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Island Windjammer Cruises

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Island Windjammer Cruises

PLANNING and SAILING made easy!

Whether you’re in the planning stages or already booked your adventure, we want to make things as easy as possible. You have questions, we have answers:

Take a look at the PLANNING GUIDE for: Airport codes, Arrival and Departure info and how to book your cruise.

Your SAILING GUIDE answers questions about: What to pack, WIFI, local currency, and tipping.

If you have questions not covered here, give us a call at 877.772.4549. We’re always standing by to assist!

See you on deck!

  • Planning Guide
  • Sailing Guide
  • Boarding Instructions

Pre-Cruise Planning Guide

We want to make it easy for you to plan your sailing adventure. You have questions, we have answers. Here, you’ll find everything you need to know before you book your cruise. From airport codes, to when you need to be there and when to disembark — not that you’re going to want to! Let’s get started!

AIRPORT CODES

When should i fly in.

Plan to arrive at least one day prior to boarding.

WHAT TIME DO WE BOARD?

Grenada:   12:30 PM Dominica | Greece | St. Kitts | St. Lucia | St. Maarten | St. Vincent | Tortola:   2:00 PM Turks and Caicos (Providenciales) - 3:00 PM

Those affected by changes to boarding information will be contacted via email.

HOW DO I GET TO THE SHIP ON BOARDING DAY?

It's a breeze to make your own way to the ship on boarding day! Taxis are readily available at hotels and guest houses. Check here for recommended transfer companies in some ports.

American, Caribbean Air, United

Air Canada, American Airlines, British Airways, Caribbean Airlines, Condor, Delta, LIAT, Virgin Atlantic

Sky Express, Aegean Air, and Olympic from Athens

American Airlines, Air Canada, Air France, British Airways, Caribbean Airlines, Delta, Jet Blue, Liat, Qantas Airways, Seaborne Airline, United Airways, WestJet, Windward Island Airways International

Air Caribe, Air Martinique, American Airlines, American Eagle, Air Canada, British Airways, Condor, Delta, JetBlue, LIAT, United, US Air, Virgin Atlantic, West Jet

Tip: The international airport in St. Lucia is 1.5 - 2 hours from our ship's anchorages.

ST. MAARTEN

Air France, American Airlines, Air Canada, Air Transat, Caribbean Airlines, Condor, Delta, KLM, LIAT, Jet Blue, Sky Service, Sun Country, Spirit, United, US Air, West Jet

ST. VINCENT

American Airlines, Air Canada, Caribbean Airlines

Tortola has a small airport on Beef Island. Most flights are through San Juan, Puerto Rico, or St. Thomas offered by Cape Air, Seaborne, and Air Sunshine with occasional service by other airlines and charter flights.

TURKS AND CAICOS (PROVIDENCIALES)

Air Canada, American, Bahamasair, British Airways, Delta, SouthWest, United

WHAT TIME DO WE LEAVE THE SHIP ON DISEMBARKATION DAY?

All cruises disembark by 10:00 AM.

WHAT’S THE EARLIEST FLIGHT I CAN TAKE WHEN I DISEMBARK?

DOMINICA  10:00 AM

GREECE  7:00 AM

GRENADA  10:00 AM

ST. KITTS  9:30 AM

ST. LUCIA  2:00 PM

ST. MAARTEN  1:00 PM

ST. VINCENT  11:00 AM

TURKS AND CAICOS (PROVIDENCIALES)  9:30 AM

TORTOLA  9:30 AM

CAN YOU RECOMMEND A HOTEL?

From bed and breakfasts to villas and resorts, you’ll find accommodations in a style and price to suit your needs. Take a look at our preferred partners on our hotels page .

SPECIAL DIETS

Vegetarian and gluten free diets are available on board; just speak with your chef when you arrive. Vegan, kosher, and other more restrictive diets cannot be accommodated. Anyone with life-threatening food allergies should not sail, as there is always the possibility of cross-contamination in our small galleys.

BOOKING YOUR CRUISE

I’m ready to book my cruise. what’s the next step.

Book online or give us a call at 877.772.4549. A non-refundable deposit of $750 pp is required on 6-night sailings, or $1500 pp on premium cabins. The non-refundable deposit on 10 and 12-night sailings is $1500 pp. Balance is due no later than 90 days prior to sailing. Full payment is required if reserving online or within 90 days of sailing.

PASSPORTS REQUIRED

Welcome aboard.

You’re about to embark on the best vacation of your life! We want to make sure that you feel comfortable every step of the way. Take a moment to read this short guide, with answers to the most commonly asked questions. If there is anything else you'd like to know, give us a call or email. We’re standing by to lend a hand!

WHERE IS THE SHIP DOCKED?

