CURATED ESCAPE ACROSS MAINE

journey through port towns, islands, and mountains
Maine’s rugged beauty defies expectations. In this founder’s trip, we’ll begin in the bustling harbor city of Portland, sail the mid-coast waters of Camden, and end under the star-filled skies of Baxter State Park. You’ll be immersed in the local culture Mainers are proud to share.

Sample Itinerary

Here’s an example of what your escape to Maine could include. We personalize each trip to your group’s size, pace, interests, and travel style.
Trip Length

8

days

When to Visit

SUMMER & FALL

late june – late september
Ideal For

small groups

of friends, families, or couples

PORTLAND

Day 1
Day 1

FLY INTO PORTLAND

Fly to Portland, Maine’s largest city.
Once you land, Christopher and his team will meet you at the airport and drive you to The Press Hotel, a boutique luxury hotel in the Old Port District.

Depending on how far you’ve traveled, you may spend the day resting from your flight. In the evening, we’ll take you to one of our favorite spots in the city for lobster rolls.

DAY 2
DAY 2

EXPLORE PORTLAND

See all that the historic city of Portland has to offer.
After breakfast, we’ll take you and your group on a guided bike tour throughout Portland. It’s one of the most scenic ways to explore the city. The city is lined with elegant 19th-century architecture and landmarks. We’ll end our tour at the picturesque Portland Head Light, a landmark lighthouse built in 1791.

For lunch, we’ll visit a nearby lobster shack for fresh seafood. After lunch, spend the afternoon walking the cobblestoned streets and shopping. For dinner, we’ll plan something amazing for you — like a curated meal at a top restaurant with a James Beard award-winning chef.

Day 3
Day 3

VISIT PEAKS ISLAND

Ferry to the island for a seaside adventure.
In the morning, we’ll take an hour-long ferry from Portland to Peaks Island. There, we can plan a variety of activities for you and your group: kayaking, biking, swimming, or simply relaxing on the beach.

We’ll return to Portland in the evening. For dinner, we can recommend several spots, depending on whether you’re craving something classic or unexpected. Portland actually has several amazing Vietnamese restaurants that we love to take our guests to!

MID-COAST: CAMDEN

Day 4
Day 4

DRIVE TO CAMDEN

Say goodbye to Portland as we head north to Camden.
In the morning, we’ll schedule private transport to take us to the scenic mid-coast town of Camden where you and your group will stay aboard a luxury windjammer.

Aboard these wooden sailing ships, you’ll find Michelin-level cuisine, live music, and more — it’s the perfect atmosphere to relax and destress. After getting settled on the boat, you’ll get the chance to sail it as we head to a nearby island to explore.

DAY 5
DAY 5

SAILING IN CAMDEN

Dig your own clams.
Wake to a beautiful sunrise on the water. After breakfast, we’ll sail the boat to a nearby spot to dig your own clams. We’ll show you how it’s done and let you and your group enjoy working with your hands. Later that evening, you’ll get to enjoy your fresh clams for dinner, paired with a crisp glass of white wine — and a sunset!

NORTH: BAXTER STATE PARK

Day 6
Day 6

DRIVE TO BAXTER STATE PARK

Luxury glamping under the stars.
In our opinion, we’ve saved the best of Maine for last. We’ll drive from Camden to Baxter State Park. Covering over 200,000 acres, this state park has some of the best fishing and hiking in the state. Christopher has family ties here and will reserve one of the most exclusive campsites in the park. You will stay in luxury, safari-style glamping tents with all the modern comforts of home.

That evening, sit back, relax — enjoy a fresh homemade dinner and watch the stars with a glass of wine in hand. Depending on the time of year, we may even see the northern lights!

DAY 7
DAY 7

EXPLORE THE PARK

Hike, fish, rock climb, and forage.
There’s so much to do in Baxter State Park. Depending on your group’s interests, we can go hiking to nearby mountain peaks, go fly fishing for Arctic char, or go foraging for wild mushrooms and blueberries. For the more adventurous, we can even take you rock climbing.

Depending on what we catch and find that day, we’ll enjoy the day’s spoils over dinner!

Day 8
Day 8

RETURN HOME FROM PORTLAND

We’ll transport you to the airport and ensure you have all of your belongings.
The last day is always the hardest part of the trip — no one wants to leave! We’ll be in touch with you after you arrive home to share a leather-bound photo book from your journey in Maine.

Disconnect from Everyday

reconnect in the wild beauty of maine

From lobster feasts to wilderness glamping, let us craft a founder-led journey that’s as restorative as it is unforgettable — tailored to your pace, curiosity, and the people you love traveling with.