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Sailing the Maine Coast: A Schooner Cruise for Your Bucket List

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Looking for a unique getaway? I just went on my very first Schooner trip sailing the Maine Coast, and it was exactly the trip i didn't know I needed!


I did a girls trip on the 4-day Fall Foliage cruise up the coast of Maine on the J&E Riggin Schooner, and couldn't get over what a perfect trip it was. Full of insanely good food, stunning views, and a fun crew, it was the perfect trip to enjoy this beautiful pocket of the US.


In this guide Im going to share with you exactly what the trip looks like, and why you should add it to your bucket list!

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Sailing the Maine Coast: About the Schooner & Where it Goes

Sailing the coast of Maine is a truly special experience, but traveling on a Schooner is really a unique feat of its own. Before diving into the details of the trip itself, here's a bit of insight into what a Schooner boat is like, the history of the J&E Riggin Schooner, and where it sails out of.

โ›ต๏ธย What is a Schooner Boat?

A schooner is a classic sailing vessel known for its elegant design and two or more masts rigged with fore-and-aft sails. Built for both speed and stability, schooners were once used for fishing, trading, and cargo along the East Coast.ย 


Today, many have been lovingly restored to carry passengers on sailing trips, offering a peaceful and nostalgic way to explore the water. Cruising on a schooner is timeless, powered only by the wind and surrounded by the beauty of the open sea, making it a true bucket list activity.

J&E Riggin -sailing the Maine coast
J&E Riggin -sailing the Maine coast
J&E Riggin -sailing the Maine coast
J&E Riggin -sailing the Maine coast

๐Ÿ“–ย The History of the J&E Riggin Schooner

Built in 1927 in Dorchester, New Jersey, the J. & E. Riggin began as an oyster dredger named after the builderโ€™s sons, Jacob and Edward.ย 


After years of hard work at sea, she was restored by the loveliest couple Justin & Jocelyn from Rockland, Maine, and transformed into the windjammer she is today. Now a National Historic Landmark, the J. & E. Riggin continues to sail along Maineโ€™s coast, offering incredible sailings along the Maine coast.


Captain Justin has been sailing for his entire life and Jocelyn is the excellent chef behind all the incredible meals onboard. They're young, fun, and an iconic duo for these sailings along the Maine coast.

J&E Riggin -sailing the Maine coast

๐Ÿ“ย Where Does the J&E Riggin Schooner Boat Sail From?

The J&E Riggin Schooner sailings depart from Rockland Maine's harbor, which is just minutes walking from the downtown area, and it sails up the coast, returning to the same port.

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Sailing the Maine Coast: How to Get to the Port

Rockland is a charming coastal town and the main departure point for many schooner cruises along Maineโ€™s rugged coast. Getting there is simple, but your route will depend on where youโ€™re coming from.

โœˆ๏ธย How to Get to Rockland, Maine

If youโ€™re flying in, the closest major airport is Portland International Jetport (PWM) in New Hampshire, about a two-hour drive south of Rockland. You can rent a car at the airport or take a private shuttle for a scenic ride up the coast.


Travelers from farther away can also fly into Boston Logan International Airport (BOS). The drive from there takes about three and a half hours, and there are also buses with the Concord Coach that take 4 hours and 15 minutes.ย 


For those already in Maine, driving is the easiest option, with Route 1 offering beautiful coastal views along the way. If you prefer public transportation, the Concord Coach Lines bus runs from Portland and Bangor directly to Rocklandโ€™s downtown station, just minutes from the harbor.

๐Ÿ…ฟ๏ธย Parking in Rockland

There is parking for all sailings right at the dock, and it is just $20 for a pass that is good for the entire trip. It's a really safe area, and we felt comfortable leaving our car there for the 4 days we were gone.

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Sailing the Maine Coast: Itineraries & Prices

Now let's dive into the itineraries and prices to expect on a Maine Coast sailing trip on the J&E Riggin Schooner!

โณย How Long are the J&E Riggin Sailings?

J&E Riggin offers several sailings, from 3-6 night sailings starting from May 22nd for their first sailing, and finishing their season with the September 30th Fall Foliage sailing. Certain sailings sell out quickly, so we recommend reserving yours as far in advanced as you can.


There are also specialized sailings such as photography cruises and knitting cruises to check out! These have a slightly higher price, but are niched and have workshops and a niched audience.

J&E Riggin sailing on the Maine coast
J&E Riggin sailing on the Maine coast
J&E Riggin sailing on the Maine coast

๐Ÿ’ตย How Much are the J&E Riggin Schooner Sailings on the Maine Coast?

Sailings on the Maine coast start at $1,295, and go to $1,660 for longer itineraries. All meals are included, and the only other expense you'd need to worry about is tipping the staff.

