Boston Cruise Ship Departures
The Boston cruise calendar is your overview of what’s sailing from Flynn Cruiseport through the year—Bermuda, New England & Canada, the Caribbean, Europe, and seasonal repositioning voyages. Dates, ships, and itineraries change with the seasons, so a single calendar view makes it easier to spot the sailings that fit your schedule and budget.
Use it to compare departure months, trip lengths, and destinations before you dig into a specific cruise. Whether you’re planning a quick getaway or a longer crossing, the Boston cruise calendar helps you see the full picture of departures from home waters in one place.
Boston Cruise Calendar - 2026
| Name | Departure | Stops | Cruise Line | Price | |
|---|---|---|---|---|---|
| 7 Night The Cape Codder | Aug 24, 2026 | 5 Stops |  | from $5,850 | Details |
| 7 Night Canada & New England: Bar Harbor & Halifax | Aug 30, 2026 | 3 Stops |  | from $879 | Details |
| 7 Night The Cape Codder | Aug 31, 2026 | 5 Stops | | from $5,850 | Details |
| 10 Night Classic Canada & New England | Sep 3, 2026 | 6 Stops |  | from $1,079 | Details |
| 12 Night Boston Maine & Canada | Sep 5, 2026 | 6 Stops |  | from $1,794 | Details |
| 14 Night Grand New England | Sep 6, 2026 | 11 Stops | | from $13,930 | Details |
| 7 Night Canada & New England: Bar Harbor & Halifax | Sep 6, 2026 | 3 Stops | | from $879 | Details |
| 7 Night The Cape Codder | Sep 7, 2026 | 5 Stops | | from $5,850 | Details |
| 14 Night Roundtrip Transatlantic Crossing | Sep 12, 2026 | Nonstop |  | from $1,849 | Details |
| 11 Night Southeast Canadian Explorations | Sep 14, 2026 | 7 Stops |  | from $6,565 | Details |
| 25 Night Star Collector: Autumn in Newfoundland & New England | Sep 14, 2026 | 11 Stops | | from $12,665 | Details |
| 7 Night The Cape Codder | Sep 14, 2026 | 5 Stops | | from $5,850 | Details |
| 14 Night Canada & New England: UNESCO Sites & Nights Collectors | Sep 19, 2026 | 8 Stops |  | from $2,608 | Details |
| 7 Night Canada & New England: UNESCO Sites & Quebecois Nights | Sep 19, 2026 | 5 Stops | | from $1,306 | Details |
| 14 Night Grand New England | Sep 20, 2026 | 11 Stops | | from $13,930 | Details |
| 7 Night Canada & New England: Bar Harbor & Halifax | Sep 20, 2026 | 3 Stops | | from $879 | Details |
| 7 Night The Cape Codder | Sep 21, 2026 | 5 Stops | | from $5,850 | Details |
| 10 Night Classic Canada & New England | Sep 23, 2026 | 6 Stops | | from $1,159 | Details |
| 24 Night Transatlantic Crossing New England & Canada | Sep 26, 2026 | 7 Stops | | from $3,869 | Details |
| 7 Night Canada & New England: Bar Harbor & Halifax | Sep 27, 2026 | 3 Stops | | from $879 | Details |
| 11 Night Magnifique L Automne | Sep 28, 2026 | 10 Stops |  | from $12,699 | Details |
| 11 Night Boston Maine & Canada | Sep 28, 2026 | 5 Stops | | from $1,598 | Details |
| 11 Night Boston Maine & Canada | Sep 28, 2026 | 5 Stops | | from $1,598 | Details |
| 7 Night Canada & New England Circle: New Brunswick | Oct 3, 2026 | 4 Stops | | from $1,221 | Details |
| 7 Night Canada & New England: Bar Harbor & Halifax | Oct 4, 2026 | 3 Stops | | from $879 | Details |
