Adventure Collective
Water Activities: Discover Sailing with Isabella Private Charters - Boston

Water Activities: Discover Sailing with Isabella Private Charters

Gloucestereasy

Difficulty

easy

Duration

1–3 hours

Fitness Level

Suitable for most ages and fitness levels, minimal physical activity required

Overview

Sail into the Massachusetts coast on the Schooner Isabella, where personalized cruises reveal hidden coastal gems and seabird-filled skies. Discover what makes this private vessel a standout for maritime adventure.

Gloucester, Massachusetts

Isabella Private Charters

Price includes up to 6 Passengers

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About This Adventure

Experience the charm of sailing aboard the Schooner Isabella, a cozy six-passenger vessel perfect for unforgettable sunsets, romantic date nights, or family adventures. With the ability to navigate unique coastal spots and the Essex River, each private charter promises a personalized journey led by an attentive captain and crew.

Affordable six-passenger charters perfect for sunsets, date nights, family day sails or customized day trips.

Built for comfort, above decks and below, the Schooner Isabella is perfectly suited for small group private charters. Her smaller size and shallower draft allows her to go places that are a lot more difficult on Ardelle such as nearby coastal villages or down the Essex River.

  • Isabella Private Charters are available throughout our sailing season from July-September, based on availability.
  • Our charters typically depart from and return to Maritime Gloucester, 23 Harbor Loop, Gloucester, MA. If you would like to arrange a charter from an alternate location, please give us a call to arrange pricing.
  • All Private Charters include the exclusive use of the vessel and the services of our Captain and crew.

Adventure Tips

Arrive early for the best sunset views

Getting on board before sunset ensures prime spots for capturing the stunning colors over the water.

Bring layers and sun protection

Weather at sea can change quickly; pack layers and sunscreen for comfort.

Capture the wildlife

Bring binoculars and a camera to spot and photograph local seabirds and marine mammals.

Book in advance for holidays

Private charters fill quickly during peak seasons, so reserve early for holidays or special dates.

Local Insights

Wildlife

  • harbor seals
  • oystercatchers

History

The Schooner Isabella has been a part of Essex’s maritime scene since the early 1900s, carrying generations of sailors and ocean lovers.

Conservation

The operation emphasizes eco-friendly practices, including waste reduction and wildlife-friendly navigation.

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Adventure Hotspots in Boston

Frequently Asked Questions

Recommended Gear

Sunscreen

Essential

Protects your skin during daytime cruises under the sun.

summer specific

Hat and sunglasses

Essential

Shield your eyes from the sun while enjoying the ride.

summer specific

Light jacket or sweater

Brisk breezes on the water may require some additional warmth.

spring; fall specific

Camera or smartphone

Essential

Capture scenic views and wildlife during your voyage.