Boston Harbor Sail

Harbor Sails Aboard Tall Ship Denis Sullivan Step aboard Denis Sullivan, a 137-foot historic tall ship, for a one-of-a-kind sailing experience on Boston Harbor. You’ll enjoy: ⚓️ Stunning views of the Boston skyline 🌊 The chance to help raise the sails or just relax on deck 🌅 Sunset sails, weekend sails, and special themed sails All proceeds support World Ocean School’s educational programs for youth in Boston and beyond. 📍 Departs from Moakley Dock, Seaport 📆 Multiple dates available June–August 🎟️ Tickets start at $55 | Advanced booking recommended Book now and experience Boston from the water — the way it was meant to be seen. <a href="https://www.worldoceanschool.org/boston-sails">[Ticket link]</a>

Courthouse Docks

Sail into Father's Day with Free Wine! 

Celebrate Dad in style this Father's Day with a sail aboard the Schooner Denis Sullivan - and with free wine generously donated by 90+ Cellars! Join World Ocean School for a two-hour sail aboard our beloved tall ship to enjoy a cruise out of Boston Harbor with family and friends. You can join our crew in raising the sails of our newest addition to our fleet—or just relax and enjoy the beautiful views. Gift Dad a unique and exclusive sailing experience aboard this historic vessel this Father's Day. Cash bar available during all sails. Our public sails are an opportunity for World Ocean School to share Denis Sullivan with the public. All proceeds from sail tickets support World Ocean School’s educational programs. Get your tickets <a href="HERE">HERE</a>.

John Joseph Moakley Courthouse Docks

Celebrate Dad in style this Father's Day with a sail aboard the Schooner Denis Sullivan - and with free wine generously donated by 90+ Cellars! Join World Ocean School for a two-hour sail aboard our beloved tall ship to enjoy a cruise out of Boston Harbor with family and friends. You can join our crew in raising the sails of our newest addition to our fleet—or just relax and enjoy the beautiful views. Gift Dad a unique and exclusive sailing experience aboard this historic vessel this Father's Day. Cash bar available during all sails. Our public sails are an opportunity for World Ocean School to share Denis Sullivan with the public. All proceeds from sail tickets support World Ocean School’s educational programs. Get your tickets <a href="https://fareharbor.com/embeds/book/worldoceanschool/items/391031/availability/1687361330/book/?full-items=yes">HERE</a>.

Pride Tea Dance aboard Tall Ship Denis Sullivan

Kick off Pride Weekend aboard Denis Sullivan. Celebrate Pride with your friends in a unique setting - aboard a tall ship! Enjoy food, drinks, and entertainment aboard this unique venue while taking in the beautiful Boston skyline. Book your tickets <a href="https://fareharbor.com/embeds/book/worldoceanschool/items/543554/calendar/2025/6/?full-items=yes">HERE</a>.

Wine on the Weekend aboard Denis Sullivan

What's better than a two-hour sail around Boston Harbor? A two-hour sail with free wine, of course! 🍷 Join us on Saturday, July 6th and Sunday, July 7th for our Wine on the Weekend sails with free wine generously provided by 90+ Cellars. Along with free wine, you'll enjoy unique views of the Boston skyline with family and friends. Raise the sails with our crew or just sit back, relax, and enjoy your time on board. Don't miss out! Children aged 3-12 and seniors aged 65+ $45/pp. Adults $55/pp.

Moakley Courthouse Dock

Father's Day aboard Denis Sullivan

Celebrate Dad in style this Father's Day with a sail aboard the Schooner Denis Sullivan! Join World Ocean School for a two-hour sail aboard our beloved tall ship to enjoy a cruise out of Boston Harbor with family and friends. You can join our crew in raising the sails of our newest addition to our fleet—or just relax and enjoy the beautiful views. Gift Dad a unique and exclusive sailing experience aboard this historic vessel this Father's Day. Cash bar available during all sails. Our public sails are an opportunity for World Ocean School to share Denis Sullivan with the public. All proceeds from sail tickets support World Ocean School’s educational programs. Ticket price: $45 for children age 3-12 and seniors 65+, $55 for adults 13-65, infants 2 and under are free.

"Dog"-side Event aboard Denis Sullivan

Swing by the Moakley Courthouse Dock in Seaport during your morning stroll with your furry friend to treat them to some Polkadog dog treats and take a deck tour of the schooner Denis Sullivan!

