3 Islands, One Trip: St Barth’s, Anguilla + St Martin

If you are looking for an out of the box style trip where you can visit three Caribbean islands very easily in one trip, look no further!

I recognize that often when people travel, they are not thinking about island hopping in the Caribbean (unless they are on a cruise) because there is typically enough to do on one island, let alone, three. 

But I promise, this is an amazing way to see all three of these islands in one trip. 

3 Islands, One Trip: St Barth’s, Anguilla + St Martin: Planning

There are  lot of moving parts that go into planning a trip like this, but I PROMISE, it will not be overwhelming or even hard. I am going to share all my best tips that will makes this relatively easy to plan. 

I do want to note, this is not an overnight planning trip. You should give yourself some time to plan it. 

Things to consider before planning this trip:

Budget: I would have a budget in mind unless you have unlimited funds. This will help dictate how you will build out this trip in many ways. For example: St Barths is the most expensive, but you could also just go for the day very easily. Knowing your budget will decide how your trip will go. 

When to go: Anguilla, St Barth’s and St Martin have a lot of closures between mid-August and into October for Hurricane season. This is not the ideal time to go. If it were up to me, I would go between December – June/July. Noting it is very hot in June and July. 

Be honest with yourself about the type of traveler you are: Knowing the type of traveler that you are or your group is, will help you a lot in the planning stages. For example: if you are big on beaches and not huge on partying, I would tell you to spend more time in Anguilla! The beaches are crystal clear and incredible.

Booking hotels, flights and excursions: I recommend booking your flights and hotels directly with whomever you flight and whatever hotels you decide to stay in. I linked activities within this post so you could easily access those. 

Note: you will be booking some one-way tickets. Make sure to pay attention to that. 

My ideal itinerary:

One-way flight to St Martin 

Round trip flight or ferry from St Martin to St Barths

One-way flight or ferry St Martin to Anguilla (caveat here – if it is cheaper to fly roundtrip from St Martin, than purchase a roundtrip ticket to Anguilla)

One-way Anguilla to home (American Airlines typically has one flight per day for Anguilla)

Language: I have never had any issues on the islands with anyone speaking English. Just note – St Barth’s everyone speaks French unless you address them in English.

Currency: I highly recommend having a credit card and mixed bills in Euros and Dollars. St Barth’s uses Euros, St Martin/Sint Maarten uses dollars, Antillian Guilder on the Dutch side and Euros on the French side, and Anguilla accepts dollars. 

Passport stamps: Yes, all three destinations will stamp your passport!

My ideal Itinerary (you are free to change this in any way that you want):

I think you should build out your itinerary in this order: St Barth’s, St Martin and finish in Anguilla. Reason being, St Barth’s offers lots of partying and beach days, St Martin is more active and Anguilla is relaxing with insane beaches. I don’t like to come home burnt out, but you are free to arrange this however you like. This is my preference. 

First, you need to get this region of the world. St Martin is going to be the best starting point if you want to start in St Barth’s or St Martin. I recommend starting in St Barth’s. 

There are a few ways to get to St Barth’s:

You can fly into St Martin (SXM) and then take a smaller plane (I like WINNAIR) for the 14 minute fight to St Barth’s. This is such an iconic flight, I highly recommend it. 

You could fly to San Juan, Puerto Rico (one-way) and then fly Tradewinds to St Barth’s. This is a little bit more expensive and just over an hour of flying time. However, this flight is more like a personal jet with more space and the price is higher for the flight. 

Lastly, you could fly into St Martin and then take a ferry (Great Bay Express) over to St Barth’s. It is 45 minutes on average and the most economical way to get there. 

St Barth’s

I recommend starting in St Barth’s because it is the place to be and be seen, but also a huge party destination and there are a lot of great beaches. 

You can access my St Barth’s guide for tons more information!

3-4 nights here I think is plenty! I did like 10 and it was a lot. You will need to rent a car to get around as taxis are scarce and there are no rideshare options. Good news: the car rental is the cheapest thing you will get here!

For resort stays in St Barth’s, I loved:

Le Sereno – if you want to stay on a beach, this resort sits on the Grand Cul-de-Sac and its stunning! The rooms come with breakfast and they are beautiful. 

Le Toiny – this is a much smaller resort, only 15 rooms I believe. They are massive rooms, each with their own pool and a lot of privacy! The hotel does sit on a beach and have a beach club, but it isn’t the best beach in St Barth’s by a long shot. 

