Caribbean Cruise Deals from MA - Boston

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Prices are average per person based on double occupancy and include all taxes, making the total cost easier to understand.

5 Matching Cruises

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was $1,690

Up to 46% off
4.0 rating out of 5 (1,740 reviews)

7 Night Repositioning

Brilliance of the Seas
Departing from: Boston, Massachusetts
Ports of Call

Sailing Dates

Bonus Offers
Ports of Call:
Royal Naval Dockyard (Kings Wharf), West End, Bermuda
St. Johns, Antigua
Tortola, British Virgin Islands
San Juan, Puerto Rico
Sailing Dates:
November 02, 2025
interior from

$910

$130pernight

oceanview from

$1,170

$167pernight

balcony from

$1,430

$204pernight

suite from

$3,494

$499pernight
All the Cruise Line Offers & More:

Kids Sail Free!Deposits are non-refundable. Book a stateroom on select Royal Caribbean sailings and kids 12 and under cruise for free! Kids (third and fourth guests) must be traveling in the same stateroom as two paying adults. All guests traveling will be responsible for paying port taxes and government fees at full price, new bookings only, additional restrictions apply. Pricing shown reflects discounts. Hurry offer ends 11:59 pm EST on 7/31/2025!

Flash Sale: Up to $700 Instant SavingsReceive up to $700 in instant savings! Instant savings offer applies to new bookings and provides savings per stateroom, varying by stateroom category booked and sailing length as follows: 5 nights or less, savings of $100 USD for Inside and Ocean View, $175 USD for Balconies, and $325 USD for Suites; 6 nights or longer, savings of $175 USD for Interior and Ocean View, $250 USD for Balconies, and $700 USD for Suites. Hurry - offer ends 7/24/2025.

60% Off Second GuestPLEASE NOTE: Deposits for this promotion are non-refundable. Book a stateroom on sailings departing on or after July 2, 2025 and the second guest will receive 60 percent savings! Pricing shown reflects a discount of 60 percent off the second guest, based on double occupancy. The 60 percent savings will display evenly distributed between the 1st and 2nd guests' cruise pricing. Third and Fourth guests traveling in same room receive 30 percent off standard cruise fare. Port taxes and government fees are at full price; new bookings only; additional restrictions may apply. Pricing displayed online reflects discounts. Hurry, offer ends 7/31/2025!

Up to $50 Bonus Savings - Call
For a limited-time, call to book and you may be eligible for up to $50 in extra bonus savings. Select sailings of 5-nights or less may be eligible for a $25 bonus savings per stateroom, and sailings of 6-nights or longer may be eligible for a $50 bonus savings per stateroom. Savings is not reflected in pricing shown. May not be combinable with all fares. Hurry - this offer is capacity controlled and will sell out without notice. Reference promotion ID 36671 when calling.

and more!
Interior from$910
($130pernight)

4.0 rating out of 5 (1,740 reviews)

View Itinerary Book Online Speak to an Expert
4.3 rating out of 5 (1,306 reviews)

10 Night Southern Caribbean

Celebrity Silhouette
Departing from: Boston, Massachusetts
Ports of Call

Sailing Dates

Bonus Offers
Ports of Call:
Willemstad, Curacao
Kralendijk, Bonaire
Oranjestad, Aruba
Ft. Lauderdale (Port Everglades), Florida
Sailing Dates:
October 20, 2026
interior from

$989

$99pernight

oceanview from

Call for availability

balcony from

$1,485

$149pernight

suite from

$4,804

$480pernight
All the Cruise Line Offers & More:

All-Included: Drinks & Wi-Fi
Interior from$989
($99pernight)

4.3 rating out of 5 (1,306 reviews)

View Itinerary Book Online Speak to an Expert

Get exclusive bonus offers

Our bonus offers vary by selected cruise but are designed to give you the best value at sea.