| 7 Night The Cape Codder | Oct 4, 2026 | 5 Stops | | from $6,915 | Details |
| 45 Night Day Legendary Ultimate Mediterranean & Atlantic Passage | Oct 8, 2026 | 11 Stops | | from $8,749 | Details |
| 7 Night North America & Canada | Oct 9, 2026 | 5 Stops |  | from $4,900 | Details |
| 11 Night Boston Maine & Canada | Oct 9, 2026 | 5 Stops | | from $1,598 | Details |
| 7 Night Canada & New England: UNESCO Sites & Quebecois Nights | Oct 10, 2026 | 6 Stops | | from $779 | Details |
| 10 Night Southern Caribbean | Oct 20, 2026 | 3 Stops | | from $1,066 | Details |
| 7 Night Bermuda: Halifax & Bermuda | Nov 1, 2026 | 1 Stops | | from $599 | Details |
| 18 Night Transatlantic Crossing & Eastern Caribbean | Nov 17, 2026 | 4 Stops | | from $2,099 | Details |
| 21 Night Roundtrip Transatlantic Crossing | Nov 28, 2026 | 3 Stops | | from $3,259 | Details |
| 23 Night Transatlantic Crossing & Caribbean Celebration | Dec 19, 2026 | 6 Stops | | from $3,539 | Details |
Boston Cruise Calendar - 2027
| Name | Departure | Stops | Cruise Line | Price | |
|---|---|---|---|---|---|
| 9 Night Eastbound Transatlantic Crossing | Jan 2, 2027 | Nonstop | | from $899 | Details |
| 14 Night Transoceanic Eastbound | Mar 23, 2027 | 3 Stops |  | from $7,800 | Details |
| 23 Night Grand Atlantic to Adriatic | Mar 25, 2027 | 11 Stops |  | from $6,499 | Details |
| 16 Night Cosmopolitan Crossing | Mar 25, 2027 | 7 Stops | | from $3,705 | Details |
| 37 Night Transatlantic Grand Voyage - Eastbound | Mar 29, 2027 | 11 Stops |  | from $9,289 | Details |
| 12 Night Transatlantic: Bermuda The Azores & Lisbon | Mar 29, 2027 | 2 Stops | | from $2,119 | Details |
| 16 Night Brilliant Bermuda & Iberia | Mar 31, 2027 | 7 Stops | | from $4,845 | Details |
| 16 Night Brilliant Bermuda & Iberia | Mar 31, 2027 | 7 Stops | | from $4,845 | Details |
| 23 Night New World to Ancient Shores | Mar 31, 2027 | 11 Stops | | from $9,099 | Details |
| 25 Night Atlantic Isles & Kingdoms | Apr 9, 2027 | 11 Stops | | from $6,599 | Details |
| 15 Night Atlantic Island Collector | Apr 9, 2027 | 5 Stops | | from $3,399 | Details |
| 14 Night MSC Grand Voyage | Apr 10, 2027 | 4 Stops |  | from $1,208 | Details |
| 12 Night MSC Grand Voyage | Apr 10, 2027 | 2 Stops | | from $1,059 | Details |
| 16 Night MSC Grand Voyage | Apr 10, 2027 | 6 Stops | | from $1,419 | Details |
| 17 Night MSC Grand Voyage | Apr 10, 2027 | 7 Stops | | from $1,365 | Details |
| 15 Night MSC Grand Voyage | Apr 10, 2027 | 5 Stops | | from $1,969 | Details |
| 15 Night Spain & Portugal Transatlantic | Apr 11, 2027 | 6 Stops | | from $1,741 | Details |
| 13 Night Transatlantic - Eastbound | Apr 11, 2027 | 2 Stops | Ritz-Carlton Yacht Collection | from $9,300 | Details |
| 14 Night Journey to Iberia | Apr 14, 2027 | 4 Stops | | from $7,299 | Details |
| 24 Night Atlantic Evenings | Apr 14, 2027 | 7 Stops | | from $15,699 | Details |
| 16 Night Transatlantic: Portugal Spain & France | Apr 16, 2027 | 7 Stops | | from $1,889 | Details |
| 21 Night Norwegian Fjords Crossing with History Channel | Apr 17, 2027 | 10 Stops | | from $1,969 | Details |