Le Carl Gustaf – if you want to be downtown in Gustavia, this is where you want to stay. The hotel overlooks the city and Shell Beach and Shellona Beach club are a quick walk down the hill. 

The Christopher – I love this resort and it is waterfront, but no beach access. This is great if you want something a bit cheaper than the others and has an incredible pool with sunset views. 

Beaches not to miss:

St Jean, Shell Beach, Saline Beach, Grand cul de sac, Gouverneur, Colombier, and Flamands Beach! 

You will need a car to get to most of these, unless you are staying at a resort that is on some of them. 

Best beach clubs:

Nikki Beach – you need a reservation here, often months in advance. The absolute best time is the 330pm seating on Sunday! This is the party spot. 

Shellona – I walked right in with no reservation and was sat pretty quickly. It’s not as popular at Nikki Beach but the beach is gorgeous and the food is amazing. 


Downtown Gustavia is lined with luxury shopping! If you love the big fashion houses, you’ll be right at home here. 

Best places to eat:

Le Sereno Al Mare, Shellona, Bonito, On the Rocks at Eden Rock, Hotel Le Toiny, Le Tamarin, and if you want to party at night, Bagatelle. 

Le Sereno Al Mare

Saint Martin

For the next island, I recommend St Martin! Arguably, there is a lot more to do on this island than the other two, but it depends on what you are into! I think 3-4 nights is also ideal here.

One thing to note about the island is that part of it is French and the other part is Dutch. So, Saint Martin is the French side and Sint Maarten is Dutch. There are a lot of options for activities and food here. 

Additionally, getting a taxi is easy and you can also rent a car if you want!

You can take the ferry back or the 14 minute small flight. The choice is yours. 

If you think St Barth’s is just a day trip for you, and it is for many people, just book a day trip ferry!

I only have one resort recommendation and it will blow you away! 

La Samanna – this is a Belmond resort and sits on the spectacular Baie Longue Beach, which is stunning. The water is glittering blue. The spa is fantastic as is the accommodation’s and restaurants. This resort is easily a 10/10.

Best beaches in St Martin:

Baie Longue, Maho Beach (where the planes fly over!) and Orient Beach. This would be the top three. 

Things to do:

Catamaran cruise with lunch and drinks

ATV adventure to explore the island

Sky Explorer and Flying Dutchman 


Day trip Ferry to Saba – if you want to add another island to your trip!

Snorkel underwater park

Caribbean culture and rum tour

Luxury private picnic on the beach

Where to eat:

Freedom Fighters Ital Shack, Ocean 82 and L’Oursin.


For the final stop, Anguilla is my top pick, and arguably one of my favorite places in the world! The beaches here are UNREAL. 

One thing to note about Anguilla, there is a cruise ship embargo, so, you won’t see any big ships here!

Anguilla is a rather quiet island compared to St Barth’s and St Martin. I feel very strongly that people come here for a true vacation to relax and enjoy the beaches and the culinary scene. 

You can rent a car or Moke here to get around or request a taxi. 

All that being said, if you cannot sit still or slow down, I would not spend a ton of time here. If St Martin and St Barth’s are more your speed of activities and partying, put more days in those destinations. 

I think three nights here is plenty. However, if this is more your style, put the majority of your time here and stay a night or two in St Martin and do a day trip to St Barth’s from St Martin. 

To get here from St Martin, you can either take the ferry or fly. The choice is yours, but the flight is the shortest international flight in the world! Which is so cool! It’s only about 8 minutes total. You can fly with Anguilla Air Services or take the ferry with Funtime Charters or Calypso Charters. 

Where to stay in Anguilla:

Four Seasons: I only have one recommendation as I have not made it back to the island, but this stay was incredible. If you have been following me for any measure of time, you have seen me talk about it. You can read about my stay here.

I love this resort because every room category except one has a pool in the room and the resort sits on two beaches! One of them being one of the best on the island: Meads Bay!

Best Beaches:

Shoal Bay, Meads Bay and Rendezvous Bay Beach. The island has 33 beaches and they are all super clear with soft white sands. 

Where to eat:

SALT and Half Shell Raw Bar. Make sure and try Johnny Cakes!! They are popular here. 


Pin for Pinterest: