Damn Good Sailfish Fishing Charters In The Caribbean Sea

Check real-time availability and compare rates on Caribbean Sea sailfish fishing trips. Confidently book your next day on the water.

Choose a Date
4.7/5 Average Rating

Recently Booked Sailfish Fishing Charters In The Caribbean Sea

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Montego Bay

Montego Bay Offshore Trip

NEW
38 ft 1 - 6 People From $700
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Punta Cana

Offshore Blue Marlin FADs Trip

100% (8)
42 ft 1 - 7 People From $2,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Punta Cana

Luxury Punta Cana Adventure

96% (25)
36 ft 1 - 6 People From $750
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Punta Cana

Offshore Trolling Adventure

96% (25)
37 ft 1 - 6 People From $600
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Punta Cana

Punta Cana Luxury Trip 3/4 Day

100% (8)
42 ft 1 - 6 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Punta Cana

Punta Cana Luxury Trip

100% (4)
38 ft 1 - 12 People From $875

Top Types of Sailfish Trips in the Caribbean Sea

What makes Captain Experiences Damn Good?

Damn Good Guides

You will only find quality, vetted guides on Captain Experiences, and we know them all on a first-name basis.

Damn Good Guides

Experts Available 24/7

Our US-based team is available 24/7 to help you with any questions or concerns.

Experts Available 24/7

100% Weather Guarantee

We want to keep everyone safe, so if the weather is bad we'll work with you to reschedule at no cost.

100% Weather Guarantee

4.9 / 5 Average Rating

We hand pick our Damn Good Guides, and our network spans across North America and beyond.

4.9 / 5 Average Rating

“Our Damn Good Guides go above and beyond, and we've handpicked every single one. We're passionate about the outdoors and look forward to getting you out on the trip of a lifetime, every time.”

Jonathan and Attison   |   Co-founders   |   Austin, Texas

More Sailfish Fishing Charters In The Caribbean Sea

Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Punta Cana

Punta Cana Luxury Trip VIP

100% (4)
43 ft 1 - 12 People From $1,220
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in George Town

Deep Sea Fishing

NEW
27 ft 1 - 12 People From $1,300
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in El Combate

Combate Private Fishing Charter

100% (4)
26 ft 1 - 12 People From $1,208
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore, Flats Fishing in Cabo Rojo

REEF FISHING EXPERIENCE

100% (2)
23 ft 1 - 5 People From $650
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Rincon

Epic Sportfishing - Rincon, PR

100% (4)
26 ft 1 - 6 People From $1,208
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Rincon

Tuna Marlin And More

NEW
35 ft 1 - 6 People From $850

Didn't Find What You Were Looking For?

Our guides are Damn Good Guides, which means they’re vetted by our team of outdoor experts who know them on a first-name basis. We hand pick each and every one of them, and our network spans all across the US and beyond.

The proof is in the pudding, and we’re incredibly proud of our 4.9 / 5 average review score. Hit the button below to see more trip options:

Everything to Know About Booking a Caribbean Sea sailfish fishing charter

What are the best sailfish fishing charters in the Caribbean Sea?

The best sailfish fishing charters in the Caribbean Sea are:

Why should I book a sailfish fishing charter in the Caribbean Sea with Captain Experiences?

Our Damn Good Guides currently offer 42 sailfish trips in the Caribbean Sea, and the most popular trips in the area are Montego Bay Offshore Trip guided by Billy, Offshore Blue Marlin FADs Trip guided by Edgar, and Luxury Punta Cana Adventure guided by Anthony.

Our guides in the Caribbean Sea are rated a 4.7 out of 5 based on 9298 verified reviews on Captain Experiences.

All guides on Captain Experiences are vetted by our team. You can access their reviews, click through trip photos, read bios to get to know them, and preview trip details like species, techniques, group sizes, boat specs and more.

Looking for kid friendly sailfish guides / fishing lessons in the Caribbean Sea? Check out our beginner and family friendly sailfish guides in the Caribbean Sea.

What types of sailfish fishing charters are common in the Caribbean Sea?

Deep Sea fishing is the most popular type of fishing for sailfish in the Caribbean Sea as well as nearshore fishing, inshore fishing, and flats fishing.

The most common fishing techniques in the Caribbean Sea are trolling, heavy tackle fishing, and bottom fishing but jigging and light tackle fishing are popular as well.

How much do Caribbean Sea sailfish fishing charters cost?

Prices for sailfish in the Caribbean Sea can range anywhere from about $650 to $3,400, but the average price for a half day trip for sailfish in the Caribbean Sea is $1,282. The average price for a full day trip for sailfish in the Caribbean Sea is $2,150.

Is booking a fishing guide worth the money?

Hiring a guide provides a number of benefits and many choose to book a fishing guide for a combination of experience, local knowledge, convenience, and cost-effectiveness.

Working with experienced fishing guides who know the best local spots and techniques can dramatically increase your odds of a great day. Having someone who is on the water every day and knows the area like the back of their hand is going to give you the best chances of success.

Booking a guide is also more cost effective, especially if you only get out a handful of times per year. When you consider all of the costs you would incur on your own such as the price of a boat, maintenance, insurance, gas, high-quality gear and tackle, repairs, and more, you’ll find that DIY is sometimes not worth the expense.

Even if you’ve got a great setup already in your home waters, booking a guide also provides a great opportunity to experience new techniques, new locations, or even a chance at a new target species to knock off the bucket list.

What month is best for sailfish fishing in the Caribbean Sea?

The most popular season for sailfish fishing in the Caribbean Sea is spring, and most anglers book their trips 23 days in advance.

Do I need a the Caribbean Sea fishing license for sailfish and what are the bag limits for sailfish in the Caribbean Sea?

See here for more information on sailfish fishing licenses in the Caribbean Sea, sailfish bag limits, and fishing season regulations for sailfish in the Caribbean Sea. When in doubt, your guide will always know all the relevant sailfish rules and regulations in the Caribbean Sea.

Recent Reviews

  • ★★★★★
    Tough day of fishing, but the crew works to catch fish. Not too much you can do when they aren’t biting, but it is a professional operation.

    Mark G. | August 3, 2026

    Trip: Offshore Blue Marlin FADs Trip

  • ★★★★★
    Crew was great!!!! Exciting catches. Boat was as expected!!!!!

    Peter O. | July 22, 2026

    Trip: Punta Cana Luxury Trip 3/4 Day

  • ★★★★★
    Excellent guide! Will definitely book again next year for more than once out! Have more photos but they are on my wife’s phone lol. Caught lots of fish and one heck of an experience! Top notch!

    William C. | July 19, 2026

    Trip: Offshore Trolling & Live Bait

  • ★★★★★
    We had a great time even though the waves were high. Only got one in the boat but Luis was amazing and very friendly. All in all great experience great time good times with good people.

    Trent P. | July 5, 2026

    Trip: La Parguera Offshore Fishing

  • ★★★★★
    Alberto was great today. He worked hard all day to find us a blue marlin. We had our chance at one but was unsuccessful. Thanks Brandon

    Brandon K. | June 30, 2026

    Trip: Deep Water Seamounts

Narrow Down Your Search

Last updated: September 11, 2026

Enter to Win a

$500 DAMN GOOD GIFT CARD

Gift Card

Sign up to win $500 towards ANY trip. Winners drawn monthly.

By subscribing, you agree to receive marketing communications from Captain Experiences. To opt-out, click the unsubscribe button at the bottom of our emails. Privacy Policy and Terms & Conditions

See All Sailfish Trips in the Caribbean Sea