Deals on vacations and trips to Gloucester
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Gloucester flight + hotel vacation packages
Sea Mist Resort by VRI Americas
Global Luxury Suites Downtown Boston
Raffles Boston
Boston Harbor Hotel
Mandarin Oriental, Boston
Top Gloucester hotels deals
Beauport Hotel Gloucester
The Hotel at Cape Ann Marina
Castle Manor Inn
The Vista
DoubleTree by Hilton Boston North Shore
Popular places to visit
Wingaersheek Beach
Why not spend a carefree afternoon at Wingaersheek Beach during your travels in Gloucester? While you're in the area, stroll along the seaside.
Good Harbor Beach
If a restful vacation is part of your travel plans, Good Harbor Beach might be the perfect place to seek out during your trip to Gloucester. While you're in the area, stroll along the seaside.
Hammond Castle
You can browse the exhibits at Hammond Castle, a museum with a story of its own, during your trip to Gloucester. Wander the beautiful beaches and seaside in the area.
Top reasons for your vacation to Gloucester
- Breathtaking Ocean Views: Gloucester, located on Cape Ann, offers stunning views of the Atlantic Ocean that will leave you in awe.
- Good Harbor Beach: This beautiful beach is perfect for sunbathing, swimming, and enjoying the refreshing waters of the Atlantic.
- Whale Watching: Embark on a thrilling whale watching tour and witness these majestic creatures up close in their natural habitat.
- Delicious Seafood: Indulge in the town's rich fishing heritage by dining on fresh and flavorful seafood at local eateries.
- Historical Monuments: Explore the historical monuments in Gloucester and learn about the town's fascinating past.
Explore the best activities and sights in Gloucester
Gloucester, located on the coast of Massachusetts, offers a perfect beach vacation for families. With its proximity to the sea, there are plenty of activities to engage in, such as whale watching, boating, and fishing. You can also explore the historical monuments and indulge in the local seafood. Enjoy the spectacular views of Ipswich Bay and Plum Cove while engaging in destination activities, cruises, and sailing. Don't miss out on the chance to spot dolphins and whales during a thrilling dolphin and whale watching tour. The fishing pier in Gloucester is also a popular spot for family fun.
- Wingaersheek Beach: Wingaersheek Beach is a picturesque beach destination that offers a truly family-friendly experience. With its pristine sandy shores, crystal-clear waters, and gentle waves, it is the perfect place to relax and unwind. The beach also provides opportunities for boating, allowing visitors to explore the surrounding area and enjoy the stunning coastal scenery. Additionally, Wingaersheek Beach offers a variety of shopping and dining options nearby, making it convenient for families to enjoy a day by the sea while indulging in delicious food and finding unique souvenirs.
- Dogtown: Dogtown is an outdoor enthusiast's paradise. This hiking trail offers breathtaking views of the sea and beach, with opportunities for visitors to venture along the port and witness the bustling boating activities. The trail also leads to areas known for their fresh seafood, perfect for enjoying a scenic picnic or a beachside meal. Dogtown is especially renowned for its stunning sunrises and sunsets, providing a captivating backdrop for nature lovers. With the chance to spot whales and explore nearby islands, this trail promises an unforgettable adventure and an immersive experience in Gloucester's natural beauty.
- Good Harbor Beach: Good Harbor Beach is a beloved beach destination that offers a delightful experience for beachgoers of all ages. Its expansive sandy shores are perfect for sunbathing, building sandcastles, and enjoying fun beach activities. The beach is conveniently located near a bustling port, adding to its charm and providing opportunities for visitors to witness boats sailing in and out. Good Harbor Beach is also known for its stunning sunrise views, setting a serene and picturesque atmosphere. With nearby shopping options and dining establishments, visitors can easily combine relaxation with delightful excursions and delicious meals.
Where to stay in Gloucester
Get ready for a beach vacation like no other in Gloucester, Massachusetts! Located on Cape Ann, this charming New England town offers breathtaking ocean views and a laid-back coastal vibe. Discover the beauty of Good Harbor Beach, where you can soak up the sun and dip your toes in the refreshing Atlantic waters. For a unique experience, embark on a whale watching tour and witness these majestic creatures up close. And don't forget to indulge in delicious seafood at the local eateries, showcasing the town's rich fishing heritage. Gloucester is the perfect destination for a fun-filled family getaway!