DOMINICA To be determined GREECE Kos Town, Kos Island GRENADA Port Louis Marina, St. George’s ST. KITTS Timothy Beach Resort, Frigate Bay ST. LUCIA Rodney Bay Marina, Rodney Bay ST. MAARTEN Great Bay, Philipsburg ST. VINCENT To be determined TURKS AND CAICOS (PROVIDENCIALES) South Bank Marina, Turks and Caicos (Providenciales) TORTOLA Village Cay Marina, Road Town

GETTING TO THE SHIP

It's a breeze to make your own way to the ship on boarding day! Taxis are readily available at hotels and guest houses.

HOW CAN I GET TO THE AIRPORT (OR MY POST-CRUISE HOTEL) AFTER MY CRUISE?

Your crew will assist you with arranging post-cruise airport or hotel transfers.

BOARDING TIME

Any changes in boarding information will be included with your final boarding instructions.

SUNSHINY DAYS

How’s the weather.

The weather is wonderful. Year round temperatures are typically in the mid 80’s, with fresh breezes during the day, and mid 70’s at night. Occasional rain showers are typical, but then the sun shines more brightly afterwards, as if to apologize!

If you're sailing the Greek Isles, prepare for cooler temperatures in May and October. A jacket and slacks are recommended.

WILL I GET SEASICK?

If you've experienced motion sickness in the past, or aren't sure how you'll adjust, please bring your preferred remedy with you. Most motion sickness medications aren't effective if taken after you start feeling sick. Play it safe if you're not sure, and take your medication before you set sail!

MONEY MATTERS

Do i need local currency.

NO CASH is accepted on board the ship.

The US dollar is accepted in most Caribbean ports. The Euro is accepted in the Greek Isles and most French Caribbean ports. Small denominations are best.

Visa and MasterCard may be used in most shops and restaurants. Avoid fraud alerts and pesky holds on your credit card by notifying the issuing bank of your intended foreign travel.

TIPS ABOUT TIPPING

Suggested amounts:

Six-night sailings: $250 per person, per week

Ten-night sailings (Lyra): $750 per person

Twelve-night sailings: $500 per person

Gratuities are payable ONLY by credit card at the end of your cruise. No cash is accepted onboard.

STAYING CONNECTED… OR NOT

Will i get cell phone coverage.

Most cell phone carriers provide international roaming service on Caribbean networks. Call your provider to ensure you have coverage, and ask about cost-saving international service plans.

DO THE SHIPS HAVE WIFI?

WIFI is available on board Lyra. There are Internet cafés on some of the islands.

SIPS ON THE SHIP

Is there a bar on board.

You may help yourself to the included beverages at any time. You're welcome to bring your own spirits on board to mix your favorite drinks. Pick it up at the duty free on your way down, or at a local market before you board.

DO YOU PROVIDE MIXERS?

Depending upon availability, we provide Cola, Diet Cola, Sprite, Ginger Ale and Tonic Water.

MUSIC TO YOUR EARS… AND OURS TOO

Can you play the kazoo? Have you mastered the art of strumming the guitar on your front porch swing? If you’re wildly entertaining, or mildly talented, bring your instrument along for the ride. Some guests enjoy center stage, while others just like to watch.

While we’re on the subject, bring your playlist, and take your turn at the dock. See what we did there? He-he.

DO YOU OFFER TOURS?

Greek Isles Your crew will explain the wonders of each island prior to your arrival, and may be able to assist if you wish to plan a special activity.

Windwards and Turks & Caicos These islands are small, beautiful, and far from the crowds. Island tours in some ports of call can be arranged with local taxi drivers, or your crew. The main activities are swimming, snorkeling, strolling around local villages, and....relaxing!

The British Virgins | Leewards | French West Indies These Islands are larger, more populated, and have a wide variety of activities and things to do. The Operations Manager will review things to do on your own, as well as a variety of optional extra excursions (not included in your cruise fare).

OF BEACH DAYS AND BEACH SIPS Please do not bring beverages ashore from the ship, as local vendors earn their livelihood selling drinks and renting chairs in some ports of call. When permissible, the crew will bring a beverage cooler to the beach for your enjoyment.

HOW ABOUT SNORKELING AND SCUBA? Snorkel gear is available onboard at no cost. If you are interested in scuba diving, research diving opportunities prior to sailing, and make arrangements while on board.

LOOK SUNSATIONAL The sun can be your best friend and give you a big dose of vitamin D — or your worst enemy. We strongly suggest using a high SPF sunscreen, and applying it often. We want you to look like you’ve been frolicking in paradise, not bathing in a cauldron of hot water. While we’re on the subject of encouraging… avoid insect bites by using insect repellent anytime you are outside. Apply after sunscreen.

THE ESSENTIALS

Island style.

Dress on board is casual. Ladies and gents planning to dine ashore may want to pack a sundress or a pair of trousers. Bath towels are provided, as are hair dryers, shampoo, and body wash.

Cabins have A/C and 110V electric outlets. There are 220V electric outlets aboard Lyra. CPAP machines are okay to bring if you require one. Pack light. Cabin storage space is limited. Did we say pack light? Why yes, yes we did.

