Itinerary for December 21, 2025 Departure Day Date Location Port of Call Guide 1Sunday, 12/21/2025Depart from Philipsburg, St. MaartenPhilipsburg, St Maarten, St Martin/St Maarten2Monday, 12/22/2025Charlestown 3Tuesday, 12/23/2025RoseauRoseau, Dominica4Wednesday, 12/24/2025Mayreau 5Thursday, 12/25/2025Les Saintes 6Friday, 12/26/2025BasseterreSt Kitts & Nevis7Saturday, 12/27/2025GustaviaGustavia, St Barthelemy8Sunday, 12/28/2025Philipsburg, St. MaartenPhilipsburg, St Maarten, St Martin/St Maarten9Monday, 12/29/2025Falmouth Harbour 10Tuesday, 12/30/2025Road Bay 11Wednesday, 12/31/2025Jost Van Dyke, Great Harbour 11Wednesday, 12/31/2025Soper's Hole 12Thursday, 01/01/2026Jost Van Dyke, Great Harbour 13Friday, 01/02/2026Virgin Gorda / Prickly Pear, British Virgin Islands 14Saturday, 01/03/2026GustaviaGustavia, St Barthelemy15Sunday, 01/04/2026Arrive at Philipsburg, St. MaartenPhilipsburg, St Maarten, St Martin/St Maarten Check Cruise Availability Total guests should not exceed 5 passengers. Adults: (ages 12-54) 0 1 2 3 4 5 Seniors: (ages 55 or older) 0 1 2 3 4 5 Kids: (ages 2-11) 0 1 2 3 4 5 Infants: (under 2) 0 1 2 3 4 5 Kid 1 Age: (at time of cruise) 0 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 Kid 2 Age: (at time of cruise) 0 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 Kid 3 Age: (at time of cruise) 0 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 Kid 4 Age: (at time of cruise) 0 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 Kid 5 Age: (at time of cruise) 0 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 US Resident? Need Airfare? Search Availability State/Province of Residence: Alabama Alaska Arizona Arkansas California Colorado Connecticut Delaware District of Columbia Florida Georgia Hawaii Idaho Illinois Indiana Iowa Kansas Kentucky Louisiana Maine Maryland Massachusetts Michigan Minnesota Mississippi Missouri Montana Nebraska Nevada New Hampshire New Jersey New Mexico New York North Carolina North Dakota Ohio Oklahoma Oregon Pennsylvania Puerto Rico Rhode Island South Carolina South Dakota Tennessee Texas Utah Vermont Virgin Islands Virginia Washington West Virginia Wisconsin Wyoming Alberta British Columbia Manitoba New Brunswick Newfoundland Northwest Territory Nova Scotia Ontario Prince Edward Island Quebec Saskatchewan St. Pierre and Miquelon Yukon Territory Departure City/Airport Code: Akron, OH (CAK) Albany, GA (ABY) Albany, NY (ALB) Albuquerque, NM (ABQ) Allentown, PA (ABE) Altoona, PA (AOO) Amarillo, TX (AMA) Anchorage, AK (ANC) Anderson, SC (AND) Appleton, WI (ATW) Asheville, NC (AVL) Atlanta, GA (ATL) Atlantic City, NJ (ACY) Augusta, GA (AGS) Austin, TX (AUS) Bakersfield, CA (BFL) Baltimore, MD (BWI) Bangor, ME (BGR) Baton Rouge, LA (BTR) Beaumont / Port Arthur, TX (BPT) Beckley, WV (BKW) Bellingham, WA (BLI) Billings, MT (BIL) Binghamton, NY (BGM) Birmingham, AL (BHM) Bismarck, ND (BIS) Bloomington, IL (BMI) Bluefield, WV (BLF) Boise, ID (BOI) Boston, MA (BOS) Bozeman, MT (BZN) Bradford-Warren, NY (BFD) Brainerd, MN (BRD) Buffalo, NY (BUF) Burbank, CA (BUR) Burlington, VT (BTV) Butte, MT (BTM) Cedar Rapids, IA (CID) Central Wisconsin Aprt, WI (CWA) Champaign / Urbana, IL (CMI) Charleston, SC (CHS) Charleston, WV (CRW) Charlotte, NC (CLT) Charlottesville, VA (CHO) Chattanooga, TN (CHA) Cheyenne, WY (CYS) Chicago - Midway, IL (MDW) Chicago - Ohare, IL (ORD) Cincinnati, OH (CVG) Cleveland, OH (CLE) Colorado Springs, CO (COS) Columbia, MO (COU) Columbia, SC (CAE) Columbus, GA (CSG) Columbus, OH (CMH) Corpus Christi, TX (CRP) Dallas - Ft. Worth, TX (DFW) Danville, VA (DAN) Dayton, OH (DAY) Daytona Beach, FL (DAB) Denver, CO (DEN) Des Moines, IA (DSM) Detroit, MI (DTW) Dubois, PA (DUJ) Duluth, MN (DLH) El Paso, TX (ELP) Elmira, NY (ELM) Erie, PA (ERI) Escanaba, MI (ESC) Eugene, OR (EUG) Evansville, IN (EVV) Fairbanks, AK (FAI) Fargo, ND (FAR) Fayetteville, NC (FAY) Flagstaff, AZ (FLG) Flint, MI (FNT) Florence, SC (FLO) Fort Myers, FL (RSW) Fort Smith, AR (FSM) Fort Walton Beach, FL (VPS) Fresno, CA (FAT) Ft. Lauderdale, FL (FLL) Ft. Wayne, IN (FWA) Gainesville, FL (GNV) Grand Forks, ND (GFK) Grand Junction, CO (GJT) Grand Rapids, MI (GRR) Great Falls, MT (GTF) Green Bay, WI (GRB) Greensboro, NC (GSO) Greenville, NC (PGV) Greenville, SC (GSP) Hagerstown, MD (HGR) Haines, AK (HNS) Harlingen, TX (HRL) Harrisburg, PA (MDT) Hartford, CT (BDL) Helena, MT (HLN) Hickory, NC (HKY) Hilo, HI (ITO) Honolulu, HI (HNL) Houston - Hobby, TX (HOU) Houston - Intercontinental, TX (IAH) Huntington, WV (HTS) Huntsville, AL (HSV) Indianapolis, IN (IND) Islip, NY (ISP) Ithaca, NY (ITH) Jackson, MS (JAN) Jacksonville, FL (JAX) Jacksonville, NC (OAJ) Johnstown, PA (JST) Joplin, MO (JLN) Juneau, AK (JNU) Kalamazoo, MI (AZO) Kalispell, MT (FCA) Kansas City, MO (MCI) Ketchikan, AK (KTN) Key West, FL (EYW) Kinston, NC (ISO) Knoxville, TN (TYS) Kona, HI (KOA) La Cross, WI (LSE) Lafayette, LA (LFT) Lancaster, PA (LNS) Lansing, MI (LAN) Las Vegas, NV (LAS) Lexington, KY (LEX) Lihue, HI (LIH) Lincoln, NE (LNK) Little Rock, AR (LIT) Long Beach, CA (LGB) Los Angeles, CA (LAX) Louisville, KY (SDF) Lubbock, TX (LBB) Lynchburg, VA (LYH) Macon, GA (MCN) Madison, WI (MSN) Manchester, NH (MHT) Mason City, IA (MCW) Maui, HI (OGG) Maui - Lahaina, HI (HKP) Mcallen, TX (MFE) Medford, OR (MFR) Melbourne, FL (MLB) Memphis, TN (MEM) Miami, FL (MIA) Midland/Odessa, TX (MAF) Milwaukee, WI (MKE) Minneapolis, MN (MSP) Minot, ND (MOT) Missoula, MT (MSO) Mobile, AL (MOB) Moline, IL (MLI) Molokai, HI (MKK) Monroe, LA (MLU) Monterey, CA (MRY) Montgomery, AL (MGM) Morgantown, WV (MGW) Myrtle Beach, SC (MYR) Naples, FL (APF) Nashville, TN (BNA) New Bern, NC (EWN) New Haven, CT (HVN) New Orleans, LA (MSY) New York - JFK, NY (JFK) New York - Laguardia, NY (LGA) Newark, NJ (EWR) Newburgh, NY (SWF) Newport News, VA (PHF) Norfolk, VA (ORF) Oakland, CA (OAK) Oklahoma City, OK (OKC) Omaha, NE (OMA) Ontario, CA (ONT) Orlando, FL (MCO) Oxnard, CA (OXR) Palm Springs, CA (PSP) Panama City, FL (PFN) Pasco, WA (PSC) Pellston, MI (PLN) Pensacola, FL (PNS) Peoria, IL (PIA) Philadelphia, PA (PHL) Phoenix, AZ (PHX) Pittsburgh, PA (PIT) Plattsburg, NY (PLB) Port Canaveral, FL (PCN) Port Charlotte, FL (FMY) Portland, ME (PWM) Portland, OR (PDX) Providence, RI (PVD) Punta Gorda, FL (PGD) Quincy, IL (UIN) Raleigh/Durham, NC (RDU) Rapid City, SD (RAP) Reading, PA (RDG) Reno, NV (RNO) Richmond, VA (RIC) Roanoke, VA (ROA) Rochester, MN (RST) Rochester, NY (ROC) Rockford, IL (RFD) Rocky Mount, NC (RWI) Sacramento, CA (SMF) Saginaw, MI (MBS) Salisbury, MD (SBY) Salt Lake City, UT (SLC) San Antonio, TX (SAT) San Diego, CA (SAN) San Francisco, CA (SFO) San Jose, CA (SJC) San Juan, PR (SJU) San Luis Obispo, CA (SBP) Santa Ana, CA (SNA) Santa Barbara, CA (SBA) Sarasota / Bradenton, FL (SRQ) Savannah, GA (SAV) Seattle/Tacoma, WA (SEA) Shreveport, LA (SHV) Sioux City, IA (SUX) Sioux Falls, SD (FSD) Sitka, AK (SIT) Skagway, AK (SGY) South Bend, IN (SBN) Spokane, WA (GEG) Springfield, IL (SPI) Springfield, MO (SGF) St. Louis, MO (STL) St. Petersburg, FL (PIE) State College, PA (SCE) Syracuse, NY (SYR) Tallahassee, FL (TLH) Tampa, FL (TPA) Taylorsville, NC (TYL) Toledo, OH (TOL) Tri-Cities, TN (TRI) Tucson, AZ (TUS) Tulsa, OK (TUL) Ufville, NC (UFT) Valdosta, GA (VLD) Washington - Dulles, DC (IAD) Washington - National, DC (DCA) Waterloo, IA (ALO) West Palm Beach, FL (PBI) Westchester County, NY (HPN) Wichita, KS (ICT) Wilkes-Barre / Scranton, PA (AVP) Wilmington, NC (ILM) Worcester, MA (ORH) Calgary, AB (YYC) Castlegar, CA (YCG) Charlottetown, PE (YYG) Edmonton, AB (YEG) Fredericton, NB (YFC) Halifax, NS (YHZ) Moncton, NB (YQM) Montreal, PQ (YUL) Montreal/Mirabel, PQ (YMX) OtYTIa, ON (YOW) Quebec, QB (YQB) Regina, SK (YQR) Saskatoon, SK (YXE) St. John - New Brunswick, NB (YSJ) St. Johns, NF (YYT) Sydney, NS (YQY) Thunder Bay, ON (YQT) Toronto, ON (YYZ) Vancouver, BC (YVR) Victoria, BC (YYJ) Windsor, ON (YQG) Winnipeg, MN (YWG) Searching Cruise for Available Rooms & Rates... Other 14 Night Caribbean Cruise Itineraries on the Wind Surf Departing Interior Oceanview Balcony Suite Dec 7, 2025-$3,699-$5,399Dec 21, 2025-$4,299-$5,999 Departing from Philipsburg, St Maarten, St Martin/St MaartenDeparture Date 12/21/2025 OCG Class Luxury Departing 12/21/2025 Interior-Oceanviewfrom $4,299Balcony-Suitefrom $5,999 Check Availability