Travelogue: Our Points and Miles Stay at Hermitage Bay Resort
Two Amex Hilton Aspire card free night certificates led to a beach cabana at one of the Caribbean's most intimate all-inclusive resorts.
The alarm on our phones went off at 3:30 in the morning on February 7, 2025. That’s the price of a same-day arrival in Antigua from Dallas, and for what we experienced at the end of it, a hell-of-a-trade.
Before I get into the trip itself, the points and miles picture: the two nights at Hermitage Bay were booked using my two Amex Hilton Honors Aspire free night certificates. Cash rate at the time: $3,900 per night. $7,800 in hotel value at no additional cost beyond the card’s annual fee. The Airbnb for the first two nights was booked through deltaairbnb.com, the Delta and Airbnb partnership portal that earns SkyMiles on every booking, and paid for with Airbnb gift cards purchased at a grocery store at 4x Membership Rewards points while working on a sign-up bonus minimum spend. Even the transit to the resort had a strategy behind it, booked through Priceline using the Capital One Offers page to earn 7x Capital One miles, in addition to the Amex Membership Rewards points.
Getting There: DFW to Antigua via Charlotte
We thought we were going to miss the first flight of our trip because the Skylink trains connecting the terminals at DFW Airport were experiencing issues. Because American changes gates and even terminals several times in the hours before your flight boards, we always park at Terminal E, regardless of what terminal we’re supposed to fly out of, so we can take advantage of Terminal E’s Clear+ PreCheck checkpoint, and then take the monorail to whatever terminal ends up being the one we need. Terminal D was quiet and nearly empty when we arrived. We were booked into first class on our flight to Charlotte and in the main cabin on the second flight. American upgraded us to first about an hour before the flight, always a pleasant surprise when flying out of DFW.
AA1702 pushed back from DFW Terminal D at 5:52 AM on February 7 (eight minutes early) on an Airbus A321 (tail N510UW, first flight March 2009, about 15 years and 10 months old at the time of the trip). First class. The flight landed in Charlotte at 9:12 AM Eastern, twenty minutes ahead of schedule.
That early arrival converted a tight 1h 23m scheduled connection into a comfortable 1h 43m actual buffer. Charlotte is a workable airport when you’re not running through it. We had time to enjoy a Starbucks coffee and pastry while we waited.
The Charlotte-to-Antigua leg was on a Boeing 737-800 (tail N959NN, about 10 years and 3 months old). AA2124 departed on time and landed at V.C. Bird International at 3:38 PM Atlantic time, 22 minutes ahead of schedule. Gate-to-gate from DFW, the actual journey took 7 hours and 46 minutes. We enjoyed lunch on the plane.
For stays of 3 nights or more, Hermitage Bay provides complimentary fast-track airport service. Upon deplaning, a representative holding a “Hermitage Bay” sign will meet you, guide you past regular lines, and escort you through priority immigration and customs queues. Because our stay at the resort was only two nights, we were not able to take advantage of this perk. It took about 45 minutes of “island time” to clear customs and immigration.
If you are going straight to the resort, getting to Hermitage Bay is typically seamless. The resort is located in Jennings, St. Mary’s—about a 35 to 45-minute drive from the airport. Because there are no rideshare apps like Uber in Antigua, your transit options are straightforward:
- Complimentary Resort Transfer: Hermitage Bay provides free private round-trip transfers from the airport for stays of 3 nights or more
- Private Taxi: If you aren’t booking a long enough stay, standard airport taxis are readily available outside the terminal. The drive takes roughly 20-35 minutes, and fixed-rate fares generally range from about $45 to about $60 per ride
- Car Rental: If you prefer to explore Antigua at your own pace, car rental agencies are available at the airport. You will need to purchase a temporary local driver’s permit.
The Thrifty rental car was waiting for us just a short walk from the front doors of the airport. With a car, Antigua opens up considerably. It’s a small island, but the points of interest are spread out enough that a rental matters for anyone who wants to move around freely rather than depending on resort transfers and taxis. We were there for a couple of days to explore the island before we checked into Hermitage Bay. We had reserved a Suzuki Jimny but ended up with a small Kia that’s not sold in the US. It was my first experience driving on the other side of the road, and I regretted not having thought this through beforehand. A YouTube tutorial before we arrived would have been helpful.
Friday Night and Saturday: Catherine’s Cafe, Nelson’s Dockyard, and Flatties Flame Grill
The first two nights were at an Airbnb in Piccadilly called Sunrise Suite, on the island’s southern end, booked through the Delta x Airbnb portal and paid with gift cards earned at the grocery store. A practical, well-located base for exploring the island before the resort stay began. The charming Airbnb featured tropical shutters that let in the island crosswinds and a stunning balcony overlooking the hills and ocean.