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Amenities on the J&E Riggins Schooner Boat

Now that you know about how much the Schooner cruises are, when the season it, and how long the itineraries, let's go over what the boat is equipped with.

๐Ÿดย Meals on the J&E Riggin

Bring some stretchy pants, because on of our favorite parts of this Maine Schooner cruise is the food. Jocelyn is an EXCELLENT chef and there is no way you'll be leaving this sailing hungry.


There are 3 fresh meals served a day, each one carefully planned with fresh, seasonal ingredients from their own garden and local vendors (and delicious desserts too!).

meals on JR Riggins Schooner - sailing on the Maine coast
meals on JR Riggins Schooner - sailing on the Maine coast
meals on JR Riggins Schooner - sailing on the Maine coast
meals on JR Riggins Schooner - sailing on the Maine coast

๐Ÿนย Drinks Onboard

Onboard there is potable water you can drink, and hot tea and coffee offered from 7 AM throughout the entire day. Alcohol is not provided, but guests are able to bring their own beverages of their choice, which can be stored in the various coolers onboard.

coffee and tea on JR Riggins Schooner - sailing on the Maine coast

๐Ÿšฝย Bathrooms on the Schooner

There are two bathrooms onboard, and they've been recently updated so that you no longer have to pump them. They're not as luxurious as a cruise ship, but let's not forget you're on a boat! There are toiletries in the bathrooms as well so that you can freshen up after.

๐Ÿšฟย Showers Onboard

There is just one shower onboard, but we never had to fight for it. It's a simple set up, and inside one of the toilets. There isย hot water - you just need to let them know so that they can turn it on. Both a bath and hand towel are given to each guest, so you don't need to worry about bringing one with you.

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Sailing the Maine Coast with the J&E Riggin Schooner

Now it's time for the fun part! I'm going to share with you exactly what a trip sailing along the Maine coast looks like, and precisely what made the J&E Riggin Schooner a special experience.

Don't have time to read the whole article and want to save it for later? Just pin it!

Sailing on the Maine coast - J&E Riggin Schooner cruise
Sailing on the Maine coast - J&E Riggin Schooner cruise
Sailing on the Maine coast - J&E Riggin Schooner cruise

Day 1: Joining the Vessel

The first day boarding starts at 5:00 pm, and around 6:00 pm when everyone is onboard there is a Captain's Meeting. You'll hear about what the sailing will look like, how the bathrooms work, and basic safety instructions.


I got a flat tire on my way up, delaying me several hours. After working on cruise ships, I totally freaked out about missing the boat or getting in trouble for not being there on time. Good thing though is that the Schooner actually doesn't sail until the morning!


Night 1 allows guests to enjoy the downtown area of Rockland by dining locally, checking out the shops, and simply getting settled in. You'll be greeted with a delicious cheese plate, and you can go back to the boat at any time of the night.

Rockland, Maine
Rockland, Maine
Rockland, Maine

Day 2: Sailing the Maine Coast

Each morning the staff brings out coffee and tea at 7 AM. Early mornings are perfect for having a hot drink and soaking up the peaceful vibes around the dock before your first incredibly delicious breakfast. We had pancakes with homemade whipped cream, fresh fruit, and bacon from a local butcher.


After we purchased our parking passes, walked a bit around town, and then around 11:00 it was time to hit the water!


One of the most interesting parts about being on the sailboat was learning how to sail and even all working together to get the sails up! It's not mandatory by any means, but we loved this part, and found it a unique and fun way to all come together and be part of the experience.

learning how to sail - sailing the Maine coast on the J&E Riggin

Once we truly set sail we simply enjoyed the entire day on the water - hanging out, eating, and enjoying hobbies like painting, knitting, and playing cards with the other passengers.


Lunch is around midday, and has an assortment of incredible dishes like clam chowder, ramen, caesar salad, grilled meats and more.

lunch on the sailboat trip in Maine

Dinner is served between 6 and 7, and typically has a specially baked dessert afterwards. To finish the evening there may be an activity, and for us we took smaller boat rides around the area that we docked, enjoyed the sunset, and had a relaxing evening anchored out in the waters of Maine.


Hang out on the deck for some stargazing, or you can head down to the galley area for a cozy indoor hangout. There are also plenty of card games, board games, and books you can enjoy.

J&E Riggin sailing on the Maine coast

Day 3: Port Visit & Lobster Bake

Every itinerary is different, but every sailing on the Maine coast will definitely include some stops in small coastal towns. On our trip we stopped in an adorable town that is home to the best lobster in Maine. We had an hour and walked around town, stopped in the coffee shop, and checked out the local gift shops.

J&E Riggin sailing on the Maine coast
J&E Riggin sailing on the Maine coast
J&E Riggin sailing on the Maine coast

Each sailing has different stops, which is part of the magic of sailing with the J&E Riggin!