| 14 Night Cultural Crossing with Bermuda Paris & Brugge | Apr 17, 2027 | 4 Stops | | from $1,059 | Details |
| 7 Night Bermuda: Halifax & Bermuda | Apr 18, 2027 | 1 Stops | | from $1,159 | Details |
| 14 Night Spain & Gibraltar Transatlantic | Apr 19, 2027 | 5 Stops |  | from $827 | Details |
| 14 Night Transatlantic Miami to Morocco & Spain | Apr 24, 2027 | 3 Stops | Virgin Voyages | from $1,540 | Details |
| 28 Night New World Old World | Apr 29, 2027 | 11 Stops | | from $19,699 | Details |
| 16 Night Shimmering Atlantic Shores | Apr 29, 2027 | 8 Stops | | from $9,799 | Details |
| 92 Night Grand Arctic | Apr 29, 2027 | 11 Stops | | from $72,969 | Details |
| 14 Night Spain & Morocco Transatlantic | May 2, 2027 | 3 Stops | Virgin Voyages | from $1,540 | Details |
| 7 Night Bermuda: Halifax & Bermuda | May 9, 2027 | 1 Stops | | from $909 | Details |
| 15 Night Transatlantic: France Spain & Portugal | May 11, 2027 | 4 Stops | | from $1,609 | Details |
| 7 Night Bermuda: Halifax & Bermuda | May 16, 2027 | 1 Stops | | from $909 | Details |
| 9 Night Eastbound Transatlantic Crossing to Hamburg | May 19, 2027 | 1 Stops | | from $1,429 | Details |
| 7 Night Eastbound Transatlantic Crossing | May 19, 2027 | Nonstop | | from $899 | Details |
| 26 Night Transatlantic & the Fjords | May 19, 2027 | 10 Stops | | from $4,939 | Details |
| 7 Night The Cape Codder | May 29, 2027 | 5 Stops | | from $6,915 | Details |
| 12 Night Atlantic Passage | May 30, 2027 | 1 Stops | Seabourn | from $5,298 | Details |
| 14 Night Grand New England | Jun 5, 2027 | 11 Stops | | from $13,930 | Details |
| 18 Night Transatlantic: New York Canada & London | Jun 10, 2027 | 9 Stops | | from $3,869 | Details |
| 14 Night Canada & New England: Maritimes & Montreal Collectors | Jun 19, 2027 | 8 Stops | | from $3,274 | Details |
| 7 Night Canada & New England: Maine Maritimes & Montreal | Jun 19, 2027 | 7 Stops | | from $1,652 | Details |
| 7 Night The Cape Codder | Jun 20, 2027 | 5 Stops | | from $7,415 | Details |
| 7 Night The Cape Codder | Jun 27, 2027 | 5 Stops | | from $7,415 | Details |
| 14 Night Independence Day Celebration | Jul 2, 2027 | 2 Stops | | from $3,099 | Details |
| 14 Night Grand New England | Jul 3, 2027 | 11 Stops | | from $13,930 | Details |
| 7 Night Canada & New England: Maine Maritimes & Montreal | Jul 3, 2027 | 7 Stops | | from $1,732 | Details |
| 7 Night Canada & New England: Maine Maritimes & Montreal | Jul 3, 2027 | 7 Stops | | from $1,732 | Details |
| 7 Night The Cape Codder | Jul 4, 2027 | 5 Stops | | from $7,415 | Details |
| 7 Night Bermuda: Halifax & Bermuda | Jul 4, 2027 | 1 Stops | | from $1,239 | Details |
| 14 Night Iconic Iceland Greenland & Canada | Jul 9, 2027 | 10 Stops |  | from $9,999 | Details |
| 7 Night The Cape Codder | Jul 11, 2027 | 5 Stops | | from $7,415 | Details |
| 14 Night Grand New England | Jul 17, 2027 | 11 Stops | | from $13,930 | Details |
| 35 Night Legendary Voyage of the Vikings | Jul 17, 2027 | 11 Stops | | from $8,632 | Details |
| 7 Night The Cape Codder | Jul 18, 2027 | 5 Stops | | from $7,415 | Details |
| 7 Night Bermuda: Halifax & Bermuda | Jul 18, 2027 | 1 Stops | | from $1,239 | Details |
