top of page
  • Allyson Rychlak

Bermuda in 5 (or 6...) Days

Another family vacation has come and gone, and Bermuda never disappoints. My family has been here several times, and needless to say, Bermuda has it all. Under 2.5 hours from Philadelphia (and much of the eastern seaboard), the island provides a quick flight to paradise. This time, we stayed at an Airbnb on the West End of the island in Sandy's Parish, an oasis with stunningly clear water and beautiful sunset views.

Kayaks and snorkels were included with our Airbnb, which had its own private beach on the West End of the island

Day 1: Monday

Our stay was slated for Monday-Friday. After we landed at L.F. Wade International Airport, we went through customs with Bermuda Travel Authorizations in hand. Our Airbnb host arranged a taxi for us, so we met the driver at the prearranged taxi pickup and took a 35-40 minute drive from the airport (in the East End) to the West End of Bermuda ($85 rate).

Tip for traveling in a post-COVID world: each country will be different, but Bermuda required Travel Authorizations, which cost $40 per person. We had to upload our vaccine cards and a PCR test taken a maximum of four days before departure; we each had tests at CVS on the Friday before we left and received the results between Saturday morning and Sunday morning. American Airlines also required VeriFLY, where we had to upload the approved Authorizations from Bermuda's government, our vaccine cards, passport info, and negative tests as well. Even though we had to have VeriFLY to check into the flight, we were still required to show them at the gate to get approved to board. It was a process, to say the least.

Regardless of the COVID regulations of the island, it was all worth it! The first photo features the entrance to our Airbnb, which was the the guest house/unit of the host's family home. We saw them only in passing and had contactless check-in. Not only did we have a private beach with kayaks and snorkels, we woke up to the sound of the ocean and saw sunset each night from our balcony. Although a resort can be great, the privacy of this spot was spectacular. If you're interested in the Airbnb details, feel free to shoot me a note.

Our first impression of the beach was one to never forget! Beware of the jellyfish.

On Monday, we snorkeled, unpacked, and headed to the grocery store to get some things for the week. We had a reservation at Breezes at the Cambridge Beaches Resort and Spa, but canceled it at the recommendation for some quality Jamaican food down the street from us. While it seemed promising, it was takeout only, and we wanted to sit. We ended up getting a taxi to Dockyard (approximately $20 each way to and from our Airbnb), where the cruise ships come to port, and ate at a pub called The Frog & Onion. Since we didn't have bus passes yet, the taxi was our next best option. For the bus, masks are required, as well as passes or exact change, so we planned to get them the next time we were at Dockyard, since the Visitor Center was not open after dinner. The night finished with an incredible sunset and the sounds of treefrogs lulling us to sleep.

Day 2: Tuesday

Our second day began with a walk to Pompano Beach Club, where my cousin Ashley got married in 2011! We grabbed coffee and water (our plan to have breakfast there was rushed since the walk was longer than expected). This is an incredible resort with a beautiful beach and golf course, so we highly recommend Pompano when choosing between hotels rather than vacation rentals. This was our pickup spot for our Bermuda Hidden Gems full-day tour, which took us cliff jumping, dry cave exploring, and cave swimming on the East End of the island. We had a wonderful guide and really enjoyed this excursion, which runs at $150 per person directly on the company's site (third-party sites run slightly higher).

Dry cave exploring... the guide asked if anyone was claustrophobic before we went in!

We had lunch at Eliana's Fine Dining by the airport and enjoyed yummy tilapia and Bermuda ginger beer, as well as the island's famous Rum Swizzles and Dark 'n Stormys. Food was included in the tour, but alcohol was not. After lunch, we swam and snorkeled at Cooper's Island Nature Reserve, which was crowd-free with clear water and lots of fish and coral to see.

Cave swimming! The water had such a high salt content, you could float without even trying to swim.

We were dropped off in Sandy's Parish around 5pm and ended up making dinner at our Airbnb that night, since the full day tour of exploring and being in the sun was quite tiring. However, this tour is a great way to see different aspects of the island, learn about the beaches and nature, and explore places you might not see on your own.

Day 3: Wednesday

Midway through our trip, we took a taxi Wednesday morning back to Dockyard to grab bus passes from the Visitor Center, which was only open 8:30am-4pm. With 2 full days left of exploring and a taxi arranged for our airport trip on Friday, we got 2-day passes for unlimited travel for $31.50 per person. We booked a half-day (9am-1pm) boat rental from Island Tour Centre and opted to do it ourselves rather than with a guide. This was a great way to have privacy as opposed to a catamaran snorkeling trip with 50+ people from the cruise ships, and allowed us to explore the spots for snorkeling that we were interested in.

