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North Shore sailing for summer 2024!

Welcome to Sunset Sail Salem, home of New England's finest classic charter fleet and your destination for a truly authentic North Shore sailing experience.

Welcoming Schooner Malabar X for 2024

When and If will be joined by her senior sister, the beautiful Malabar X this Summer as we welcome her into our fleet for the first time. Widely considered to be the magnum opus of John Alden's prestigious schooner portfolio, Malabar X smashed records in the Newport-Bermuda race of 1932 and is available for private charter this Summer with Sunset Sail Salem!

Get inspired with our most popular trips!

Morning sails.

Blow away those cobwebs and start your day right with a morning sail on When And If. Saturday mornings are Mimosa Mornings so let our crew tell you about today’s signature cocktail with a twist, or enjoy a soft drink as we sail into the morning sun.

Afternoon excursions

The best way to escape the heat on those sweltering Summer days! It’s at least 10 degrees cooler on the water and if there’s a breeze out there we’ll find it. Leave the hustle and bustle behind to join us out in the cool blue where the bright sky meets the dark water as we sail through the afternoon.

Sunset sails

Take advantage of these long warm evenings and come enjoy a sail on a beautiful historic yacht, plying some of the finest sailing grounds around! Watch the sun set on another lazy hazy summer day as the twilight rolls in and we return to the dock.

Sail away to paradise with our exceptional trips

We are grateful to have such a supportive and loyal customer base, and we hope you will join them in experiencing the Sunset Sail Salem difference.

Sunset Sail Salem

Salem and the North Shore are home to some of loveliest sailing in New England. We offer daily sailing and private charters on the beautiful Salem Sound.

Come sail on our unique historic yacht and take in the views of Boston's North Shore, the scenic islands, picturesque lighthouses and abundant wildlife as wind fills the sails.

This summer marks our sixth season sailing the beautiful schooner When And If from the Salem landing. Hop onboard as we gracefully sail by up to 5 of Salem Sounds majestic lighthouses while sipping on your favorite cocktail in comfort and style!

A beautiful classic

The Historic Schooner When And If, built in 1939 for General George S Patton to sail around the world.

"When the war is over, and If I live through it, Bea and I are going to sail around the World" are the worlds of then Colonel Patton as he named his now historic yacht. The elegant classic schooner yacht now takes up residence with Sunset Sail Salem under the care of owner and Captain Seth Salzmann. This vessel is your chance to enjoy truly glorious sailing with room for up to 32 guests on private charters and 28 guests on our shared sailings. Set sail in class and style on this stunning example of the golden years in American yachting under sail!

Perfect sailing

Escape the crowds and take to the sea for an experience unlike any other. Watch as your experienced captain and crew cast-off lines and the yacht glides out of the harbor. Sit back and relax or lend a hand as we raise sail and turn off the engine. You’ll experience the thrill of the sails catching the wind and the schooner picking up speed as we sail past majestic lighthouse, beautiful beaches, rocky shores and numerous islands in the well protected waters of Salem Sound.

Enjoy from our array of craft cocktails, wines and beer as our Captain and crew share stories of the history of the ship and nautical tales of Salem Sound's storied landmarks and out islands. Misery island, Bakers island, Children’s Island and Marblehead neck are among the many sights to be scene on a regular basis. Keep in mind, that we go where the wind takes us and no two trips are the same!

Our happy customers share their experiences

At Sunset Sail Salem, we pride ourselves on delivering exceptional sailing excursions to our guests. Don't just take our word for it – read what our satisfied clients have to say about their experiences with us.

“Been onboard multiple times for a few day sails and also booked a private charter for my mom and dad’s 30th anniversary last year. Phenomenal experience every time.”

“We had the best sail we could have hoped for. Captain Eric was fun and informative. Will go again and recommend you all do the same. 👍🏻”

“So much fun, and so relaxing. The captain and crew are awesome and really do their best to make your experience amazing. This is a must do.”

Sail into adventure! Our upcoming events

Join us as we set sail and explore the beauty of the open water. Check out our events to see what's coming up and sign up today for an unforgettable adventure on the water!

Sunset Sail on When & If

Set sail on a classic sailing yacht, gliding through the calm waters while the evening breeze fills the sails. The experience of sailing during the sunset is a memory that will last a lifetime

Private Charter on Malabar X

The beautiful Malabar X, (1930) joins our fleet for the first time this Summer. With space for up to 20 guests and a sailing experience matched only by that aboard her younger sister When And If, a private charter on Malabar is truly the finest classic sailing on the North Shore.

Private Sunset Sail

An excellent option for those seeking a unique, unforgettable and exclusive experience. Your Private charter can accommodate up to 32 guests .

