaway or a longer vacation, Gloucester House Rental - Belle View is the perfect choice for your next trip to Gloucester.

Little House Gloucester is a charming and cozy real estate and travel agency located in the heart of Gloucester, Massachusetts. Our dedicated team of professionals is committed to helping our clients find their dream home or plan the perfect getaway. Whether you're looking to buy or rent a property, or seeking assistance in booking your next vacation, we are here to provide personalized and attentive service. Visit us at 37 Cherry Street and let us help you make your real estate or travel dreams a reality.

Welcome to Martin St/Winthrop St (Bank Gloucester), your convenient transit station located in the heart of Essex, Massachusetts. Situated in the charming community of Essex, our station serves as a vital hub for local commuters and visitors alike. Whether you're traveling for business or leisure, our strategic location at Essex, MA 01929 ensures easy access to various destinations in the region. Our station is designed to provide a seamless and efficient transit experience, with well-maintained facilities and friendly staff ready to assist you. We are committed to making your journey as smooth as possible. Discover the convenience of Martin St/Winthrop St (Bank Gloucester) as your preferred transit point in Essex.

Maritime Heritage Charters is a unique institution located in Gloucester, Massachusetts, United States. As a museum and travel agency, we offer visitors the opportunity to immerse themselves in the rich maritime history of the area. Our location at 23 Harbor Loop provides easy access to the waterfront and a chance to explore historic ships, artifacts, and exhibits. Whether you're interested in booking a charter to sail the open seas or simply want to learn more about the maritime heritage of Gloucester, Maritime Heritage Charters is the perfect destination for maritime enthusiasts of all ages.

Cape Ann Cruises is a reputable travel agency located at 63 Rogers Street in Gloucester, Massachusetts. They specialize in offering a variety of exciting cruise experiences along the beautiful Cape Ann coastline. Whether you're looking for a relaxing harbor cruise, a whale watching excursion, or a sunset cruise, Cape Ann Cruises has something for everyone. Their knowledgeable staff is dedicated to providing top-notch customer service and ensuring that every guest has a memorable and enjoyable experience on the water. Visit Cape Ann Cruises for an unforgettable adventure on the scenic waters of Massachusetts.

Wicked Pissah Fishing is a popular tourist attraction and travel agency located at 75 Essex Avenue in Gloucester, Massachusetts. Known for its exciting and memorable fishing excursions, Wicked Pissah offers visitors the opportunity to experience the thrill of deep sea fishing in the beautiful waters of the Atlantic Ocean. With experienced guides and top-of-the-line equipment, guests are sure to have an unforgettable adventure on the water. Whether you're a seasoned angler or a beginner looking to try your hand at fishing, Wicked Pissah Fishing is the perfect destination for a fun and exciting day out on the water.

The Schooner Thomas E. Lannon is a renowned travel agency located at 63 Rogers Street in the picturesque coastal town of Gloucester, Massachusetts. Specializing in unforgettable sailing experiences, the agency offers a variety of excursions aboard the historic Schooner Thomas E. Lannon, a beautifully restored 65-foot wooden vessel. Guests can enjoy breathtaking views of the Atlantic Ocean, learn about the rich maritime history of the area, and even participate in sailing the ship themselves. Whether you're looking for a romantic sunset cruise or a family-friendly adventure on the water, the Schooner Thomas E. Lannon promises a memorable and unique experience for all who come aboard.

Accommodations At Rocky Neck offers cozy and comfortable lodging in the heart of Gloucester, Massachusetts. Located at 43 Rocky Neck Avenue, this charming institution provides a peaceful retreat for guests looking to relax and unwind by the sea. With its convenient location just steps away from the beach and local shops and restaurants, Accommodations At Rocky Neck is the perfect choice for travelers seeking a tranquil getaway. The well-appointed rooms and friendly staff ensure a pleasant stay for all visitors. Whether you're exploring the historic sights of Gloucester or simply enjoying a leisurely day at the beach, Accommodations At Rocky Neck is the ideal place to call home during your stay in this picturesque coastal town.

