top of page
AdobeStock_208138553.jpeg

CHARTERS

Join Us for an Unforgettable Sailing Charter

Whether you're looking for a peaceful escape, an adventurous day on the water, a luxurious sailing getaway, or a way to celebrate a special occasion, we offer custom sailing experiences designed just for you.

Choose from a sunset cruise, a private captained charter, or a week-long sailing trip to Maine, Cape Cod, the Islands, or the Caribbean in winter. We also host memorable team-building events, birthdays, and anniversary sails — all departing from Marblehead or Salem, MA.

Our private sailing charters are a magical way to explore the water with family, friends, or colleagues aboard your own private yacht.

Don't just dream about sailing — make it a reality.


Contact us today to start planning your perfect on-the-water adventure. We’ll help you every step of the way.

Why Choose Satori Sailing?

  • Tailored Experiences
    Every sailing charter is customized to match your vision, goals, and group size.

  • Experienced Captains
    Our friendly, knowledgeable skippers ensure your safety and enjoyment from start to finish.

  • Top Destinations
    From Boston’s North Shore to the Caribbean, we’ll help you create unforgettable sailing memories.

Sunset Cruises

Duration: 2 hours
Group Size: Private charter for 2–6 guests

Experience Level: No experience necessary
Location: Marblehead, MA

Vessel: 22' Capri. or 27' Hunter keelboat

Price: $399

Enjoy a peaceful, early-evening sunset cruise along the scenic coastlines of Salem, Beverly, and Marblehead. Departing from either Marblehead or Salem, this private sailing experience is perfect for couples, families, or small groups looking to unwind on the water.


Your USCG-licensed captain can provide local insights about the area or light sailing instruction — it's entirely up to you.


We provide water and light snacks, and you're welcome to bring your own beverages and food. (Please note: red wine is not permitted to avoid staining the boat.)


Treat yourself to a romantic coastal cruise or a memorable New England evening with friends.


Book your sunset sail today directly through our online booking system.

Sunset Cruises

Day Trips & Excursions

Duration: Full-day (8 hours)
Group Size: Private charter for 2–6 guests

Experience Level: No experience necessary
Location: Marblehead, MA

Vessel: Based on availability and group needs

Price: $1,499 per day

Spend the day aboard your own private sailing yacht exploring the stunning coastline of Boston’s North Shore. Departing from Marblehead or Salem, your captain will guide you along scenic islands, beaches, and hidden coves for an unforgettable summer escape.


You can pack a picnic, stop at one of several seaside restaurants for lunch, or just relax and enjoy the views. Your experienced captain can provide local insight or offer light sailing instruction throughout the day.

  • Water and snacks are included

  • Guests may bring their own food and beverages (note: red wine is not allowed due to staining concerns)

This full-day private sailing charter is perfect for families, friend groups, or couples looking to make the most of New England's sailing season.


Book your day trip now and let us help you plan the perfect custom sailing adventure.

Day Trips & Excursions

Special Event Charters

Duration: Hourly (Min 2 Hrs)
Group Size: Private charter for 2–6 guests

Experience Level: No experience necessary
Location: Marblehead, MA

Vessel: Based on availability and group needs

Price: $199 per hour (Min 2 hrs)

Celebrate your next birthday, anniversary, or special occasion with a custom private sailing charter. Departing from Marblehead or Salem, enjoy a relaxing sail around Salem Sound, taking in the coastlines of Salem, Beverly, and Marblehead, along with the area’s many islands, beaches, and coves.


Your captain can offer local insights or light sailing instruction if you’d like to learn as you go.

  • Water and snacks provided

  • Bring your own food and beverages (red wine not permitted due to staining risk)

Whether it’s a relaxing Friday evening or a once-in-a-lifetime celebration, let us help you create a memorable experience on the water.


Corporate & Team Building Sails

Looking for a unique and meaningful summer outing for your team? Satori Sailing offers customized team-building sailing experiences that combine fun on the water with valuable group dynamics.  Using real sailing maneuvers, your team will practice communication, coordination, and leadership in a hands-on and unforgettable way.

  • Perfect for corporate outings, client entertainment, or small group retreats

  • Hosted by experienced captains who facilitate a supportive and safe environment

  • Water and snacks included; guests may bring food and drinks (no red wine)

Get out of the office and onto the water — contact us to plan a private, team-focused sailing experience that your group will be talking about long after the sails are down

Special Event Charters

Crewed Charters

Duration: Full-day (8 hours) or multi-day/week
Group Size: Private charter for 2–6 guests

Experience Level: No experience necessary
Location: New England (June–Sept) or the Caribbean (Dec–April)

Vessel: Beneteau 40' or Dufour 41'

Price: $1,499 per day

Experience the ultimate sailing adventure with a fully crewed charter. Whether you’re dreaming of a long weekend on the New England coast or a week in the Caribbean, we’ll help you create an unforgettable journey.


From June to September, sail north to Maine’s rugged coastline or south through the Cape Cod Canal to explore Cape Cod and the Islands. From December to April, we relocate to the U.S. and British Virgin Islands, where turquoise waters, coral reefs, and warm winds await.


Sail with one of our experienced instructors and choose to relax or enhance your skills with hands-on sailing instruction, including:

  • Anchoring, docking, and mooring practice

  • Navigating currents in Woods Hole or the Cape Cod Canal

  • Bluewater cruising experience

  • Caribbean sailing techniques

Our well-appointed yachts provide a comfortable liveaboard setting so you can enjoy the cruising lifestyle in some of the world’s best sailing destinations.


Whether you're here for relaxation, education, or a bit of both — contact us today to plan your custom crewed sailing experience.

Crewed Charters
Satori Sailing logo – Sailing School in Marblehead, MA

Satori Sailing offers certified sailing lessons and private charters in the protected waters of Salem Sound. Serving Boston’s North Shore, including Marblehead, Salem, Swampscott, Manchester, Beverly & Gloucester.

Call: 781-797-0433

Email: info@sailsatori.com

  • Satori Sailing Facebook Icon
  • Satori Sailing Instagram Icon
Marblehead Chamber of Commerce Business Member Logo - Satori Sailing - Sailing School and Private Charters in Marblehead - Boston Area
Marblehead Chamber of Commerce Logo - Satori Sailing - Sailing School and Private Charters in Marblehead - Boston Area

Based in Marblehead, Massachusetts

Pride Flag

© Satori Sailing LLC
Designed by Prototype Media

bottom of page