Windstar Cruises

Windstar Cruises runs 58 repositioning sailings in our directory, on 5 ships.

58 cruisesfrom $5705 ships

Regions:Asia Atlantic - North America Caribbean Central America Hawaii / Mid-Pacific Mediterranean Northern Europe Pacific - North America Western Europe

58 Windstar Cruises repositioning cruises

VancouverCanadaTokyoJapan

Star Seeker · Windstar Cruises

TranspacificGrand Voyage

Sat, Aug 22, 202624 nightsOcean crossing

August

Sat, Aug 22, 2026

24 nights

Ocean crossing

$15,800

from · Inside · est.

$658/night

ReykjavikIcelandBostonUSA

Star Pride · Windstar Cruises

TransatlanticGrand Voyage

Mon, Aug 24, 202621 nightsOcean crossing

August

Mon, Aug 24, 2026

21 nights

Ocean crossing

$11,550

from · Inside · est.

$550/night

ReykjavikIcelandMontrealCanada

Star Pride · Windstar Cruises

TransatlanticGrand Voyage

Mon, Aug 31, 202625 nightsOcean crossing

August

Mon, Aug 31, 2026

25 nights

Ocean crossing

$12,240

from · Inside · est.

$490/night

ReykjavikIcelandBostonUSA

Star Pride · Windstar Cruises

Transatlantic

Mon, Aug 31, 202614 nightsOcean crossing

August

Mon, Aug 31, 2026

14 nights

Ocean crossing

$6,240

from · Inside · est.

$446/night

SewardUSA (Alaska)Kobe-OsakaJapan

Star Seeker · Windstar Cruises

TranspacificGrand Voyage

Wed, Sep 2, 202624 nightsOcean crossing

September

Wed, Sep 2, 2026

24 nights

Ocean crossing

$14,490

from · Inside · est.

$604/night

SewardUSA (Alaska)TokyoJapan

Star Seeker · Windstar Cruises

Transpacific

Wed, Sep 2, 202613 nightsOcean crossing

September

Wed, Sep 2, 2026

13 nights

Ocean crossing

$4,230

from · Inside · est.

$325/night

BarcelonaSpainBridgetownBarbados

Wind Star · Windstar Cruises

TransatlanticGrand Voyage

Sat, Oct 31, 202624 nightsOcean crossing

October

Sat, Oct 31, 2026

24 nights

Ocean crossing

$7,790

from · Inside · est.

$325/night

BarcelonaSpainBridgetownBarbados

Star Legend · Windstar Cruises

TransatlanticGrand Voyage

Wed, Nov 4, 202623 nightsOcean crossing

November

Wed, Nov 4, 2026

23 nights

Ocean crossing

$6,650

from · Inside · est.

$289/night

LisbonPortugalColonPanama

Wind Star · Windstar Cruises

TransatlanticGrand Voyage

Tue, Nov 10, 202625 nightsOcean crossing

November

Tue, Nov 10, 2026

25 nights

Ocean crossing

$2,030

from · Inside · est.

$81/night

LisbonPortugalBridgetownBarbados

Wind Star · Windstar Cruises

Transatlantic

Tue, Nov 10, 202614 nightsOcean crossing

November

Tue, Nov 10, 2026

14 nights

Ocean crossing

$4,230

from · Inside · est.

$302/night

MalagaSpainBridgetownBarbados

Star Legend · Windstar Cruises

Transatlantic

Thu, Nov 12, 202615 nightsOcean crossing

November

Thu, Nov 12, 2026

15 nights

Ocean crossing

$3,300

from · Inside · est.

$220/night

BridgetownBarbadosPuntarenasCosta Rica

Wind Star · Windstar Cruises

Panama Canal

Tue, Nov 24, 202618 nightsOcean crossing

November

Tue, Nov 24, 2026

18 nights

Ocean crossing

$1,460

from · Inside · est.

$81/night

BridgetownBarbadosPanama CityPanama

Star Legend · Windstar Cruises

Panama Canal

Fri, Dec 4, 202616 nightsOcean crossing

December

Fri, Dec 4, 2026

16 nights

Ocean crossing

$5,610

from · Inside · est.

$351/night

ColonPanamaPuntarenasCosta Rica

Wind Star · Windstar Cruises

Panama Canal

Sat, Dec 5, 20267 nightsOcean crossing

December

Sat, Dec 5, 2026

7 nights

Ocean crossing

$570

from · Inside · est.

