CURATED ESCAPE ACROSS MAINE
Sample Itinerary
Trip Length
8
days
When to Visit
SUMMER & FALL
Ideal For
small groups
PORTLAND
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.
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.
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
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.
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
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!
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!
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.