That first evening, still running on the energy of a same-day arrival from Dallas, we drove to English Harbour for dinner at Catherine’s Cafe on Pigeon Point Beach. Catherine’s Cafe is a French-Caribbean restaurant right on the sand, where you walk in from a dirt path and sit down to a menu that takes the beach setting seriously. We had lobster, grilled steak, an Old Fashioned Rum Punch, and finished with a soufflé and an apple tarte. The bill came to XCD 563.63, which the server handwrote at the bottom as USD $217. For two people, beachfront, with lobster and two desserts, it was not a bad deal.
Saturday, we stopped at an amazing roadside coffee hut, You & Me Cafe, and enjoyed a couple of delicious Sri Lankan iced coffees and the comfy seating they have under the trees behind the stand, on an ocean-side dock. Then, we were off to the Antigua Naval Dockyard and Related Archaeological Sites (known to most as Nelson’s Dockyard) in English Harbour on the island’s southern coast. It’s the only continuously operating Georgian-era dockyard in the world, built in the early 18th century, abandoned by the British Royal Navy in 1889, and a UNESCO World Heritage Site since 2016.
Admiral Horatio Nelson served here from 1784 to 1787 during his first commission, and the restored buildings still carry that history in their stonework and proportions. The marina today hosts mega and superyachts alongside the 18th-century structures, which creates an unusual visual contrast: centuries of naval architecture framing contemporary sailing wealth. The museum, the restored sail loft, the views across English Harbour, and the general quality of the restoration make it worth at least half a day. We enjoyed lunch at Nelson’s Dockyard and made a friend of the waitress. She told us she also worked at a jerk-chicken spot, and we immediately made plans to eat there for dinner.
Saturday night was a deliberate contrast to Friday’s French-Caribbean dinner. Flatties Flame Grill sits on Dockyard Drive in English Harbour, a stone’s throw from Nelson’s Dockyard. The sign out front reads “Pioneers of Peri Peri chicken in Antigua,” and that’s exactly what it is: South African and Portuguese flame-grilled food served outdoors with Carib beers and a crowd that mixes locals and tourists in roughly equal measure. Rustic, loud, and reasonably priced. After a day walking the Dockyard in the heat, it was a nice respite.
Sunday: Through the Rainforest to Sheer Rocks, Then Hermitage Bay
The drive from English Harbour to Hermitage Bay felt like crossing from one Antigua into another. Leaving behind the polished marina, colonial stonework, and clipped sails of English Harbour, the road slipped inland and began to climb through a greener, wilder part of the island. The air grew softer and heavier, the light filtering through banana leaves, palms, and tangled fruit trees as the road curved past small villages, roadside stalls, and flashes of hillside opening suddenly toward the sea.
The drive made the island feel intimate: not just beaches and blue water, but rainforest, red earth, and the scent of something tropical ripening. By the time Hermitage Bay appeared, tucked against the western coast, it felt less like an arrival than a transition from Antigua’s historic harbor to its hushed, hidden edge.
As we got close to Hermitage Bay, we decided to have lunch at a nearby resort.
The Sheer Rocks restaurant sits within Cocobay Resort on Antigua’s west coast, positioned along a cliff edge overlooking the Caribbean. It’s consistently ranked among the best restaurants in the Caribbean, open to locals, yacht visitors, and well-informed travelers, not just resort guests. The setup is a series of open-air dining pavilions with private plunge pools and panoramic ocean views. The menu runs Mediterranean-Caribbean fusion with fresh seafood and locally sourced ingredients. The culinary program is led by Head Chef Jamal Warner and Group Chef Simon Christey-French, who have built a seasonally changing menu centered on Antigua’s farmers, fishermen, and producers.
The restaurant’s Tapas Journey is a vibrant shared-dining experience centered on signature small plates, from fresh seafood to indulgent bites. One patron described staying from a 1:00 PM lunch until sunset without any particular intention.
From Sheer Rocks, the drive to Hermitage Bay follows Antigua’s west coast to St. Mary Parish, where the resort sits on its own private beach at Jennings New Extension. Check-in was at 3:00 PM.
Sunday Afternoon and Monday: Hermitage Bay
Hermitage Bay is a small property: 30 suites spread across the beach and up a hillside, adults-only, all-inclusive. The all-inclusive structure covers food and top-shelf liquor. Premium wines and the spa are charged separately. There is no buffet, no DJ at the swim-up bar, and no daily activity schedule with forced participation. The design principle is intimacy and quiet.
We arrived and received a full White Lotus experience: we were greeted by name at the entrance and enjoyed welcome cocktails on the veranda while the staff delivered our bags to our cabana.
The only event that required pre-booking was the sunset sushi. Prepared while you watched and served at the amazing Tree Bar, an open-air, thatched-roof beachfront bar built around an ancient tree. The sushi can be enjoyed alongside the resort’s famous Hermitage Rum Punch, a Pineapple Caipirinha, or an Antigua Sunset as the sun goes down over the water. I never seek out sushi, but I enjoyed it immensely. Interestingly, the chef was a young Russian.
