tall ship cruises

8 Incredible Tall Ship Destinations for Your Dream Vacation

If you’ve decided to book a tall ship cruise as your next vacation, or as part of your next vacation, you probably have questions. Where are the best places to go? What are the prices like? How long will the trip last? What should I expect when I’m on board?

In this article, we’ll take a look at some tall ship cruise options and discuss prices, routes, and what to expect when you arrive.

Where Are the Best Tall Ship Routes?

For this article, we’ll frame our discussion from a US standpoint. The United States has the most tall ships out of any country (64) and therefore has the most opportunities to book a tall ship cruise.

Ps: You can click the name to jump directly to the relevant details.

1 Day2-6 Days7 Days or more
Domestic RoutesLiberty Fleet and The Adirondack – Boston, MA

Lady Washington – Grays Harbor, WA

Maritime Museum – San Diego, CA

Traverse Tall Ship Co – Traverse City, MI

Navy Pier – Chicago, IL

Liberty Fleet – Boston, MA

Lady Washington – Grays Harbor, WA

Traverse Tall Ship Co – Traverse City, MI

International RoutesLiberty Fleet – Bahamas

Star Clippers – Caribbean, Mediterranean, Central America, Ocean Crossings

Tall Ships Races 2022 – Denmark, The Netherlands, Belgium

Domestic Routes and Daysails

1. Liberty Fleet and The Adirondack – Boston, MA

The Liberty Fleet has two boats, The Liberty Clipper and the Liberty Star, which sail out of Boston Harbor. They offer a couple of domestic cruise options – harbor day sailing, transit passages, and an Atlantic Seaboard cruise.

Day Sailing around the harbor is a fun, family-friendly activity and a great way to see Boston Harbor if you’re staying in the city. Liberty Fleet offers a basic daysail, a sunset cruise, and a historical tour.


  • Basic Daysail – $39, 1.5 hours
  • Sunset Cruise – $45, 1.5 hours
  • Historical Tour – $45, 1.5 hours

If you’re looking for a little more adventure, Liberty Fleet also offers transit cruises and racing. These are overnight or week-long trips that require passengers to get their hands dirty by helping to crew the ship.

You could take part in a three-day roundtrip sail aboard the Liberty Clipper over Labor Day weekend (this includes participating in the Gloucester Schooner Race), or help transit the Liberty Clipper from her homeport in Boston to New York City during the first week in October.


  • Gloucester Schooner Race – call for prices. You can choose to participate in the full three-day race or choose either the Northbound or Southbound leg.
  • Fall Transit Cruise – From $799. Saturday, Oct. 3 – Thursday, Oct. 8. Meals provided.

A third tall ship, The Adirondack, also operates out of Boston Harbor. This tall ship offers day sailing only, and special occasion cruises such as on Valentine’s Day, Independence Day, Christmas, and New Year’s Eve. You’ll sail past many of the historical sights in the harbor. Beer, wine, cocktails, and other drinks are available to purchase, and you can bring a snack or picnic lunch to enjoy.

2. Lady Washington – Grays Harbor, WA

The Lady Washington is the West Coast’s premier tall ship, and sails out of Grays Harbor in Washington. She sails up and down the West Coast all year, so if you live on the West Coast, you might be able to tour the lady Washington at the dock when she stops in your hometown.

A trip up to Washington opens up many other cruising options aboard this historic ship, including sunset sails, adventure daysails, passages and charters. Sunset sails are best if you’re just looking to relax and enjoy a cocktail, while adventure sails are longer trips where you will be invited to join the crew in hauling lines and setting sails.


  • Sunset Sail – $39, 2-3 hours
  • Adventure Sail – $69, Friday – Sunday

You can also join the Lady Washington crew for a transit passage, a multi-day sail where you will be expected to stand watch, steer the ship, climb aloft and participate in other daily chores.

For a truly unique experience, the Lady Washington is available for private charter, for events such as weddings, workplace team building, and private parties.


  • Passage Sail – the price depends on the length of the leg
  • Private Charter – call for prices.

