Idyllic Island Honeymoon: 8-Nights on Anguilla and St. Barth

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Curated By

Sebastian Luxe Travel

  • Tropical Vacations

  • Honeymoons

  • Couples Travel

  • Luxury Travel

  • Anguilla

  • St. Barths

  • Island

Advisor - Idyllic Island Honeymoon: 8-Nights on Anguilla and St. Barth
Curator’s statement

Anguilla and St. Barth are close enough to combine easily in one Caribbean honeymoon, but different enough that the trip genuinely feels like two vacations. I like starting in Anguilla, where the beaches are extraordinary and there is very little pressure to do anything at all, then finishing in St. Barth with its restaurants, shopping, beach clubs and distinctly French sense of fun. Four nights on each island gives you enough time to settle in, and the logistics between them are surprisingly easy.

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Day 1: St. Maarten touchdown and sail to Anguilla

The honeymoon begins on Maundays Bay, where the water looks almost suspiciously turquoise.

Start the honeymoon by flying into St. Maarten and taking the boat directly to Anguilla. This is my favorite way to begin the trip because you skip another airport connection, get onto the water almost immediately and arrive in Anguilla already feeling like the honeymoon has started. The transfer is easy enough that the journey feels like part of the vacation rather than another travel day.

Once you arrive in Anguilla, head to Cap Juluca on Maundays Bay. Check in, put on a swimsuit and do almost nothing for the remainder of the afternoon. Maundays Bay has the sort of bright turquoise water that makes even very reasonable sightseeing plans seem unnecessary.

For your first night, stay at the hotel for dinner. After a wedding and a travel day, there is absolutely no need to prove anything by immediately crossing the island for a reservation.

Day 2: Maundays Bay and a proper resort day

A couples massage at Cap Juluca, because honeymoon scheduling should occasionally consist of nothing more ambitious than deciding which robe is yours.

Do not book an excursion your first morning. Have a long breakfast, swim in Maundays Bay and allow yourselves a full resort day at Cap Juluca. This is a particularly good day for a couples massage, paddle boarding, a long lunch or several uninterrupted hours on the beach.

One of the reasons Anguilla works so well at the beginning of a honeymoon is that there is very little pressure to sightsee. You can have an excellent day without doing much more than moving between the water, your beach chair and lunch.

In the evening, leave the resort for dinner and start exploring Anguilla's excellent restaurant scene. I would choose one special dinner reservation rather than trying to fit cocktails, dinner and nightlife into the same evening. The entire point of starting here is to slow down.

Day 3: Private boat day around Anguilla

A private boat day is one of the few things I would consider essential during four nights in Anguilla.

Today is the day to book a private boat. Spend several hours exploring Anguilla from the water, with time for swimming and snorkeling and the flexibility to stop wherever conditions are best that day.

I prefer a private charter to an overly structured group excursion on a honeymoon because you can decide how ambitious you actually feel once you are out there. Stay somewhere beautiful longer than planned, stop for lunch or spend most of the afternoon swimming. There should be very little clipboard energy involved.

Keep dinner relatively easy that evening. After a day of sun and saltwater, this is generally not the night anyone wants an elaborate itinerary.

Day 4: Explore more of Anguilla

Live music at Leon’s on Meads Bay, where dinner comes with sand under your feet and one of Anguilla’s best backdrops.

Use your final full day to see another side of the island. Spend some time around Meads Bay, visit Shoal Bay or simply decide that Maundays Bay is too good to leave and stay exactly where you are.

This is also a good day for a long beach lunch. Anguilla's restaurant scene is unusually good for such a small island, and I would never recommend spending the entire trip eating only at your resort.

For your final evening in Anguilla, make one of your favorite dinner reservations of the trip and linger. By this point, you should have adjusted completely to island time, which is convenient because tomorrow's journey to St. Barth is almost comically easy.

Day 5: The 12-minute flight to St. Barth

Twelve minutes in the air and suddenly the honeymoon feels like an entirely different vacation.

After breakfast, head to Anguilla’s tiny airport and fly directly to St. Barth. The flight takes about 12 minutes, and both airports are so small and easy that changing islands feels far simpler than people expect when they first see a two-island honeymoon itinerary.

This little flight is one of the reasons I love pairing Anguilla and St. Barth. You get two completely different Caribbean experiences without losing half a day to complicated transfers. You are barely in the air long enough to settle into your seat before St. Barth appears below you.