The accommodation was a beach cabana with a private plunge pool, a Beach Pool Villa in the resort’s room category structure. It was located directly on the beach, with direct access to the water and a private pool for when the Caribbean is not quite what you’re looking for. Guests at Hermitage Bay have plenty of space to spread out. The beachfront villas have large decks with lounge chairs, a daybed, sliding glass doors that open onto the villa, a full minibar, and four-poster beds with bug netting. Ours was on the second row, farther from the beach with more privacy.
The resort has a laid-back, relaxing atmosphere with Caribbean-rustic design features. During a typical stay, guests range from honeymooning couples to points-and-miles enthusiasts cashing in Hilton Honors points, with evenings often featuring live music.
Hilton doesn’t offer many all-inclusive properties, even with the SLH offerings. We had not been to an all-inclusive resort in more than two decades and enjoyed the opportunity to dine without worrying about the cost.
Two nights, two Aspire free night certificates. Cash value: $3,900 per night. The effective out-of-pocket cost beyond the Aspire card’s annual fee: nothing.
We did get a kick out of a sign we spotted attached to a large tree. Maybe because of our aging eyes, we had to get pretty close to the small sign to read it.
The Experience
The experience at the resort was amazing. The bartenders remembered drink orders, and the staff anticipated needs. We were even given the opportunity to select the items available in our complimentary minibar. There were personal notes from the staff and management, inspirational quotes, and turn-down service when the mosquito netting was installed around the bed. The menu was limited at the restaurants, but the food was delicious. Amy had lobster every meal, it seemed.
Antigua is renowned for its Caribbean Spiny Lobsters, an entirely different species from the clawed Maine lobsters. Spiny lobster meat is firmer and slightly less sweet, but just as good. The staff could not have been more gracious or attentive.
Tuesday: Checkout and the Long Way Home
Hermitage Bay checkout was at 11:00 AM on February 11. The return flights out of V.C. Bird didn’t depart until 1:56 PM, which left a comfortable margin to return the Thrifty car, clear security, and head to the airport’s Executive Lounge.
AA3015 to Miami operated on a Boeing 737 MAX 8 (tail N313SB, first flight January 2019, about 6 years old at the time of the trip). We were in first class, again. The flight departed on time and arrived at Miami International three minutes early, at 4:33 PM Eastern.
The Miami connection ran 2h 33m actual against 2h 34m scheduled, essentially unchanged. AA2115 home to DFW operated on a Boeing 737-800 (tail N837NN, about 14 years and 9 months old), departing four minutes early from Miami Terminal N and arriving at DFW Terminal C at 9:19 PM Central, seventeen minutes ahead of schedule.
Four segments, four early arrivals: AA1702 by 20 minutes, AA2124 by 22 minutes, AA3015 by 3 minutes, AA2115 by 17 minutes. For a routing with two connections over a five-day trip, that kind of execution takes friction out of every handoff.
The Points Breakdown
Airbnb gift cards are available at most major supermarkets. The Amex Gold and many premium cards earn 4x on U.S. supermarket purchases. When you’re working toward a minimum spend requirement on a new card, a planned Airbnb booking becomes a double-to-triple opportunity: the stay earns Delta miles through the portal, and the payment earns 4x points on the card, plus the points from the store’s loyalty program. Nothing complicated, just a decision made before going to the Airbnb website. At the time, we were able to take advantage of higher multiples on gift cards at Tom Thumb, Albertsons, Vons, Carrs, etc., to move those grocery store points out west towards Alaska, adding another layer of points stacking.
The Aspire free night certificates were really the centerpiece. The Amex Hilton Honors Aspire card comes with two free night certificates per year (one per card; I carry two Aspire cards). The certificates work at nearly any Hilton worldwide, including Hilton SLH properties like Hermitage Bay. At $3,900 per night, using one certificate per night for two nights yields $7,800 in hotel value against an annual fee of $550 per card ($1,100 total for both cards). The math on the Aspire does not require much persuasion.
The Wins
The portal + gift card combination for the Airbnb. Booking through deltaairbnb.com adds SkyMiles to a booking you were going to make anyway. Paying with grocery store gift cards earned at 4x while meeting a minimum spend adds another layer. Neither move requires more than ten minutes of advance planning.
First class on the flights. The upfront seats made a 7-hour trip to the Caribbean much more comfortable.
Sheer Rocks as the anchor for the transition day. A 10 AM checkout and a 3 PM check-in could have been a wasted three hours. Instead, it was the best lunch of the trip.
Hermitage Bay’s scale. Thirty suites on a private beach with a ratio of staff that consistently gets called out in every review. The resort’s model: small, all-inclusive, adults-only, no filler, is exactly what it advertises.
All four flights early. In a trip where the travel days bracket a resort experience that deserves to start and end without airport friction, four for four is the outcome you want.
The Loss
Antigua is not overly LGBTQ-friendly.
Flights operated on February 7 and February 11, 2025. Flight times and aircraft details from Flighty. Aircraft ages are calculated from the first-flight date to the trip date.
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