Dreaming of Sanibel: Using flexible points for a Florida beach cottage getaway

Editor’s note: The team at The Points Guy loves to travel, but now is not the time for unnecessary trips. Health officials say the fastest way to return to normalcy is to stop coming in contact with others. That includes ceasing travel. We are publishing travel guides because we should all use this time to think about and plan our next adventures. TPG doesn’t advise booking travel until later this year — and even then, be mindful of cancellation policies.

Everyone who loves exploring the globe is thinking about their first trip after coronavirus. TPG editors have some cool dream trips in the works, including an epic trek to Mongolia, a journey to French Polynesia and a hop across the pond to the Mediterranean. All of those points-fueled trips sound amazing! But my first trip once it’s safe to travel will be much closer to home: Sanibel Island, a barrier island off Florida’s Gulf Coast.

Maybe I’m getting more conservative as I get older — or maybe I’m just scared of getting a respiratory illness since I have historically had a tough time recovering from bouts of bronchitis — but my husband and I don’t picture ourselves jetting off to Africa or Argentina anytime soon. Close-to-home destinations are more appealing right now.

Sanibel Lighthouse
Sanibel is an amazing vacation for couples and families alike. (Photo © The Lee County Visitor & Convention Bureau)

Also, we just love Sanibel and visit several times a year — when there’s not a pandemic, of course. It’s rustic Old Florida at its best. Residents have fought for conservation for decades so you won’t find high-rise beachfront condos here. Accommodations are two to four stories maximum. There are no traffic lights anywhere on the island but you will find 15 miles of seashell-strewn beaches, 25 miles of wide paths and the J.N. “Ding” Darling National Wildlife Refuge where you could see Florida bobcat, alligators, river otters and an incredible array of birds from pink roseate spoonbills to American white pelicans to Eastern screech-owls.

Related: How to plan a family trip to Fort Myers and Sanibel Island

Shelling on Sanibel Island - Florida
When you shell on the island, you’re doing the “Sanibel stoop” — leaning over to pick up specimens for your collection. (Photo © The Lee County Visitor & Convention Bureau)

We love the natural setting — many roads are made of crushed shells instead of asphalt — and the lack of commercialism. You won’t find chain restaurants here, with the sole exception of a Dairy Queen outpost. But that also means there are no points hotels on the island. Don’t let that stop you from visiting! Here’s how to plan a trip to Sanibel using miles and flexible points.

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In This Post

Getting to Sanibel

Since we live in northeast Florida, it usually doesn’t make much sense for us to fly to Southwest Florida International Airport (RSW) in Fort Myers on the opposite coast. There are no nonstop flights from our home airport of Jacksonville and the connecting flights that are available on American and Delta are usually more expensive than we’d like to pay. I say usually because right now there are some incredibly well-priced flights well into the fall — when, hopefully, we’ll feel comfortable traveling.

Round-trip Delta flights in Basic Economy are just $105.20 per person in late September. It’s hardly worth putting the miles on our car to make the six-hour drive with prices like that. If we wanted to lock in advance seat assignments, we could pay another $70 per ticket for main-cabin seats. Even Comfort+ seats are just $209 each round-trip for advance seat assignments, extra legroom and priority boarding.

(Screenshot courtesy of Delta)

Those low-priced Delta tickets are enticing but we could also fly with American Airlines. Although the cash prices are much higher ($752 per person for round-trip main-cabin flights), award seats are available for most dates from September through December for 25,000 AAdvantage miles plus $11.20 per person round-trip.

Screenshot courtesy of American Airlines
(Screenshot courtesy of American Airlines)

The American award flights aren’t a bad choice, but Delta’s flight durations and departure/arrival times are better. We prefer to arrive on the island around lunchtime so we can enjoy a leisurely meal at Doc Ford’s Rum Bar and Grille on Island Inn Road before doing some grocery shopping at Bailey’s General Store on Periwinkle Way.

