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Holland America Line · Oosterdam

11-Day Eastern Caribbean: Windward & Leeward Islands

Dec 11, 2027 – Dec 22, 202711 nightsRound trip from Fort Lauderdale

1 / 21

RelaxAway Half Moon Cay

Bahamas

Day
11
Date
Dec 21, 2027
Arrive
8:00 AM
Depart
3:00 PM

RelaxAway, Half Moon Cay is Holland America Line's award-winning private island, a Bahamian paradise reserved for our guests. Designed to inspire effortless relaxation, this idyllic retreat includes a Beach Club, serene lounging spaces, island-only menu items, and much more.

Oosterdam

Guests
1,964
Year built
2004
Deck plans

Oosterdam

Guests
1,964
Year built
2004
Deck plans

Philipsburg

Sint Maarten

Day
4
Date
Dec 14, 2027
Arrive
10:00 AM
Depart
9:00 PM

Philipsburg, the bustling capital of the Dutch side of Sint Maarten, offers visitors a fascinating mix of cultures, scenic beaches, and excellent shopping opportunities.

Basseterre

St. Kitts & Nevis

Day
5
Date
Dec 15, 2027
Arrive
7:00 AM
Depart
5:00 PM

The dual-island nation of St. Kitts and Nevis beckons travelers with a storied past, evident in the British architecture of Basseterre and sprawling colonial plantations.

Fort-De-France

Martinique

Day
6
Date
Dec 16, 2027
Arrive
8:00 AM
Depart
11:00 PM

Some three centuries after Columbus landed here, the French-speaking island of Martinique had established strong economic and cultural ties to New Orleans, thanks to its sugar and rum production. That came to an abrupt halt when Mount Pelee erupted in 1902, destroying the island's rich trading port of St. Pierre.

Roseau

Dominica

Day
7
Date
Dec 17, 2027
Arrive
8:00 AM
Depart
5:00 PM

Roseau, the capital of Dominica, is nicknamed "the nature island" for good reason. The island, flanked by Guadeloupe and Martinique, offers some of the Caribbean's most stunning landscapes.

St. Johns

Antigua & Barbuda

Day
8
Date
Dec 18, 2027
Arrive
7:00 AM
Depart
4:00 PM

St. Johns, Antigua, a treasure trove of 365 pristine beaches, offers an unmatched Caribbean adventure. With Holland America, explore the intriguing Nelson's Dockyard, relax on sun-swept shores, and take in panoramic views from Shirley Heights Lookout for a memorable escape.

San Juan

Puerto Rico

Day
9
Date
Dec 19, 2027
Arrive
8:00 AM
Depart
5:00 PM

San Juan, Puerto Rico, is a treasure trove of culture, history, and natural beauty. On a Holland America Line cruise, discover the cobblestone streets of Old San Juan, a UNESCO World Heritage Site, taste local culinary delights like fried plantains, or unwind on the sun-soaked shores of Condado Beach.

Pinnacle Suite

1,290 sq ft

Our premier 1,290 sq. ft. Pinnacle Suite features floor-to-ceiling glass doors, a large private Whirlpool verandah, living, dining, and dressing rooms, and lush sleeping accommodations with luxurious Duxiana® king beds. These elegant suites sleep up to four guests and include a deep soaking tub and an independent, full-size shower stall, dual-sink vanities, and guest toilets.

Pinnacle Suite floor plan, OosterdamFloor plan

Neptune Suite

465–502 sq ft

From $6,999 per person

Featuring floor-to-ceiling glass doors, a spacious private verandah, expansive sitting areas, and comfortable sleeping accommodations with Mariner’s Dream™ beds, our 465–502 sq. ft. suite sleeps up to four guests and boasts a deep soaking tub and an independent, full-size shower stall, dual-sink vanities, premium bathrobes, pillow menus, fresh flowers, and binoculars.

Neptune Suite floor plan, OosterdamFloor plan

Signature Suite

393–400 sq ft

From $5,499 per person

These elegant 393–400 sq. ft. suites feature a sitting area with floor-to-ceiling glass doors overlooking a private verandah. Signature Suites accommodate up to four guests with two beds that convert to a queen- or king-size bed — our signature Mariner’s Dream™ bed, and a Murphy, Pullman, or sofa bed, depending on configuration.

Verandah

228–405 sq ft

From $3,699 per person

Floor-to-ceiling glass doors lead to your private balcony, infusing these coveted 228–405 sq. ft. staterooms with natural light. Enjoy a private verandah overlooking the ocean, a spacious sitting area for unwinding, and our signature Mariner’s Dream™ bed that can convert from one queen to two beds.

Ocean View

From $3,199 per person

With a view of the ocean through a window or porthole, these expansive staterooms include a sitting area, two beds that convert to one queen-size bed — our signature Mariner's Dream™ bed with plush euro-top mattress — premium massage showerheads, and a host of amenities.

Inside

143–225 sq ft

From $2,599 per person

These comfortable 143–225 sq. ft. staterooms feature ample storage space and two beds that convert to one queen-size bed — our signature Mariner's Dream™ bed with plush euro-top mattress — premium massage showerheads and a host of amenities.