3. Maritime Museum – San Diego, CA

If the cold of the Pacific Northwest or Northeast US isn’t your thing, you might opt for a trip aboard one of the tall ships docked in the port at sunny San Diego. The San Diego Maritime Museum offers historic bay cruises and adventure sails aboard their fleet.

Those passengers wanting a quick, relaxed trip might opt for the 45-minute historic cruise aboard Pilot. Though not a tall ship, this historic vessel was launched in 1914 and performed regular operations until 1996.

For those seeking a splash of adventure, try a four-hour adventure sail aboard either the Californian or the San Salvador, where you will be invited to assist the crew as they sail out of San Diego bay.


  • Historic Bay Tour – $30 general admission (access to tour most boats at the dock) + $10 Pilot add-on
  • Adventure Sail – $59-$99. 11:30 AM to 4 PM daily

4. Traverse Tall Ship Co – Traverse City, MI

The Traverse Tall Ship Company has two ships – Manitou and Scout – both of which sail out of Grand Traverse Bay. They offer a brunch cruise, daysails, multi-day windjammer cruises, and private charters, all of which offer passengers the chance to explore the scenic beauty of Northern Lake Michigan.

The Scout also offers a 6-hour island package, in which you sail out to Power Island and get off the boat to spend the day hiking, picnicking, and swimming on the island.

If you’d like to experience spending the night aboard, but aren’t ready to do so at sea, Scout also offers the option to enjoy a sunset cruise followed by an overnight stay on the boat at the dock in Center Point Marina.


  • Brunch Cruise – $70, 10 AM – 12 PM, weekends only.
  • Daysail – $330, 2 hours. Snacks and soft drinks provided, BYOB for alcohol.
  • Sunset Cruise – $380, 2 hours
  • Windjammer Cruise – $895-$1170, 4 or 5 days. Offered in September only.
  • Power Island Package – $750, 6 hours.
  • Dockside Overnight – $350-$600, 2 hours + overnight

Another option for East Coast residents is the tall ship Windy, Chicago’s Official Tall Ship. Windy sails from Navy Pier at the south end of Lake Michigan, and offers day sailing options only, as well as private charters and a few special sails like the Chicago Air Show sail.


  • Chicago Skyline Sail – $39, 1.25 hours
  • Fireworks Cruise – $43, 1.5 hours, alcoholic drinks available for purchase
  • Marshall Vente Sail – $75, 2.5 hours, includes a live band performance
  • 2021 Chicago Air Show – $79, 3 hours, watch the air show from the water

International Routes

1. Liberty Fleet – Bahamas

As well as offering daysail and transit options, the Liberty Fleet in Boston also runs the Windjammer sailing vacation to the Bahamas. The trip lasts six nights and offers guests the chance to explore the outer islands of the Bahamas.

Aboard the Liberty Clipper, you’ll leave from Nassau in the Bahamas and spend seven days island hopping to various tropical locations before returning to Nassau. This is a vacation cruise, so passengers are treated as guests, not crew, and are not expected to help with running the ship.

Guests can purchase shared or private cabins, at either standard or premium prices. Guests are also expected to pay their own airfare to the Bahamas and provide their own accommodation if they need it before boarding the boat.


  • Shared Single Cabins – $1399 standard, $1599 premium
  • Private Single Cabins – $2098 standard, $2298 premium
  • Private Double Cabins – $2798 standard, $2998 premium, $3198 en suite

2. Star Clippers – Caribbean, Mediterranean, Central America, Ocean Crossings

Star Clippers has a fleet of three ships – the Royal Clipper, Star Clipper, and Star Flyer – and runs a number of cruises at various destinations around the world. Trips in the Caribbean, Mediterranean and Central America are vacation packages that typically run for about seven days and include stops at several different ports along the way.

Star Clippers

Caribbean cruises happen aboard the Star Flyer during the winter season, while the Star Clipper sails in the Mediterranean in the spring. The Royal Clipper sails in both locations and offers the chance to partake in an ocean crossing in-between seasons for those brave souls who want to experience a true tall ship adventure.

Visit the Star Clippers website for pricing and details – there are too many options to list here. You can also find brochure rates and discounts of up to 65% on some trips on the Star Clippers website.

