Two-, three-, and four-hour private sails along Boston’s North Shore, Salem Harbor, and beyond.
Private Two Hour, Three Hour, and Four Hour Sail options aboard a cozy Cal 36.
boat-charters · Marblehead
Set sail from Marblehead Harbor on a private four-hour Cal 36 charter for up to six guests. Cruise past Magnolia’s coves, head toward Gloucester’s working waterfront, and watch seals and ospreys against a glacially scoured coastline.
Emma Rose Sailing Charters is a Marblehead, Massachusetts-based company offering private sailing experiences aboard a cozy Cal 36. The business provides short and mid-length trips on Boston’s North Shore and area harbors, including Two Hour Sail, Three Hour Sail, and Four Hour Sail options. Each cruise is private and accommodates small groups, making the charters suitable for families, friends, and intimate gatherings.
Trips depart from Marblehead and explore local coastline and historic sights. The Two Hour Sail follows scenic coastal routes past historic homes and shoreline vistas. The Three Hour Sail ventures toward Salem Harbor and Boston’s Gold Coast, offering extended coastal views. The Four Hour Sail sails beyond Marblehead harbor and combines relaxation with the thrill of open-water sailing. All cruises emphasize a relaxed, well-equipped sailing experience aboard the Cal 36.
Bookings are arranged per private charter for guests seeking a tailored coastal outing. The fleet description and guest capacity note a cozy private boat for six. Typical activities on these trips include scenic viewing, relaxed time on deck, and active sailing depending on wind conditions. Photography, sightseeing, and small group celebrations are a natural fit for these private charters.
Emma Rose Sailing Charters presents a clear, location-focused offering for travelers and locals wanting coastal sailing from Marblehead, Massachusetts. The business listing highlights private, small-group sailing on a Cal 36 with multiple trip lengths to match guest schedules and preferences. Reservations are made directly for private charters departing from Marblehead, with clear trip options and availability.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Charters depart from Marblehead
Cozy private boat capacity
Two, three, and four hour sails
Sailing aboard a cozy Cal 36
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Emma Rose Sailing Charters listing.
Emma Rose Sailing Charters offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Reserve a Two, Three, or Four Hour Sail aboard the Cal 36 for small groups; private charters fill quickly.
boat-charters · Marblehead
Set sail from Marblehead Harbor aboard the Cal 36 EMMA ROSE for a private two-hour cruise along Boston’s North Shore. This intimate charter showcases historic shoreline architecture, rocky ledges, and lively sailing for up to six guests.
boat-charters · Marblehead
Board a private Cal 36 in Marblehead for a three-hour coastal sail to Salem Harbor and along Boston's Gold Coast. Small groups (up to six) get close views of granite headlands, historic harbors, seabirds, and seaside estates—an ideal half-day introduction to New England sailing.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.