Adventure Awaits Experience

Explore the beautiful Virgin Islands from the water! We offer private charters, group charters, sunset charters, snorkeling, special events, bar hopping, beach hopping, food stops and more! Check out different islands: St Thomas, St John, Lovango, Great St James, Little St James, Water Island, and Buck Island to name a few. We also frequent the ever so popular Lime Out and Pizza Pi.  ​Each trip includes the basics: snacks, water, coolers with ice, snorkeling equipment, paddleboards, and large rafts. If you book a private charter we will discuss with you what type of itinerary you would like to do. Each family is different and may want to see or do different things making each trip unique, no "cookie cutter" trips here! If you are unsure of the places you may want to go our higly experienced crew can help you decide. We also offer group charters (Day charter or Sunset Charter). This trip is also unique, we may have a food destination in mind or it may just be a snorkeling trip but the stops in between vary. 

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Sailing Catamaran 
Experience

We are excited to announce this option is now available! This is a brand new 2022 Leopard 42 Sailing Catamaran! Be one of the first to come aboard! You will be sure to get a unique experience on a trip booked with Second Wind. This catamaran combines the perfect mixture of luxury with adventure. We run the sails as much as possible to really get the true experience of sailing. We can head unique secluded spots and drop anchor so you can get some snorkeling in or maybe you prefer cliff jumping. We also can make stops at popular destinations like Magens Bay. We have a dinghy available to take you up to the beach to enjoy your favorite cocktail. We also have multiple levels with plenty of seating area if you prefer to lounge in style on the boat. It's your day, your way! We will do everything we can to make sure this is the trip of a lifetime! 

Private Charters
 

 
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Private 8 Hr. Trip

8 Hour Cruise
Up to 12 Guests

$1920 plus tax

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Private 6 Hr. Trip

6 Hour Cruise
Up to 12 Guests

$1450 plus tax

$200 Off (Book before Nov 30)

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Private 8 Hr. Trip

8 Hour Cruise
Up to 12 Guests

$1920 plus tax

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Private 6 Hr. Trip

6 Hour Cruise
Up to 12 Guests

$1650 plus tax

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Private 4 Hr. Trip 

4 Hour Cruise
Up to 12 Guests

$990 plus tax

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Private Sunset

2 Hour Cruise
Up to 12 Guests

$510 plus tax

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Private 4 Hr. Trip 

4 Hour Cruise
Up to 12 Guests

$1,100 plus tax

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Private Sunset

2 Hour Cruise
Up to 12 Guests

$550 plus tax

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Group Charters on Adventure Awaits
St Thomas or St John Pick Up Options

 
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Day on the Water

(Bring a Lunch)

6 Hour Cruise
Up to 12 Guests

$125/person

$85/Child plus tax

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Group Charter

Lime Out Trip 

8 Hour Cruise
Up to 12 Guests

$150/person

$125/Child plus tax

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Group Charter

Pizza Pi & Snorkeling

6 Hour Cruise
Up to 12 Guests

$125/person

$85/Child plus tax

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Group Charter

Sunset Swim

4 Hour Cruise
Up to 12 Guests

$95/person

$75/Child plus tax

 
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'Round Town Picnic Boat Charters
 

 
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Departure: Waterfront of Emancipation Garden in Charlotte Amalie, St Thomas 00804
Check-In: 15 minutes prior to departure time

'Round Town Picnic Boats is the newest excursion that has left our guests with a feeling of closeness and intrigue with Charlotte Amalie Harbor. You can enjoy a 90 minute excursion taking in the sights from the water of Charlotte Amalie, Hassel Island, Yacht Haven, while you enjoy complimentary mimosas, rum punch or red and white wines. This excursion has proved to be an exciting new tour for locals and tourist alike from business lunch hour to after work drinks.  

Customize A Unique Trip 

Looking for a longer excursion? Want to do a cooperate event or a private party celebration? Maybe you want to do a trip to Hassel Island or Water island....or both? This option allows you to book a 4 hour trip with the option to select additional time. 

Excursions available are Mimosa Mornings, Rum Punch Lunch,  Wine Down Time, and City Lights Tour.

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What Are Picnic Boats?

These unique round boats offer the perfect setting for friends or families to gather. Think about it, circles create a sense of wholeness and balance, making us conscious of context. Sitting in a circle helps us to fully see each other as peers sharing meaning, creativity, and a common center.