Self-Guided Tour

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  • Length
  • 7 days/6 nights
  • Departure Dates
  • Jun 07 – Sep 19, 2021
  • Tour Cost
  • $2190 per person
    +$850 single supplement
Reserve this Tour
Included 2-nights Beauport Hotel
2-nights North Conway Inn (Cranmore, Bernerhof, or similar)
2-nights Sugar Hill Inn, Franconia, NH
Breakfast 6 days
Packing list
Area information
Sightseeing suggestions and activities in Gloucester, MA & White Mountain National Forest, NH
Detailed step-by-step descriptions and maps with hiking routes


Summer in the northeast would not be complete without exploring the rocky coast of the North Atlantic, or the rugged peaks of the White Mountains. Our self guided New England Sea to Summit Adventure does both, with opportunities for exploration at every turn. Set out for a paddle by kayak or SUP, enjoy a swim at the beach, or treat yourself to a sunset sail.  Then head north for a variety of day hike options.  Accommodations range from luxury hotels to cozy inns.

Located north of Boston on Cape Ann, Gloucester is America’s oldest continuous seaport. Although it was fished for centuries by many cultures before it was settled by Europeans in 1623, one of the earliest well-known records of the area is Samuel de Champlain’s 1606 account.  His charts refer to Gloucester as “le beau port” or beautiful harbor, and once you arrive it’s immediately easy to understand why.  You’ll spend your first two nights here in beachfront luxury.

Home to 48 peaks over 4,000 feet, the White Mountains of New Hampshire are one of the greatest outdoor playgrounds in the northeast. With so many trails to choose from, there’s something for everyone.  We’ve picked out some of our favorites for you.  Tackle the challenging summit of Mount Washington–the highest peak east of the Mississippi–or explore the areas near Franconia and Crawford Notches.  North Conway and Franconia, New Hampshire bookend all of it, and you’ll spend two nights each here as a base for your mountain adventures. 


Day 1

Gloucester, Ma — After landing at Boston Logan International, you’ll rent a car and drive 45 minutes to quaint and scenic Cape Ann, on the North Shore of Massachusetts.  Gloucester boasts a rich history not only for being one of the most prominent American fishing ports, but also for it’s productive granite and shipbuilding industries. It’s also home to the one of the oldest art colonies in America, as well as over 4000 acres of conservation land. You might spend the afternoon relaxing at Good Harbor Beach or at the Beauport Hotel’s roof-top pool, before having dinner overlooking the harbor.

  • Beauport Hotel

Day 2

Gloucester, Ma — Today, the island is your oyster and there are many activities to choose from based on the weather and your taste. Explore Gloucester Harbor by stand-up paddle board or the nearby Essex River by kayak. Browse the shops on Main Street’s historic West End or the galleries and art studios along Rocky Neck. Venture out for a relaxing sail on board the immaculate Schooner Thomas E. Lannon, traditionally built based on the local design of a 1903 swordfishing vessel.

  • Beauport Hotel
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  • Ravenswood Loop and other local activities

Day 3

North Conway, NH — In the morning you’ll drive 3 hours north towards Crawford Notch in New Hampshire’s White Mountains. You might consider stopping for an optional excursion to Portsmouth, NH where you’ll find a variety of nice restaurants and shops.  Arriving in the mountains around midday will allow plenty of time for a moderate afternoon hike.  Head up Mount Chocorua for spectacular 360 degree views of the region, or a shorter excursion up Mount Willard are good choices for today.  

  • Cranmore, Bernerhof Inn, or similar
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  • Mount Chocorua or Willard

Day 4

North Conway, NH — Your hike for the day begins at Pinkham Notch, just 30 minutes north of your inn.  The well-traveled Ravine Trail climbs quickly up through the bowl of Tuckerman’s Ravine to a broad shoulder of Mount Washington with Mt. Pierce, Mt. Eisenhower, and Mt. Monroe coming into view.   If the weather is clear, you can continue up to tackle the summit of Mt. Washington, the highest peak in New England.  Enjoy the world above treeline with sweeping views of the Presidential Range.  

  • Cranmore or Bernerhof Inn
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  • Mount Washington via Tuckerman's Ravine

Day 5

Sugar Hill, NH —   One of our favorite routes in the White Mountains is the traverse along Franconia Ridge between Mount Lafayette and Lincoln.  It’s a demanding hike with some steep climbing but the endless panoramic views from the ridge make it worth the effort!  Stop in at the AMC’s Greenleaf Hut for a quick refreshment before finishing your descent to Franconia Notch.  Finish the day with a spectacular dinner at the classy but cozy dining room at the Sugar Hill Inn, just outside of Franconia, NH.  

  • Sugar Hill Inn
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  • Franconia Ridge Traverse

Day 6

Sugar Hill, NH — After breakfast hit the trail for the last day of hiking on your journey, on the west side of White Mountain National Forest.  Though not as high as Washington or Lafayette, Mount Mousilauke boasts views of equal splendor, with a more moderate climb up to its summit at 4803′.  Your ascent follows Gorge Brook for much of the way up, and offers a few hidden opportunities for swimming and collecting water before reaching the top.  For a shorter version you can return the way you came, but we like to take the Asquam Ridge Trail down, for a longer but more gradual descent.  You’ll spend a second night at the perfectly quaint Sugar Hill Inn.  

  • Sugar Hill Inn
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  • Mount Mousilauke

Day 7

Departure — Today you’ll say goodbye to the mountains of New England and return to Boston or your other post-tour destinations.

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