Many destinations in the Caribbean can be reasonably priced vacations if you plan correctly and take advantage of some of the tools available to you. I booked a trip to St. Martin on a whim because when I returned from Kenya, I just felt I needed another vacation that was more relaxing and low energy.

For this trip, my strategy looked a little different, because I had nearly 50,000 Delta Skymiles points that I wanted to be able to use for my flight. My hope was that most, if not all, of the flight would be covered by accrued miles, and it turned out, a trip to St. Martin would only cost me 27,000 points plus $98, noting that a 15% discount was also applied for being a Skymiles member.

I searched Expedia and found a beautiful luxury hotel property in the Oyster Pond neighborhood called Princess Heights Luxury Boutique Condo Hotel, which I was able to book for $1200. Being an Expedia member also means discounts on bookings, access to properties that non-members don’t have, and earning rewards points that can be used toward future bookings.

Finally, I booked experiences through Viator, an island tour for $60 and a day trip to Anguilla for $150, which brought me to just over $1500.

This $1500 trip included:

St. Maarten (a dual Dutch/French island with stunning beaches, delicious food, and shopping)
Anguilla (known for white-sand beaches and a luxury island experience)

Here’s exactly how I made it work.

Why St. Maarten Is a Budget Traveler’s Secret Weapon

If you’re trying to stretch your travel dollars in the Caribbean, St. Martin is one of the best places to start, because:

It’s a major regional hub with frequent flights from the U.S.
It offers direct access to multiple nearby islands by ferry or by plane
You get two cultures on one island (French + Dutch)
Excursions are plentiful and competitively priced

From St. Maarten, you can easily reach:

Anguilla (ferry or day cruise)
St. Barths
Antigua
St. Kitts
Nevis
Saba
Statia (St. Eustatius)

This makes it an ideal base if you want the island hopping experience without paying for multiple long-haul flights.

How I Saved on Flights: Airline Points & Flexibility

Flights are usually the biggest expense and where the biggest savings live.

As I mentioned earlier, I booked my flight using Delta airline miles, which significantly reduced my out-of-pocket cost to $98. If you’re sitting on points, you can check the special offers to see if there’s a deal for a destination you’re interested in or search for a destination you have in mind, making sure to toggle on dollars + miles.

Tips:

Be flexible with travel dates; I generally try to leave on a Tuesday when flights can be cheapest
Use points for Caribbean routes where cash prices spike seasonally

Even partial point redemptions can knock hundreds off your total.

Use Hotel Rewards to Lower Costs

For this trip specifically, I used a few Expedia reward points toward my stay, but I do want to note that there are other hotel chains and third party sites that offer reward points for booing stays. You can lean into programs like Marriott Bonvoy or Hilton Honors to find stays that you know will be reliable, clean, and well-located. Pairing a mid-range hotel with points or member discounts is one of the easiest ways to keep Caribbean travel affordable.

The Game-Changer: Booking Experiences Instead of DIY Planning

Here’s how this trip really came together. Instead of planning everything myself, I used Viator to book excursions that gave me a comprehensive experience of the island as a first-time visitor.

Full Island Tour of St. Maarten – $60

This guided tour covered:

French and Dutch sides of the island
Major hotspots like Maho Beach, Orient Bay, and Marigot
Historical context you wouldn’t get driving yourself

For $60, it eliminated transportation costs and guesswork while I got to experience the beaches and everything in between on the island.

Anguilla Day Cruise – $150

This was a 7-hour cruise with:

Multiple beach stops
Time in Anguilla without an overnight stay
Lunch, snacks, and drinks included

Considering Anguilla is often marketed as ultra-luxury, this is a great budget-friendly way to experience it without paying extremely high prices.

Memberships That Save You Money

The perks that come with memberships have to stack before you can use them, but it’s worth it to prioritize earning points wherever you can and for the brands you use often. Here are some that I utilize:

AMEX credit card rewards: great for flights, statement credits, and travel protection
Expedia membership: discounted hotel rates and bundled savings
Marriott Bonvoy: free nights, member pricing, and late checkout perks
Viator: safe and reasonably priced experiences that you earn reward dollars for

None of these require exorbitant spending, just consistency.

The Reason This Trip Worked

This trip wasn’t about finding the cheapest option for everything. It just worked because I:

Used points where they mattered
Chose a reasonable mid-range hotel
Booked comprehensive experiences instead of piecing things together
Picked a destination that naturally supports island hopping

Caribbean Travel Is More Accessible Than You Think

St. Maarten + Anguilla for $1,500 was totally about strategy, and if i’m being honest, I could have strategized even better to be able to visit other islands like St. Barths as well. The great thing about learning as you go is that the next time you go to plan a trip to the same location or a nearby destination, you have more than enough information to make it even more fulfilling the next time around.

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