sailboat charter rockland maine

We look forward to sailing with you again in May 2024.

A Morning in Maine

Sailing tours on beautiful penobscot bay, featured sailing trips.

• Most Popular!
• Clock 2 Hours
• Users All Ages

2-Hour Sailing Trip

Join Captain Tyler Waterson aboard the beautiful 55′ ketch Morning In Maine, as he points out the natural and historic features unique to Penobscot Bay.

• Clock 6 Hours

Monroe Island Adventure

Your island adventure awaits! Maine has over 3,000 miles of coastline, and almost half of that is on islands only accessible by boat.

• Clock 2.5 Hours

Science under Sail

Join us and a science educator from our partners at Herring Gut Coastal Science Center in Port Clyde as we set sail to learn about the ecology of Penobscot Bay!

Day Sails on Penobscot Bay

Enjoy the Maine Coast’s beauty from the deck of Morning In Maine. Relax and watch the seabirds and harbor seals as the ketch glides through the waters of Penobscot Bay… or lend a hand in sailing the boat!

On most Maine sailing trips we see Rockland Breakwater Lighthouse, Owls Head Lighthouse, and historic schooners. Monday morning is the best time for a day sail in Rockland, Maine, where we watch the schooners sail out of the harbor for their week-long cruises.

We look forward to having you aboard!

The boat accommodates 21 passengers and can fill up quickly, so make your reservations early!

#1 Outdoor Activity in Rockland, Maine! Our Customers Love Us!

Maine is best by sailboat.

“Loved our afternoon on Morning in Maine. The wind was great and the boat is really lovely. Capt Tyler and George were great crew. Saw eagles, a harbor seal and all the sights you’d want to see in Rockland. Sailing really is the best way to get to know Maine.”

Best "boat ride" in Maine

“As Mainers, we have had the opportunity to go on various “boating adventures” along the Maine coast. This was the most pleasant and fun one ! 2 hours was perfect. The captain allowing the kids to help with the sails was very cool and even steer… Totally made their day. The captain was very personable and made the trip interesting. I was concerned about getting seasick, but the ride was actually very smooth.”

“We had a wonderful time on our sailing expedition and learned a lot about the area. Definitely worth the time to spend some time on the water with folks that live in the area sharing lots of good stories.”

Great experience!

"Our sail on a Morning in Maine was one of the highlights of our trip. The views were beautiful and the ride was smooth and relaxing. It was a great experience and one that I highly recommend!"

Schooner American Eagle

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Dump out your bucket list.

This is the adventure you’ve been looking for..

Windjamming is, quite literally, like nothing else on Earth. By turns exhilarating, relaxing, surprising, and nurturing, it’s like no other vacation you’ve ever experienced.

Wake up to the quiet solitude of Maine’s coast, find renewal in the wind and sun, and surprise yourself as you help steer the ship. Aboard our vessels, with itineraries tossed to the wind, our guests find both a spark of adventure and time to reflect.

Is there a sailor in your soul?

Welcome to the Maine Windjammer Association – the largest fleet of traditional tall ships in the Americas. Our iconic windjammers offer multi-day, all-inclusive, sailing adventure cruises in one of the most acclaimed cruising grounds in the world.

When you sail aboard a Maine Windjammer Association vessel, you can be sure that your hosts hold themselves to the highest standards of safety and quality. As your captain and guide they will treat you to honest, heartfelt Maine hospitality and personalized attention.  Explore our fleet and offerings to find your perfect cruise.

The Windjamming Experience

Simply put, windjamming is about reconnecting with our essential enjoyment of life. It’s about gorgeous scenery, human connection, soul-nourishing meals, and taking time for both adventure and reflection. Our playground is the sparkling sea and the spruce-clad granite islands that rise from it.

Whether you join us for a three-night cruise or a week, we promise you a total escape from the ordinary. Be prepared to get closer than you ever have before to breathtaking wildlife like eagles, seals and porpoises, to visit some of North America’s most spectacular coastal scenery, charming villages and unspoiled islands, and to savor the freshest, fire-cooked Downeast fare. With only 16-31 guests on our ships, you’ll experience the kind of honest, heartfelt hospitality that keeps our guests coming back year after year.

Welcome to the only place in the world where schooners play in abundance. Where steady breezes, glittering bays, and literally thousands of islands make Penobscot Bay one of the most revered cruising grounds on earth.