Walk the Plank with World Ocean School

Ten lucky people, chosen by the community, will be plunging into Boston Harbor from the plank of one of Boston’s 57 National Historic Landmarks - the 96 year old schooner Roseway! In the weeks leading up to the event, the courageous people making a splash are competing in a real time donation leaderboard to see who can raise the most money for World Ocean School's life-changing student programs. Walk the Plank will feature each spectacular leap into the harbor, along with food, drinks, and music, all included in the cost of your ticket! There will also be a raffle to participate in during the event with fantastic prizes and gift cards to some of your favorite spots in Boston. Join us on Thursday, August 18 to watch these brave plank walkers take the plunge into the Boston Harbor dressed head to toe in costume! Enjoy food, drinks, and music, all while supporting World Ocean School's high-impact programs aboard the historic schooner Roseway. Sponsored by: Munroe Morrow Wealth Management Legal Sea Foods Lord Hobo Seaport BOSToday Jessica Scranton Photography

S22: conversations

Wondering what to do in Boston? Places to eat? Free activities? Good for a group? Date night spot? Girls night out? The best things to do? Ask Joyraft!

Best places to go in Boston? Things to do? Places to eat?

Questions & answers about things to do in Boston

Recs 💬

Community recs 💬

S4: top picks

The most fun, cool and unique things to do in Boston. Can’t miss events, shows and experiences. Concerts, restaurants, bars, free things in Boston and beyond.

The most fun and cool events happening around Boston

Hot and new things to do in Boston

Hot & new

Hot & new 🔥

S11: happening this weekend

What to do in Boston this weekend? From festivals, concerts, performances, free events, screenings and more, Joyraft has the best things to do in Boston.

25+ things to do in Boston/Cambridge/Somerville this weekend

Things to do in Boston this weekend

This wknd

This weekend for you

S21: roundups

Our top picks: outdoor dining, free events, spring festivals, best bars, upcoming concerts, museum parties - the latest in and around Boston.  Slug: joyraft-top-picks-best-things-to-do-boston-ma

Top picks of the best things to do in and around Boston

Joyraft picks: Boston’s best things to do

Roundups ⭐️

Curated by Joyraft ⭐️

S28: calendar experiences

This week in Boston

This week in Boston 📆

This week 📆

S20: c+d experiences

Discover new, unique events and experiences happening in and around Boston. Perfect for date night, good for a group or with a friend. Be the first to know.

The newest events happening in and around Boston

The newest events on Joyraft

Just added

Just added to Joyraft

S16: editor picks

The most unique and can’t miss things coming up in Boston / Cambridge / Somerville and beyond. Festivals, food, drinks, fairs, concerts, art and free activities.

Unique and Can’t Miss Things to Do in Boston

Can’t-miss things to do in Boston 🚨

Can't-miss things to do 🚨

S2 (A): top experiences

The most popular things to do on Joyraft. Concerts, restaurants, bars, events, parties, openings, kid friendly, date ideas, free things in Boston and beyond.

Top 20 things to do in Boston

Top 20: Joyraft’s most popular

Top 20

Top 20 on Joyraft

S3 (A): trending experiences

Discover can’t miss events and things to do in Boston. The most fun, unique and cool events coming to the Boston area this spring and summer.

The hottest events happening in Boston

Trending events on Joyraft

Trending 📈

S17: interest based

Your guide to everything free in and around Boston. From events, to fairs, to festivals, to outdoors. Joyraft has all the free events happening near you.

100+ free things to do in Boston and beyond

Free things to do in Boston

Free things to do

S19: interest based

Kid-friendly events in Boston

S18: interest based

Where to eat and drink in Boston? Joyraft has Boston’s newest bars, restaurants and specials. Drinks and pre fixe dinner menus. Cambridge & Somerville too.

worldoceanschool

Experiences

Boston Harbor Sail

Boston Harbor Sail

Sail into Father's Day with Free Wine!

Sail into Father's Day with Free Wine!

Pride Tea Dance aboard Tall Ship Denis Sullivan

Boston Harbor Sail

Boston Harbor Sail

Boston Harbor Sail

Boston Harbor Sail

Wine on the Weekend aboard Denis Sullivan

Father's Day aboard Denis Sullivan

"Dog"-side Event aboard Denis Sullivan

Walk the Plank with World Ocean School