Length
11 nights
Departs
Dec 11, 2027, Fort Lauderdale
Returns
Dec 22, 2027, Fort Lauderdale
Ports of call
8
Days at sea
3
Ship
Oosterdam

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Offers on this sailing

  • Have It All Early Booking Bonus

Itinerary

  1. Day 1Dec 11

    Fort Lauderdale, Florida, United States

    Depart 9:00 PM

    Embark

  2. Day 2Dec 12

    At sea

  3. Day 3Dec 13

    At sea

  4. Day 4Dec 14

    Philipsburg, Sint Maarten

    Arrive 10:00 AMDepart 9:00 PM

    Philipsburg
  5. Day 5Dec 15

    Basseterre, St. Kitts & Nevis

    Arrive 7:00 AMDepart 5:00 PM

    Tender

    Basseterre
  6. Day 6Dec 16

    Fort-De-France, Martinique

    Arrive 8:00 AMDepart 11:00 PM

    Fort-de-France
  7. Day 7Dec 17

    Roseau, Dominica

    Arrive 8:00 AMDepart 5:00 PM

    Roseau
  8. Day 8Dec 18

    St. Johns, Antigua & Barbuda

    Arrive 7:00 AMDepart 4:00 PM

    St. Johns
  9. Day 9Dec 19

    San Juan, Puerto Rico

    Arrive 8:00 AMDepart 5:00 PM

    San Juan
  10. Day 10Dec 20

    At sea

  11. Day 11Dec 21

    RelaxAway Half Moon Cay, Bahamas

    Arrive 8:00 AMDepart 3:00 PM

    Tender

  12. Day 12Dec 22

    Fort Lauderdale, Florida, United States

    Arrive 7:00 AM

    Disembark

Oosterdam

Guests
1,964
Year built
2004
Dining and venues
  • Dining Room
  • Canaletto
  • Pinnacle Grill
  • Morimoto By Sea
  • Lido Market
  • 24-Hour Room Service
  • Dive-In
  • Crow’s Nest Café
  • Crow’s Nest Bar
  • Lido Bar
  • Pinnacle Bar
  • Ocean Bar
  • Sea View Bar
  • Explorer’s Lounge
  • Art Studio
  • Casino
  • Game Room
  • Kids Club
  • High Score!
  • Library
  • Meeting Rooms
  • Pickleball
  • Sport Court
  • The Shops
  • Effy Fine Jewelry
  • Art Gallery
  • Photo Gallery
  • Portrait Studio
  • Lido Pool
  • Sea View Pool
  • Hydropool
  • Hot Tubs
  • Spa & Salon
  • Fitness Center
  • Neptune Lounge
  • Tai Chi

Videos

  • Staterooms and suites

  • Casino

  • Entertainment

  • Spa and salon

All Oosterdam sailings

Deck plans

Open after 120227 plan (PDF)

after 120227
Oosterdam, after 120227 deck plan

Staterooms

Per person, double occupancy

  • Inside, Oosterdam

    Inside

    Inside (143–225 sq ft)

    These comfortable 143–225 sq. ft. staterooms feature ample storage space and two beds that convert to one queen-size bed — our signature Mariner's Dream™ bed with plush euro-top mattress — premium massage showerheads and a host of amenities.

    $2,599

  • Ocean View, Oosterdam

    Ocean View

    Ocean View

    With a view of the ocean through a window or porthole, these expansive staterooms include a sitting area, two beds that convert to one queen-size bed — our signature Mariner's Dream™ bed with plush euro-top mattress — premium massage showerheads, and a host of amenities.

    $3,199

  • Verandah, Oosterdam

    Verandah

    Verandah (228–405 sq ft)

    Floor-to-ceiling glass doors lead to your private balcony, infusing these coveted 228–405 sq. ft. staterooms with natural light. Enjoy a private verandah overlooking the ocean, a spacious sitting area for unwinding, and our signature Mariner’s Dream™ bed that can convert from one queen to two beds.

    $3,699

  • Signature Suite, Oosterdam

    Signature Suite

    Signature Suite (393–400 sq ft) · Signature Suites

    These elegant 393–400 sq. ft. suites feature a sitting area with floor-to-ceiling glass doors overlooking a private verandah. Signature Suites accommodate up to four guests with two beds that convert to a queen- or king-size bed — our signature Mariner’s Dream™ bed, and a Murphy, Pullman, or sofa bed, depending on configuration.

    $5,499

  • Neptune Suite, Oosterdam
    Neptune Suite floor plan, OosterdamFloor plan

    Neptune Suite

    Neptune Suite (465–502 sq ft) · Neptune Suites

    Featuring floor-to-ceiling glass doors, a spacious private verandah, expansive sitting areas, and comfortable sleeping accommodations with Mariner’s Dream™ beds, our 465–502 sq. ft. suite sleeps up to four guests and boasts a deep soaking tub and an independent, full-size shower stall, dual-sink vanities, premium bathrobes, pillow menus, fresh flowers, and binoculars.

    $6,999

Taxes and fees included.

Dates and prices

11 nights, 11-Day Eastern Caribbean: Windward & Leeward Islands

On Oosterdam

No other dates of this itinerary on Oosterdam are listed. See all Oosterdam sailings

Same itinerary on other ships

Inside$2,599
CabinRequest