Your St. Thomas Off-Season Survival Guide!

Getaway Girlfriend
Sep 8
7 min read

It is no secret that this is one of my favorite times of year...mainly because I am mostly on VACATION MODE. We own two charter businesses and this is when we shut everything down for both slow season and to be prepared for any storms that come this way....Thank You Erin for turning North!

Slower days on island are great for us but can also be fantastic for you for so many different reasons. Lower rates on your favorite beachfront condos or resorts, popular beaches that become your own private oasis and no crowds or reservations to plan way ahead of time. The only caveat is that a lot of other businesses are closed this time of year as well. Thankfully, St. Thomas, being the hub of commerce tends to remain mostly open. We'll highlight the best of the best for you here so you can make the most of your off-season travel to St. Thomas and also point out the DON'T MISSES to BOOK NOW for next season!

Why Travel in the Off-Season?

If you're flexible with travel and on top of the weather updates (shout out to VI Weather Lady)...this is the best time to:

✨ Actually hear the waves crash while relaxing on the beach.
💆‍♀️ Enjoy spa days and hotel resorts without a crowd...no kids!
💸 Book luxury villas and beachfront condos at a fraction of the price.
📸 Capture the kind of photos that will never happen in regular season!

Yes, it’s storm season but it’s also slooowwww season. With smart planning (that’s me!), you’ll have a restorative, low-key, and peaceful getaway that still checks every box.

Where to Stay: Boutique & Blissful

These are our top GG-approved spots to unwind, recharge, and indulge:

Bolongo Bay Beach Resort

I will never stop hyping Bolongo Bay....we absolutely adore the Doumeng family that owns it and fully endorse them as the only All Inclusive on St. Thomas. True, it is not a typical AI like Sandals or resorts in Mexico but you will never get a staff that cares as much about their guests as you will find here.

Breakfast/Lunch/Dinner/Cocktails all included
Live Music & Karaoke nights weekly
Fun events, on site excursions and included water sports with your stay!

Sapphire Beach Resort & Surrounding Properties

St Thomas Off Season Guide Sapphire Beach Sunrise — Sapphire Beach Sunrise

I live and work here full time can definitely vouch for the vibe. These beachfront condos can go for upwards of $7-$800/night in season so if you want to get these views for less than half the price, this is the time!

On site breakfast, lunch and dinner spots as well as live music and beach bar🍹)
Endless excursions can be found at the adjacent marina (boat rentals, day sails, sunsets, jet skis, parasail, etc...)
Direct Bookings available to save even more money without the fees from www.sbrmbookings.com

Buoy Haus Frenchman's Reef

I have only visited Buoy Haus for the day as I have my own home and no real need to stay here but if you're looking for a luxury resort for a great price, Buoy Haus in off season would definitely be my pick!

Tons of dining choices on property...Salt Shack, Sand Bar, Isla Blue, Sugarfin, etc...
One of the best pool views and settings we've seen with the ocean steps away.
On site hobie cats, snorkeling and water activities included.

Don't Miss Excursions for Off-Season in St. Thomas

We do know that some of our favorites are closed for this time but listed below are our top picks to still get those bucket list items checked off!

🤿 OS "Do it All" Trip for $99/pp:

Snorkel at 2-3 beautiful beaches with turtles and other marine life.
Open bar, sodas, waters and food included...plus champagne for later.
Sunset cruise back with above mentioned champagne.
Trip runs from 2-7pm out of American Yacht Harbor.
Book this trip for now or later HERE OS Do It All Trip

⛰️ Stormy Pirates Virgin Gorda & White Bay Trip $300/pp:

Have The Baths at Virgin Gorda all to yourself....you will never get it like this in regular season.
Swim and snorkel at Spring Bay & Devil's Bay with no crowds
A White Bay afternoon with open bar on the boat and the pristine beach with no people.
Learn More and Book for now or future HERE Virgin Gorda & White Bay BVI Trip

🌅 Sunset Cruise on Snorkel Cat $110/pp:

Sunset cruise from 5-7pm out of Margaritaville on Snorkel Cat
Appetizers and Open Bar included
Great views and plenty of space to relax and take in the golden hour
Learn More and Book for now or future HERE Snorkel Cat Sunset Cruise

Where to Eat: Breakfast to Dinner & Drinks

September and October may be quieter, but the island is still delicious. Here are 10 GG-approved spots to keep you fueled all day:

Breakfast & Coffee

Latte’s in Paradise (Red Hook) ☕Island-famous lattes, smoothies, muffins, sandwiches and more. Open from 6am-2pm
Frenchtown Deli & Coffee Shop A huge favorite on island on the South Side serving breakfast, lunch and dinner. Definitely a neighborhood vibe with great harbor views. Open from 7am-8pm

