York Harbor, Maine

York Harbor, Maine Tour

October 5 - 10, 2025

(5 nights)

Tour Size: 10 Women - currently, 9 spaces are available.

Autumn Splendor: Exploring York Harbor, Maine, in October

York, Maine is located on the southernmost coast of Maine and was founded by the Europeans in 1624 and is one of the oldest settlements in North America.

Explore the enchanting beauty of York Harbor, ME, in October with our captivating travel tour. York Harbor unveils its picturesque charm as the crisp autumn air sets in, blending stunning coastal vistas with rich historical heritage. 

The average daytime temperatures in early October range from the low 50’s to the low 70’s, rarely going below 45 degrees in the evening. It is a perfect time to visit Maine, as the summer crowds will have departed, and the fall foliage is in all its splendor. Here is a glimpse of what you can experience during your visit:

Highlights:

· York Harbor Inn: Enjoy your own private room at the York Harbor Inn (directly across the street from the ocean). All guest rooms at the York Harbor Inn are unique in size, character, and amenities. This Inn is representative of quintessential New England. The hotel has no elevators, so be prepared to climb some stairs to reach rooms on the upper floor. We will enjoy breakfast each morning and two dinners in the Inn’s famous 1637 at York Harbor restaurant, which has been featured in Food & Wine Magazine, Gourmet, Taste, and other fine food publications. They feature local seafood and fresh seasonal ingredients, all in an ocean-view setting.

· Historic York Village: Explore York’s history in the heart of York at York Village. Stroll along tree-lined streets adorned with colonial-era architecture, including the iconic Old Gaol (jail) and the historic Jefferds Tavern. Delve into the town’s past at the Museum of Old York, where exhibits offer insights into York’s maritime and cultural heritage.

· Nubble Lighthouse: We will visit the iconic Nubble Lighthouse, possibly the most photographed lighthouse in Maine.

· Dining Delights: We will indulge our taste buds with fresh seafood delights at waterfront restaurants offering panoramic views of York Harbor. Savor locally sourced lobster rolls, clam chowder, and other New England culinary delights.

· Fall Foliage: Immerse yourself in nature’s vibrant palette as the foliage transforms into a tapestry of reds, oranges, and golds. We will visit Mount Agamenticus and walk the Cliff Walk, where will get a fantastic panoramic view of nature’s fall display in all its splendor.

· Art and Culture: Discover the areas thriving arts scene with visits to galleries showcasing local artists’ works. We will attend a live performance at the Ogunquit Playhouse, which is one of the last remaining summer theatres. Creative teams are brought in from around the world.  Casting for each show is hand-picked from Broadway and Regional actors in New York, Los Angeles, and across the country.

· Distillery Visit: We will visit a local small-batch distillery (Wiggly Bridge Distillery) where we will get a private tour, tasting and even learn how to mix cocktails!

· Coast Encounters (Tide Pooling Exploration): Weather and tides permitting, we will enjoy an excursion led by Carol Steingart with Coast Encounters to do some tide-pooling where she will teach us about the local tidal ecosystem during low tide where we will get a hands-on experience finding the sea creatures that reside in the tide pools. If the weather and/or tides don’t cooperate; no fear Carol will bring the tidal pools to us indoors where we will listen to her speak about the ecosystem and have a hands-on experience with over 30 sea creatures. Truly a unique experience, as Carol is the only person licensed in all of Maine that offers these excursions. If you have water shoes bring them, but if not, Carol will provide them for us.

· Coastal Cruise: We will enjoy a 3-hour, private boat tour with Seacoast Maritime Charters on board the Shining Star which departs out of the harbor in Kittery.  The boat has an indoor, heated area if the day is chilly. Captain Jack will take us along the coast to view the coastline from a different vantage point.

· Shopping: We will have ample time to explore boutique shops and artisanal stores in York and the nearby villages.

Experience the magic of York Harbor, ME in October, where coastal beauty, historical intrigue, and autumn splendor converge to create unforgettable memories.

Itinerary:

Day 1 - Sunday, October 5, 2025

Plan to fly into the Boston Logan International Airport (BOS).  Please use the C & J Bus service from the airport to take you to Portsmouth, NH. All C & J coaches pick up downstairs, outside baggage claim near the orange “Scheduled Bus” sign. The service runs every hour to Portsmouth and costs $27 one way. Be sure to purchase your ticket on the bus in advance. You will have a QR code on your phone that they will scan as your ticket. From Portsmouth, NH drop off, take an Uber to the hotel (short 10-minute drive).