$81/night

PuntarenasCosta RicaColonPanama

Wind Star · Windstar Cruises

Panama Canal

Sat, Dec 12, 20267 nightsOcean crossing

December

Sat, Dec 12, 2026

7 nights

Ocean crossing

$3,770

from · Inside · est.

$539/night

Oranjestad ArubaArubaPanama CityPanama

Star Legend · Windstar Cruises

Panama Canal

Sat, Dec 12, 20268 nightsOcean crossing

December

Sat, Dec 12, 2026

8 nights

Ocean crossing

$3,260

from · Inside · est.

$408/night

ColonPanamaPuntarenasCosta Rica

Wind Star · Windstar Cruises

Panama Canal

Sat, Dec 19, 20267 nightsOcean crossing

December

Sat, Dec 19, 2026

7 nights

Ocean crossing

$3,570

from · Inside · est.

$510/night

PuntarenasCosta RicaColonPanama

Wind Star · Windstar Cruises

Panama Canal

Sat, Dec 26, 20267 nightsOcean crossing

December

Sat, Dec 26, 2026

7 nights

Ocean crossing

$4,770

from · Inside · est.

$681/night

PuntarenasCosta RicaColonPanama

Star Legend · Windstar Cruises

Panama Canal

Mon, Dec 28, 20268 nightsOcean crossing

December

Mon, Dec 28, 2026

8 nights

Ocean crossing

$3,960

from · Inside · est.

$495/night

ColonPanamaPuntarenasCosta Rica

Wind Star · Windstar Cruises

Panama Canal

Sat, Jan 2, 20277 nightsOcean crossing

January

Sat, Jan 2, 2027

7 nights

Ocean crossing

$4,270

from · Inside · est.

$610/night

ColonPanamaPuntarenasCosta Rica

Star Legend · Windstar Cruises

Panama Canal

Tue, Jan 5, 20277 nightsOcean crossing

January

Tue, Jan 5, 2027

7 nights

Ocean crossing

$3,360

from · Inside · est.

$480/night

PuntarenasCosta RicaColonPanama

Wind Star · Windstar Cruises

Panama Canal

Sat, Jan 9, 20277 nightsOcean crossing

January

Sat, Jan 9, 2027

7 nights

Ocean crossing

$570

from · Inside · est.

$81/night

PuntarenasCosta RicaColonPanama

Star Legend · Windstar Cruises

Panama Canal

Tue, Jan 12, 20277 nightsOcean crossing

January

Tue, Jan 12, 2027

7 nights

Ocean crossing

$3,360

from · Inside · est.

$480/night

ColonPanamaPuntarenasCosta Rica

Wind Star · Windstar Cruises

Panama Canal

Sun, Jan 17, 20277 nightsOcean crossing

January

Sun, Jan 17, 2027

7 nights

Ocean crossing

$570

from · Inside · est.

$81/night

ColonPanamaPuntarenasCosta Rica

Star Legend · Windstar Cruises

Panama Canal

Tue, Jan 19, 20277 nightsOcean crossing

January

Tue, Jan 19, 2027

7 nights

Ocean crossing

$4,060

from · Inside · est.

$580/night

PuntarenasCosta RicaColonPanama

Wind Star · Windstar Cruises

Panama Canal

Sun, Jan 24, 20277 nightsOcean crossing

January

Sun, Jan 24, 2027

7 nights

Ocean crossing

$4,370

from · Inside · est.

$624/night

PuntarenasCosta RicaColonPanama

Star Legend · Windstar Cruises

Panama Canal

Tue, Jan 26, 20277 nightsOcean crossing

January

Tue, Jan 26, 2027

7 nights

Ocean crossing

$4,060

from · Inside · est.

$580/night

ColonPanamaPapeeteFrench Polynesia

Wind Star · Windstar Cruises

Panama CanalGrand Voyage

Sun, Jan 31, 202729 nightsOcean crossing

January

Sun, Jan 31, 2027

29 nights

Ocean crossing

$8,910

from · Inside · est.

$307/night

ColonPanamaPuntarenasCosta Rica

Wind Star · Windstar Cruises

Panama Canal

Sun, Jan 31, 20278 nightsOcean crossing

January

Sun, Jan 31, 2027

8 nights

Ocean crossing

$4,770

from · Inside · est.