Love our Salem sailing excursions?

If you've enjoyed our Salem sailing excursions, you'll definitely want to check out our sister sailing companies!

Sunset Sail Key West

Sunset Sail Key West is more than just a private sailing charter, it is the culmination of decades of experience and a lifetime of passion for sailing, and for Key West.

When and If

A beautifully restored 1939 John Alden schooner, When and If was designed for American General George S. Patton to sail around the world.

Looking for fun events? Top 5 things to do around Tallahassee

Let there be sunshine and electricity this weekend. It's been a rough week.

Arts groups were among many hit hard by the May 10 storm and tornadoes. They had to act fast and make changes to keep shows going.

The Tallahassee Symphony Orchestra is dusting off at Adderley Amphitheater and picking up the baton with a guest conductor for the 2nd Annual Freedom's Eve Emancipation Concert on Friday. Pas de Vie Ballet moved its concert from the FAMU Campus to FSU's Fallon Theatre.

Food drives and special donations are planned to help others. Come out and support the arts as the community pulls together.

Here's a roundup of entertaining events around Tallahassee, culled from emails, the  Council on Culture & Arts  online listings and elsewhere.

Need a break? Play the USA TODAY Daily Crossword Puzzle.

Benefit: Fundraiser for Railroad Square set for Saturday in Downtown Tallahassee | Brew Bend

Tallahassee bistro: Sample fine vintages, schnitzel, oysters and music at Tallahassee's cozy Wine House

UPDATE: Friday's Freedom Eve concert moved to The Moon

Due to forecasted rain and thunderstorms Friday evening, the 2nd Annual Freedom's Eve Emancipation Concert with the Tallahassee Symphony will now be at The Moon. Food trucks, entertainment by local organizations, and information booths will open at 5:30 p.m. The orchestra concert begins at 7 p.m. This event is free and open to the public. Seating is general admission. The parking lot at The Moon is open to all attendees for this event. Additional parking can be found across Lafayette Street in the shopping center.

FOOD and BEVERAGE: A cash bar will be open at The Moon starting at 5:30 p.m. Food Trucks will begin sales at 5:30 in The Moon parking lot: Blow’s Buss Down Food Truck, Fired Up Pizza, Street Chefs.

1. 2nd Annual Freedom's Eve Concert

The Tallahassee Symphony Orchestra will proceed with the 2nd Annual Freedom's Eve Emancipation Concert as scheduled from 6-9 p.m. Friday at Adderley Amphitheater in Cascades park. There will be a reading of the Emancipation Proclamation and a full schedule of events to celebrate Florida's Emancipation Day.

This will be an uplifting, free, community gathering including performances by the Capital Battery Line, Ayoka Afrikan Drum and Dance, historical reenactments, and several local vendors, followed by a performance by the TSO. The symphony will introduce guest conductor Chelsea Tipton, who will perform with Marques Jerrell Ruff and Jay Williams & Total Praise to lift community spirits. Pre-concert entertainment and vendors start at 6 p.m. concert starts at 8 p.m.

TSO will host a food and supply drive at the concert for Sabal Palm Elementary School, located in one of the hard-hit neighborhoods. The school is back open but supplies are depleted. School administrators have requested non-perishable food items and fresh produce. Cash donations or store gift cards (Walmart, Publix, Target) also accepted and will be collected at the TSO table on the plaza behind the amphitheater.

In case of bad weather or rain, the concert will be moved to The Moon and all activities will be moved to the Moon parking lot.

2. Spotlight on Pas de Vie Ballet

There's been a venue change because of the storms but Pas de Vie Ballet's Spotlight on Dance concert will go on as planned this weekend with all performances at FSU's Fallon Theatre, 503 W. Call St.

Artistic direct Natalie Botha is celebrating the ballet's 35th year of guiding young artists and producing critically-acclaimed dance pieces. The children's performances of "Peter and the Wolf" will be at 11 a.m. Friday, May 17. Tickets are $5. The Spotlight on Dance concert will be at 7:30 p.m. Saturday, May 18, and 2:30 p.m. Sunday.

Tickets are $10-$25 each (pay what you can). For more information, visit pasdevieballet.com .

3. Be uplifted with New 76ers at concert series

Catch the heartfelt vocal harmonies of the acoustic folk "family" trio, The New 76ers, when they play a show at the Holy Comforter Episcopal Church Concert Series on Friday, May 17. Doors open at 7 p.m. with the concert beginning at 8 p.m. There is plenty of parking in the school parking lot.

