Celebrity has one of the strongest Boston programs of any premium line, especially in fall. Here’s what’s sailing from Boston’s Flynn Cruiseport in 2027.
Celebrity Silhouette: Canada and New England round trips
Celebrity Silhouette, a Solstice-class ship with the Lawn Club, sails round-trip Canada and New England cruises from Boston in September and October 2027. Expect ports such as Portland, Bar Harbor, Saint John and Halifax, timed for peak foliage.
Repositioning cruises from Boston
- Celebrity Silhouette, October 16, 2027: 10 nights from Boston to Fort Lauderdale via Aruba, Curaçao and Bonaire. It’s a Southern Caribbean cruise that starts an hour from home.
- Celebrity Summit, October 20, 2027: 9 nights from Boston to San Juan via Bermuda (Hamilton and St. George’s), St. Barts and Virgin Gorda.
Repositioning cruises are often among the best per-night values Celebrity sells. You’ll need a one-way flight home.
Why sail Celebrity from Boston?
- About an hour from southern New Hampshire
- No outbound flight
- Peak foliage itineraries
- Rare chances to start a Caribbean cruise in New England
Packing
Fall sailings need layers: a waterproof jacket, a sweater and walking shoes. Repositioning cruises need both cool-weather and beach clothes. See our Canada and New England packing guide.
FAQ
When should I book a Celebrity foliage cruise from Boston?
9–12 months ahead. Late September and early October sell out first.
Do I need a passport?
For closed-loop round trips, a birth certificate and ID work for U.S. citizens, but a passport is strongly recommended. One-way repositioning cruises typically require a passport.
Keep planning
We’re a New Hampshire agency and book Boston departures every week. Get a free quote or call 860-951-8312.