🥗 Casual Lunch & Daytime Bites

The Shack @ Hull Bay 🍔 Laid-back surfer vibes...burgers, fish tacos, and local beers. A true Northside secret. Movie nights hosted on the lawn some nights as well!
Tarpon's Table (Red Hook) Think🦞 for dinner, mimosas and biscuits for breakfast and fresh poke bowls for lunch and a breezy deck overlooking the water. I go here at least twice a week.
The Greenhouse (Downtown) 🍛Iconic Caribbean flavors...stuffed lobster, conch fritters, and jerk chicken. A must for first-timers and repeat visitors alike and a menu selection that will make your head spin. They literally have everything!

🍷 Dinner with a View

PRIME at Paradise Point 🥩🦞Surf & turf with breathtaking views over Charlotte Amalie harbor. Date-night pick for a trip without the kids.
SeaSalt (Sapphire Beach) 🍸Trendy, modern and the perfect setting overlooking the ocean. Creative cocktails, fresh seafood, and open air seating on the upper balcony.
Cutlass & Cane 🌄Sunset dinners with one of the best views on island. Local Caribbean-meets-American plates and a cozy, boutique feel.

🍹 Cocktails & Late-Night Fun

Box Bar (Yacht Haven Grande) 🎶 Live music some nights, strong pours, and a welcoming crew. Great local hangout or evening stop for the perfect downtown escape.
XO Bistro (Red Hook) 🍷Cozy wine bar with small plates...perfect for winding down the night with friends, laughter, and a second bottle....always. The crowd here...especially in off season is always a good time.

💡 GG Insider Tip: Always double-check seasonal hours (especially Mondays/Tuesdays). I keep tabs on what’s open so you don’t have to...ask me before you go, and I’ll build your personalized dining itinerary.

🎶 What to Do When It Rains

Because sometimes it does...this is storm season and as long as we don't have anything major coming our way, then these Caribbean "Snow Days" can be a lot of fun!

Lucky Street – Indoor fun, cocktails + games
Sudi’s Caribbean Bar & Grille – Live music + local happy hour specials and they have a generator for those power outages we all know so well.
Mountain Top – Shopping + the best banana daiquiris with a panoramic view.

Can’t Miss Events

September Highlights

🏝️ Sapphire Sundays – Live music on the beach every Sunday at Sapphire from 3-6pm
🎤 Soundbite Wednesdays – Tapas + sunset tunes from Island Favorite, Jon Gazi at Isla Blue x Sand Bar
🛍️ Bordeaux Farmers Market – Shop handmade + local on Sept 14 & 28
SUNDAZE at The Westin – DJ Cypha sets the backdrop with the ultimate pool party on island!

Trips to Book Now for Peak Season (Closed or Limited in Off-Season)

Some of the best island adventures hit pause during September and October but that just means now is the perfect time to book early for high season before they sell out.

🚤 Private Boat & Yacht Experiences

NOVA Luxury Yacht Charters – Picture this: champagne in hand, cruising to gorgeous beaches aboard your own private yacht. NOVA’s fully crewed charters are peak-season perfection for intimate groups or milestone trips. 🛥️✨
GoMojo Tender Rentals – Want to captain your own adventure? These customized RIBS are perfect for a day of DIY beach-hopping with friends and family. Easy, flexible, and 5 stars across the board!

🐠 Family-Friendly & Unique Adventures

Adventures of Saltwater Taffy – A local-favorite experience blending storytelling, snorkeling, and fun on the water. Saltwater Taffy has got to be the highest rated sailing trip on island. Catered breakfast, lunch, cocktails, snorkel guide and your own photo assistant for the day! Perfect for a lighthearted group day. 🐬

🏝️ Must-Do Excursion: Jost Van Dyke

Ocean Surfari’s Jost Trip – An island getaway isn’t complete without a stop at the Soggy Dollar Bar for Painkillers. This trip makes the BVI run easy, fun, and unforgettable. $149/pp plus customs fees gets you the perfect day at White Bay (Passport required!) 🍹

💡 GG Tip: These are the types of experiences that sell out in advance once the season kicks in. Secure your spot now, and you’ll thank yourself when you’re sipping cocktails at White Bay while everyone else is stuck on a waitlist. 😉

Feedback from a GG Traveler

“I came in September expecting a ‘quiet’ vacation with nothing going on. What I got was a perfect week of rest, laughter and friendly faces. I had almost every beach to myself and was lucky enough to catch the full moon party at Sapphire as well. 10/10 recommend.” – GG Guest, Stephanie Atkins 2025