Island Life
We've been heading to Great Diamond Island for as long as we can remember. So we have all of the insider information you need to know to have an amazing stay. Whether you're headed down for your first time or you want to learn some more insider tips, you’ve come to the right spot. Let us share everything we know so that you can have an amazing experience at The Woodbury Cottage!
Transportation to Great Diamond Island
Casco Bay Lines
The easiest way to get both your crew and your gear to Great Diamond Island is Casco Bay Lines. You will want to make sure to give yourself enough time to drop everything off, find parking and buy tickets. The first step is to deal with your gear. To do that, you just need to pull up to the garage doors at the ferry terminal. They have carts you’ll load everything into. Everything needs to be checked in at least one hour prior to departure. Once you pay, the next time you’ll see your gear is on the dock at Great Diamond. So easy! If you want to make it even easier on yourself you can call ahead and set up an account by putting a credit card on file with the Freight Department. That way, if you are planning on or think you might be planning on having anything delivered to you during your stay, it will make things go much more smoothly for you and you’ll get your deliveries quicker.
Make sure you pay close attention to the ferry schedule as it changes quarterly. Also, make sure you’re going by the Great Diamond schedule and NOT the Diamond Cove one. Diamond Cove is the stop after Great Diamond and it’s on the opposite side of the island. You don’t want to make it harder on yourself by having to walk back to the Cottage—especially since you can’t take the golf carts on the Diamond Cove side of the island.
Fogg’s Water Taxi
If the ferry schedule doesn’t fit your travel schedule, you can always call ahead for a water taxi. While the water taxi is a quicker and more direct way of getting to the island it’s not as cost-effective. This option is just for transporting people and won’t work if you’re trying to take all of your gear with you. In Portland, they pick you up and drop you off at the public dock which is next to the Fire Boat and in front of Casco Bay Lines. On Great Diamond, they will drop you off and pick you up from the ferry dock. The dock in front of The Woodbury Cottage is not part of the property, so guests can’t use it and should not trespass on it.
Since the ferry terminal and the water taxi pick up location are next to each other, the parking and driving directions are the same for both.
Driving and Parking
Getting to Casco Bay Lines
No matter what the GPS tells you, make sure to take I-295 to Exit 7 (Franklin St). Franklin St is a straight shot down to the ferry terminal and lets you avoid the craziness of Commercial Street. It’s highly suggested that you ship all of your gear on the ferry. That way, you can really enjoy the trip down the bay and unwind after your travels on the mainland. Everything needs to be at the cargo drop-off at the minimum one hour before departure. The full ferry schedule can be found here. Just make sure you build in plenty of extra time. It can take a while to get through that part of the city in the summer, especially when you have to drop things off at the ferry, go back out to find parking and make it back to board the ferry in time. Casco Bay Lines is very punctual and will not hold a boat for anyone.
Parking
There is a parking garage right at the ferry terminal, but it is the most expensive option--and it's usually full. The best two alternatives are both outdoor lots. One is $5/day, but it is a 15-20 minute walk to the ferry. The other is $15/day which is next to the ferry terminal. At both, you pay at a meter and put the sticker on your dashboard or you can download the Passport App and manage it all from your phone. The $5/day is on the corner of Park Street and Commercial Street. The $15/day is at the Ocean Gateway Lot at 2 Commercial St.
No matter what you decide, definitely build in some extra time into your plan because that part of Portland is a zoo during the summer.
Local Grocery Shopping
The most convenient for location and process is Whole Foods Market located at 2 Somerset Street in Portland. It’s right off the Franklin St exit of I-295. If you stop to shop there, just tell the cashier that it's a Provisions order. They’ll collect your info to make sure it gets to the right island then they’ll handle it all from there. They will pack it up and deliver it to the ferry and it will be shipped right to the island. You just need to pick it up at the dock and bring it back to the cottage. They do charge additional for ice sheets and insulated bags, but it is well worth it! More info can be found here: Whole Foods Provisions Information.
Another option to shop in person is at Hannaford Supermarkets. The easiest location to shop yourself is 295 Forest Ave, Portland, ME 04101. They also offer Hannaford To Go where you order online and pick up curbside at the store. The best store for this option is the Maine Mall.
Trader Joe’s is located at 87 Marginal Way in Portland and it’s close to the route to the ferry terminal. It’s near the Whole Foods, just not as close to the highway exit. Just be aware that the parking lot is very small and it’s always busy.