- Annisquam: Annisquam is a charming neighborhood in Gloucester, Massachusetts. Known for its quaint New England vibe, this region offers a unique experience for a beach vacation with your family. With its picturesque views of the Annisquam River and beautiful coastline, it is a perfect spot for relaxing by the beach and enjoying water activities like swimming and kayaking. Annisquam also has a rich history and is home to historic buildings, including the Annisquam Village Church. Explore the neighborhood's narrow streets lined with charming cottages, visit local art galleries, and indulge in delicious seafood at waterfront restaurants.
- Magnolia: Magnolia is another popular neighborhood in Gloucester, Massachusetts, renowned for its family-friendly atmosphere and stunning beaches. This region offers a range of activities for the whole family, from building sandcastles and sunbathing on the beach to exploring tide pools and collecting seashells. Magnolia also has a variety of shops, perfect for browsing unique souvenirs and beach essentials. After a day of fun in the sun, dine at one of the neighborhood's cozy restaurants and savor fresh seafood dishes. Magnolia's relaxed and welcoming ambiance makes it an ideal destination for a beach vacation with your family.
The travel seasons of Gloucester
Trips to Gloucester show a small change in popularity throughout the year. The peak season to visit is from June to August, with July being the highest month. Off-peak season starts from November to January, and December sees the least travelers.
Gloucester has something in store for you whenever you visit. January is the coldest month of the year, while July is hottest, with average temperatures up to 69.6 degrees Fahrenheit. The wettest month in Gloucester is July, so pack accordingly.
 Calendar Month |  Temperature |  Precipitation |  Cloudiness |
| January | 31.1°F (-0.5°C) | Light Rain | Mostly Sunny |
| February | 31.8°F (-0.1°C) | Light Rain | Mostly Sunny |
| March | 36.7°F (2.6°C) | Light Rain | Mostly Sunny |
| April | 45.1°F (7.3°C) | Light Rain | Mostly Sunny |
| May | 54.3°F (12.4°C) | Light Rain | Mostly Sunny |
| June | 62.4°F (16.9°C) | Light Rain | Mostly Sunny |
| July | 69.6°F (20.9°C) | Light Rain | Mostly Sunny |
| August | 69.4°F (20.8°C) | Light Rain | Mostly Sunny |
| September | 64.0°F (17.8°C) | Light Rain | Mostly Sunny |
| October | 55.2°F (12.9°C) | Light Rain | Mostly Sunny |
| November | 45.1°F (7.3°C) | Light Rain | Mostly Sunny |
| December | 37.4°F (3.0°C) | Light Rain | Mostly Sunny |
Food and dining in Gloucester
Gloucester, Massachusetts, known for its rich sea-faring communities, offers a variety of local cuisines that will satisfy any food lover's cravings. One must-visit restaurant is the Azorean Restaurant & Bar, a highly-rated European Mediterranean restaurant. Indulge in their diverse menu featuring dishes like fresh seafood and casserole specialties. For Asian cuisine enthusiasts, Midori is a popular spot offering flavorful Chinese dishes. And don't miss out on The Gloucester House Restaurant, a highly-rated North American restaurant with a stunning oceanfront view. With its array of dining options, Gloucester promises a delightful culinary experience for your family vacation.
How do I find my perfect vacation package with Travelocity?
Ensure your entire crew has an abundance of fun on your next trip. When searching for a vacation package tailored to your needs, utilize our family-friendly filters to explore destinations suitable for your children's age groups, along with accommodations offering additional amenities. Selecting the ideal package can help save you money and prevent any tantrums.
Why should I book with Travelocity?
Conference calls, to-do lists and, of course, football practice. Busy lives and packed schedules call for trips that are hassle-free. Our aim is to provide worry-free travel every time you and your family book with us so that you can spend less time fretting and more time creating cherished memories. To achieve this, we will assist you in finding and planning your ideal trip, along with offering transparent pricing and reliable reviews, and 24/7 guaranteed customer support before, during, and after your vacation.
How can I save money on my trip to Gloucester?
Save money by visiting Gloucester during the off-peak season from November to January. Take advantage of discounted prices by bundling your flights, hotel, and car bookings. While in Gloucester, enjoy affordable local attractions such as exploring the beautiful beaches, taking a whale watching tour, and indulging in delicious seafood. With its close proximity to the sea, Gloucester offers a variety of inexpensive activities for the whole family to enjoy.
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