On our small ship cruises, we have complete liberty to explore secret anchorages, remote fishing villages, and charming gallery towns. Schooners have been an intrinsic part of the Maine Coast for centuries, and there is something very special about rounding the point and arriving at anchorage under sail. Come touch this culturally distinct, pristine and physically breathtaking part of America.

Explore by Schedule

Use our cruise finder below to explore sailing options that fit your schedule. If your dates are flexible, or you just want to learn more, visit our fleet page and each vessel’s website. Reservations can be made directly with the Windjammer of your choice. Have fun exploring! Whichever vessel you choose, you are sure to have the sailing adventure of a lifetime.

Find My Trip

Best ever bucket list item! Absolutely wonderful Captain & Crew which made the whole experience a 5 star bucket list event for me. Sailing on an antique vessel was thrilling and boy could the crew make her preform!

Stay in the Know

With our monthly newsletter, you’ll receive tips and hints from folks who have sailed as well as information about the best dining and attractions the area has to offer, special packages, windjammer history, events, and more!

You can request a mailed or digital packet of brochures, or you can find individual ships’ brochures under each listing on the fleet page.

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Convenience 

Quality .

Spend more time having a good time, instead of planning to have a good time. By not spending so much time and effort trying to figure out where to eat, where to go and what to do - you'll have more vacation in your vacation. 

One of the main benefits of a Private Charter is that the quality of your experience will be better. Doing things as a group is about connection. With more time spent together, you'll connect more. This is the whole point of a group experience. 

Time together, along the coast of Maine, aboard your own private schooner, is an exclusive experience without equal. Our Private Charters afford you unparalleled freedom, privacy and options.  

 A  Private Charter improves the quality of your group experience.

Have maine all to yourself.

Maine is " Vacationland." It's all about getting away from it all. But. How do you get away from all the other people trying to get away from it all?

You book a Private Charter, aboard our charming 1882 schooner, Grace Bailey. 

What about planning? How do you make planning a group vacation easier? You will love our solution. Don't do it. Plan nothing.  ​

We take care of everything. Accommodations - done, meals - done, activities - done, destinations - done. You don't have to do any planning.

Just get here, and get going. 

Private Charters

"Trip of a lifetime." 

Vancouver CAN

"It allowed me and the guys to connect."

San Diego CA

We take our favorite restaurant with us. Our chef will plan all the meals. Would you like chocolate cake for dessert? We can do that.

We can create your favorite meals for you. We can also let the chef freestyle the menu and spoil you with the fruits of her travels. Beyond your preferences, we can cater to any allergies or diets.

We hope you are beginning to see the many benefits of a Private Charter.

Note that we can only make plans on trips that are not yet booked for next year. We encourage you to contact us as soon as you have some dates in mind from next year's schedule . 

Call or Contact us to feel the relief of making a good decision. Relief and excitement. We look forward to hearing from you.

Spend  more time having a good time, instead of planning to have a good time. 

Private Charter Inquiry

Thank you for submitting your Private Charter inquiry. We will contact you back quickly about your plans. You have chosen well.

CONTACT FORM

Take care 

of Everything

A private charter aboard grace bailey includes:.

An island lobster bake / steak dinner

This applies to any length trip; from a 3 night jaunt to a 6 night adventure. ​

The lobsters will be sourced and picked up fresh along the way. 

All meals, made fresh three times daily with dessert at lunch and dinner. ​ ​

Wine is served with dinner. Beyond that is BYOB. We have a quite large cooler. Imbibe as you wish.

Our chef can accommodate allergies, conditions and preferences with skill and taste. ​​

Every member of the party will enjoy equal quality, regardless of meal variant. 

Full run of the ship. If you want to swim, we'll anchor. If you want to leisurely enjoy our small boats to explore our chosen anchorage, you will. We will still adhere to our policy of chasing the best winds; safety and logistics takes precedent. ​

Convenience

EVENING STAR YACHT CHARTERS

Maine Bareboat Yacht Charters

Sail the Coast of Maine on a Beautiful Classic Sailboat

Looking to charter a bareboat yacht on the coast of Maine?   Evening Star   is a 45' traditional sailboat available for bareboat charter from Belfast Harbor in the heart of Penobscot Bay!   The yacht Evening Star is equipped with Hood Stowaway roller furling masts and has two double staterooms, each with its own head and shower.  

