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Caribbean October 2026 Boston
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Cruises from Boston

Find the Best Cruises from Boston for you. Easily compare prices and find out when to book your dream vacation with our cruise search..

Very good price

Compared to other cruises

10 Night Caribbean Southern
Celebrity Silhouette
4.0 "Very good"

PORTS

Boston; Willemstad; Kralendijk; Oranjestad; Fort Lauderdale

SAIL DATE:   Oct 20, 2026   -   Oct 30, 2026

Interior

$770 $77/night
Price Curve

Oceanview

$892 $89/night
Price Curve

Balcony

$1314 $131/night
Price Curve

Suite

$4668 $466/night
Price Curve

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Very good price

Compared to other cruises

13 Night Caribbean Southern
Norwegian Sky
3.6 "Good"

PORTS

Boston; Royal Naval Dockyard, West End, Bermuda; Great Stirrup Cay Bahamas; Cabo Rojo, Dominica... Tampa

SAIL DATE:   Oct 23, 2026   -   Nov 05, 2026

Interior

$1179 $90/night
Price Curve

Oceanview

$1379 $106/night
Price Curve

Balcony

$2919 $224/night
Price Curve

Suite

$6049 $465/night
Price Curve

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Very good price

Compared to other cruises

7 Night Bermuda
Norwegian Breakaway
3.5 "Good"

PORTS

Boston; Halifax; Royal Naval Dockyard, West End, Bermuda; Royal Naval Dockyard, West End, Berm... Boston

SAIL DATE:   Oct 18, 2026   -   Oct 25, 2026

Interior

$664 $94/night
Price Curve

Oceanview

$809 $115/night
Price Curve

Balcony

$1052 $150/night
Price Curve

Suite

$1213 $173/night
Price Curve

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Very good price

Compared to other cruises

7 Night Bermuda
Norwegian Breakaway
3.5 "Good"

PORTS

Boston; Halifax; Royal Naval Dockyard, West End, Bermuda; Royal Naval Dockyard, West End, Berm... Boston

SAIL DATE:   Oct 25, 2026   -   Nov 01, 2026

Interior

$699 $99/night
Price Curve

Oceanview

$899 $128/night
Price Curve

Balcony

$1129 $161/night
Price Curve

Suite

$1299 $185/night
Price Curve

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Set sail from Boston on the best cruise for you for the best price! No matter where you go, you can count on cruisewatch.com to make sure you get there in style and help you find the best price. Thanks to our innovative price prediction and free automatic alerts, we can save our customers up to 70% off cruises from Boston! Plus, explore our database of expert tips and advice to make the most out of your dream cruise vacation. Pack your bags and get ready - your perfect cruise from Boston is now closer and more affordable than ever!