| 7 Night Eastbound Transatlantic Crossing | Jul 23, 2027 | Nonstop | | from $899 | Details |
| 28 Night Norwegian Fjords | Jul 23, 2027 | 7 Stops | | from $4,059 | Details |
| 7 Night The Cape Codder | Jul 25, 2027 | 5 Stops | | from $7,415 | Details |
| 14 Night Grand New England | Jul 31, 2027 | 11 Stops | | from $13,930 | Details |
| 7 Night The Cape Codder | Jul 31, 2027 | 5 Stops | | from $7,415 | Details |
| 7 Night The Cape Codder | Aug 7, 2027 | 5 Stops | | from $7,415 | Details |
| 14 Night Grand New England | Aug 14, 2027 | 11 Stops | | from $13,930 | Details |
| 7 Night The Cape Codder | Aug 14, 2027 | 5 Stops | | from $7,415 | Details |
| 14 Night Grand New England | Aug 28, 2027 | 11 Stops | | from $13,930 | Details |
| 7 Night Canada & New England: Eastport & Halifax | Aug 29, 2027 | 3 Stops | | from $989 | Details |
| 14 Night Iconic Iceland Greenland & Canada | Aug 29, 2027 | 10 Stops | | from $8,999 | Details |
| 11 Night Boston Maine & Canada | Sep 2, 2027 | 5 Stops | | from $1,598 | Details |
| 7 Night Canada & New England: UNESCO Sites & Quebecois Nights | Sep 4, 2027 | 6 Stops | | from $1,694 | Details |
| 7 Night The Cape Codder | Sep 4, 2027 | 5 Stops | | from $7,415 | Details |
| 7 Night Canada & New England: Eastport & Halifax | Sep 5, 2027 | 3 Stops | | from $989 | Details |
| 14 Night Grand New England | Sep 11, 2027 | 11 Stops | | from $13,930 | Details |
| 11 Night Boston Maine & Canada | Sep 13, 2027 | 5 Stops | | from $1,809 | Details |
| 24 Night Transatlantic Crossing New England & Canada | Sep 17, 2027 | 9 Stops | | from $4,659 | Details |
| 21 Night Transatlantic Crossing New England & Canada | Sep 17, 2027 | 7 Stops | | from $3,909 | Details |
| 7 Night Canada & New England Circle: New Brunswick | Sep 18, 2027 | 4 Stops | | from $1,709 | Details |
| 11 Night Boston Maine & Canada | Sep 24, 2027 | 5 Stops | | from $1,598 | Details |
| 11 Night Boston Maine & Canada | Sep 24, 2027 | 5 Stops | | from $1,598 | Details |
| 11 Night Boston Maine & Canada | Sep 24, 2027 | 5 Stops | | from $1,598 | Details |
| 14 Night Grand New England | Sep 25, 2027 | 11 Stops | | from $13,930 | Details |
| 14 Night Canada & New England: UNESCO Sites & Nights Collectors | Sep 25, 2027 | 6 Stops | | from $3,469 | Details |
| 7 Night Canada & New England: UNESCO Sites & Quebecois Nights | Sep 25, 2027 | 6 Stops | | from $1,694 | Details |
| 19 Night Roundtrip Transatlantic Crossing | Oct 1, 2027 | 2 Stops | | from $2,979 | Details |
| 7 Night Anthony Inglis & the National Symphony Orchestra | Oct 1, 2027 | Nonstop | | from $1,239 | Details |
| 10 Night Eastbound Transatlantic Crossing | Oct 1, 2027 | 2 Stops | | from $1,839 | Details |
| 12 Night Canada & New England Intensive: Portland Saguenay & Montreal | Oct 4, 2027 | 11 Stops | | from $4,219 | Details |
| 11 Night Boston Maine & Canada | Oct 5, 2027 | 5 Stops | | from $1,659 | Details |
| 11 Night Boston Maine & Canada | Oct 5, 2027 | 5 Stops | | from $1,659 | Details |
| 11 Night Leaves & Lobsters | Oct 13, 2027 | 10 Stops | | from $12,099 | Details |
| 11 Night Leaves & Lobsters | Oct 13, 2027 | 10 Stops | | from $12,099 | Details |