Now Taking Reservations for 2024      Available Bareboat or with Captain

The Sailing Yacht BLUE VAYU

Your Captain Linda Hanson

Capt. Linda Hanson is the owner and operator of BLUE VAYU. She holds a 100-ton license. Linda has cruised and raced sailboats on the Atlantic Ocean and the coast of New England for the past 30 years. In her opinion, Penobscot Bay offers spectacular sailing and is the jewel of the Maine coast. 

As a former teacher of French and Spanish, Hanson has traveled extensively in Europe and South America. Sh

Sail beautiful Penobscot Bay on your own private charter. Come aboard BLUE VAYU and discover the adventure and the beauty of a well-balanced yacht under sail.  The Blue Vayu is a classic Swedish sloop built in 1974 and extensively restored to display her mahogany and teak topsides.  Her classic European design and graceful demeanor turn heads wherever she goes.

Your private charter is $150. per hour with a two hour minimum. The fare is for parties of up to six people. Snack and beverage is provided.  

Custom excursions

Custom excursions are between two and six hours. Trips between two to three hours allow ample time to sail to inner harbor lighthouses and  observe the lobstering culture. Longer excursions may visit nearby islands and harbors.

* weather permitting

Photo Gallery

Captain Hanson on a day trip to Pulpit Harbor, North Haven Island, Maine with sailor and extreme skier Dan Egan.

Husband and wife comment on their three day trip to Mt. Dessert Island

Set sail aboard Blue Vayu and improve your sailing skills with Captain Linda Hanson

1 Harbor Park, Rockland, Maine

207-749-1289

[email protected]

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Your Maine Adventure Awaits!

Come experience a Maine windjammer vacation along the rocky coast on the historic Schooner J.& E. Riggin . Enjoy 3, 4, 5, or 6-day eco-friendly sailing vacations as your windjammer cruise, departing from Rockland Maine, takes you past the spruce clad islands, unequaled rocky coastline and legendary lighthouse-dotted bays of Penobscot Bay.

This unforgettable travel experience is why over 65% of our passengers return year after year, not to mention the food!

Book Your Maine Sailing Adventure Today!

What’s new?

• Our 2023 Sailing Schedule will feature NEW cruises like Sip & Sail Adventures featuring local mixologists, distillers, and brewers!
• Jocelyn is making a Pumpkin & Sweet Potato Curry Soup to beat the chill.
• The stays’l & jib are in the loft of Gambell & Hunter where they are being measured for replacement.

Noteworthy…

Named “Best Windjammer Fare” – a Maine Classic in the Best of New England by Yankee Magazine as well as one of the places to visit along New England’s “Maritime Trail” and “8 Perfect New England Weekend Getaways”.

Latest from the blog

Caulking the Deck : “One of the best things we can do to keep everyone comfortable on board the J. & E. Riggin is keep things dry. Especially in the cabins. The best way to keep the cabins dry, is to make sure there is plenty of material in between the pine planks that form the deck. The gaps between the planks are called seams and they are packed tightly with cotton and oakum before being sealed with a layer of hot pitch .”

About the Riggin

Schooner J. & E. Riggin is a proud member of the Maine Windjammer Association

Copyright © 2018 - 2024 Schooner J. & E. Riggin. All rights reserved.

Explore, Discover The Ocean

NorthPoint Yacht Charters arranges sailing and power boat cruising charters in Maine and Northern New England.

• Charter Gallery

Enjoy The Ocean With Your Family

NorthPoint Yacht Charters offers a wide variety of boats owned and managed by individual owners including both power and sailboats from 28-80 feet.

• How To Charter

Charter with NorthPoint Yacht Charters

Both bareboat and crewed charters are available. We also offer transportation, concierge services, bed and breakfasts, custom itineraries, provisioning, catering as well as special events. We are proud of our boats and take the extra time to make sure that your cruise will be pleasurable and trouble free.

About NorthPoint Yacht Charters

Welcome to the 2024 Charter Season

NorthPoint Yacht Charters arranges sailing and power boat cruising charters in Maine, Northern New England and the Canadian Maritimes. We offer a wide variety of boats owned and managed by individual owners including both power and sailboats from 28-80 feet.

Both bareboat and crewed charters are available. We also offer transportation, concierge services, bed and breakfasts, custom itineraries, provisioning, catering as well as special events.  We are proud of our boats and take the extra time to make sure that your cruise will be pleasurable and trouble free. 