After we got back to the boat we had some coffee and hung out before heading over to a deserted island where we had our incredible lobster bake. There were dozens of local lobsters caught, along with fresh corn, mushrooms, potatoes, cheeses, and mouth watering steak.


It was honestly one of the best meals I've had in my life, and an absolute highlight of any sailing the J&E Riggin has.

J&E Riggin sailing on the Maine coast
J&E Riggin sailing on the Maine coast
J&E Riggin sailing on the Maine coast
J&E Riggin sailing on the Maine coast

Day 4: A Day at Sea

Our 4th day involved lots of eating, drinking, and relaxing. Depending on your itinerary and the weather you may stop at a small town, or simply enjoy sailing for the day. Expect lots of food and enjoying a calm day on the water.

Day 5: Back to Rockport

Our final morning we enjoyed the best breakfast ever! (We aren't going to spoil it for you - but get excited!) Enjoy your final hours on the calm seas before heading back to Rockport. You'll take your group photo, get your stuff together, and say goodbye to your group after an amazing trip sailing the coast of Maine.

J&E Riggin sailing on the Maine coast
J&E Riggin sailing on the Maine coast
J&E Riggin sailing on the Maine coast
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Sailing the Coast of Maine: Rules, Safety, & Tips

Now that you know how much fun you're going to have sailing the Maine coast on the JR Riggins Schooner, here's some important info to keep in mind to keep you healthy and safe.

๐ŸŒŠย Rules at Sea

There aren't too many rules you need to worry about while sailing the Maine Coast. Sustainability is key though, so make sure you never throw anything overboard, limit your water consumption, and respect the nature around you.


The first night of the trip there will be a captain's meeting, and they'll give you the scoop about everything!

๐Ÿฉบ Health & Safety

There isn't too much to worry about in terms of safety. The Schooner sails pretty slowly, and it typically doesn't move as much as larger boats do. Sea Sickness is not common, but if you are prone to motion sickness it's always good to have dramamine with you just in case.

โœ… Tips for Preparing for Your Schooner Cruise

  • Book your trip in advance, as there are limited spots each sailing.
  • Bring a bathing suit in case you want to go for a swim.
  • If you have a hobby then bring it with you as there is plenty of down time.
  • Try ALL the food - we promise you'll regret missing out on anything.
  • Let the company know in advance of any allergies/ dietary restrictions. They're super accomodating!
  • Don't go to bed too late - the sunrise is worth the early wake up call!
  • Bring your camera! It really is stunning out there.
  • Make sure to tip your hardworking staff - they deserve it!
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Other Things to Keep in Mind for the Maine Sailing

Now you know what to expect for your sailing along the Maine coast! But before you go, here are a few other things to keep in mind for your trip.

โ˜€๏ธ Weather in Coastal Maine

Coastal Maine experiences mild, breezy summers with average highs in the 70sยฐF (20sยฐC) and cool evenings perfect for sailing or seaside walks. Winters are cold and snowy, while spring and fall bring crisp air and colorful scenery along the rocky coast.

๐Ÿ“†ย The Best Time for Sailing the Maine Coast

The best time to sail the coast of Maine is from June through October, when the weather is warm, the winds are steady, and the waters are calm. July and August offer the most reliable sailing conditions which are great for swimming, while October brings gorgeous Autumn colors perfect for photography.

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๐ŸŽ’ How to Prepare for Your Schooner Cruise

Here is a packing list for your sailing trip on the J&E Schooner:


  • Sneakers, deck shoes or soft soled shoes (2 pairs)
  • Wool socks (2 pairs โ€“ for June and September sailing)
  • Slacks, jeans, or sweatpants (elastic waists are really comfortable)
  • Rain jacket and pants, pants being as important as the jacket. No rain ponchos, as they can present a hazard.
  • Shorts and shirts (both long- and short-sleeved)
  • Long underwear (for June and September sailing)
  • A heavy sweater or two
  • Windbreaker
  • Bathing suit and an extra beach towel for swimming
  • Hat
  • Sunglasses
  • Sunscreen
  • bug repellant
  • Flashlight or headlamp for the evenings (the sun sets early in the fall)
  • Binoculars
  • Camera (along with batteries and memory card)
  • Drone (only fly it when anchored)
  • Craft projects
  • Ear plugs (for light sleepers)
  • Reusable water bottle
  • USB charging cords for your cell phone
  • Wet wipes
  • SPF lip balm
  • Rolled sleeping pad, sleeping bag, and small pillow (if sleeping on deck in the summer)

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So are you ready to experience the incredible JR Riggins Schooner sailing the Maine coast? It's the relaxing getaway you didn't know you needed, and you'll really experience some of the best meals of your life.


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