Discover the freedom of a private sailing adventure around Boston Harbor. Explore islands, swim, and enjoy a personalized day on the water with your friends or family.
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Difficulty
easy
Duration
6–8 hours
Fitness Level
Suitable for all fitness levels; minimal physical exertion required as the crew manages sailing tasks.
Wildlife
History
Boston Harbor played a pivotal role during the American Revolution, including the famous Boston Tea Party event.
Conservation
Efforts to maintain water quality and protect local marine habitats are active, with charters committed to eco-friendly practices.
Polaris Maritime LLC - D.B.A Classic Sail Boston
Discover the freedom of a private sailing adventure around Boston Harbor. Explore islands, swim, and enjoy a personalized day on the water with your friends or family.
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 Sunscreen and Hat
Protect yourself from sun exposure while on the open water to avoid sunburn.
Pack Snacks & Drinks
Since it’s a private charter, bring your favorite refreshments to stay energized.
Wear Non-Slip Footwear
Choose shoes with good grip to safely move around the deck.
Inform Crew of Swimming Ability
Let the crew know your swimming comfort level for safe island hopping stops.
Sunscreen
Protects skin from UV rays during long exposure on the water.
summer
Light Jacket or Windbreaker
Keeps you warm against cool sea breezes while sailing.
spring
Waterproof Bag
Keeps your valuables dry and safe during the trip.
Non-Slip Boat Shoes
Ensures safe footing on the deck throughout the day.