1. Home
  2. Cruise Lines
  3. Island Windjammers
Island Windjammers

Free Price Drop Alerts
Get Island Windjammers price drops
250,000+ people have entered their email

Island Windjammers Cruise Highlights


Why Go?

Three windjammer-style tall ships that carry 10 to 30 passengers

Casual and social onboard atmosphere

Fares include drinks and snorkeling equipment

Find a Cruise

Easily compare prices from multiple sites with one click

Island Windjammers Awards

Cruisers’ Choice Destination Awards

2018 Top-Rated Eastern Caribbean, Bahamas & Bermuda Cruise Lines
2018 Top-Rated Southern Caribbean Cruise Lines

Island Windjammers Overview

Island Windjammers is barefoot cruising at its most essential. Launched in 2008, it has become the cruise line of choice for would-be sailors who want to try their hand at hoisting the sails and climbing the mast in warm-weather locales throughout the Caribbean.

Who goes on Island Windjammers cruise ships?

Come prepared to socialize; with no more than 30 passengers onboard, it's hard to be anti-social on an Island Windjammers sailing. Most cruisers are a mix of solo travelers, friends traveling together and couples. While most passengers fall into the 45- to 65-year-old age range, there usually is a sprinkling of older and younger passengers. The company also attracts families onboard, as it welcomes children 8 and up year-round, except for a few themed cruises, and offers discounted youth fares in the summer. (Given the size of the ships, families often charter an entire ship -- or part of a ship -- for a family reunion.)

Do I have to dress up on an Island Windjammers cruise?

No, Island Windjammers wholeheartedly embraces the concept of casual cruising. Swimsuits, cover-ups and T-shirts are typical daytime attire, and dressing for dinner usually means nothing more than putting on a clean shirt.

What are Island Windjammers' most popular activities?

Island Windjammers' ships are intentionally short on typical cruise ship amenities, such as fitness centers and theaters, with passengers preferring to relax or if they're feeling up to it, help to raise the sails and even take a turn at the helm.

The upper deck is a popular place to congregate; passengers use its cushioned benches to chat and nap. You can also swim and snorkel directly from the ship. The more adventurous opt for the stand-up paddle-boards or the rope swing.

The flexible Windjammer schedule leaves plenty of time to explore on land, and cruisers enjoy hiking, swimming, snorkeling and checking out the colorful smaller islands the ships visit.

Is everything free on Island Windjammers?

Not quite. Island Windjammers' cruise fares include all meals and snacks, beverages (beer, wine, rum punch, soft drinks and tonic water) and the use of snorkeling equipment.

Shore excursions and gratuities cost extra, and there is no Wi-Fi onboard.