$596/night

ColonPanamaPuntarenasCosta Rica

Star Legend · Windstar Cruises

Panama Canal

Tue, Feb 2, 20277 nightsOcean crossing

February

Tue, Feb 2, 2027

7 nights

Ocean crossing

$3,960

from · Inside · est.

$566/night

Panama CityPanamaOranjestad ArubaAruba

Star Legend · Windstar Cruises

Panama Canal

Tue, Feb 16, 20276 nightsOcean crossing

February

Tue, Feb 16, 2027

6 nights

Ocean crossing

$3,660

from · Inside · est.

$610/night

Panama CityPanamaBridgetownBarbados

Star Legend · Windstar Cruises

Panama Canal

Tue, Feb 16, 202714 nightsOcean crossing

February

Tue, Feb 16, 2027

14 nights

Ocean crossing

$6,790

from · Inside · est.

$485/night

BridgetownBarbadosBarcelonaSpain

Star Legend · Windstar Cruises

TransatlanticGrand Voyage

Tue, Mar 2, 202723 nightsOcean crossing

March

Tue, Mar 2, 2027

23 nights

Ocean crossing

$6,350

from · Inside · est.

$276/night

BridgetownBarbadosLisbonPortugal

Star Legend · Windstar Cruises

Transatlantic

Tue, Mar 2, 202715 nightsOcean crossing

March

Tue, Mar 2, 2027

15 nights

Ocean crossing

$3,770

from · Inside · est.

$251/night

San JuanPuerto RicoLondonEngland

Star Pride · Windstar Cruises

Transatlantic

Tue, Mar 30, 202716 nightsOcean crossing

March

Tue, Mar 30, 2027

16 nights

Ocean crossing

$3,640

from · Inside · est.

$228/night

Kobe-OsakaJapanSewardUSA (Alaska)

Star Seeker · Windstar Cruises

TranspacificGrand Voyage

Mon, May 10, 202721 nightsOcean crossing

May

Mon, May 10, 2027

21 nights

Ocean crossing

$9,930

from · Inside · est.

$473/night

TokyoJapanVancouverCanada

Star Seeker · Windstar Cruises

TranspacificGrand Voyage

Thu, May 20, 202723 nightsOcean crossing

May

Thu, May 20, 2027

23 nights

Ocean crossing

$8,580

from · Inside · est.

$373/night

TokyoJapanSewardUSA (Alaska)

Star Seeker · Windstar Cruises

Transpacific

Thu, May 20, 202711 nightsOcean crossing

May

Thu, May 20, 2027

11 nights

Ocean crossing

$2,620

from · Inside · est.

$238/night

VancouverCanadaSapporo-OtaruJapan

Star Seeker · Windstar Cruises

TranspacificGrand Voyage

Sat, Aug 21, 202723 nightsOcean crossing

August

Sat, Aug 21, 2027

23 nights

Ocean crossing

$9,380

from · Inside · est.

$408/night

ReykjavikIcelandBostonUSA

Star Pride · Windstar Cruises

TransatlanticGrand Voyage

Thu, Aug 26, 202721 nightsOcean crossing

August

Thu, Aug 26, 2027

21 nights

Ocean crossing

$8,590

from · Inside · est.

$409/night

SewardUSA (Alaska)Kobe-OsakaJapan

Star Seeker · Windstar Cruises

TranspacificGrand Voyage

Wed, Sep 1, 202724 nightsOcean crossing

September

Wed, Sep 1, 2027

24 nights

Ocean crossing

$9,850

from · Inside · est.

$410/night

SewardUSA (Alaska)Sapporo-OtaruJapan

Star Seeker · Windstar Cruises

Transpacific

Wed, Sep 1, 202712 nightsOcean crossing

September

Wed, Sep 1, 2027

12 nights

Ocean crossing

$2,420

from · Inside · est.

$202/night

ReykjavikIcelandMontrealCanada

Star Pride · Windstar Cruises

TransatlanticGrand Voyage

Thu, Sep 2, 202725 nightsOcean crossing

September

Thu, Sep 2, 2027

25 nights

Ocean crossing

$9,740

from · Inside · est.