Tickets are $20, payable cash or check at the door, or available for advanced pick up at the Church office at 2015 Fleischmann Road.

4. Music for Food Tallahassee concert

Just in time to lift spirits after the storms, Music for Food Tallahassee presents “Happy Shoes,” a concert to benefit the FSU Food For Thought Pantry, at Grace Lutheran Church, 2919 Miccosukee Road, from 4-5:30 p.m. Sunday, May 19.

Sunday's “Happy Shoes” features one of Franz Schubert’s most beloved songs, the beautiful “Shepherd on the Rock,” for soprano, clarinet, and piano. Next is the Folk Suite for violin and harp, written in 2008 by Taiwanese composer Chiayu Hsu. The program closes with the sunny and delightful Piano Quartet by Robert Schumann.

Performers include Deborah Bish, Mitchell George, Deloise Lima, Galen Dean Peiskee, Jr., Corinne Stillwell, Marcy Stonikas, Benjamin Sung, Noël Wan, and Laurel Yu.

Music For Food is a musician-led initiative to fight hunger in our community, part of a national organization with 22 chapters across the country. The concert is free but there's a collection for non-perishable food and monetary donations to benefit the FSU Food for Thought Pantry. Donations may be made at musicforfood.net. Suggested donation: $20/adult; $5 student.

4. Jump into cleanup at Riverpalooza in Apalachicola

Apalachicola Riverkeeper plans a celebration of the Apalachicola River, Bay, and Floodplain with Riverpalooza on Saturday, May 18, at the Apalachicola Bay Yacht Club, 170 Water St, Apalachicola,

The day begins with a community, coastal cleanup sponsored by OceanAid 360. Collect trash however you like – walk around and find trash by foot, grab your bike and pedal around, paddle the kayaks along the shoreline, or take your boat out to collect trash by boat. There will be a dumpster at the Apalachicola Yacht Club (AYC) for trash and debris disposal.

After the clean up, gather at the Apalachicola Yacht Club for a celebration with music, food, and a good time. Join us for fun and a chance to win exciting adventure gear. Music will be played throughout the day by Clayton Mathis, Chris Matechik, Flying Fish, and the Funky Taters.

Tickets can be purchased in advance at the Water Craft Brewing Company and Riverkeeper’s office in Apalachicola. Tickets also can be purchased on the day of the event at the Apalachicola Yacht Club! Tickets are $10 each; 5 for $40 or 10 tickets for $75.

5. Get in the groove at Havana Reggaefest

The 14th year of Havana Reggaefest gets the beat going from noon-8 p.m. Saturday, May 18, at 5F Farm Event Center, 8583 Salem Road in Quincy.

This cultural experience features seven bands featuring Alex Marley and six other bands includingTobacco Rd. Attendees can also visit the kitchen and learn authentic cultural cooking and shop the antique thrift and gift shop. Tickets are $10 pre-concert at G&G restaurant. Day of tickets are $15-$25. Visit simpletix.com. Call 850-766-3955.

Bonus event: 'Demon Barber' opens in Monticello

The Monticello Opera House gets bloody with "Sweeney Todd: The Demon Barber of Fleet Street," by Stephen Sondheim and Hugh Wheeler, opening on Friday, May 17.

The production runs through June 2 at the Monticello Opera house, 185 W. Washington St., Monticello. Tickets are $27. Visit monticellooperahouse.org . Due to violent content, this show is not recommended for children.

In this infamous tale drawn from a "penny dreadful" story from the Victorian era, Sweeney Todd, an unjustly exiled barber, returns home to 19th century London, seeking vengeance against the lecherous judge who framed him and ravaged his young wife. The road to revenge leads Todd to Mrs. Lovett, a resourceful proprietress of a failing pie shop, above which, he opens his new barber practice. Mrs. Lovett's luck sharply shifts when Todd's thirst for blood inspires the integration of an ingredient into her meat pie.

Bonus event: Millstone's Spring Harvest Tour

Millstone Institute of Preservation in Tallahassee is presenting a new community event with its Spring Harvest Tour of farms. Take a self-guided tour and road trip to over 30 farms, ranches and orchards on May 18-19.

Modeled after the popular Fall Farm Tour, now in its 17th year, this new event presents people with the opportunity to get out in spring and visit local farms, ranches, orchards, and gardens. Farmers are excited to showcase their spring crops and animals. The Madison County Tourist Development Council is the Patron Sponsor of the Spring Farm Tour. Make sure you download the guide book to know which farms are participating.

Via the Tour Guidebook, you read about each farm/garden and decide which you’d like to see. The Tour has stops in 10 different counties. Purchasing products at each site will be available. Some sites have created their own festivals around the tour! Download your Spring Harvest guide via Facebook.

