Luxury cruises from Boston: Regent, Seabourn, Oceania, Azamara and Windstar

Luxury cruises from Boston are a short list of autumn voyages on small ships, most of them one way to Montreal by way of Maine, Nova Scotia, Prince Edward Island and Quebec. This guide covers the five lines that run them, what each says its fare includes, and what they cost per night.

We group these lines by the size of their ships and what their fares include, not by any rating. Holland America, Celebrity and Princess also sail Canada trips from Boston, and they are covered near the end.

Which luxury cruise lines sail from Boston?

Regent Seven Seas, Seabourn, Oceania Cruises, Azamara and Windstar all start voyages in Boston on the schedule we track. Each sends one or two ships, and every departure is in September or October. The smallest ship, Windstar's Star Pride, carries 312 guests.

Ship	Line	Size, from the line's own page	Boston sailings	First listed	Lowest fare	Cheapest cabin listed
Seven Seas Grandeur	Regent Seven Seas	746 guests	1	13 October 2027	$13,849	Suite
Seven Seas Prestige	Regent Seven Seas	818 guests	2	21 September 2028	$13,799	Suite
Seabourn Quest	Seabourn	458 guests	1	16 October 2028	$8,998	Suite
Oceania Vista	Oceania	607 suites and rooms	1	29 September 2027	$8,099	Balcony
Oceania Aurelia	Oceania	238 suites and staterooms	1	4 October 2028	$7,899	Balcony
Azamara Quest	Azamara	736 guests	1	4 October 2027	$4,789	Interior
Star Pride	Windstar	312 guests	6	16 September 2027	$4,477	Ocean view

Fares are the lowest on 3 November 2026, per person for the cheapest cabin listed, two sharing, with taxes and fees included. Oceania's pages give room counts rather than guest numbers, so those two rows are not directly comparable with the others.

What does a luxury cruise fare from Boston include?

It depends on the line. Of the five, only Regent lists unlimited shore excursions in its fare, along with drinks, every specialty restaurant, Wi-Fi and prepaid gratuities. Oceania and Azamara include gratuities and some drinks, Seabourn includes drinks and says tipping is not expected, and Windstar includes all dining. The details below come from each line's own pages.

Regent Seven Seas

Regent's what's-included page lists unlimited shore excursions, unlimited drinks including fine wines and specialty coffees, every specialty restaurant at no added cost, an in-suite minibar restocked daily, unlimited Wi-Fi, prepaid gratuities, valet laundry, 24-hour in-suite dining and use of the spa facilities. Concierge suites and higher add a one-night hotel stay before the cruise. The same page says 99% of Regent's suites have a private balcony.

Regent lists Seven Seas Grandeur at 746 guests and 548 crew, and Seven Seas Prestige at 818 guests and 630 crew. Prestige is new. Regent says she debuts in December 2026, and her Boston voyages are in September and October 2028.

Seabourn

Seabourn's what's-included page says all dining venues are complimentary, along with premium spirits, fine wines, a welcome Champagne and an in-suite bar. Its FAQ says tipping is neither required nor expected.

On the Seabourn Quest page, complimentary Wi-Fi is listed for Owner's Suites and above, and the spa is marked as an extra charge. None of the Seabourn pages we read lists shore excursions as included. Seabourn gives Quest 458 guests and a 2011 launch.

Oceania Cruises

Oceania's Your World Included page lists specialty restaurants, shipboard gratuities, Wi-Fi, specialty coffees, sodas, cold-pressed juices, still and sparkling water and free launderettes as included for every guest. You then pick one of two extras: wine and beer by the glass at lunch and dinner, or a shore excursion credit.

Oceania's page gives Oceania Vista, built in 2023, 607 suites and rooms. It gives Oceania Aurelia 238 suites and staterooms and nearly 500 crew, lists 2000 as the year she was built, and calls her 2027 and 2028 voyages inaugural sailings.

Azamara

Azamara's home page lists dining venues, beer, wine and spirits, AzAmazing Evenings, onboard gratuities and unlimited self-service laundry as always included. Its FAQ narrows the drinks to select standard spirits, international beers and one red and one white wine by the glass, and says shore excursions carry a fee. Azamara's Quest page says the AzAmazing Evenings event comes on most voyages.

Two specialty restaurants, Prime C and Aqualina, carried a surcharge of $49.95 per person for most guests when we checked the FAQ on 3 November 2026. Azamara's ship facts give Azamara Quest 736 guests at double occupancy and a refurbishment in November 2026.

Windstar

Windstar's Star Pride page says all dining is included, specialty restaurants too, and its offers page adds 24-hour room service. Windstar's All-Inclusive Package adds gratuities, unlimited Wi-Fi and select beer, cocktails and wine by the glass.

When we checked on 3 November 2026, Windstar was giving that package free on bookings made by 17 November 2026 for voyages through 2027, with terms attached, so check what applies when you book. Windstar describes Star Pride as an all-suite ship for 312 guests.

Where do luxury cruises from Boston go?