4.0 rating out of 5 (767 reviews)

14 Night Eastern Caribbean

Zuiderdam
Departing from: Boston, Massachusetts
Ports of Call

Sailing Dates

Bonus Offers
Ports of Call:
San Juan, Puerto Rico
Charlotte Amalie, St. Thomas, U.S.V.I.
Philipsburg, St. Maarten
Castries, St. Lucia
Bridgetown, Barbados
Willemstad, Curacao
Half Moon Cay, Bahamas (Cruiseline Private Island)
Miami, Florida
Sailing Dates:
October 18, 2025
interior from

$1,249

$89pernight

oceanview from

$1,299

$93pernight

balcony from

$1,499

$107pernight

suite from

$2,599

$186pernight
All the Cruise Line Offers & More:

Exclusive: Up to $150 to Spend on Board - CallCall to book a stateroom on a qualifying 2025-2027 Holland America sailing and receive a bonus of up to $150 FREE onboard spending! Amount of onboard spending is per stateroom, length of sailing, and category purchased. This offer is for new reservations only. This offer is not combinable with all sailings or fares displaying online. Call for more information. Hurry, offer ends 07/24/2025. Reference promotion ID 36906 when calling.

Exclusive: Up to $300 to Spend on Board - CallFor a limited time, call to book select 2025 or 2026 Holland America sailings and receive up to $300 to spend on board. Use it any way you choose; towards specialty dining, at the spa, in the shops, and more. On board spending is based on stateroom category booked. Interior rooms receive $25 per person (max $50 per stateroom); Oceanview rooms receive $50 per person (max $100 per stateroom), Balcony rooms receive $75 per person (max $150 per stateroom), and Suites receive $150 per person (max $300 per suite). New bookings only, may not be combinable with all fares. Hurry - this offer ends at 11:59 PM PST on 07/31/2025. Reference promotion ID 36862 when calling.

Free Drinks, Dining, and Excursions with Select FaresBook your Holland America cruise vacation under select fares and you can "Have It All!" Included in this fare, Guests 1 & 2 will enjoy a Signature Beverage Package, included Shore Excursions (the longer you sail, the more you get!), a Specialty Dining Experience, and Wi-Fi throughout your journey. Restrictions apply - not all pricing displaying online qualifies. Have It All may be added for 3rd & 4th guests but you must call to do so. New bookings only, subject to availability.

Travel By Sea Sale: Up to 40% Off, Gratuities Included & More

and more!
Interior from$1,249
($89pernight)

4.0 rating out of 5 (767 reviews)

View Itinerary Book Online Speak to an Expert
was $5,287

Up to 68% off
4.3 rating out of 5 (1,306 reviews)

10 Night Repositioning Caribbean

Celebrity Silhouette
Departing from: Boston, Massachusetts
Ports of Call

Sailing Dates

Bonus Offers
Ports of Call:
Willemstad, Curacao
Kralendijk, Bonaire
Oranjestad, Aruba
Ft. Lauderdale (Port Everglades), Florida
Sailing Dates:
October 10, 2025
interior from

Call for availability

oceanview from

Call for availability

balcony from

$1,674

$167pernight

suite from

$5,627

$563pernight
All the Cruise Line Offers & More:

Exclusive: $125 Specialty Dining CreditBook a balcony or higher stateroom on select 5 + night Celebrity Cruises sailings and we will give you a FREE $125 Specialty Dining Credit! Offer is only available on select Celebrity sailings, new bookings only created July 1, 2025 - July 30, 2025 and is per stateroom. May not be combinable with all fares or promotions displaying online. Other restrictions may apply. Call for additional details! Hurry offer ends 11:59 PM EST on 07/31/2025!