If you want to shop local, Rosemont Market & Bakery, Micucci Grocery and Lois’ Natural Marketplace are all great options. Lois’ has a location a block from the ferry terminal. This is a great option if you head in town and only need a few things, you can pop in before you get on the ferry back to the island.
Once you're on the island, Whole Foods, Rosemont Market & Bakery and Lois’ Natural Marketplace will ship food on the ferry for you so you don't have to go into town. All require a minimum 24-hour advance notice. Depending on the length of your stay, it’s easier most times to just plan ahead and bring food. If you are planning on shopping for food ahead of time, Casco Bay Lines has banana boxes for you to use that simplifies and organizes the process of getting your food to the island.
More information:
*Island delivery also available. See below.
Once You’re On The Island
Directions to The Woodbury Cottage:
Exact directions will be emailed to paid & confirmed guests prior to arrival. It’s only a 7-10 minute walk from the ferry dock. Just be aware that the lock on the entry door is a combination lock. The code for you will be the last four digits of your contact phone number. The combination needs to be lined up on the top line (not the middle line like most combination locks).
Golf Cart:
The golf cart will be waiting for you at the cottage. It’s best to leave your gear at the dock and head up to the house then go back to the dock. We aren’t allowed to leave our golf cart at the dock because we aren’t allowed into the Diamond Island Association because there is no public access to The Woodbury Cottage. So, you need to keep that in mind when you head into town. You’ll need to plan extra time to get to the dock and leave the golf cart at the cottage. As far as your gear goes, the island is super safe and everyone leaves stuff on the dock and is super respectful of each other’s things.
In order to use the golf cart as part of the rental of the cottage, you will be required to sign a separate contract since VRBO doesn’t cover golf carts in its contract. Please note that you will receive the contract electronically for you to e-sign either the day before or the day of your arrival. This is because the contract includes pictures of the golf cart in the exact shape it is handed over to you. That means it’s inspected after the previous guest and pictures are retaken so you are not held responsible for any damage that happened before your arrival.
A sample contract can be found here. Please note, the text will be the same, but the pictures will be different for each guest.
Island Grocery Delivery
The following stores deliver directly to Great Diamond Island via Casco Bay Lines. The selection and ordering timeframes differs between them, but no matter where you order from, all you have to do is pick up your purchase on the ferry dock.
Island Dining
There are great dining options available on the island. All three are located on the opposite side of the island in Diamond Cove. You’ll feel secluded at the Cottage but you can still go out for a meal. It’s really the best of both worlds. Please note that you can drive the golf cart to the entrance gate to Diamond Cove, but you’ll need to leave the golf cart there and walk the rest of the way. Golf carts are not permitted to pass through the gate.
Not only is this our absolute favorite spot on Great Diamond Island, but it’s also one of our favorite restaurants in all of Portland. Make sure you plan to have at least one meal here. You won’t regret it! However, the secret is out about this place so expect a wait or plan to go in between ferry arrivals because people flock here from Portland. Reservations are always a good idea.
In the back of the Crown Jewel is the General Store is open in the morning. They offer coffee, breakfast sandwiches, candy, beverages (alcoholic & non-alcoholic), basic provisions and Crown Jewel merchandise. More information can be found here.
This was the first restaurant on the island. Offering lunch, dinner, bar bites and brunch on the weekends, you can either dine inside, on the covered deck, or on the lawn overlooking Diamond Cove. This is the best place to accommodate bigger parties.
The Inn has a classic hotel bar and a cafe that’s best for lunches. You can dine inside or outside on their side patio. In the morning, the bar offers Starbucks brand coffee. Walking over to get a coffee is one of our favorite ways to start our day.
Island Activities
Beaches
In addition to the beach in front of the cottage there is a big beach behind Elwell Hall that faces Portland. It is a great place to watch the sunset. There are beaches on the Diamond Cove side of the island but since it is a private community, guests of The Woodbury Cottage aren’t allowed on them. They are not afraid or shy about enforcing their rules.
Hiking
There are over 80 acres of woodland behind the cottage. All you have to do is literally walk about the back door and into the woods. It’s fun to hike through the woods and explore that part of the island. You’ll eventually end up in Diamond Cove at which point you can take the island roads back or turn around and hike back through the woods. There is also a trail along the waterline if you want to enjoy ocean views during your hike.
It’s also fun to head over to Little Diamond Island at low tide. The sandbar appears at low tide that you can walk or bike over. The golf carts CANNOT be taken over because of how soft the sand can get. Make sure you pay close attention to the tides. You don’t want to get stuck and either have to wait for a ferry or wade through the water back to Great Diamond.