Cape Ann Whale Watch is a premier tourist attraction and travel agency located at 415 Main Street in Gloucester, Massachusetts, United States. Embark on a thrilling adventure with experienced guides as you set sail to witness majestic whales in their natural habitat. Enjoy breathtaking views of the Atlantic Ocean while learning about these incredible creatures. Don't miss the opportunity to create unforgettable memories with Cape Ann Whale Watch.

7 Seas Whale Watch, located at 63 Rogers Street in Gloucester, Massachusetts, is a top tourist attraction and travel agency offering daily whale watching trips to the Stellwagen Bank National Marine Sanctuary. Ranked #2 on Tripadvisor's list of top family-fun activities in the world in December 2023, and #1 local attraction based on traveler reviews from 2012-2023, 7 Seas Whale Watch has been providing unforgettable experiences since 1983. With a focus on education, inspiration, and conservation, our tours aim to deepen visitors' understanding and appreciation of the marine environment. Our family-owned business, with three generations of career captains, has a genuine love and respect for the ocean and its inhabitants.

Coastal Fishing Charters, located at 415 Main Street in Gloucester, Massachusetts, is a top-rated travel agency specializing in fishing charters. From tuna charters to striped bass trips, deep sea fishing, and more, their trips run from May through October. With over 35 years of experience, they offer affordable and unforgettable experiences for up to 6 people. Captain Nick Danikas, a licensed coast guard captain, leads the trips and ensures a safe and enjoyable adventure. Whether you're looking to catch some haddock, cod, striped bass, or even bluefin tuna, Coastal Fishing Charters has you covered. Book your trip today and experience the thrill of fishing on the Massachusetts coast!

Connemara Bay Fishing Charters is a travel agency located at 47 Crafts Road in Gloucester, Massachusetts, United States. Specializing in deep sea fishing excursions, lobstering tours, and clambake/lobsterbake cruises in the waters off Cape Ann, including Gloucester, Rockport, Manchester, and Ipswich. Whether you're looking to reel in striped bass, haddock, cod, tuna, or even giant bluefin tuna, Connemara Bay Fishing Charters has you covered. With experienced guides and top-of-the-line equipment, you're sure to have an unforgettable fishing experience. Additionally, you can book a lobstering tour to learn about the sustainable commercial fishery and even take home a lobster for dinner. The charter boats, Connemara Bay II and Silver Lining, offer ample deck space, modern amenities, and all necessary safety equipment for a safe and enjoyable trip. After your fishing excursion, you can have your catch cooked to perfection at Lobsta Land Restaurant. So, whether you're a seasoned angler or a beginner looking for a fun day on the water, Connemara Bay Fishing Charters has something for everyone.

Harborview Inn, located at 71 Western Avenue in Gloucester, Massachusetts, offers comfortable lodging with a stunning view overlooking Stacy Boulevard and Gloucester’s outer harbor. As America’s oldest and most scenic working waterfront, guests can enjoy easy access to beaches, museums, downtown galleries, shops, and restaurants within walking distance. Owned and operated by John, a lifelong resident of Cape Ann, guests can expect a warm welcome and insider’s perspective on the area. Most rooms feature a breathtaking harbor view, private baths, cable TV, and air conditioning. Guests can enjoy a complimentary continental breakfast with fresh fruits and pastries from the Cape Ann area.

Located in the picturesque town of Gloucester, Massachusetts, Wingaersheek Inn & Motel offers comfortable and affordable lodging for visitors looking to explore the stunning beaches and historic sites of Cape Ann. Situated at 46 Concord Street, this charming inn and motel provides cozy rooms with modern amenities, friendly service, and easy access to nearby attractions. Whether you're in town for a weekend getaway or an extended vacation, Wingaersheek Inn & Motel is the perfect home base for your stay in Gloucester.

