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.

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. Ride past elegant 19th-century architecture, historic landmarks, and bustling harbor views. 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.

Say goodbye to Portland as we head north to Camden.
In the morning, we’ll arrange private transport to the scenic mid-coast town of Camden. There, we’ll stay at the Grand Harbor Inn. After lunch, we’ll take you to nearby Megunticook Lake, a glacier-carved freshwater lake perfect for boating, tubing, swimming, or simply relaxing.

Stay on a luxury wooden windjammer.
Today, we’ll check out of our hotel and take your group to stay in a luxury windjammer in Camden. Aboard these historic wooden sailing ships, you’ll be treated to Michelin-level cuisine, live music, and the kind of storytelling sailors have passed down for generations — the perfect atmosphere to unwind and reconnect.

After settling in, you’ll even have the chance to take the helm as we sail to a nearby private island.

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, enjoy your fresh clams for dinner, paired with a crisp glass of white wine — and a sunset!

To see whales breaching and take in coastal beauty.
In the morning, we’ll head north along the scenic coast to Bar Harbor, the gateway to Acadia National Park. You will stay at the elegant Bar Harbor Grand Hotel.

In the afternoon, we’ll set out on a private whale-watching cruise. Keep your eyes peeled for whales — plus curious harbor seals and puffins. Depending on the season, you may even have the chance to pull lobster traps alongside local fishermen.

Hike to the top of Cadillac Mountain.
Spend the day exploring Acadia National Park, one of New England’s most stunning landscapes. Hike to the top of Cadillac Mountain — the highest point on the U.S. eastern seaboard — where sweeping views stretch across glaciated coastlines and forested islands. For those looking for a slower pace, we can arrange a scenic bike ride through the park.

In the evening, we’ll take you to our favorite restaurant for a classic Maine lobster dinner.

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.