3. Tall Ships Races 2022 – Denmark, The Netherlands, Belgium

The Tall Ships Races is an annual event run by Sail Training International that happens in Europe during the summer. Every year, four different European cities are chosen as host ports, and over 100 tall ships participate in a race between them. In 2022 the boats will start in Esbjerg, Denmark, and race two legs to Harlington in The Netherlands and Antwerp in Belgium, before returning to Denmark to finish in Aalborg.

Because there are so many tall ships involved in the race, you have to choose which ship you would like to crew and book a spot on that ship. This is an official race, and the crew will be required to participate in all the tasks necessary to perform well in the race, including watches, sail trimming, and managing lines. The Sail Training website has information on each ship that will participate, including how many crew can fit, and the special considerations for each ship.

What is it Like to Travel by Tall Ship?

Traveling by tall ship is an experience like no other, and it can be as challenging or as easy as you like, depending on the vacation that you choose.

  • If you’re up for the challenge of crossing an ocean or being part of a tight-knit crew racing to beat a fleet of other boats, then a trip to the Tall Ship Races or an ocean crossing aboard the Royal Clipper might be for you.
  • If you’re simply looking to sip on a cocktail and watch the sunset, you should opt for a two-hour cruise aboard the Lady Washington or Liberty Fleet.

No matter which option you pick, there are a few things you’ll want to know ahead of time.

Do I Need to Know How to Sail?

tall ship sailing vacation

No! The great thing about booking a tall ship cruise is that no sailing experience is necessary – even for an ocean crossing or the Tall Ship Races! Part of the fun of crewing on a tall ship cruise is that you learn as you go. Your captain and the tall ship’s paid crew will teach you everything you need to know and help you perform your assigned job.

Be aware that if you are booking a spot in the races or on an ocean crossing, you will be expected to perform all tasks, and you should be able to perform them well. Life at sea can be a matter of life or death, and your captain will not hesitate to let you know when you are doing something wrong. A tall ship adventure is a tough experience not to be entered into lightly.

What Do I Need to Bring?

For a multi-day or multi-week tall ship adventure, you will need to bring everything you need to live on a boat for that length of time.

For an ocean crossing or transit passage when you will be helping crew the boat, this will include a few changes of clothes, closed-toe shoes, a waterproof jacket and pants if you have them, warm clothes including a hat and gloves, work gloves for handling lines and a headlamp with a redlight setting for seeing at night. You will probably also want to bring some kind of entertainment like a book, deck of cards, or device for watching movies during your downtime.

For a windjammer-style vacation where you will not be expected to work as a crew, you won’t need nearly as much – just whatever clothes you’d like to wear, layers to stay warm at night, a bathing suit, and something to entertain yourself during downtime.

For a daysail, it’s a good idea to bring a snack and bottle of water, sunscreen, and layers.

Will I Get Seasick?

There’s no one right answer here, as seasickness susceptibility differs from person to person, but it’s always a good idea to prepare for the worst, even if you’re only going out for a couple of hours. If the water you’ll be sailing on is relatively calm – i.e you’re staying inside the bay and not going out onto the open ocean – it’s safe to assume you probably won’t get seasick.

If you are working as crew on a multi-day passage, the chance of getting seasick becomes much higher. Even the most seasoned sailors often get sick for the first two or three days of a passage. Don’t be embarrassed – it happens to the best of us!

If you do find yourself getting seasick, the best way to combat it is to go up on deck and look at the horizon. The fresh sea air will feel much better than the stuffy air below deck, and having a stable point to focus on will help your body adjust to the motion of the boat. Other remedies are a ginger beer or any light, carbonated beverage, salted pretzels or other easily digested snacks, and motion-sickness pills like Dramamine.

Can I Bring My Pets?

No. Pets are not allowed on any tall ship cruises. Service animals are permitted under certain circumstances – inquire with the company running your trip. If you plan to bring a service animal, be sure to research the animal importation regulations for any foreign countries you may be visiting.

Sail Away on Your Next Adventure

Whether you sail for a day, a week, or a month, the majesty and splendor of these spectacular boats will be something you remember for the rest of your life. With the tips and information outlined in this article, you should be prepared to book the adventure of a lifetime!