Capt. Bill & Sons Whale Watch is a renowned travel agency located at 24 Harbor Loop in Gloucester, Massachusetts, United States. With years of experience in providing unforgettable whale watching experiences, they offer top-notch tours led by knowledgeable captains and crew members. Their comfortable vessels provide the perfect platform for spotting majestic whales in their natural habitat. Whether you're a wildlife enthusiast or just looking for a unique adventure, Capt. Bill & Sons Whale Watch is the perfect choice for an exciting and educational experience on the open seas.

Surfari is a trendy clothing store located at 88 Bass Avenue in Gloucester, Massachusetts. Our store offers a wide selection of surf-inspired apparel and accessories for both men and women. Whether you're hitting the waves or just looking to add some beachy vibes to your wardrobe, Surfari has everything you need to ride the wave of style. Come visit us today and experience the laid-back, coastal atmosphere of our store.

Sunreayz Transportation is a reliable and efficient transportation service located at 13 Pond Road in Gloucester, Massachusetts. With a commitment to providing safe and comfortable rides, Sunreayz Transportation offers a range of services including airport transfers, corporate transportation, and special event transportation. Their professional drivers are knowledgeable about the area and dedicated to ensuring a smooth and enjoyable journey for all passengers. Whether you need a ride to the airport or transportation for a special occasion, Sunreayz Transportation is the go-to choice in Gloucester.

The Vista is a charming lodging institution located at 22 Thatcher Road in Gloucester, Massachusetts, United States. Situated in a picturesque setting, this cozy retreat offers comfortable accommodations and stunning views of the surrounding landscape. Whether you are looking for a relaxing getaway or a convenient place to stay while exploring the area, The Vista is the perfect choice. With its warm hospitality and inviting atmosphere, this institution is sure to make your stay memorable.

Julietta House is a charming lodging institution situated at 84 Prospect Street in the picturesque town of Gloucester, Massachusetts, United States. This cozy bed and breakfast offers a warm and inviting atmosphere for guests looking to relax and unwind in a serene setting. With comfortable accommodations and friendly staff, Julietta House is the perfect choice for those seeking a peaceful getaway in the heart of New England. Enjoy a relaxing stay at Julietta House and experience the beauty of Gloucester during your visit.

Salt Water Grille is a bar and restaurant located at 226 Washington Street in Gloucester, Massachusetts. We specialize in delicious seafood dishes, such as Fish and Chips, Sauteed Shrimp, and Shrimp in sweet and spicy sauce. Our menu also includes fresh salads with a variety of toppings, tacos, and other mouthwatering options. Whether you're looking to host an event or simply don't feel like cooking, Salt Water Grille is here to provide you with top-notch service and cuisine. Our friendly and attentive staff will ensure that your dining experience is nothing short of exceptional. Customers have raved about our delicious mussels, fish tacos, and cocktails, making us a must-visit spot in Gloucester.

Cape Ann Harbor Tours is a popular tourist attraction and travel agency located at 66 Harbor Loop in Gloucester, Massachusetts, United States. Offering a variety of scenic boat tours and excursions, visitors can experience the beauty of Cape Ann's historic harbor and coastline. From narrated sightseeing tours to private charters, Cape Ann Harbor Tours provides a unique opportunity to explore the area's rich maritime history and stunning natural landscapes. Whether you're a local looking for a fun day out on the water or a visitor wanting to discover the charm of Gloucester, a trip with Cape Ann Harbor Tours is sure to be a memorable experience.

Plum Cove Beach is a picturesque natural feature located at 1000 Washington Street in Gloucester, Massachusetts, United States. This stunning beach offers pristine sandy shores, crystal-clear waters, and breathtaking views of the Atlantic Ocean. Visitors can enjoy sunbathing, swimming, beachcombing, and picnicking in this tranquil seaside setting. Plum Cove Beach is the perfect spot for a relaxing day by the ocean, surrounded by the beauty of nature.