SeaDream's Caribbean Voyages

SeaDream Yacht Club / Specials / SeaDream's Caribbean Voyages
Cruise Line SeaDream Yacht Club
Prices From $4,419
Expires 4/30/25

Experience the Caribbean like never before on a small-ship luxury cruise with SeaDream Yacht Club!

On a voyage with SeaDream, you'll experience a casual yachting atmosphere while still being pampered with luxurious amenities by an award-winning crew. Plan your tropical getaway with SeaDream and get extra perks from us like bonus savings or shipboard credit.

Search the sailings below or connect with our experts at 1 (877) 734-6858 to start planning your Caribbean vacation with SeaDream.

Connect With A CruiseInsider Expert About This Special Offer!

Submit the form below or call us at 1 (877) 734-6858

Includes free extras and bonus savings available only from CruiseInsider.

8-night British & French Islands Explorer Cruise

St. Maarten (Philipsburg) to San Juan

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream II
Departs
3/8/25
From
$6,179
7-night Windward & British Virgin Islands Cruise

Bridgetown (Barbados) to St. Maarten (Philipsburg)

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream I
Departs
3/8/25
From
$4,419
7-night Windward Islands Explorer Cruise

St. Maarten (Philipsburg) to Bridgetown (Barbados)

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream I
Departs
3/15/25
From
$5,419
7-night French West Indies & The Grenadines Cruise

Roundtrip Bridgetown (Barbados)

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream I
Departs
3/22/25
From
$4,819
6-night Leeward Islands Adventure Cruise

Roundtrip San Juan

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream II
Departs
3/23/25
From
$5,859
7-night West Indies Explorer Cruise

Bridgetown (Barbados) to St. Maarten (Philipsburg)

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream I
Departs
3/29/25
From
$5,419
7-night Turks & Caicos Cruise

San Juan to Palm Beach

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream II
Departs
3/29/25
From
$6,419
13-Night Transatlantic Spring Voyage I Cruise

St. Maarten (Philipsburg) to Malaga

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream I
Departs
4/19/25
From
$4,719
13-night Transatlantic Autumn Voyage I Cruise

Malaga to San Juan

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream I
Departs
11/2/25
From
$4,719
7-night Windward Islands Discovery Cruise

Marigot, St. Martin to Bridgetown (Barbados)

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream II
Departs
11/16/25
From
$4,419
7-night The Glorious Grenadines Cruise

Roundtrip Bridgetown (Barbados)

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream II
Departs
11/23/25
From
$4,819
7-night Leeward Islands Discovery Cruise

Roundtrip St. Thomas (Charlotte Amalie)

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream I
Departs
11/29/25
 
Call For Pricing
7-night Windward & British Virgin Islands Cruise

Bridgetown (Barbados) to San Juan

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream II
Departs
11/30/25
From
$4,419
7-night Grand Island Adventure Cruise

St. Thomas (Charlotte Amalie) to San Juan

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream I
Departs
12/6/25
 
Call For Pricing
7-night Leeward Islands Adventure Cruise

Roundtrip San Juan

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream II
Departs
12/7/25
From
$4,919
7-night Spanish & British Caribbean Delight Cruise

San Juan to St. Maarten (Philipsburg)

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream I
Departs
12/13/25
From
$4,419
7-night Caribbean Islands Adventure Cruise

San Juan to St. Thomas (Charlotte Amalie)

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream II
Departs
12/14/25
From
$4,419
7-night Leeward Islands Celebration Cruise

St. Maarten (Philipsburg) to San Juan

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream I
Departs
12/20/25
From
$5,419
7-night Leeward Islands Celebration Cruise

St. Thomas (Charlotte Amalie) to San Juan

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream II
Departs
12/21/25
From
$5,419
7-Night Tropical New Year's Cruise

San Juan to St. Thomas (Charlotte Amalie)

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream I
Departs
12/27/25
 
Call For Pricing
7-night Tropical New Year's II Cruise

San Juan to St. Thomas (Charlotte Amalie)

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream II
Departs
12/28/25
From
$10,419
7-night Caribbean Island Adventure Cruise

San Juan to St. Thomas (Charlotte Amalie)

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream I
Departs
1/31/26
From
$4,919
7-night British Islands Discovery Cruise

St. Thomas (Charlotte Amalie) to San Juan

Cruise Line
SeaDream Yacht Club
Cruise Ship
SeaDream I
Departs
2/7/26
From
$5,319

Terms and Conditions

Fares/rates are per person, based on double occupancy for select sail and travel dates; are capacity controlled and subject to availability at time booking and may be pulled without notice. We reserve the right to correct errors. Information and pricing is subject to change without notice. While we do our very best to ensure that information and pricing appearing in this website is complete and accurate, we cannot be responsible for incomplete and inaccurate representations, which may or may not be under our control. In the event of a pricing error, misrepresentation or omission, we reserve the right to adjust the pricing or make any other corrections.