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BalconyNo inventory on the latest successful check
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SuiteNo inventory on the latest successful check
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FARES
Cabin pricing
2 adults · checked 11/1/2026, 6:03:12 AM UTC
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Portland
Highest guest ratings first, with more reviews breaking ties. Unrated tours appear last.
24 of 24 loaded tours match your filters.
Starting prices vary by date, guests and tour option. A date search is not a confirmed reservation. Check the meeting point, tour time and return-to-ship buffer before booking.
6–8 hours
Private White Mountains Tour with Mount Washington Cog Railway
Experience the breathtaking beauty of New England’s White Mountains on this private guided tour from Portland, Maine. This full-day adventure combines spectacular mountain scenery, historic rail travel, charming villages, and iconic landmarks that showcase New Hampshire’s famous mountain region.
The highlight of the tour is the Mount Washington Cog Railway, where guests board the historic train and travel to the summit of Mount Washington, the highest peak in the northeastern United States. At the summit, guests can enjoy panoramic views, explore the observation area, and visit the small museum.
The tour also includes scenic drives along portions of the famous Kancamagus Highway, widely considered one of the most beautiful mountain drives in the country. Along the way we visit picturesque villages such as Jackson and North Conway, see the historic Mount Washington Hotel, and stop at scenic overlooks and waterfalls that make the White Mountains unforgettable.
★ 5.0 (7 reviews)Check current price
Check dates and timing on Viator. Prices checked 10/6/2026, 12:34:32 AM UTC.Pickup, options & cancellationSee tour & check dates ↗
2–6 hours
Private Yacht Tour in Portland, Maine 2hr, 4hr and 6hr Available
Explore the stunning scenery and rich maritime history of Casco Bay on a private 2hr, 4hr or 6hr powerboat cruise. Ideal for families, friends, or small groups, this exclusive charter offers a personal adventure, allowing you to encounter marine wildlife, view iconic lighthouses, and discover unique islands at your own pace. With flexible scheduling and customizable experiences, this cruise promises an unforgettable day on the water, complete with opportunities for swimming and exploring Maine’s rugged coastline.
- Private cruise for up to 6 passengers, ensuring an exclusive experience
- Encounter marine wildlife like seals, porpoises, and seabirds
- View famous lighthouses including Portland Head Light and Bug Light
- Flexible departure times and customizable itineraries available
– Alternative pickup available in Portland for added cost, saves 30 min of driving, contact us for availability
★ 5.0 (4 reviews)Check current price
Check dates and timing on Viator. Prices checked 10/6/2026, 12:34:32 AM UTC.Pickup, options & cancellationSee tour & check dates ↗
8–10 hours
Private Portland to Cape Ann, MA Castles & Coast
Discover coastal New England on this private day tour from Portland, Maine to Massachusetts’ North Shore and Cape Ann. This thoughtfully curated experience blends grand seaside estates, medieval-style architecture, colonial history, and authentic harbor towns into one unforgettable journey.
Admission is included to the breathtaking Crane Estate at Castle Hill in Ipswich, where sweeping lawns lead to panoramic Atlantic views. A favorite filming location for major Hollywood productions, its dramatic setting feels timeless and cinematic. You’ll also enjoy a guided tour inside Hammond Castle, a stunning 1920s seaside castle overlooking the ocean.
Explore historic Ipswich, one of America’s oldest towns, and visit Gloucester’s iconic Fisherman’s Memorial while strolling its working harbor.
With private transportation and relaxed pacing, this tour offers an elegant and memorable way to experience the beauty, history, and charm of coastal Massachusetts in a single day.
★ 5.0 (3 reviews)Check current price
Check dates and timing on Viator. Prices checked 10/6/2026, 12:34:32 AM UTC.Pickup, options & cancellationSee tour & check dates ↗
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PLAN YOUR TRIP
Booking & getting there
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CURRENT OFFERS
Available promotions
Shown for 2 adults
Offer names are shown exactly as returned with the current fare. Displayed totals already reflect applicable discounts; eligibility, combinability, and final terms are confirmed during booking.
The chart shows the earliest captured price, changes between captured prices and the latest observation. Dates without a plotted change do not establish that the fare stayed available throughout that period.
DAY BY DAY
Itinerary with local times
DAY1
BostonEMBARK
DEPART6:00 PM
DAY2
PortlandDOCKED
ARRIVE7:00 AMDEPART5:00 PM
DAY3
RocklandTENDERED
ARRIVE7:00 AMDEPART4:00 PM
DAY4
HalifaxDOCKED
ARRIVE10:30 AMDEPART6:00 PM
DAY5
SydneyDOCKED
ARRIVE10:00 AMDEPART7:00 PM
DAY6
CruisingCRUISING
Times unavailable
DAY7
Quebec CityDOCKED
ARRIVE11:00 AM
DAY8
Quebec CityDOCKED
DEPART3:00 PM
DAY9
CruisingCRUISING
Times unavailable
DAY10
CharlottetownDOCKED
ARRIVE7:00 AMDEPART3:00 PM
DAY11
CruisingCRUISING
Times unavailable
DAY12
BostonDEBARK
ARRIVE7:00 AM
ROUTE AT A GLANCE
Itinerary map
Follow the sailing in order. Tap a numbered port to see its stop name.