Experience the excitement of the Round Island Regatta in Portsmouth, NH—an annual sailing race around Round Island that celebrates maritime heritage with thrilling competition and vibrant shoreside viewing.
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Difficulty
moderate
Duration
3–5 hours
Fitness Level
Moderate fitness needed for walking around viewing areas and possibly sailing if participating in the race.
Wildlife
History
Portsmouth’s maritime tradition dates back centuries, with Round Island historically serving as a strategic navigation point for local fishermen and traders.
Conservation
Local groups actively monitor and maintain water quality and shoreline habitats to preserve the delicate estuarine ecosystem here.
Gundalow Company
Experience the excitement of the Round Island Regatta in Portsmouth, NH—an annual sailing race around Round Island that celebrates maritime heritage with thrilling competition and vibrant shoreside viewing.
Gundalow Company preserves and interprets regional maritime heritage through authentic sailing experiences aboard the Piscataqua, a reproduction of historic gundalow barges. The organization offers an array of public sails, special events, and private charters that highlight the Piscataqua River, Portsmouth harbor, and the 6,000-acre Great Bay estuary. Experiences include short harbor sails, a Great Bay exploration, sunset cruises, the annual Round Island Regatta, a Sail to Wood Island and Life Saving Station Tour, and a rotating Speaker Series focused on maritime and naval history.
Families are welcomed aboard with hands-on sailing activities and one free child ticket included per adult on designated Kids Sail Free departures. Crews encourage passenger participation, offer educational commentary, and prioritize passenger safety and comfort.
Gundalow Company supports community events, partners with local historians and guest experts for weekly lectures during the Speaker Series, and provides customizable private charters for groups seeking specialized itineraries. All sails emphasize environmental stewardship, regional history, and accessible, memorable outings for visitors and residents.
Booking information, schedules, and trip details are published seasonally and updated frequently to reflect weather and tidal conditions. Rain-or-shine events such as the Round Island Regatta proceed with adjustments as needed. Trained crew members maintain the Piscataqua to historic standards while following current safety regulations.
Through a combination of historically inspired vessels, educational programming, and family-focused activities, Gundalow Company offers reliable, culturally rich maritime experiences that connect passengers with New England’s coastal heritage. Advanced bookings are recommended to secure preferred dates, routes, and private charter options today.
Tours Offered
9 Experiences
Diverse sailing options and events
Kids Policy
1 free child
One free child ticket per adult
Sailing Area
Piscataqua & Great Bay
River, estuary, and harbor routes
Typical Duration
1.5–2 hours
Short sails and extended trips available
Secure a spot for a harbor cruise, sunset sail, or private charter — book now to guarantee preferred dates.
Check tide schedules
Tides strongly affect race conditions; consult local tide charts for the best race-day strategy.
Arrive early for best viewing spots
Peirce Island and Back Channel shores fill quickly—arriving early guarantees a prime vantage point.
Bring waterproof gear
Portsmouth weather can be unpredictable; waterproof jackets and shoes keep you comfortable rain or shine.
Use binoculars for detailed views
Binoculars enhance your experience by letting you track boats’ maneuvers from the shore.
Water-resistant jacket
Keeps you warm and dry during unpredictable spring weather on the water.
spring
Binoculars
Enhances your ability to follow race details from shore.
Comfortable walking shoes
Essential for navigating rocky or uneven shoreline viewing areas.
Sun protection kit (hat, sunscreen)
Protects skin from strong sun exposure during long outdoor viewing.
summer