$390/night

ReykjavikIcelandBostonUSA

Star Pride · Windstar Cruises

Transatlantic

Thu, Sep 2, 202714 nightsOcean crossing

September

Thu, Sep 2, 2027

14 nights

Ocean crossing

$6,340

from · Inside · est.

$453/night

LisbonPortugalPhilipsburg St MaartenSint Maarten

Wind Surf · Windstar Cruises

TransatlanticGrand Voyage

Fri, Nov 5, 202723 nightsOcean crossing

November

Fri, Nov 5, 2027

23 nights

Ocean crossing

$4,690

from · Inside · est.

$204/night

San JuanPuerto RicoPuntarenasCosta Rica

Star Pride · Windstar Cruises

Panama CanalGrand Voyage

Mon, Nov 22, 202721 nightsOcean crossing

November

Mon, Nov 22, 2027

21 nights

Ocean crossing

$7,320

from · Inside · est.

$349/night

San JuanPuerto RicoPuntarenasCosta Rica

Star Pride · Windstar Cruises

Panama Canal

Mon, Nov 29, 202714 nightsOcean crossing

November

Mon, Nov 29, 2027

14 nights

Ocean crossing

$4,990

from · Inside · est.

$356/night

ColonPanamaPuntarenasCosta Rica

Star Pride · Windstar Cruises

Panama Canal

Mon, Dec 6, 20277 nightsOcean crossing

December

Mon, Dec 6, 2027

7 nights

Ocean crossing

$3,360

from · Inside · est.

$480/night

LisbonPortugalSan JuanPuerto Rico

Star Legend · Windstar Cruises

Transatlantic

Mon, Dec 6, 202714 nightsOcean crossing

December

Mon, Dec 6, 2027

14 nights

Ocean crossing

$2,640

from · Inside · est.

$189/night

PuntarenasCosta RicaColonPanama

Star Pride · Windstar Cruises

Panama Canal

Mon, Dec 13, 20277 nightsOcean crossing

December

Mon, Dec 13, 2027

7 nights

Ocean crossing

$3,360

from · Inside · est.

$480/night

ColonPanamaPuntarenasCosta Rica

Star Pride · Windstar Cruises

Panama Canal

Mon, Dec 20, 20277 nightsOcean crossing

December

Mon, Dec 20, 2027

7 nights

Ocean crossing

$3,050

from · Inside · est.

$436/night

PuntarenasCosta RicaColonPanama

Star Pride · Windstar Cruises

Panama Canal

Mon, Dec 27, 20277 nightsOcean crossing

December

Mon, Dec 27, 2027

7 nights

Ocean crossing

$3,760

from · Inside · est.

$537/night

ColonPanamaPuntarenasCosta Rica

Star Pride · Windstar Cruises

Panama Canal

Mon, Jan 3, 20287 nightsOcean crossing

January

Mon, Jan 3, 2028

7 nights

Ocean crossing

$3,560

from · Inside · est.

$509/night

PuntarenasCosta RicaColonPanama

Star Pride · Windstar Cruises

Panama Canal

Mon, Jan 10, 20287 nightsOcean crossing

January

Mon, Jan 10, 2028

7 nights

Ocean crossing

$3,560

from · Inside · est.

$509/night

ColonPanamaPuntarenasCosta Rica

Star Pride · Windstar Cruises

Panama Canal

Mon, Jan 17, 20287 nightsOcean crossing

January

Mon, Jan 17, 2028

7 nights

Ocean crossing

$3,560

from · Inside · est.

$509/night

PuntarenasCosta RicaColonPanama

Star Pride · Windstar Cruises

Panama Canal

Mon, Jan 24, 20287 nightsOcean crossing

January

Mon, Jan 24, 2028

7 nights

Ocean crossing

$3,560

from · Inside · est.

$509/night

ColonPanamaPuntarenasCosta Rica

Star Pride · Windstar Cruises

Panama Canal

Mon, Jan 31, 20287 nightsOcean crossing

January

Mon, Jan 31, 2028

7 nights

Ocean crossing

$3,560

from · Inside · est.

$509/night

PuntarenasCosta RicaColonPanama

Star Pride · Windstar Cruises

Panama Canal

Mon, Feb 7, 20287 nightsOcean crossing

February

Mon, Feb 7, 2028

7 nights

Ocean crossing

$3,560

from · Inside · est.

$509/night

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