Kenny’s Virgin Islands Bachelor Party Guide

In February 2020, my fiancé Kenny, founder of the resortwear brand Kenny Flowers, went on his bachelor party to the Virgin Islands, and I had my bachelorette party in Miami. We both were so lucky to have had the most incredible bachelor and bachelorette parties, and trust me when I say his bachelor party was one for the RECORD BOOKS.

I was so jealous of this trip. I mean come on, the incredible Virgin Islands for a bachelor party!? The BVI’s and the US Virgin Islands are amazing, and one of my favorite places I’ve ever been.  It’s surprisingly easy to get down to paradise (most of his guys were flying from NYC, where they were able to get roundtrip direct airfare for around $250), the beach bars are out of this world, and the general vibe makes it the best bachelor party destination for good chill beach vibes, and warm weather any time of year. 

So of course I solicited him to help us write this ultimate bachelor party guide for the Virgin Islands, and I think it’s super helpful for anyone planning a Caribbean bachelor party.   

What To Do for a Bachelor Party in the Virgin Islands

Stay on St. Thomas for ease

STT is the easiest airport to fly into for the USVI/British Virgin Islands, making it an easy home base for a bachelor party. On Friday, take the ferry over to Water Island, and head straight to Dinghy’s at Honeymoon Beach. It’s the perfect place to hang for the day, cure hangovers with hammock naps, or keep the buzz going with a drink in hand surrounded by beautiful Caribbean-blue waters. They also have a beach volleyball setup, so before you crush some chicken fingers for lunch and get a few games in. 

Do a big boat day Saturday

Get a yacht for the big day and go full send. Snorkeling around the Indian rocks and Norman caves, Willie T’s for drinks/lunch aboard a pirate ship, iconic Soggy Dollar afternoon. 

Other options

  • Sunset Booze Cruise: For $100 each, open bar two hour cruise at sunset time. We didn’t do this, but it’s worth looking into for a Thursday or Friday evening activity. 
  • Magen’s Bay or Sapphire Beach – if you’re looking for a nice beach to hang at on Saint Thomas island.

Where to stay in the USVI for a bachelor party

Margaritaville – it’s on St. Thomas, making it super easy to get to and from the airport. You’re right on the beach with two pool options – one with a swim up bar and view over the beach, and one with a pool volleyball set up. They of course have cheeseburgers in paradise and alllllll the margaritas and painkillers. What worked out great about this place for a Virgin Islands bachelor party, is that it was so laid-back and comfortable. We were able to sleep well and wake up relatively energized for the next day of debauchery. Also, a boat day doesn’t end when you hit the dock at 4pm. In fact, you get back to the swim up bar just in time for 5pm happy hour and a solid couple hours of clowning with ocean views from the top. 

It was easy for arrivals and we didn’t leave the resort Thursday – too busy playing pool volleyball, slurping down frozen cocktails, and catching up with the boys… There doesn’t need to be much on the agenda that first afternoon, especially if people are arriving at different times.. it makes it easy for them to roll up to the resort and quickly reunite with the fellas. 

Margaritaville comfortably sleeps 3-4 to a room, meaning it’s great for groups of all sizes, and comes with a huge fridge and of course a blender to make your own drinks. 

If you’re a smaller crew, look into renting one or a few boats and just staying on them. Like a yacht week bachelor party, but way better. 

Other options for epic accom in the USVI: rent a big oceanfront villa like these ones


Where to eat and go out in St. Thomas

When you’re ready for some evening mayhem, throw on matching bachelor party shirts and journey to downtown Red Hook – where you’ll find the lively bars and restaurant options, like Duffy’s Love Shack, which is known for its finely-crafted cocktails, fun staff, live music and island-inspired eats.

We had the most fun at Duffy’s on Friday night, going there for dinner and not leaving til past midnight, but there’s also XO bar and a couple other places in the area.  

If you’re looking for nice group dinner spots around Red Hook, we went to Secret Harbour Hotel Restaurant. The open air dinner was great and it’s a perfect spot to throw a few boozy toasts/speeches. 

How to get to the Virgin Islands

One of the most appealing aspects of the Virgin Islands, was how surprisingly cheap and easy it was to get there. Search Skyscanner, and you’ll find great nonstop options with Delta, American, and United from NYC, Miami, etc. for less than $300 Round Trip. I recommend a Thursday morning + Sunday afternoon flight combo to maximize the long weekend of leisure.

Island Transportation Tip 

Set up a van beforehand. My best man had the incredible idea to arrange a driver in advance, that would shuttle us around from airport to hotel, hotel to dinner, hotel to port, port to hotel, etc. It was pure convenience for everyone, and made the accounting easier in the end too. We used Big Mo and it was beyond convenient to not have to worry about taxis and finding transport every time we needed to go out, retreat back to the resort or get picked up from a port. 

Also – US$ was used everywhere, so that was easy. 

Don’t forget your passport!

Even if you’re staying in the USVI, the boys will all need a passport and $70 cash to enter the BVI’s if you do the boat trip for the day (which I highly recommend)

Expenses of a bachelor party in the Virgin Islands

Financially there were no surprises, everyone knew what they were in for, and with cheap flights, and beers cheaper than the mainland, it was an easy set up to celebrate without breaking the bank. In the Virgin Islands, you’re not going to get a surprise $10k table charge that you have to split and explain to your fiance.

The Perfect US / British Virgin Islands Bachelor Party Itinerary

Thursday: Arrive to Margaritaville, thrive at Margaritaville for the afternoon/evening/sunset, go out for dinner

Friday: ferry to Dinghy’s, go out to Red Hook at night

Saturday: big yacht outing to British Virgin Islands, boys night in with beers and pizza by the pool (check out airbnb for boat rentals)

Sunday: Chill on the beach til afternoon flights

There’s not much to worry about in advance for a USVI / British Virgin Islands Bachelor Party, but here’s a checklist to make sure you have the bases covered, and the rest will fall in place

What to wear on a bachelor party in St. Thomas / BVI

Kenny Flowers vacation shirts and swim trunks, of course


Check out Kenny Flowers vacation shirts here, and vacation swim trunks here

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Christina is a leading luxury lifestyle and travel blogger with over 2 million readers. Follow her on instagram @jetsetchristina.