Mostly to Montreal, one way. The Regent, Seabourn, Oceania and Azamara voyages, and Windstar's September voyages, sail from Boston through Maine, Halifax and Prince Edward Island, then into Quebec, and end in Montreal. Windstar's October 2027 voyages head south instead, through Bermuda to the Caribbean, and end in San Juan.

These are the sailings on the schedule we track:

Leaves	Ship	Nights	Ends	Ports of call
16 September 2027	Star Pride	11	Montreal	Portland, Bar Harbor, Halifax, Charlottetown, Gaspé, Quebec City
16 September 2027	Star Pride	25	Montreal	The 11-night route, then on from Montreal to the Saguenay, Saint-Pierre, Newfoundland and Labrador and back
29 September 2027	Oceania Vista	11	Montreal	Portland, Bay of Fundy, Halifax, Sydney, Charlottetown, Havre-Saint-Pierre, Sept-Iles, Quebec City
4 October 2027	Azamara Quest	12	Montreal	Portland, Rockland, Saint John, Halifax, Charlottetown, Baie-Comeau, Saguenay, Quebec City, Trois-Rivieres
13 October 2027	Seven Seas Grandeur	11	Montreal	Bar Harbor, Saint John, Halifax, Sydney, Charlottetown, Gaspé, Saguenay, Quebec City
22 October 2027	Star Pride	10	San Juan	Hamilton and St. George's in Bermuda, Gustavia, Virgin Gorda
22 October 2027	Star Pride	17	San Juan	The 10-night route, then a week around the Virgin Islands, St. Kitts and St. Maarten
14 September 2028	Star Pride	11	Montreal	Portland, Bar Harbor, Halifax, Charlottetown, Gaspé, Quebec City
14 September 2028	Star Pride	25	Montreal	As in 2027
21 September 2028	Seven Seas Prestige	11	Montreal	Bar Harbor, Saint John, Halifax, Sydney, Charlottetown, Gaspé, Quebec City
4 October 2028	Oceania Aurelia	11	Montreal	Portland, Bay of Fundy, Halifax, Sydney, Charlottetown, Baie-Comeau, Saguenay, Quebec City
13 October 2028	Seven Seas Prestige	11	Montreal	Portland, Saint John, Halifax, Sydney, Charlottetown, Gaspé, Quebec City
16 October 2028	Seabourn Quest	12	Montreal	Portland, Halifax, Charlottetown, Cap-aux-Meules, Gaspé, Saguenay, Quebec City

Every one of these ends away from Boston, so plan a flight home. To fly back into the United States, CBP lists a valid U.S. passport or a Trusted Traveler card such as NEXUS for U.S. citizens. The cruise documents guide covers the rest, and the Canada and New England guide describes the ports.

How much does a luxury cruise from Boston cost per night?

On 3 November 2026 the lowest fare per night was $1,254 on Regent, $750 on Seabourn, $718 on Oceania, $399 on Azamara and $355 on Windstar, per person, two sharing, taxes and fees included. Norwegian's lowest was $60. Those figures buy different cabins and inclusions, so they do not compare like for like.

Line	Lowest fare	Lowest per night	Cheapest cabin listed	Shore excursions	Gratuities
Regent Seven Seas	$13,799	$1,254	Suite	Unlimited, included	Prepaid, included
Seabourn	$8,998	$750	Suite	Not listed as included	Tipping not expected
Oceania	$7,899	$718	Balcony	A credit, if you choose it	Included
Azamara	$4,789	$399	Interior	A fee per tour	Included
Windstar	$4,477	$355	Ocean view	Not listed as included	In the All-Inclusive Package

The cheapest cabin decides a lot here. Regent's and Seabourn's lowest fares buy a suite, while Azamara's buys an interior cabin, so a higher fare can mean a larger room as well as more included.

On a mainstream ship the extras are added one by one. For Norwegian Breakaway, Cruisebound lists drinks packages, gratuities, Wi-Fi and specialty dining as add-ons. Even so, Regent's lowest fare per night was more than ten times Norwegian's on 3 November 2026, by our arithmetic, so the inclusions narrow the gap without closing it.

What about Holland America, Celebrity and Princess from Boston?

They also sail Canada and New England trips from Boston, at lower fares and with fewer extras in the fare. On 3 November 2026 the lowest fare was $1,234 on Holland America, $904 on Celebrity and $949 on Princess. All three add a daily gratuity for each guest on top.

On 3 November 2026 those gratuities were $18 a day per guest in a standard cabin on Holland America and Princess, and $19.50 on Celebrity, from the lines' own pages. Holland America's Volendam also sails voyages of up to 35 nights to Greenland, Iceland and northern Europe, which the Europe and transatlantic guide covers.

When do luxury cruises leave Boston?

In September and October. Every Regent, Seabourn, Oceania, Azamara and Windstar departure on the schedule we track falls in those two months, which are also Boston's busiest overall. Tourism Nova Scotia says late September to mid-October is typically the strongest window for fall color there, with Cape Breton tending to peak before the south of the province.

The cruise season guide shows what else leaves in each month, and the month pages for September 2027 and October 2027 list every departure.