Bucket-List Cruise Adventures

Pick your sailing — we plan the whole adventure

14 sailings across 23 cruise lines, each one priced and planned end to end: the ports it calls at, the one unmissable thing to do at each, and the flights and nights either side. A balcony averages about $166 a night on Carnival and about $414 on Disney, per person with taxes in — what a night costs on every line. Leaving within three weeks?

Bucket-list adventures at every port — where to fly in, and what to do the day(s) before and after.

When are you free? — only cruises that fit entirely inside your dates
My result then click any cruise row to open it
Where to? tap as many as you like Caribbean Mediterranean Alaska Bahamas Mexico Northern Europe Hawaii Bermuda Europe Asia Australia & South Pacific Panama Canal South America North America Pacific Middle East Africa
Trip tap one or more Round-trip One-way Repositioning
Length tap one or more 3–5 nights 6–8 nights 9–12 nights 13+ nights
Cruise level tap one or more Luxury Premium Contemporary River
+ pick specific cruise lines
Luxury Azamara Explora Journeys Oceania Regent Seabourn Silversea Viking Ocean Windstar River AmaWaterways Avalon Viking River Premium Celebrity Cunard Disney Holland America Princess Virgin Virgin Voyages Contemporary Carnival Costa MSC Cruises Norwegian Royal Caribbean
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Showing 14 of 14 sailings
11-night to Rockland & Halifax from BostonRound-trip
Celebrity · Celebrity Silhouette
Balcony: typical fare in the usual range↑ 11% balcony, 38d
North America 11 nights Sep 2 – Sep 13, 2027
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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Balcony $3,123 pp
Book This Cruise@ Cruisebound
11-night to Rockland & Halifax from BostonRound-trip
Celebrity · Celebrity Silhouette
Balcony: above average 24% over usual↑ 8% balcony, 38d
North America 11 nights Sep 13 – Sep 24, 2027
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Quebec City, Quebec · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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Balcony $3,458 pp
Book This Cruise@ Cruisebound
11-night to Rockland & Halifax from BostonRound-trip
Celebrity · Celebrity Silhouette
Balcony: above average 78% over usual↑ 63% balcony, 38d
North America 11 nights Sep 24 – Oct 5, 2027
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Portland, Maine · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgBridgeClimb Sydney +3 more
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Balcony $4,962 pp
Book This Cruise@ Cruisebound
12-night Boston to MontrealOne-way
Azamara · Azamara Quest
Balcony: low fare 18% under usualAll grades open
North America 12 nights Oct 4 – Oct 16, 2027
Boston, Massachusetts · Portland, Maine · … · Montreal, Quebec12 ports
Boston, Massachusetts · Portland, Maine · Rockland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Corner Brook, Newfoundland · Havre St. Pierre, Quebec · Sept-Iles, Canada · Saguenay Fjord, Canada · Quebec City, Quebec · Troisrivieres, Canada · Montreal, Quebec
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Luxury Camden Sailing Experience on Penobscot BayReversing Falls & Fundy Tidal Bore +7 more
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Balcony $6,379 pp
Book This Cruise@ Cruisebound
11-night to Portland & Rockland from BostonRound-trip
Celebrity · Celebrity Silhouette
Balcony: above average 22% over usual↓ 12% inside, 38d
North America 11 nights Oct 5 – Oct 16, 2027
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Portland, Maine · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Luxury Camden Sailing Experience on Penobscot BayPeggy's Cove & Lunenburg +3 more
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Balcony $3,390 pp
Book This Cruise@ Cruisebound
12-night to Portland & Rockland from BostonRound-trip
Celebrity · Celebrity Summit
Balcony: low fare 16% under usualAll grades open
North America 12 nights Sep 1 – Sep 13, 2028
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Portland, Maine · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Quebec City, Quebec · Charlottetown, Prince Edward Island · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Luxury Camden Sailing Experience on Penobscot BayPeggy's Cove & Lunenburg +3 more
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Balcony $2,566 pp
Book This Cruise@ Cruisebound
11-night New York to MontrealOne-way
Silversea · Silver Spirit
Suite: low fare 6% under usual
