A Caribbean New Year: Sail, Learn & Celebrate in the Virgin Islands

 

Ring in the New Year aboard Sail Libra as we explore the U.S. and Spanish Virgin Islands on a 7-day cruising adventure designed for learning, sailing, and total relaxation. Starting and ending in St. Thomas, we’ll spend the week island-hopping through St. John, St. Croix, and possibly Culebra or Vieques, discovering hidden anchorages, quiet bays, and vibrant island charm along the way.

 

This is the perfect end-of-year passage for anyone looking to unplug, connect with the rhythm of the sea, and welcome the New Year under the stars — from the helm of a classic offshore sailing yacht.

 

 

Day 1: Welcome Aboard in St. Thomas

 

We’ll meet in Charlotte Amalie on December 28th, get everyone settled in, and walk through safety, systems, and basic seamanship. Depending on arrival time and conditions, we may enjoy a short shakedown sail before anchoring for the night and kicking off the week.

 

 

Days 2–3: Coastal Cruising & Exploration

 

We’ll begin by heading to St. John for a stop in Maho Bay or another scenic anchorage. From there, we’ll ease into the cruising lifestyle, sailing through protected waters and learning along the way. Depending on conditions and crew interest, we may sail offshore to St. Croix for a more open-ocean leg.

 

Topics covered during this stretch:

 

• Sail trim and helm basics
• Anchoring and mooring techniques
• Weather awareness and route planning
• Watchstanding and sailing under tradewind conditions

 

 

New Year’s Eve at Anchor

 

We’ll find a quiet, beautiful anchorage — perhaps Culebra or Christmas Cove — to celebrate New Year’s Eve as a crew. The plan is simple: good food, good company, and an unforgettable night under the stars. Whether it’s a quiet toast aboard or a swim under fireworks, it’ll be a New Year to remember.

 

 

Days 4–6: Open Water & Spanish Virgin Islands

 

If weather and timing allow, we’ll make a short open-water sail to the Spanish Virgins — with possible stops in Culebrita, Ensenada Honda, or Sun Bay, Vieques. These less-traveled islands offer great sailing, turquoise waters, and quiet beaches ideal for exploring and relaxing.

 

Expect opportunities for:

 

• Downwind and beam reach sailing
• Line handling and sail reefing
• Chart reading and GPS navigation
• Snorkeling and beach walks when at anchor

 

 

Day 7: Return to St. Thomas

 

We’ll sail back by noon to St. Thomas on January 3rd for you to disembark.

 

Why This Passage is Special

 

• Celebrate the New Year by Sail – Step into 2026 on the water with a fresh breeze and Caribbean sun
• Island Variety – Explore the U.S. and maybe the Spanish Virgin Islands, from bustling bays to remote coves
• Learn by Doing – Perfect for beginner and intermediate sailors, with an open, supportive learning environment
• Relaxed and Meaningful – A blend of seamanship, sailing, swimming, and simple celebration

 

 

Life on Board Libra

This is a laid-back but purposeful cruising passage. You’ll participate in helm work, sail trim, anchoring, and onboard routines — learning through action and repetition. Libra’s pace allows time to relax, swim, ask questions, and enjoy being off-grid during the holiday week.

 

Meals are hearty, fresh, and celebratory — with plenty of snacks, tropical ingredients, and good company around the table. The Mate will ensure everyone’s well-fed and fueled for each day of sailing and exploring.