Northern Caribbean Island Hopping Itinerary

I had an expiring Delta certificate from a flight bump a year ago and the New York JFK – St. Maarten flight was nearly the exact amount left on the cert. Off-season Caribbean here I went. If you have been following me on Instagram, facebook or twitter you’ve seen the pictures as I darted around the islands.

In this series:

Saba 01

Saba Island

I am not a beach person and not much for chilling out, so my goal was a rapid-fire survey of the islands, see what might qualify for a languid trip with my wife, and scoop up a few Travelers’ Century Club locations. This is not the recommend way for most people to see the Caribbean, quite against the spirit of doing nothing, however I had a lot of fun.

What was clear is to avoid cruise ships and peak season. These are small islands with limited infrastructure. I can’t imagine St. Kitt’s with a bunch of mega ships at dock. They taper off by April, so May-June, ahead of hurricane season, is a nice time to visit.


The challenge was to scoop up as many places as possible without attempting to fly LIAT, which everyone with Caribbean experience says to avoid at nearly all costs. In my short visit I saw plenty evidence of their massive delays. So I turned to St. Maarten-based WinAir and ferries. WinAir really impressed me with every flight on their fleet of four DHC-6 Twin Otter planes arriving early and the flexibility to change to earlier different flights as needed. Being offseason some flights had only a couple people but none were canceled.

Booking WinAir was more of a challenge. Trying to book all my flights together had the allure of savings through ITA and Hipmunk but I never was able to get any to ticket. I played the Orbitz “this fare has sold out” game for a while as well as at other sites. Eventually I had to book the first segment as a one-way on Priceline and the rest as a multi-city on Expedia, in total $60 less than booking on WinAir but $150 more than the theoretical savings on Hipmunk. It would have been even pricier to book each roundtrip separately. If you book them, play with some combinations to see what works.

Day 1:

  • New York – St Maarten (SXM) on Delta, arriving 13:05.
  • Original plan was to try to catch the 13:20 WinAir to Saba (SAB) rather than the 17:45 I booked, but WinAir took off 20 minutes early, which is typical for them.
  • Alternate: taxi to the French side of the island, St Martin, for the ferry to Anguilla.
  • 1.5 hour taxi tour of Anguilla.
  • Ferry back to St Martin, taxi to St Maarten, 17:45 flight to Saba.
  • Overnight at budget guesthouse El Momo Cottages on Saba.

Day 2:

  • Dawn hike up to Mt. Scenery (took a nasty tumble on the way down, spent the morning bandaging up and washing my  clothes).
  • 10:55 flight back to St Maarten, connecting to St. Barth’s (SBH).
  • Walk from St. Barth’s airport to Gustavia and around the town. Rarely wear sandals and forget to put sun block on my feet: ouch!
  • 14:05 flight back to St Maarten (originally booked 16:10 but I had seen enough of $18 crepes and hamburgers).
  • Overnight at Travel Inn Hotel in Simpson’s Bay near St Maarten airport (only recommended as a cheap, transit hotel; no beach).

Day 3:

  • 08:15 flight to St Kitt’s (SKB).
  • Rental car with Hertz and drive to UNESCO-listed Brimstone Hill Fortess and around the island plantations.
  • Found ripe soursops to eat:  if I ever live on a tropical island by base reuqirement is ample supply of soursop, passion fruit and coconut.
  • Unplanned addition: ferry to Nevis and back, just in case they ever exercise their independence option. The ferry was most pleasant than sitting in St Kitt’s heat.
  • Walking tour of Charlestown, Nevis, including the Alexander Hamilton birth house.
  • 19:25 flight from St Kitt’s back to St Maarten via Nevis (at one point I had looked at booking from Nevis, however that was breaking my fare. I did call WinAir and they said I could probably walk up at Nevis and get it sorted for a $35 change fee).
  • Overnight at Travel Inn Hotel again.

Day 4:

  • Already visited Anguilla so morning was clear and I stayed at hotel and caught up on work.
  • 14:15 Delta flight back to New York.

In the following posts I will give my thoughts on each of the islands. In this cluster I only missed St Eustatius. Preview: Saba was my favorite.

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  • Alan

    How much did you spend?
    I did something like this except SKB for a 3 nights trip to SXM… But all on ferry.

  • @Alan – with the low season the Saba ferries were reduced and the St Barth’s ferry seemed about a wash in costs when adding get to from the port on St Maarten since I didn’t rent a car and by combining the WinAir it seemed to help with the St Kitts airfare. The Delta was $390 paid by a cert, WinAir came to $550, others including cheapie hotels about about $400 to the trip, not a cheap region to dart around. That was all put together last week, so some of the WinAir segments were in their higher buckets.

    Which did you like best?

  • I am so envious of you! I have wanted to visit Saba for years, and it just never worked out. I’m also not a beach person, but rather enjoy scenery. My husband loves aviation, so he would totally be into Saba’s shortest runway in the world. Look forward to more on it!

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  • guera

    Looking forward to this one! When its all said and done, I hope you’ll which islands are worth visiting if you are not interested in beaches and going to restaurants.

    For years St. Bart’s was on my list, because people had ranted about how wonderful it was. About 3 years ago, I had the opportunity to fly from San Juan, PR to St. Barts because my daughter was working as a pilot for a charter outfit in PR. I spent several hours driving around the island, and then spent an afternoon sipping wine at that beach restaurant at the end of the runway watching airplanes take off. It was a pleasant day.

    However, the island visitors consist of French tourists who come there and rent a house, and then alternate going to the beach and to the many restaurants. For me, this is fine for a day or two, then I am ready for something else.

    So I am interested in hearing about islands which have some interesting (to me) things to do, like hike to waterfalls, or have good beach snorkeling.

  • @Guera – and many of those vaunted French restaurants in St Barth’s seem to specialize in either crepes or hamburgers, not as inspiring as advertised.

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  • john

    Thank you for this. Its interesting. I was once on SXM for work and was toying with doing similar day trips. In the end I was dissuaded by cost and hassle.
    When I looked at needing a rental car on each island (so paying for two each day doing day trips), plus the flight/ferry costs…. oye.. and for what?
    I did not know there were public transport options on SXM. I share your disdain for the place.

    One major detractor for me was all the immigration hassle. being on island time and doing two border crossings a day just seems like a nightmare. Did you not waste a lot of time in immigration since each island is its own entity? I mainly have experience of this in the ABCs where a twenty minute flight requires actually takes ~three hours between rental car drop off/pick up, check in, and immigration (oh and island time). Is it not so bad up around SXM?

  • @john – perhaps because of off-season and the big intl flights to SXM cluster midday, I had no lines to speak of anywhere for my morning and evening comings and goings, all were fast and cursory. All the regional airports were deserted or nearly so, for instance my St Kitt’s flight was me and one other guy in the whole airport. Only the smallest hiccup was on St Kitts, the first immigration officer said, “I’m eatin'” and made me go to the next guy in the empty hall. Saba was particularly efficient, once you check in, you go to immigration to get stamped out, continue waiting by the cafe in the only room of the airport, and once the incoming plane arrives you dart out and the entire turn is less than 10 minutes.

    There are minimal security hassles on the islands, other than SXM which follows the full liquids, belts, shoes thing.

    Costs were a bit of a pain, I only rented a car in St Kitts. Anguilla I hired a taxi for 1.5 hours. St Barth’s I walked, Saba a taxi up the mountain to the town and walked while there, Nevis I walked for the hour I was there. Nonetheless, costs did add up and this was primarily rationalized as a Travelers’ Century Club trip.

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