Sail Añejo offers a unique sailing experience in Gloucester, MA, allowing guests to explore America’s Oldest Seaport from the deck of a beautiful sailboat. Visitors can choose from private sails or sunset cruises, enjoying scenic views of Cape Ann, historic landmarks, and the famous fishing vessels from the show "Wicked Tuna." The boat departs from 19 Harbor Loop, providing a tranquil escape from the noise and crowds of the city. Guests consistently praise the exceptional hospitality of the Captains, who are known for their friendliness and helpfulness. The atmosphere aboard Sail Añejo is described as welcoming, safe, and comfortable, making it perfect for special celebrations or casual outings. Many reviews highlight the ease of booking and the great value offered compared to other options. Whether celebrating a milestone birthday, an anniversary, or simply enjoying a girls' weekend, guests leave feeling relaxed and enchanted by the experience. The customized tours and engaging commentary from the Captains add a personal touch that makes each sailing memorable. With many customers eager to return for another sailing adventure, Sail Añejo stands out as a must-visit destination for anyone looking to enjoy the beauty of Gloucester from the water.
We had the most amazing time on the Anejo! We rented time for a girls trip and had so much fun, relaxed, and learned more about the area. Stephanie and Michael were extremely kind, personable, and helpful. I would certainly use their services again and recommend this to anyone wanting an afternoon of leisure on cape Ann!
July 2025
Stephanie and Captain Birch were incredibly helpful, friendly and just made the whole experience enchanting!! Can’t wait to go sailing with them again!
June 2024
Best experience we could’ve asked for! Did the sunset sail for engagement photos and was 100% worth it. They were super accommodating and I would recommend to anyone looking for a photo session or just a fun date night!