SAMPLE PACKING LIST

  • Swimsuit (2)
  • T-Shirts & Shorts
  • Sundress/Trousers
  • Light Jacket/Sweatshirt
  • Sunglasses / Reading Glasses
  • Comfortable Walking Shoes
  • Beach Towel
  • Re-usable water bottle
  • Personal Toiletries
  • Personal Medication (pack in carry-on)
  • Suntan Lotion / Sunscreen
  • Insect Repellent / Towelettes
  • Mask & Snorkel if you prefer your own
  • Water Shoes

Island Windjammers Trading Co. Check out our limited-edition ship logo shirts, hibiscus ball caps, and beach towels.  Click here to shop.

DON’T FORGET YOUR BOARDING INSTRUCTIONS, RETURN FLIGHT INFORMATION, AND PASSPORTS. KEEP THEM IN YOUR HAND LUGGAGE, ALONG WITH YOUR MEDICATION.

Travel delays and emergency contact:

877.772.4549

SEE YOU ON DECK!

Shore leave, even sailors need a little shore time.

Our home ports offer accommodations in styles and prices to suit your needs, from bed and breakfasts to villas and resorts. Browse online, or check out some of our guest favorites, featured here.

Albergo Gelsomino Hotel, Kos Town

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Kos Aktis Art Hotel, Kos Town

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Kosta Palace Hotel, Kos Town

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Sea Glass Place, St. Georges

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Allamanda Beach Resort, St. Georges

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Radisson Grenada Beach Resort, St. Georges

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True Blue Bay Boutique Resort, St. Georges

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Bay Gardens Beach Resort and Spa, Rodney Bay

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Timothy Beach Resort, Frigate Bay

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Marriott’s St. Kitts Beach Club, Frigate Bay

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Holland House, Philipsburg

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Pasanggrahan Boutique Hotel, Philipsburg

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Seaview Beach Hotel, Philipsburg

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Maria’s by the Sea Hotel, Road Town

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Sebastian’s on the Beach, Apple Bay

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TURKS & CAICOS

Ports of call resort, grace bay.

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The Sands at Grace Bay, Providenciales, Turks and Caicos

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Sibonne Beach Hotel, Grace Bay

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Pre and Post Cruise Transfers

Getting around the islands is a breeze. Taxis are readily available at airports and hotels in all of our ports of call.

You may prearrange arrival airport-to-hotel transfers, and hotel-to-ship transfers on boarding day, in Grenada or St. Lucia using our known drivers.

Your crew can assist with arranging post-cruise airport or hotel transfers in all ports.

The Other Tour St Lucia

Airport transfers, hotel to ship transfers, and boutique island tours Website: theothertourstlucia.com Email: [email protected] 758.716.2267 Use promo code IWJ10 when booking your transfer online, and receive a 10% discount

Kerry Cyrus, aka Foxy

Airport Transfers, hotel to ship transfers, and island tours Email: [email protected] Cell/WhatsApp: 473.409.4473

Island Windjammers Boarding Instructions

Passport and flight documents.

Please carry your cruise confirmation, your passport, and proof of return flight. Your passport must be valid for at least six months beyond the dates of your trip. Some airlines will not allow you to board if this requirement is not met.

Your passport serves as your boarding pass.

BOARDING INSTRUCTIONS

Early boarding is not permitted.

GREECE, KOS TOWN Boarding time 2 PM. Lyra will be docked in the main harbor of Kos Town, along the main promenade, directly across from City Hall (Address: Akti Kountouriotou 7, Kos). You may drop your luggage at the yacht any time after 12 noon. There are numerous cafes, restaurants, and shops along the harbor front to keep you busy until boarding time!

GRENADA Your meeting place is the Knife and Fork Cafe in Port Louis Marina. Please leave your luggage outside the cafe, as space is limited. You’ll be met by a crew member at 12:30PM, and accompanied to the ship.

ST. KITTS Your meeting place is the outside deck of Sunset Cafe, located at Timothy's Beach Resort. You’ll be met there by a crew member at 2PM, and accompanied to the ship.

ST. LUCIA Your meeting place is Café Ole /Boardwalk Bar located at Rodney Bay Marina. You'll be met there by a crew member at 2PM, and accompanied to the ship.

ST. MAARTEN Your meeting place is the Greenhouse Restaurant located in Philipsburg (not Simpson Bay). You'll be met there by a crew member at 2PM, and accompanied to the ship.

ST. VINCENT To be determined.

TURKS AND CAICOS (PROVIDENCIALES) Your meeting place is South Bank Marina located at 1 Long Bay Highway at 3 PM. The marina restaurant is closed on Sunday. For your comfort, we suggest arriving as close to boarding time as possible.

TORTOLA Your meeting place is the restaurant at Village Cay Marina in Road Town. You'll be met there by a crew member at 2PM, and accompanied to the ship.

Disembarkation in all Ports of Call:

Disembarkation is no later than 10 AM

FLIGHTS HOME

The following is the earliest recommended departure flight time for each port:

GREECE  12:00 PM

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