Sail away on a private 4-hour charter around Boston Harbor Islands with your own captain. Perfect for families, friends, and all skill levels looking for a unique outdoor adventure on the water.
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Difficulty
easy
Duration
4 hours
Fitness Level
Suitable for all fitness levels; minimal physical exertion required aside from light movement on deck.
Wildlife
History
Boston Harbor Islands played a strategic role in colonial and revolutionary history, with forts and lighthouses marking their legacy.
Conservation
The Boston Harbor Islands National Recreation Area prioritizes sustainable tourism and protects sensitive habitats from human impact.
Polaris Maritime LLC - D.B.A Classic Sail Boston
Sail away on a private 4-hour charter around Boston Harbor Islands with your own captain. Perfect for families, friends, and all skill levels looking for a unique outdoor adventure on the water.
Polaris Maritime LLC - D.B.A Classic Sail Boston operates private sailing charters from Boston, MA. The company offers three signature private charters that showcase Boston Harbor and the Harbor Islands. Each charter sails with a captain and is designed for family outings, small groups, and special occasions.
The Two Hour Private Sail Charter is a focused, 2-hour cruise around Boston Harbor with views of Seaport, Castle Island, and waterfront landmarks. Guests can relax, listen to music, and celebrate with friends while enjoying complimentary refreshments and an option to BYOB.
The Private Half Day Sail Charter is a 4-hour private voyage that explores the Boston Harbor Islands. This customizable half-day trip allows passengers to work with the captain to choose destinations, extend island time, and swim along sheltered anchorages.
The Private Full Day Sail Charter delivers a day of island hopping, lighthouse views, and opportunities to swim and explore multiple islands at leisure. Guests may bring snacks and drinks for a personalized on-deck experience.
Bookings are arranged from Boston, MA, and each charter emphasizes private, customizable sailing time on the water. Trip summaries note amenities and options included with each private charter. Polaris Maritime LLC - D.B.A Classic Sail Boston presents straightforward private sailing experiences that focus on Boston Harbor exploration, customizable itineraries, and shared time with family and friends.
Reservations are available for family gatherings, celebrations, and group outings; scheduling and destination choices are coordinated with the captain to match guest preferences for a tailored Boston Harbor sailing experience today.
Location
Boston, MA
Departing from Boston Harbor
Private Charters
3 Trip Options
Three private sailing experiences available
Durations
2-hour to full day
Options from 2 hours to full day
Captain Onboard
Includes Captain
Private charters include a captain
Book a Two Hour, Half Day, or Full Day private sailing experience around Boston Harbor with captain-led customization.
Bring layered clothing
Sea breeze and sun exposure can vary, so pack layers to stay comfortable throughout your sail.
Stay hydrated
Even on cooler days, it's important to drink water while out on the water to stay energized.
Wear non-slip shoes
Deck surfaces can get slippery, so sturdy, non-slip footwear is recommended for safety.
Protect your skin
Apply waterproof sunscreen to avoid sunburn, especially during longer exposure on the water.
Layered clothing
Keep warm and comfortable as temperatures and wind conditions change during the sail.
Waterproof sunscreen
Protect your skin from UV rays during extended sun exposure on open water.
summer
Non-slip shoes
Helps maintain footing on wet or slippery deck surfaces.
Reusable water bottle
Staying hydrated is key for comfort and safety while sailing.