All-Included: Drinks & Wi-Fi
Balcony from$1,674
($167pernight)

4.3 rating out of 5 (1,306 reviews)

View Itinerary Book Online Speak to an Expert
4.0 rating out of 5 (767 reviews)

21 Night Eastern/Western Caribbean

Zuiderdam
Departing from: Boston, Massachusetts
Ports of Call

Sailing Dates

Bonus Offers
Ports of Call:
San Juan, Puerto Rico
Charlotte Amalie, St. Thomas, U.S.V.I.
Philipsburg, St. Maarten
Castries, St. Lucia
Bridgetown, Barbados
Willemstad, Curacao
Half Moon Cay, Bahamas (Cruiseline Private Island)
Miami, Florida
Grand Turk Island, Turks & Caicos
Sailing Dates:
October 18, 2025
interior from

$2,230

$106pernight

oceanview from

$2,280

$109pernight

balcony from

$2,480

$118pernight

suite from

$3,990

$190pernight
All the Cruise Line Offers & More:

Exclusive: Up to $150 to Spend on Board - CallCall to book a stateroom on a qualifying 2025-2027 Holland America sailing and receive a bonus of up to $150 FREE onboard spending! Amount of onboard spending is per stateroom, length of sailing, and category purchased. This offer is for new reservations only. This offer is not combinable with all sailings or fares displaying online. Call for more information. Hurry, offer ends 07/24/2025. Reference promotion ID 36906 when calling.

Exclusive: Up to $300 to Spend on Board - CallFor a limited time, call to book select 2025 or 2026 Holland America sailings and receive up to $300 to spend on board. Use it any way you choose; towards specialty dining, at the spa, in the shops, and more. On board spending is based on stateroom category booked. Interior rooms receive $25 per person (max $50 per stateroom); Oceanview rooms receive $50 per person (max $100 per stateroom), Balcony rooms receive $75 per person (max $150 per stateroom), and Suites receive $150 per person (max $300 per suite). New bookings only, may not be combinable with all fares. Hurry - this offer ends at 11:59 PM PST on 07/31/2025. Reference promotion ID 36862 when calling.

Free Drinks, Dining, and Excursions with Select FaresBook your Holland America cruise vacation under select fares and you can "Have It All!" Included in this fare, Guests 1 & 2 will enjoy a Signature Beverage Package, included Shore Excursions (the longer you sail, the more you get!), a Specialty Dining Experience, and Wi-Fi throughout your journey. Restrictions apply - not all pricing displaying online qualifies. Have It All may be added for 3rd & 4th guests but you must call to do so. New bookings only, subject to availability.

Travel By Sea Sale: Up to 40% Off, Gratuities Included & More

Exclusive: Free Canaletto Dinner for 2 - Call
Call to book select staterooms on a qualifying 2025 Holland America sailing and we'll give you a free dinner for 2 at the Canaletto where you can indulge in authentic Italian classics. New bookings only, may not qualify with all fares and promotions shown. Oher restrictions apply, call for more details and to book today. Hurry - offer ends 11:59 PM EST on 11/15/2025. Reference promo ID 36337 when calling.

and more!
Interior from$2,230
($106pernight)

4.0 rating out of 5 (767 reviews)

View Itinerary Book Online Speak to an Expert

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We're sorry.

7 Night Repositioning

Brilliance of the Seas

10 Night Southern Caribbean

Celebrity Silhouette

14 Night Eastern Caribbean

Zuiderdam

10 Night Repositioning Caribbean

Celebrity Silhouette

21 Night Eastern/Western Caribbean

Zuiderdam

Cruise Search Results

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Your Selections:

Destination (Any) selected

Departure date filter (Any) selected

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We're sorry.

7 Night Repositioning

Brilliance of the Seas

10 Night Southern Caribbean

Celebrity Silhouette

14 Night Eastern Caribbean

Zuiderdam

10 Night Repositioning Caribbean

Celebrity Silhouette

21 Night Eastern/Western Caribbean

Zuiderdam

Filters Any

Destination Any selected

Departure date filter Anyselected

Departure port Any selected

Cruise length Any selected

Cruise line Any selected

Cruise ship Any selected