Bonus event: Maclay Tour of Gardens

The 29th Annual Maclay Tour of Gardens – an event of the Friends of Maclay Gardens, a nonprofit Citizens Support Organization that has assisted Maclay Gardens State Park in meeting critical needs for over 30 years – will take place from 9 a.m. until 3 p.m. on Friday and Saturday, May 17 and 18.

This year’s Tour will highlight seven Tallahassee residential landscapes, all garden-owner created and maintained. Tour attendees will be treated to a continental breakfast at Maclay Gardens State Park beginning at 8:30 a.m. and will receive Tour booklets detailing locations and descriptions of the gardens.

Maclay Tour of Gardens one-day tickets (Friday, May 17, or Saturday, May 18) are available on the Friends of Maclay Gardens website,  friendsofmaclaygardens.org.

OTHER EVENTS

Apalachicola Area Historical Society : Spring Speaker Program featuring Jack Rudloe at 4 p.m., Saturday, May 18, at the Raney Carriage House, 126 Market Street, Apalachicola. Jack Rudloe is the founder of Gulf Specimen Marine Laboratory in Panacea, a unique environmental education center and public aquarium that supplies marine organisms to schools and research laboratories. He is the author of seven well-known books on Florida natural history and marine life.

Blue Tavern: Start the weekend with Two Clever from 5-7 p.m. Friday, May 17, at Blue Tavern , 1206 N. Monroe St., followed from 8-11 p.m. with Will Fulkerson Jazz Night at the Tavern with Leon Anderson & Rodney Jordan. After the trio plays the first set, alto saxophonist extraordinaire Jonathan Gray will join the band for the rest of the night. $10 cover. Its 3rd Saturday Trad Irish Session from 4-7 p.m., followed at 8 p.m. by the Corey Hall Trio. Corey Hall is a folksinger with a hot band. $10 cover.

On Tuesday from 5-7 p.m. catch happy hour with Bronwyn Chelette, followed at 8 p.m. by Bluesday Tuesday with Bubbles Brown, a singer-songwriter, multi-instrumentalist, and two-piece outfit from Chicago, now headquartered in New Orleans. $5 Cover. On Wednesday from 5-7 p.m., Rick Redmond plays, followed at 8 p.m. by Open Mic Night. On Thursday from 5-8 p.m. catch Therese Whichello with adult recital and student showcase, followed at 8 p.m. by free movie night with movies featuring Roger Corman movies, who died at age 98 last week.

Downtown Market : Acoustic duo Hot Tamale will be entertaining at the Downtown Market in the Chain of Parks from 10 a.m.-1:30 p.m. Saturday, May 18. Hot Tamale is known for their upbeat shows and their family-friendly repertoire.

LeMoyne Arts: Last chance to see "Soulful Feelin: A Folk Art Celebration” at LeMoyne Arts, 125 N. Gadsden St., from 11 a.m.-6 p.m. Saturday, May 19. The exhibit features renowned folk artists such as O.L. Samuels, Eddy Mumma, and Thornton Dial, Sr., alongside contemporary voices such as Mary Proctor.

Great Oaks Pub at Southwood: The “Rhythm Remedy” makes a return visit to the Great Oaks Pub, 3750 Grove Drive, combines the vocal power of Mark Blair from Crooked Shooz and the horns from Acme R&B , and sprinkles in other local musical stars to achieve a cornucopia of dance oriented, horn driven classic soul, funk, and rock. Join Mark, Mike Brawer, Kent Rodriguez, Steve VanGorder, Greg Moore, Bill Landing and Tom Buchanan for a funkadelic adventure this Friday. $3 cover for members and $7 for public. Call 850-942-4653 for reservations.

Rock Type One to None Concert: Three bands will perform at fundraiser for Type 1 diabetes research at Dreamland Bar-B-Q, Centre Of Tallahassee, from 4-7 p.m. Saturday, May 18. Performers include Tallahassee guitarist and vocalist Chris Manuel and his band Midnight Caravan. Also on the bill is a relatively new group of young rockers called Fallen Timber, whose journey as a band started while attending Chiles High School. Unicorn Wranglers, who have organized this event for several years, will close the show.

Wine House : Corine Samwel and Douce Ambiance will be performing at The Wine House on Market Street from 7-10 p.m. on Friday, May 17. This will be  an evening of European art songs, standard jazz songs, and Gypsy Jazz instrumentals in a warm ambiance with good food and drinks. Think Edith Piaf, Jacques Brel, Marlene Dietrich. Cover charge $10.

Have an event coming up? Email details to [email protected].