Boat Rentals in Gloucester, MA | Top Waterfront Rentals & Adventures



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Gloucester Boat Rentals harbor with boats and kayaks; a wooden shack offers life vests.


Boat Rentals in Gloucester, MA | Best Harbor & Cape Ann Boat Rentals


Gloucester, Massachusetts, is one of New England’s most iconic coastal towns, known for its rich fishing history, scenic harbor, and access to the open waters of Cape Ann. Whether you want to cruise along the shoreline, go fishing, or enjoy a private sunset ride, boat rentals in Gloucester, MA offer something for every type of boater.


Below is a complete guide to the best boat rental options in Gloucester, including self-drive boats, captained charters, and specialty water experiences.


Best Boat Rentals in Gloucester, MA



Gloucester Boat Rental

White motorboat with blue canopy docked at a wooden pier. Harbor with other boats in background.


One of the most popular and trusted options in town, Gloucester Boat Rental offers easy, self-captained powerboat rentals right in Gloucester Harbor.


  • Half-day and full-day boat rentals
  • No boating license required (valid driver’s license needed)
  • Fishing gear rentals are available
  • Beginner-friendly instructions provided
  • Convenient harbor location on Rogers Street

This option is ideal for visitors who want full freedom to explore Gloucester Harbor, nearby coves, and the scenic Cape Ann coastline at their own pace.


Online Boat Rental Platforms in Gloucester



GetMyBoat – Gloucester, MA

Sailboat with yellow sail on blue water at sunset, followed by other sailboats.


GetMyBoat is a popular platform that connects renters with a wide variety of boats in and around Gloucester.


  • Powerboats, sailboats, yachts, and fishing boats
  • Options with or without a licensed captain
  • Hourly, half-day, and full-day rentals
  • Ideal for groups, special occasions, and custom trips

This platform is perfect if you’re looking for flexibility, unique boat types, or a captained experience.


Boatsetter – Gloucester Area Rentals

White motorboat on water with a city skyline in the background, lit by a sunset.


Boatsetter offers another convenient way to book boats in Gloucester and nearby coastal towns.



  • Wide selection of motorboats and yachts
  • Captained and bareboat options available
  • Easy online booking and price comparisons
  • Great for sightseeing cruises and private events

Boatsetter works well for travelers who want a smooth booking process and premium boat options.


Private Charters & Specialty Boat Experiences



Cape Ann Cruises

Two people take a selfie on a boat, sailing on the ocean under a blue sky.


If you prefer a relaxed, fully guided experience, Cape Ann Cruises provides private charters and scenic cruises.



  • Private yacht charters
  • Sunset and harbor cruises
  • Great for celebrations, events, and group outings
  • Professional crew included

This is a great choice for visitors who want to enjoy the water without handling the boat themselves.


Sailing Yacht Charters

People sailing on a boat under a partly cloudy sky, some standing and looking out.


For a classic New England experience, sailing yacht rentals are available through select charter providers.



  • Half-day and full-day sailing trips
  • Professional captain included
  • Ideal for couples, families, and special occasions
  • Peaceful way to explore Cape Ann waters

Sailing charters are perfect for those looking for a slower, more scenic experience on the water.


Kayak & Paddleboard Rentals in Gloucester



While not traditional boat rentals, kayaking and paddleboarding are popular water activities in Gloucester.


  • Rentals available near Bearskin Neck and Annisquam
  • Great for calm harbor waters
  • Ideal for beginners and nature lovers
  • Affordable and family-friendly

These options are perfect if you want a casual way to enjoy Gloucester’s coastal beauty.


Tips for Renting a Boat in Gloucester, MA


  • Best season: Late spring through early fall
  • Book early: Summer weekends and holidays fill up fast
  • Bring essentials: Sunscreen, water, snacks, and a camera
  • Check weather conditions: Coastal winds can change quickly
  • Choose the right boat: Self-drive for freedom, captained charters for relaxation


Final Thoughts on Boat Rentals in Gloucester, MA


From self-drive powerboats to luxury yacht charters, boat rentals in Gloucester, MA make it easy to experience the city’s historic harbor and stunning Cape Ann coastline from the water. Beyond boating, Gloucester offers plenty of things to do—from exploring scenic lighthouses and art galleries to strolling historic streets. 


When it’s time to refuel, the city’s best restaurants serve everything from fresh seafood to cozy local fare. For those looking to extend their stay in style, luxury vacation rentals provide the perfect home base, combining comfort with spectacular waterfront views.


Whether you’re planning a fishing trip, sightseeing cruise, or private celebration, Gloucester has boat rental options and experiences for every travel style and budget.


FAQs About Boat Rentals in Gloucester, MA

  • Do I need a boating license to rent a boat in Gloucester?

     Most self-drive boat rentals only require a valid driver’s license. Captained charters include a licensed captain, so no experience is needed.


  • What types of boats can I rent in Gloucester?

    You can rent powerboats, sailboats, yachts, fishing boats, and even kayaks or paddleboards, depending on your preference.

  • Are there guided or captained boat options?

    Yes! Many rental platforms and local providers like Cape Ann Cruises offer captained charters for sightseeing, sunset cruises, or private events.

  • When is the best time to rent a boat in Gloucester?

     Late spring through early fall is peak boating season, with the best weather and calmer waters. Booking in advance is highly recommended for summer weekends.


  • Can I fish from a rental boat in Gloucester?

    Absolutely! Many boats come with fishing gear rentals or allow you to bring your own. Gloucester is famous for its rich fishing waters.


  • Where should I stay while visiting Gloucester?

     For a luxurious experience, consider waterfront vacation rentals. They offer stunning views, easy harbor access, and a comfortable home base for exploring the city’s attractions, restaurants, and activities.


  • What else can I do in Gloucester besides boating?

    Check out local things to do, including visiting lighthouses, exploring art galleries, walking the historic streets, or dining at some of the city’s best seafood restaurants.


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