York Harbor Inn – located at 480 York Street, York Harbor, ME.

6:30 pm: Plan to attend a private, welcome dinner at the hotel at 6:30 pm at the 1637 York Harbor restaurant (includes a cocktail or a glass of wine/beer).

Day 2 – Monday, October 6, 2025

Enjoy breakfast at the hotel restaurant (1637 at York Harbor) from 7:30 am to 10:00 am.

The morning is free, and lunch on your own.

Time Estimate 1:30 pm to 7:30 pm (subject to change dependent on when low tide occurs): We have a 3-hour excursion planned led by Carol Steingart, of Coast Encounters to do some tide pooling. Carol is the only person in Maine that offers this unique experience. This date will be a full moon, creating the best low tide experience, and will open a unique location and is very safe for walking. It’s a public conservation trust island we can walk to by crossing a creek. Because of the low water level during a full moon period, walking across the creek to the island will only be up to our knees. This will allow us to explore the tidepools on the island with ease. This location does not have much seaweed, and the terrain is like walking on a sandy beach. We will be in the tidepools with ankle to knee-deep water and pebbly substrate. Water shoes will be provided if you don’t have your own. Snacks will be provided.

Dinner on your own.

Day 3. – Tuesday, October 7, 2025:

Enjoy breakfast at the hotel restaurant (1637 at York Harbor) from 7:30 am to 10:00 am.

11 am - We have private transportation arranged from the hotel to the Kittery Point harbor.

Noon – 3 pm: Seacoast Maritime Charter. Private 3-hour excursion aboard the 46-foot Shining Star, which departs from the Kittery Point Harbor. The boat offers an indoor, heated area if the weather is chilly. Captain Jack will take us on a tour to showcase the coastline from a different perspective. We will visit an offshore island and get to see some iconic lighthouses from the sea.

6:30pm: Dinner @ Shearwater Restaurant at Stage Neck Inn (across the street from the York Harbor Inn). We will enjoy a private dining experience in an ocean-view room (includes a cocktail or a glass of wine/beer).

Day 4 – Wednesday, October 8, 2025:

Enjoy breakfast at the hotel restaurant (1637 at York Harbor) from 7:30 am to 10:00 am.

We will be picked up at the hotel at 9:30 am to be taken to Mount Agamenticus for a private tour and brief, easy 1 mile hike to the summit for a panoramic view of the surrounding area. We depart around Noon to be driven to Ogunquit, with a stop along the way to visit the iconic Nubble Lighthouse (the most photographed lighthouse in all of Maine), to enjoy some free time to shop on Shore Road and grab lunch on your own. Be sure to walk the Marginal Way Walking Path (which is a cliff-side path). We will depart Ogunquit around 3:00 pm to head back to the hotel.

Dinner on your own.

7 pm: We will be picked up and transported to Ogunquit, where we will enjoy a Broadway-caliber show (TBD) at the Ogunquit Playhouse from 8 pm – 10 pm before heading back to the hotel for the night.

Day 5 – Thursday, October 9, 2025:

Enjoy breakfast at the hotel restaurant (1637 at York Harbor) from 7:30 am to 10:00 am.

11:00 am - We will be picked up and taken to the Wiggly Bridge Distillery, where we will be given a welcome cocktail, private tour, and tasting from Noon – 2 pm.

6:30 pm: Plan to attend a private, farewell dinner at the hotel at 6:30 pm at the 1637 York Harbor restaurant (includes a cocktail or a glass of wine/beer).

Day 6 – Friday, October 10, 2025:

Enjoy breakfast at the hotel restaurant (1637 at York Harbor) from 7:30 am to 10:00 am.

Plan to return to Boston Logan International Airport using the same service with C & J Bus. Uber to Portsmouth, NH to pick up the bus. The fare one way back to the airport will be $27. Buses run every hour. Purchase your return trip in advance.

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What is not included:

· Airfare or other transportation not included in the tour.

· Airport transfers

· Some meals and activities are not included in the tour, where indicated in the itinerary

· Beverages that are not specified

· Any personal expenses or expenditures

· Travel Insurance

· Gratuity for the Tour Leader

Pricing & Payment Dates

The cost of the tour is $3,000/pp. Upon booking, you will be required to make a 20% deposit ($600.00). An additional 40% deposit of $1,200 will become due March 31, 2025, and the remaining 40% or $1,200 balance is due 45 days prior to the tour start date or August 21, 2025. 

No refunds for cancellations for any reason, which is why we require you to obtain travel insurance.