Water-Based Experiences in Gloucester, Massachusetts | Book Boats, Tours & Activities with Varoom

In Gloucester, Massachusetts coastal adventures await you right on the Gloucester waterfront, from whale watching cruises and harbor sightseeing to art and cultural experiences at the Cape Ann Museum and the city’s maritime heritage. Enjoy Water-Based Events with family-friendly options along the Cape Ann coastline, explore iconic spots like Fisherman's Memorial and Gloucester Harbor, and unwind at beaches such as Good Harbor Beach while planning multi-day trips and easy bookings through Varoom. USA

In Gloucester, Massachusetts, USA, you’ll find a harbor-driven escape built for Water-Based adventures, from whale-watching excursions to sailing, kayaking, and scenic harbor tours. Here, this destination unfolds with coastal art, seafood feasts, and family-friendly days along the shores of Cape Ann, inviting you to explore iconic landmarks and seaside neighborhoods while discovering stays that fit your plans. The area rewards explorers with landmark spots like the Fishermen’s Memorial and historic waterfront streets, plus vibrant galleries and authentic shorefront dining that keep the momentum going for Art & Culture, Tours & Sightseeing, and Food & Drink experiences. Whether you’re planning a multi-day escape, a romantic retreat, or a Group-Friendly outdoor itinerary, here you’ll uncover a curated mix of Events and activities that highlight the Water-Based possibilities and easy access to the region’s best attractions.

Activities

Top Water-Based in Gloucester

Salem Historic Schooner Sailing Tour
10
Excellent
186 Reviews
5-Star Rating Recommendation
From
US $55Per Person
Whale Watching Trips to Stellwagen Bank Marine Sanctuary. Guaranteed sightings!
10
Excellent
2193 Reviews
5-Star Rating Recommendation
From
US $45Per Person
Schooner Fame Sailing Tour
10
Excellent
571 Reviews
5-Star Rating Recommendation
From
US $51Per Person
Sailing on Historic Schooner Yacht in Salem, MA
10
Excellent
186 Reviews
5-Star Rating Recommendation
From
US $55Per Person
Gloucester Harbor Kayak Tour Explore Coastal Beauty and Sea
10
Excellent
1 Reviews
5-Star Rating Recommendation
From
US $130Per Person

Top sights in Gloucester

Explore Gloucester's top sights-from the working harbor and lighthouse views to the Cape Ann Museum and scenic Stage Fort Park-as you plan Water-Based adventures with Varoom, letting you book stays nearby and experience the area's coastal culture, nature, and family-friendly activities without missing a beat.

From sightseeing to restaurants
there’s plenty of things to do in Gloucester

Whether you love exploring landmarks or tasting local cuisine, you’ll find endless adventures here.

Other tours in Gloucester

Salem History and Ghost Walking Tour With Night Option
10
Excellent
15099 Reviews
5-Star Rating Recommendation
From
US $36Per Person
History and Hauntings of Salem Guided Walking Tour
10
Excellent
15099 Reviews
5-Star Rating Recommendation
From
US $36Per Person
Whale Watching Tour in Gloucester
10
Excellent
4515 Reviews
5-Star Rating Recommendation
From
US $48Per Person
Salem Voodoo, Vampires, and Ghosts Guided Walking Tour
10
Excellent
1975 Reviews
5-Star Rating Recommendation
From
US $28Per Person
Bewitched Walking Tour of Salem
10
Excellent
1926 Reviews
5-Star Rating Recommendation
From
US $35Per Person
Salem Award-Winning Witchy Walking Tour with Guide
10
Excellent
1926 Reviews
5-Star Rating Recommendation
From
US $35Per Person
Satanic Salem Walking Tour
10
Excellent
1679 Reviews
5-Star Rating Recommendation
From
US $30Per Person
Mysteries and Murders of Salem Guided Night-Time Walking Tour
10
Excellent
1515 Reviews
5-Star Rating Recommendation
From
US $36Per Person
Wicked Awesome Tours: Witch Trial History and Salem Haunts!
10
Excellent
1215 Reviews
5-Star Rating Recommendation
From
US $29Per Person
Salem Witch Trials and Haunted Sights Walking Tour
10
Excellent
1215 Reviews
5-Star Rating Recommendation
From
US $29Per Person
2.5-Hour Salem History & Sightseeing Guided Walking Tour
10
Excellent
852 Reviews
5-Star Rating Recommendation
From
US $40Per Person
Salem History & Sightseeing Guided Walking Tour
10
Excellent
852 Reviews
5-Star Rating Recommendation
From
US $40Per Person

Top-rated places to stay near Gloucester

Discover top-rated stays near Gloucester, Massachusetts, that pair Water-Based adventures with comfortable, guest-focused amenities.
From the area’s scenic coastlines to accessible tours and family-friendly options, you’ll find places that align with your plans and Events here.
Book with Varoom and connect your Gloucester-area getaway to the experiences you care about, whether you’re seeking adventure, relaxation, or multi-day experiences by the water.

New
Apartment
Map-icon
4 Bedrooms 2 Baths 10 Guests 1300 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $717/Night 7 Nights - US $5,018
star-icons-4
House
Map-icon
like-icon10.0
Exceptional
(7 Reviews)
3 Bedrooms 1 Bath 6 Guests 1001.04 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $396/Night 7 Nights - US $2,772
star-icons-3
Hotel
Map-icon
like-icon9.6
Exceptional
(478 Reviews)
1 Bath
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $440/Night 7 Nights - US $3,081
New
House
Map-icon
3 Bedrooms 3 Baths 6 Guests 24757 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $626/Night 7 Nights - US $4,385

Know more about Gloucester

To book, start with the listing for the Water-Based experience in this destination, select your preferred date and party size, then submit your booking request. For the exact cancellation terms, payment options, and any host-specific requirements, refer to the listing or contact the owner through Varoom.
Cancellation terms differ by host and listing. Check the listing’s policy and any timeframes for refunds, and contact the owner if you need clarification before you book.
Parking options and transportation details are listed by the host. Check the listing for access instructions or nearby options, and contact the owner if you need help planning arrival times.
The area experiences seasonal changes, so review the listing for climate-specific guidance and what to expect. If you have concerns about weather contingencies, contact the host before your trip.
Amenities and inclusions vary by listing, so review the specific Water-Based experience on the page. You’ll find details about equipment, access, and any extras; if anything isn’t clear, reach out to the host before reserving.
Age requirements and capacity limits are set by the host for each experience. Review the listing details and ask the owner directly if you have a specific group or participant with special needs.
Item suggestions vary by activity, so consult the listing for a packing checklist. If you’re unsure, ask the host about essential gear, safety items, and any items provided on-site.
Some hosts offer snacks or drinks, while others do not. Check the listing for inclusions and consider contacting the owner to confirm any food or beverage arrangements for your dates.