Biking
Most of the bikes are mountain bikes. You can either take them through the woods to do some actual mountain biking or you can ride around the roads. Heading to Little Diamond at low tide is also fun. But make sure you time the tides right, otherwise, you’ll get stuck there.
Tennis
There is a tennis court in the middle of the island. There are four tennis rackets and tennis balls at the house. It is a clay court so please be courteous and sweep the court when you are done.
Swimming
Obviously, you can wade in and take a dip on either of the beaches. But our favorite way to get in the water is jumping off the State Pier. Just be careful because the lower the tide, the higher your jumps will be. There are ladders on each side of the pier to make it easy to get back out of water. Be advised that jumping is technically not allowed so if you choose to do it just be extra cautious and mindful of the boat traffic.
Board Games & Puzzles
We’ve tried to make sure all of the best board games are at the cottage. If we’re missing one, let us know! Board games are in the coffee table in the living room and the puzzles are under the bed in the front bedroom on the first floor. The list of the entire inventory of games can be found here.
The Store at Elwell Hall
This is the place to go for Great Diamond Island swag, a look into the history of the island or a frozen treat. Hours are pretty limited so make sure you check out their Facebook page so you know it’s open when you want to head over. They do a great job of keeping everyone up to date on everything that is going on here.
Kayaking
Whether you bring your own or you need to rent, enjoying Great Diamond and surrounding islands from the water is super fun. If you need to rent, Portland Paddle is the place to go. They will ship the boats on Casco Bay Lines. They also offer guides that will take you on excursions throughout the bay. If you choose to rent boats for your entire stay, you can still hire a guide for whatever day works best for you. The guides will even meet you out front of the Woodbury Cottage. If you store your boats on the beach you need to make sure you pull them very far up on the beach because the high tide takes over almost the entire beach. Make sure you secure them to a tree as well.
Island Hopping
It’s fun to take a day trip to another island. Peaks Island is great but if you want to get there by ferry you have to go back into Portland to get the ferry to Peaks. Long Island is the best island to head to from Great Diamond. It has a beautiful white sand beach you can spend the day at. It also has a sandwich shop, an ice cream shop and a convenience store. If you’re not afraid of a long walk, exploring Long Island can be done on foot. But if you want to get around quickly, taking the bikes is also an option. Visitor information for Long Island can be found here.
Waste Removal
Trash
All your normal trash that can’t be recycled or composted should be collected in normal trash bags in the silver upright canister in the kitchen. When you have a really full bag, you need to put it into a purple City of Portland trash bag and bring it over to where the trash cans are located for weekly pick up. Regular trash bags and the purple City of Portland trash bags can be found in the cabinet under the counter in the pantry. The trash cans that belong to The Woodbury Cottage are in the cluster of trash cans on the left just after you pass the triangle of grass (and golf cart parking) at the top of the hill as you walk up from the ferry dock. Trash pick-up is Monday morning.
Recycle
Please try to recycle as much as possible. The blue recycling receptacle is located under the counter in the pantry. Blue recycling bags can be found with the trash bags—in the cabinet under the counter in the pantry. Recycle is dropped off in the designated recycling cans located at the same spot that the trash cans are. It is also picked up on Mondays.
Clynk
In Maine, any recyclables that have a bottle deposit are recycled separately. Cans and bottles that have a bottle deposit are collected in the green trash can located under the counter in the pantry. You need to use the green Clynk bags. They can be found with the trash bags & recycle bags in the cabinet under the counter in the pantry. Once full, they can be brought down to the dock house on the ferry dock on Tuesday mornings. They need to have the barcode sticker on the front of the bag for them to be taken in town. The barcode stickers can be found in the box of bags.
Compost
There is a compost bin under the back deck. There is a list of what can and cannot be composted on the refrigerator. There is also a copy here.
Our Favorite Portland Restaurants, Bars & Breweries
If you’re looking to explore Portland and check out the amazing culinary scene, these are our favorite places. You don’t want to miss the ferry back to Great Diamond Island so making reservations where you can is a great idea.
Restaurants
Bars
Breweries
Departure Checklist
There isn’t much we ask you to do before you leave, but it is much appreciated for you to do everything on the list. It makes turnover much easier and quicker!
☐ All dishes cleaned & put away.
☐ All windows & doors closed & secured.
☐ Golf cart parked at the house with the key locked inside the cottage.
☐ Grills covered.
☐ All electronics & lights plugged in but turned off.
☐ All trash, recycling & bottle returns taken to the proper disposal spot.
☐ Used beds turned down, but not stripped. Just make it obvious what beds were used.