North America 11 nights Sep 7 – Sep 18, 2028
New York, New York · Boston, Massachusetts · … · Montreal, Quebec9 ports
New York, New York · Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & Lunenburg +4 more
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Suite $7,200 pp
Book This Cruise@ Cruisebound
12-night to Portland & Rockland from BostonRound-trip
Celebrity · Celebrity Summit
Balcony: low fare 16% under usualAll grades open
North America 12 nights Sep 13 – Sep 25, 2028
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Portland, Maine · Rockland, Maine · Charlottetown, Prince Edward Island · Quebec City, Quebec · Sydney, Nova Scotia · Halifax, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Luxury Camden Sailing Experience on Penobscot BayGreen Gables House & Anne of Green Gables Island E… +3 more
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Balcony $2,566 pp
Book This Cruise@ Cruisebound
7-night to Rockland & Saint John from BostonRound-trip
Royal Caribbean · Jewel of the Seas
Balcony: typical fare in the usual rangeAll grades open
North America 7 nights Sep 22 – Sep 29, 2028
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Rockland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +1 more
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Balcony $1,570 pp
Book This Cruise@ Cruisebound
12-night to Rockland & Halifax from BostonRound-trip
Celebrity · Celebrity Summit
Balcony: low fare 16% under usualAll grades open
North America 12 nights Sep 25 – Oct 7, 2028
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts8 ports
Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Corner Brook, Newfoundland · Charlottetown, Prince Edward Island · Quebec City, Quebec · Sydney, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & LunenburgGros Morne National Park +3 more
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Balcony $2,544 pp
Book This Cruise@ Cruisebound
11-night New York to MontrealOne-way
Silversea · Silver Spirit
Suite: typical fare in the usual range
North America 11 nights Sep 29 – Oct 10, 2028
New York, New York · Boston, Massachusetts · … · Montreal, Quebec9 ports
New York, New York · Boston, Massachusetts · Rockland, Maine · Halifax, Nova Scotia · Sydney, Nova Scotia · Charlottetown, Prince Edward Island · Saguenay Fjord, Canada · Quebec City, Quebec · Montreal, Quebec
★ Bucket-list Manhattan Helicopter TourPrivate Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayPeggy's Cove & Lunenburg +4 more
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Suite $7,600 pp
Book This Cruise@ Cruisebound
7-night to Rockland & Saint John from BostonRound-trip
Royal Caribbean · Jewel of the Seas
Balcony: typical fare in the usual rangeAll grades open
North America 7 nights Oct 6 – Oct 13, 2028
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Rockland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +1 more
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Balcony $1,530 pp
Book This Cruise@ Cruisebound
12-night to Portland & Rockland from BostonRound-trip
Celebrity · Celebrity Summit
Balcony: typical fare in the usual rangeAll grades open
North America 12 nights Oct 7 – Oct 19, 2028
Boston, Massachusetts · Portland, Maine · … · Boston, Massachusetts9 ports
Boston, Massachusetts · Portland, Maine · Rockland, Maine · Charlottetown, Prince Edward Island · Quebec City, Quebec · Sydney, Nova Scotia · Halifax, Nova Scotia · Saint John, New Brunswick · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourPortland Head Light & Casco Bay Scenic Lighthouse…Luxury Camden Sailing Experience on Penobscot BayGreen Gables House & Anne of Green Gables Island E… +4 more
View →
Balcony $2,671 pp
Book This Cruise@ Cruisebound
7-night to Rockland & Saint John from BostonRound-trip
Royal Caribbean · Jewel of the Seas
Balcony: typical fare in the usual rangeAll grades open
North America 7 nights Oct 13 – Oct 20, 2028
Boston, Massachusetts · Rockland, Maine · … · Boston, Massachusetts6 ports
Boston, Massachusetts · Rockland, Maine · Saint John, New Brunswick · Halifax, Nova Scotia · Sydney, Nova Scotia · Boston, Massachusetts
★ Bucket-list Private Luxury Boston TourLuxury Camden Sailing Experience on Penobscot BayReversing Falls & Fundy Tidal BorePeggy's Cove & Lunenburg +1 more
View →
Balcony $1,520 pp
Book This Cruise@ Cruisebound

Itineraries from the Cruisebound catalog + our enrichment; schedules cross-checked against official port authorities. Booking via Cruisebound and CruiseDirect — we may earn a commission, at no extra cost to you.