Once you arrive, check into your hotel and give yourselves the afternoon to settle in. Depending on where you stay, that might mean Flamands Beach, Grand Cul-de-Sac, a private pool overlooking Toiny Bay or somewhere closer to Gustavia. I would resist the temptation to start sightseeing immediately. Have lunch, swim, unpack and enjoy wherever you chose to stay.

That evening, head into Gustavia for dinner. After four wonderfully quiet nights in Anguilla, the harbor, restaurants and people-watching immediately make the second half of the honeymoon feel like a different trip.

Day 6: Gustavia, shopping and Shell Beach

Gustavia is small enough to wander without a plan and stylish enough that wandering somehow still involves shopping.

Spend the morning slowly exploring Gustavia. Wander around the harbor, browse the shops and stop for coffee without feeling any obligation to turn the morning into serious sightseeing.

Then walk over to Shell Beach for a long lunch and some time by the water. This is one of my favorite ways to structure a day in Gustavia because you can combine shopping, lunch and the beach without spending the entire day driving back and forth across the island.

Return to your hotel in the late afternoon for a swim and some downtime before dinner. St. Barth has plenty going on, but you do not have to participate in all of it simultaneously.

Day 7: Discover a quieter island side

Some of St. Barth’s best moments are the quiet ones, especially when they happen from a private pool suite at Cheval Blanc.

Spend today seeing the less social side of St. Barth. Gouverneur and Saline are both beautiful options when you want a beach without a beach-club scene, while Colombier feels even more removed and can be reached by hiking or by boat.

One of the misconceptions about St. Barth is that the entire island revolves around restaurants, beach clubs and seeing people you vaguely recognize from somewhere. It does not. Some of its most beautiful places are wonderfully quiet.

You could also make this a day to enjoy your hotel. If you are staying at Le Toiny, spend some time at the beach club or by your private pool. At Le Barthélemy, Grand Cul-de-Sac is ideal for swimming and water sports. Wherever you are staying, leave enough time in the afternoon to actually enjoy it.

Choose somewhere atmospheric and romantic for dinner that evening. After a quieter day, this is a good night for one of the island’s special restaurants.

Day 8: A long lunch and one last day in paradise

Save a little room in the itinerary for doing absolutely nothing. It is still a honeymoon.

For your final full day, choose your level of activity carefully. Make it a proper St. Barth beach-club day with a long lunch somewhere lively, or decide that your hotel is too lovely to leave and spend the afternoon exactly where you are.

This is the day I would avoid trying to check anything else off a list. Have a late breakfast, swim, order lunch somewhere beautiful and leave yourself enough time to enjoy the hotel you paid a considerable amount of money to stay in.

For the final evening, return to Gustavia for one last dinner or arrange something quieter and more private. This is the night for whichever version of St. Barth feels most like you, whether that means getting dressed up and going out or having dinner barefoot near the water.

There is no prize for leaving St. Barth having successfully visited every restaurant.

Need to know

For this itinerary, I recommend doing the islands in this order: Anguilla first and St. Barth second.

Starting in Anguilla gives you a few days to come down from the wedding, sleep late, swim and spend an unreasonable amount of time looking at turquoise water. St. Barth then changes the energy completely with Gustavia, excellent restaurants, shopping, beach clubs and a little more nightlife.

Where you stay in St. Barth changes the personality of the second half of the trip. Cheval Blanc is ideal for a polished beachfront stay on Flamands, Le Barthélemy has a relaxed setting on Grand Cul-de-Sac, and Le Toiny is wonderful for couples who want more privacy and a private-pool villa feel. There is no single “best” hotel for every honeymoon. The right one depends on how social, private, beach-focused or scene-adjacent you want the trip to be.

That contrast between the islands is exactly why the combination works. You are not simply switching hotels midway through your honeymoon. The second half genuinely feels like a new trip.

I recommend at least four nights on each island. If you have ten nights rather than eight, even better. I would add an extra night to each island rather than trying to squeeze a third destination into the itinerary.

Restaurant and beach-club openings in St. Barth can be seasonal, so exact plans should always be confirmed based on your travel dates.

If you are planning an Anguilla and St. Barth honeymoon and would like help choosing the right hotels, room categories, transfers, restaurants and experiences, feel free to reach out.

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