But we have another consideration that makes flying a potential no-go. We adopted a puppy in March, joining our 2-year-old bearded collie, and we feel that the first year is pivotal in building bonds with a new family member. Since Sanibel is so pet-friendly — and we’ve vacationed there with our animals many times in the past — we’ll likely skip the flights this time around and make the drive so we can bring the entire gang.

Related: New to TPG? Read our Beginner’s Guide

Booking beachfront accommodations

When you visit Sanibel, you may as well stay right on the beach. There are several condo complexes, beach cottages and home rentals. Just be aware that many accommodations have a minimum seven-night stay — though that is usually relaxed in off-seasons (like summertime or between Thanksgiving and Christmas). Almost all home rentals require a minimum 28-night stay — through there are a few exceptions.

Our favorite spots include Sundial Beach Resort & Spa, Mitchell’s SandCastles and Island Inn. For full house rentals, we like the Island House and Harbour House, which you can rent from Sanibel Vacation House Island Rentals. You want to be on Middle Gulf Drive, West Gulf Drive or any side street that allows for a quick walk to a public beach access path. East Gulf Drive (follow Causeway Boulevard to Lindgreen Boulevard and then turn left) is also lovely and it’s closer to the island’s famed lighthouse but we just happen to prefer mid-island and west side accommodations and beaches.

Related: Must-do activities when visiting Fort Myers and Sanibel with kids

Sanibel Lighthouse
Sanibel lighthouse on the island’s east end. (Photo © The Lee County Visitor & Convention Bureau)

Using fixed-value points to book a cottage

For this trip, we’d like to use as little cash as possible. That’s why we’ll look to our fixed-value points as a method of paying for our accommodations. We could dip into our Barclaycard Arrival miles, which we can redeem at a rate of 1 cent each toward a statement credit to offset a purchase that’s coded as “travel.” I earn those miles with the Barclaycard Arrival Plus® World Elite Mastercard®, which unfortunately isn’t taking new applicants at this time.

We could also book a Sanibel beachfront cottage using Chase Ultimate Rewards points that we earn with our Chase Sapphire Reserve®, Chase Freedom® and Ink Business Preferred® Credit Card.

The information for the Chase Freedom and Ink Business Preferred has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

I was pleasantly surprised to see so many popular Sanibel accommodations listed at Chase’s travel portal. Even one of our favorites, Sundial Beach Resort & Spa, can be booked. The thing about Sundial though is that many units are individually owned so the decor differs condo to condo. We prefer to rent direct from owners so we can pick out the interior vibe and the view we’re looking for.

Chase Ultimate Rewards Sanibel resorts
(Screenshot courtesy of Chase’s travel portal)

Another one of our favorite spots — Island Inn — is also bookable with Chase Ultimate Rewards points.

Sanibel Island Inn
(Screenshot courtesy of Chase’s travel portal)

An entry-level Gulfview Deluxe Room runs 11,152 points per night on our desired dates.

But when we go to Sanibel, we prefer a full-on view of the beach so we’d likely book a Gulf Front Cottage. The Gulfview room is just 295 square feet with two queen beds, but the Gulf Front Cottage is much larger at 635 square feet and it’s got two queen beds as well as a queen sleeper sofa. It’s going for 20,232 points per night.

(Screenshot courtesy of Chase’s travel portal)

That’s interesting but for just a few points more — 22,752 points per night — we could book an entire 1,399-square-foot house on the beach! It’s got one king bed, two queens, two twin beds and two queen sleeper sofas.

Screenshot courtesy of Chase
(Screenshot courtesy of Chase’s travel portal)

All of these options are intriguing but none of them are a “great” deal on Ultimate Rewards points since TPG values them at 2 cents each. Each of these options comes in under that value when you do the math so we could get more out of them by booking elsewhere. But if our goal is to spend no cash on this vacation — and we have plenty of UR points — it could still be worth it to us.

Related: Why mile and point valuations don’t always have to rule your world

For our purposes though, it will likely make more sense to book directly with Island Inn, pay with our Barclaycard Arrival Plus® World Elite Mastercard® and then apply previously earned points to “erase” the travel-coded charge on our statement after the trip.

Related: How to maximize Chase Ultimate Rewards points

Island dining

We love Sanibel for all of its mom-and-pop restaurants — most of which are devoted to fresh local seafood. We end up dining out a lot on our vacation but since we almost always book a condo or cottage — with a complete kitchen or kitchenette — we also do some of our own meal prep. That’s why we always stop off at Bailey’s General Store upon arrival. We stock up on a few must-haves, like the store’s famous Key lime pie. (You cannot eat enough Key lime pie when you’re on the Gulf of Mexico!)

There’s also a terrific farmers market behind the town library on Sundays.

Sanibel Island Farmers Maarket
Sanibel Island Farmers Market. (Photo by Brian Tietz/The Beach of Fort Myers and Sanibel)

If you plan a similar vacation and start with a grocery shopping expedition, be sure to use a card that offers the best rewards for those purchases. The American Express® Gold Card rewards 4x points per dollar spent up to $25,000 per year at U.S. supermarkets; then 1x. We don’t have that card so we usually use our no-annual-fee Amex EveryDay® Credit Card from American Express that rewards 2x points per dollar up to $6,000 per year at U.S. supermarkets, plus a 20% bonus when you use the card 20 times a month.

Related: The best credit cards for grocery shopping in 2020

If you plan to dine out a few times on the trip, also pack a credit card that rewards you best for dining. I use the Chase Sapphire Reserve for dining to earn 3x Ultimate Rewards points per dollar. But, I’ll admit, there are tastier options, including:

The information for the Citi Prestige, Capital One Savor card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

If you head to Sanibel, check out some of our favorite restaurants on the island and neighboring Captiva:

  • Doc Ford’s Rum Bar and Grille: Start with the restaurant’s signature Yucatan shrimp — steamed peel-and-eat shrimp with garlic butter, Colombian chilies, cilantro and Key lime juice. Messy but delicious! I like to follow that up with a calamari salad with fresh Everglades greens, cucumbers, tomatoes and wonton crisps tossed in a sweet-and-sour vinaigrette.
  • The Clam Shack: This New England-style seafood shack has everything from steamers to Ipswich clams to lobster rolls to chowder. We like to split the clambake special or go for a steamed lobster dinner with all the fixings.
  • Cip’s Place: Cip’s has a terrific kids menu — pasta with butter or marinara, hot dogs, hamburgers and chicken strips — and the adult menu is equally enticing with buttermilk fried chicken, Reuben sandwiches, Danish baby back ribs and shrimp stir-fry.
  • Lazy Flamingo: With a fun laid-back atmosphere, this is the place for peel-and-eat shrimp and a grouper sandwich.
  • Sunset Grill: At breakfast, I always choose the Key lime pie French toast but other diners prefer biscuits and gravy with hash browns or bagel with smoked salmon.
  • Keylime Bistro: On Captiva with indoor and outdoor seating. Go here for the walnut-crusted snapper with a tropical fruit salsa and end the meal with the best Key lime pie in the entire state of Florida.

Related: The best credit cards for dining in 2020

Bottom line

Sanibel is one of the most beautiful beach destinations in Florida. If you gravitate to quiet, nature-based getaways, you will love it. I’ve been visiting the island since I was a toddler and it feels like home. The thrill of seeing dolphins right off the coast — especially at sunset — never fades. And I could spend hours watching pelicans dive-bomb the water as they fish for a meal. We’ve seen bobcats and turtles and even a few manatees over the years. We can’t wait to get back and we look forward to paying for the entire stay with miles and points.

For more future trip inspiration:

Featured image by Jason Boeckman/© The Lee County Visitor & Convention Bureau

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