Once you find a trip you like, review our Travel Policies, and contact us to get signed up.
2022
Key Largo
February – October, 2022
With several great trip leaders!
These trips make for the perfect getaway: easy to get to, short, 6-diver max, personal boat, and personal on-site accommodations within walking distance of the boat!
Since they’re so popular, we’re running 16 of them in 2022! Each trip only takes 5 divers, so sign up now! If you don’t see a date you want, contact us about custom trips.
Availability listed with dates on the trip page
Bonaire
April 9 – April 16, 2022
With Randy
Bonaire has some very easy, yet incredibly beautiful dive sites, giving new divers an excellent chance to gain a LOT of bottom time and experience. Then, it has some more challenging sites for more experienced divers. Plus great infrastructure, including excellent first-responder services and an excellent grocery store. The people are friendly, and it’s located below the hurricane belt, so the constantly sunny, never too-hot climate is almost boring.
Sold Out
Cozumel
May 21 – May 28, 2022
With Paul
Cozumel is one of those places you can go back to year after year. In fact, Paul does just that! This trip is one of our cheaper trips, but still includes everything you need! All you can eat and drink at the resort, several restaurants, a short walk to the boats, and a beautiful beach to return to.
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Cocos Islands
June 11 – June 21, 2022
With Dennis Z
After a beautiful air-conditioned bus ride through a very scenic Costa Rica, you get to board the Okeanos Aggressor II for 10 days! There will be tons of diving where you’re sure to see some amazing things.
1 Spot Open
St. Lucia
July 2 – July 9, 2022
With Billy
St. Lucia is a diving destination unlike any other. The beautiful island isn’t just for divers. Within the resorts, are acres of wildlife to explore. Lounge on the beaches, bike through the mountains, explore French ruins, or just sit back and enjoy the most delicious food.
Sold Out
Bonaire
September 3 – September 10, 2022
With Randy
Bonaire has some very easy, yet incredibly beautiful dive sites, giving new divers an excellent chance to gain a LOT of bottom time and experience. Then, it has some more challenging sites for more experienced divers. Plus great infrastructure, including excellent first-responder services and an excellent grocery store. The people are friendly, and it’s located below the hurricane belt, so the constantly sunny, never too-hot climate is almost boring.
Sold Out
Dominica
September 3 – September 10, 2022
With Billy
Explore the dramatic topography of the sea and the land, whether it’s watching sea turtles and whales or canyoning or hiking to waterfalls, there are tons to see! Above water, you’ll have bird watching, fishing, hiking, canyoning, and waterfalls to see! Underwater, you’ll see volcanic ledges, reefs, and walls filled with seahorses, frogfish, batfish, flying gurnards, jawfish, upside-down jellyfish, and flamingo tongue snails.
1 Spot Left
Cayman Brac
November 5 – November 12, 2022
With Laine
Cayman Brac is an excellent trip! It’s fairly easy to get to, the resort is beautiful, and the food is delicious Caribbean fare that can’t disappoint. We conveniently dive with the resort and simply walk back for a wonderful lunch.
Sold Out
2023
The Emperor Explorer in the Maldives
February 26th – March 5th, 2023
With Shannon and Jen McDonald
Join us aboard the magnificent Emperor Explorer. Discover the beauties of the pacific from mantas to mola-mola. Then, for our shark lovers, enjoy whale sharks, grey reef sharks, oceanic black tip sharks, hammerhead sharks, and occasional bull sharks!
4 Spots Left
Cayman Aggressor in the Cayman Islands
June 24 – July 1, 2023
With Randy
During your Caymans Island liveaboard scuba diving trip, the Cayman Aggressor V will dive the best of all three islands, which includes the Northwall and Southwall in Grand Cayman, Bloody Bay Wall in Little Cayman & everyone’s favorite, Stingray City. The Oro Verde, Doc Poulson, Russian Destroyer and Kittiwake wrecks are bustling artificial reefs that disguise once magnificent ships and are a must see for every diver.
Truk Odessey in Truk Lagoon
July 1 – July 8, 2023
With Billy
This is a once-in-a-lifetime type of trip. It takes a few days to get there, but it is well worth it! The wrecks are unbelievably preserved. Every detail of the engine room, bunks, and bridge is as it was almost 80 years ago.
Sold Out
Komodo Islands
July 16 – July 25, 2023
With Dennis Z
It is said that half the fun is getting there. So let’s get to the Komodo Islands in traditional style aboard an all teak 132′ Pinisi sailing vessel, the Aurora! Traditional style with all the modern conveniences. That means 8 spacious cabins each with private bathrooms and air conditioning.
Sold Out
Blackbeard’s Sailboat in the Bahamas
September 2 – September 8, 2023
With Lauryn
The Blackbeards sail/dive charter is an adventure that we’ve been doing at Gypsy since the late 80’s – it’s fun, it’s dive-intensive, and it’s great value for the money. Dive sites are in the Out Islands of the Bahamas. You get it all: reefs, wrecks, walls, blue holes, drift, night, deep and shark feeding dives.
Bonaire
September 2 – September 9, 2023
With Randy
Bonaire has some very easy, yet incredibly beautiful dive sites, giving new divers an excellent chance to gain a LOT of bottom time and experience. Then, it has some more challenging sites for more experienced divers. Plus great infrastructure, including excellent first-responder services and an excellent grocery store. The people are friendly, and it’s located below the hurricane belt, so the constantly sunny, never too-hot climate is almost boring.
2024
Aqua Cat in the Bahamas
June 22 – June 29, 2024
With Randy
We’re headed back to the Aqua Cat! If you’ve been in our store within the past year, you’ve noticed our screen playing our last Aqua Cat trip. We had such a great time, we’re going back!
Bonaire
August 31 – September 8, 2024
With Randy
Bonaire has some very easy, yet incredibly beautiful dive sites, giving new divers an excellent chance to gain a LOT of bottom time and experience. Then, it has some more challenging sites for more experienced divers. Plus great infrastructure, including excellent first-responder services and an excellent grocery store. The people are friendly, and it’s located below the hurricane belt, so the constantly sunny, never too-hot climate is almost boring.
2025
Humboldt Explorer in the Galapagos
June 16 – June 23, 2025
With Randy
Your Galapagos Liveaboard diving adventures will encompass everything from sharks to nudibranchs and more. The islands are best known for amazing shark diving around Wolf and Darwin Islands. These small and remote islands are best reached by liveaboard vessels for divers. Your diving experience here will generally include Galapagos sharks, silky sharks, and lots of schooling hammerheads being cleaned by king angelfish. Seeing marine turtles, schools of tuna, eagle rays, and sea lions are very common. And seeing a whale shark is very possible from June through November. All the islands you travel to are amazing sites for underwater photography.