Sail Anejo

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We want to thank EVERYONE who has supported us over the years. We are pausing charters. Stay tuned for what the next chapter holds.

Sail Charter in Gloucester, Massachusetts serving Cape Ann, the North Shore of Boston and beyond.

10/27/2026

One last goodbye to Gloucester! ⚓️❤️

We’ve loved being part of this incredible community and are so grateful for the friendships we’ve made along the way. These are the kind of friends who will remain a part of our lives for years to come. ❤️

We’ll miss the sailing, the schooners, and the magic of a harbor so rich in history. ⛵️ There’s something truly special about Gloucester that will always hold a piece of our hearts.

As we turn the page to our next adventure, we’re leaving with full hearts and so many beautiful memories.

On to the next chapter… we’re on to our next waypoint! 🌊✨

10/22/2026

⛵️ Añejo has arrived in Newport, RI! 🌊

Captain Chris departed Onset before dawn, cruised through the Cape Cod Canal, and continued on to Newport. Now we wait for the transport boat that will carry Añejo to the Bahamas! 🇧🇸☀️

In the meantime, Newport might just be one of the best places in the world for a sailboat to be. ⚓️⛵️ Beautiful harbor, gorgeous boats, and that unmistakable sailing spirit.

Next stop: The Bahamas! 🌴🌊

SailboatLife CaptainChris LifeOnTheWater

10/19/2026

⚓️💙 A new chapter begins for Añejo! 💙⚓️

Today, Añejo said goodbye to Gloucester and began her journey to her new berth in Gulfport, Florida! 🌴☀️

While it’s bittersweet to leave the “Oldest Seaport in the U.S.,” we’re taking so many wonderful memories with us that will forever hold a special place in our hearts. ❤️⚓️

Over the next couple of weeks, we’ll be documenting her journey south, sharing the sights, the stops, and the adventures along the way! ⛵️🌊

We hope you’ll all come along for the ride as Añejo begins this exciting new chapter! 💙

📍 Gloucester, MA ➡️ Gulfport, FL

JourneySouth BoatLife MakingMemories

08/14/2026

This summer has been one for the books. ☀️
We’ve closed the chapter on chartering, made the move south to St. Pete, and now there’s just one last move to make…

Añejo. ⛵️

And what a move it will be.

Stay tuned as we bring her south and begin our next chapter in Florida—post-hurricane season. 🌴🌊

The adventure continues. ✨

05/24/2026

As we set sail for new horizons, we're filled with gratitude for the incredible journey we've shared with you in Gloucester! 🌊❤️ We're excited to trade in our winter coats for sun-kissed days, where every moment can be a celebration of freedom and joy! Stay tuned for Añejo's next chapter, where the sea meets endless possibility! 🌴

05/23/2026

First shake down sail of the season. It might cold but it is the only place we want to be!

11/09/2025

Went to visit Añejo. We miss not being in the water.

11/02/2025

That's a wrap on sailing season! Bittersweet farewell to Añejo, but we're stoked for winter adventures. Stay tuned for the journey!

10/06/2025

Not often night is Añejo on a dock in Gloucester, but when she is, she sure does look good.

09/28/2025

As the season winds down, we think about all the days aboard Añejo and all the places we went.

Address

Solomon Jacobs Landing
Gloucester, MA
01930

Telephone

+19788528016

Website

https://www.sailanejo.com/

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