Announcements

Luxury yachts.

Select from wide variety of boats including both power and sailboats 20-80 feet:

View Gallery

Curve of Time Morris Ocean 32 32‘

Lucky Dog Sabre 36 36‘

Tailwind Sabre 36 36‘

Pax Sceptre 41 41‘

Thira Catalina 30 30‘

Presence J/35 35‘

Osprey Hinckley Pilot 35 36‘

Sweetness Cape Dory 36 36‘

View Full Charter Gallery

What Customers are Saying...

KOAN performed beautifully. …. The engine runs great . MC

Our charter of Blue Goose two was excellent. She is the only boat I have ever charter or used including my own that there was nothing to fix. She was very clean, well outfitted with towels, linens and basic condiments.

We had a great cruise on Alliance. We visited Pulpit, Castine, NE Harbor, Seal Harbor (Vinalhaven), Islesboro and Tenants. RE

Get In Touch With Us

NorthPoint Yacht Charters arranges sailing and power boat cruising charters, we offer a wide variety of boats owned and managed by individual owners including both power and sailboats from 28-80 feet.

• Crewed Charters
• Experience Resume
• Charter Resouces
• Charter FAQs

SCHOONER HERITAGE

Experience the very best  of

the Maine coast!

Unleash Your Inner Sailor on a Windjammer Adventure in Maine!

Sail aboard the newest and largest vessel in the fleet!

Welcome Aboard!

Join us aboard the Heritage this season for an unforgettable Maine windjammer cruise. Every trip is special. Capts. Sean and Ben are your hosts aboard every trip. In addition to sailing the vessel, they enjoy entertaining their guests by playing live music in the evenings. The food is delicious with restaurant quality dishes made with fresh local ingredients. Daily breads, cookies, and desserts are all freshly baked aboard.

Each trip we enjoy an all-you-can-eat lobster cookout on a pristine island beach. Hear about the islands, vessels and people of Mid-Coast Maine as well as the many lighthouses we see. Wildlife abounds with birds both ashore and at sea as well as marine mammals. Best of all you can enjoy sailing aboard a schooner built with your comfort in mind.

Enjoyed the trip of a lifetime with my daughter (age 29)! The Captains and crew were kind and engaging and the food was incredible! The main coast is full of beautiful little islands and sailing felt like such an adventure! The captains entertained us one evening and surprised us with their notable talents!

We have a trip for everyone aboard the Schooner Heritage. Whether you want to sail with the fleet, explore in search of lighthouses, tour Acadia, bond with family, gaze at shooting stars, or just relax and sail the Maine coast with no itinerary. We can always promise stunning views, delicious food, and an unforgettable experience. Summers in Maine are a time for growth and rejuvenation. The season is short so as Mainers we celebrate and make the most of it. Join us in this celebration as we explore hidden places not accessible to most and with 3,478 miles of tidal coastline, see Maine the way it was meant to be seen.

Coasting schooners, like the Heritage, were designed for accessing shallow passages and ports allowing us to travel to more secluded places where comparable sized vessels can’t access. This makes Heritage the perfect choice when choosing a windjammer to sail on.

Enjoy an evening beverage and sing along with Captains Sean and Ben during lively music nights.  Whether up on deck, or down in the galley, music nights aboard the Schooner Heritage are the best on the bay! 

Performing different genres of music, and the songs you know and love, as well as songs you may have never heard before that will surely be added to your playlist after you get home. 

We look forward to you joining us!

Photo: Nick Parson

Relax  & Unwind

You'll feel like you've stepped into another time and place aboard Heritage. Each day is filled with a little adventure and plenty of relaxation. We leave Rockland headed for parts unknown; wherever the wind, weather, and tides take us. The coast of Maine is spotted with over 3,000 islands topped with lush evergreen forests and lined with rugged granite shores. Row ashore and stretch your legs in local fishing villages and towns rich with art and culture. In the evenings we will anchor in hidden coves where you’ll enjoy coastal wildlife, spectacular sunsets, and endless stars.

Maine Windjammer Cruises®

Maine Windjammer Cruises

Swift is a very special vessel designed in 1935 by Murray Peterson, a masterful naval architect famous for his coaster designs.  Originally intended as a luxury yacht, she was launched in 1983 after nearly twenty years of love and dedication to build her.

A diagram of Swift below decks and a more detailed description is on our Accommodations page.

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