| 11 Night Leaves & Lobsters | Oct 13, 2027 | 10 Stops | | from $12,099 | Details |
| 10 Night Boston to Fort Lauderdale | Oct 16, 2027 | 3 Stops | | from $898 | Details |
| 7 Night Canada & New England: Eastport & Halifax | Oct 17, 2027 | 3 Stops | | from $989 | Details |
| 30 Night Roundtrip Transatlantic Crossing | Oct 20, 2027 | 5 Stops | | from $4,759 | Details |
| 7 Night Eastbound Transatlantic Crossing | Oct 20, 2027 | Nonstop | | from $899 | Details |
| 9 Night Repositioning | Oct 20, 2027 | 5 Stops | | from $854 | Details |
| 7 Night Bermuda: Halifax & Bermuda | Oct 31, 2027 | 1 Stops | | from $989 | Details |
| 20 Night Transatlantic Crossing & Eastern Caribbean | Nov 19, 2027 | 6 Stops | | from $3,449 | Details |
| 7 Night Literature Festival at Sea | Dec 2, 2027 | Nonstop | | from $1,149 | Details |
| 26 Night Caribbean Celebration | Dec 23, 2027 | 9 Stops | | from $4,959 | Details |
Explore Cruises from Boston
Boston Cruise Calendar
Find the best cruises out of Boston that match your schedule and budget.
Cheapest Cruises from Boston
Cruises out of Boston can be surprisingly affordable starting at $600 a week.
Cruises to Europe
Explore transatlantic cruises to to British isles, the Mediterranean, and Northern Europe, right from your home.
Bermuda
The perfect blend of convenience and tropical escape. Enjoy pink-sand beaches and turquoise waters just a couple of days from Boston.
New England
Autumn color, coastal flavor, and a real sense of adventure awaits you here. Experience harbor towns, taste lobster , and wake up to the rugged coastline.
Cape Cod
Explore the Cape's famous beaches, lighthouses, and classic New England towns. Enjoy fresh sea air and harbor views right from the start.
Visit Boston
Visiting Boston means discovering a city full of history, culture, and everyday charm. Top attractions and easy exploring routes help you see the highlights, while shopping and great food add plenty of local flavor. World-class museums offer deeper insights, and a wide choice of hotels makes it simple to find the right place to stay. Together, these experiences create a memorable visit that mixes the classic and the contemporary.
Attractions
Walk the Freedom Trail, explore the Waterfront, and then cross over to the Common - Boston’s neighborhoods and attractions are easy to reach.
Exploring
Walk Boston’s Revolutionary landmarks, then wander over to Beacon Hill, Back Bay, and the North End - enjoy shopping, history, and neighborhood life all within easy reach.
Shopping
From the upscale boutiques of Newbury Street to the designer stores at Copley Place, shoppers can find everything from global luxury brands to local boutiques.
Food
From lobster and chowder to the North End’s Italian favorites, Boston’s food scene is an easy highlight—great meals close to the main attractions.
Museums
From the Museum of Fine Arts and the Isabella Stewart Gardner to the Science Museum and ICA on the waterfront, Boston museums are not to be missed!
Hotels
From waterfront stays to classic Back Bay hotels, find a base that fits your plans and puts Boston’s main attractions within easy reach.