Hello, Lykkers! Let's talk about sailing in Boston—a unique and refreshing way to experience a city that's brimming with history, beauty, and sea breeze.
Whether you're a first-timer looking for a gentle cruise or someone craving the thrill of wind in your sails, Boston offers the perfect backdrop.
And trust me, this isn't just about boats—it's about soaking in skyline views, discovering hidden harbor islands, and uncovering the salty soul of the city. So, here's your complete guide to sailing in Boston and nearby attractions you won't want to miss.
Why Boston Is Perfect for Sailing
Boston has one of the most scenic harbors in the U.S., surrounded by ancient architecture, historic ships, and sparkling city lights.
The calm waters of Boston Harbor and the Charles River offer ideal sailing conditions. The city is home to several sailing schools, boat rental companies, and guided cruises—so whether you're just looking to relax or get hands-on with the ropes, you'll find your fit.
How to Get to Boston and Around
Fly into Boston Logan International Airport (BOS), just 15–20 minutes from downtown. Taxis or Ubers cost $25–$35, the Silver Line Bus to South Station is free, and water taxis run $15–$20 (costs may vary). The MBTA "T" subway covers most of the city, with a 1-day pass around $12 (cost may vary). Boston is compact, walkable, and has plenty of bike rentals.
Where to Sail and What to Book
Boston Harbor Sailing Club
Located on Long Wharf, this club offers everything from sailboat rentals to certified sailing lessons.
Estimated cost: $75–$100 for a 2-hour rental (cost may vary)
Boston Harbor Sailing Club
Liberty Fleet of Tall Ships
Sail on a historic schooner and experience Boston Harbor like they did centuries ago. They offer day sails and sunset cruises with city skyline views.
Estimated cost: $45–$55 per person (cost may vary)
Boston Harbor Cruises
Want something more laid-back? Book a narrated cruise or a sunset drinks sail to enjoy the scenery without lifting a rope.
Estimated cost: $30–$60 per person (cost may vary)
Attractions Near the Water
After your sail, stick around to explore these nearby gems:
Boston Tea Party Ships & Museum
Just steps from the water, this interactive museum lets you relive one of the most iconic moments in U.S. history.
New England Aquarium
A family favorite with penguins, sea turtles, and a giant ocean tank—just a short walk from Long Wharf. Entry ticket is $43.78 (cost may vary).
New England Aquarium
Harborwalk
A scenic path that stretches along the waterfront, ideal for walking or biking with harbor views and public art along the way.
Boston Harbor Islands National and State Park
Accessible by ferry, this group of islands offers hiking, beachcombing, picnicking, and even old forts to explore.
Where to Eat After Sailing
Legal Sea Foods – Harborside
Classic New England seafood and sweeping views. Try the clam chowder, fried oysters, or lobster roll.
Estimated cost: $25–$40 per person (cost may vary)
Legal Sea Foods - Harborside
The Barking Crab
A laid-back waterfront spot with picnic tables, local drinks, and lots of crab, shrimp, and fried clams.
Estimated cost: $20–$35 per person (cost may vary)
Where to Stay
YOTEL Boston
Sleek, tech-friendly, and located in the Seaport near the harbor.
Estimated cost: $340 per night (cost may vary)
YOTEL Boston
The Envoy Hotel
A boutique option with rooftop views and a fantastic location close to both the waterfront and downtown.
Estimated cost: $750 per night (cost may vary)
HI Boston Hostel
Budget-friendly and centrally located. Great for solo travelers or backpackers.
Estimated cost: $262–$400 per night (cost may vary)
Final Thoughts
Sailing in Boston is more than just a pastime—it’s a different way to experience the city's heart and soul. Whether you're taking in skyline views at sunset or skimming past historical wharfs, every moment on the water is unforgettable. Pair it with great food, cozy stays, and a little historical exploration, and you’ve got the perfect Boston getaway.
Want help planning a full 3-day itinerary or finding the best time to go? I'm here to help!
