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What is the best USVI cruising itinerary? 

The Best USVI Cruising Itinerary | Go Sail Virgin Islands

The Best USVI Cruising Itinerary | Go Sail Virgin Islands


The best USVI cruising itinerary is the itinerary that best meets your needs and goals. In this post we discuss how to make an informed decision when choosing a USVI cruising itinerary and provide you with a sample itinerary so you know what to expect aboard. 

What’s the best length for a USVI cruise?

If you want to really get the feel for sailing, look for USVI cruises that are 7 days. There are multiple reasons for this. For one, it takes a day or two to get oriented to a boat. That’s the case even if you have prior sailing experience because every sailboat is different. Then, you’ll want a few days to increase your skills and truly enjoy yourself without feeling rushed. Lastly, you’ll want a day to unhurriedly prepare for life back on land. 

What activities are included with the best USVI cruising itineraries? 

A good USVI cruising itinerary won’t have you wandering the US Virgin Islands aimlessly. Everyday will have a great purpose. For example, you may sail to an area that’s known for fantastic snorkeling, white sandy white beaches, or pristine conditions to practice your sailing skills.  

Can I request an individualized USVI cruising itinerary? 

All Go Sail Virgin Islands itineraries are personalized to the specific group aboard. For example, if you have a specific island you would like to explore or an activity you’d like to focus on, we can make it happen. Our goal is to ensure that your USVI cruising itinerary meets all your sailing dreams.

Does USVI have a sample USVI cruising itinerary? 

Below is a sample USVI cruising itinerary for a Go Sail Virgin Islands trip. For further reading, the Go Sail Virgin Islands “Captain’s Log” posts on our “Discover” page provide readers with real-life examples of USVI cruising itineraries. 

The first night: Sleeping aboard

Go Sail Virgin Islands invites guests to spend the night aboard the boat the day before we set sail. This allows students the opportunity to get their “sea legs” and feel comfortable calling their sailboat home for the coming days. Additionally, your captain will talk to you about the current wind and weather to help you plan your USVI cruising itinerary. 

The first day: Setting sail

You’ll wake up to a fabulous breakfast, complete with coffee and tea. From there, your captain will walk you through expectations, course requirements, and the sailing skills for the day. Then it’s time to set sail! As with most days, the sailing day will include a lunch break snorkel and then wrap up in the early evening. This gives you plenty of time to relax on deck or in the water before the sun sets. 

Day two and beyond: Sailing and exploring

Each day brings a new adventure with it. Generally, each day begins around 8am with breakfast. From there, you’ll complete any classroom ( galley table) activities planned for the day before setting sail. 

Each sailing adventure includes practicing hands-on skills until it’s time to break for lunch. You’ll have time to make a delicious wrap or sandwich and work with your captain to plan out the rest of the day. Activities include more sailing as well as options for snorkeling, exploring islands on foot, swimming, and other fabulous adventures. 

Dinner may be made aboard the boat or you may choose to eat ashore, trying one of the many wonderful USVI restaurants. Your captain is sure to have a few fabulous suggestions for you!

The last day: Wrapping up

The final day of your USVI cruising itinerary involves finalizing paperwork for certifications, logbooks, and sea-time forms before setting sail to the marina. By 10 AM, you’ll be back to shore with plenty of time to clean up and pack up before saying goodbye. Go Sail Virgin Islands is also happy to arrange a taxi to pick you up at the marina. 

Booking your USVI cruising experience

Customize your USVI cruising itinerary and book your dream trip on Go Sail Virgin Islands.  On the website, you can view trip availability in real time or contact a Bareboat Cruising Expert with any questions you have about your trip. We look forward to seeing you aboard!