My brother, aka the captain, taking us to the shipwreck off the West End of the island for snorkeling

We took the bus back to the stop 1/2 mile from our Airbnb and got ready for dinner that evening in Hamilton. It took us around 30 minutes, give or take waiting for the bus. Bus schedules for the island can be found here. Taking a taxi is the best bet if you're trying to get somewhere by a certain time, but the buses are clean, always have air conditioning (as opposed to some taxis), and so reasonable. Our reservation was at 1609 Restaurant at the Hamilton Princess & Beach Club, one of the island's finest resorts with a great location in the heart of Hamilton and right on the marina.

The Mamacita margarita was fabulous - mezcal, passoa liquor, lemon juice, agave, and bitters

With views of the marina and an open air set up, 1609 is breathtaking and worth the trip to Hamilton. My mom got the catch of the day ceviche, among 4 ceviche dishes on the menu which features a wide range of Mexican-inspired seafood and vegetarian options. The tuna & avocado tostada ceviche, shown below, was so fresh and delicious. We celebrated my mom's birthday with a variety of desserts and caught the bus back to our end of the island as the sun went down.

Day 4: Thursday

The food was so good at the Hamilton Princess we had to return; we had brunch Thursday morning at the Crown & Anchor, craving coffee and a full breakfast. Since it was a Bermuda holiday with the 2022 Cup Match going on Thursday and Friday on the West End of the island, most of the shops were closed in Hamilton, and we avoided returning to Dockyard. Cricket is still a mystery to us, but if anyone has an easy explanation of the game (our taxi driver attempted to educate us), we're all ears. The buses also followed a holiday schedule, so we took a taxi into Hamilton and a bus back.

After lounging by our beach in the afternoon, we headed to Boundary Sports Bar & Grille at the Fairmont Southampton, Bermuda's largest resort on the island with close to 600 guest rooms. It is currently closed due to change in ownership, but our tour guide told us to expect a 2023 open date. This hotel is also in close proximity to Horseshoe Bay, Bermuda's most iconic beach, which I highly recommend for first-time visitors to the island. The sports bar overlooks the 18-hole, par 3 course at Turtle Hill Golf Club. The staff was so lovely, and after our delicious meal we played shuffleboard while waiting for our taxi back to the Airbnb.

A special on the menu: peach margarita inside a pineapple!

Day 5: Friday

The plot thickens on what we anticipated to be our final day on the island. We headed to the airport around 10am for our 1pm flight (a 35-40 minute taxi at $110 due to holiday pricing). My brother and I were checked in separately from my parents since I used bonus points from American to book our tickets and secured seats ahead of time. When checking in on Thursday, my parents were not able to view mobile boarding passes or receive their seats, and a message told them to visit the desk to check in and receive seating arrangements. Needless to say, the flight was overbooked and they were not guaranteed seats.

Traveler tip: Always book seats ahead of time. Lesson learned!

The gate agents asked for 4 volunteers to give up seats to be put on the flight tomorrow in exchange for compensation. Since my parents didn't have seats to begin with, my brother and I gave ours up (because who doesn't want an extra night in Bermuda courtesy of American Airlines?). American gave us vouchers for transportation to and from the hotel, 2 rooms, and dinner and breakfast. Additionally, we were awarded flight vouchers to use by 7/30/23.

Traveler tip: If you can swing it with your schedule to stay another night, volunteer your seat. The airline should take care of the majority of the costs for your extra night, and the voucher (per person, as well) was worth it for future trips.

Due to this strange turn of events, we ended up at Grotto Bay Beach Resort & Spa, only minutes from the airport. Dinner was paid for by the airline, so we covered only the alcohol and lunch that afternoon, since being in an airport from 10:30am - 2pm can work up your appetite.

Day 6: Saturday

While it ended up working out in the end, we waited at the desk to pick up our boarding passes for close to an hour, since the agents realized that my parents were rebooked yesterday, but my brother and I were not. After the agents finally figured that situation out, we waited to board through a delay, took a flight to Charlotte, and sprinted off the plane at 5:50pm to make our 6:10pm flight from Philadelphia to Charlotte. Travel can be a nightmare these days, but it certainly makes for a good story!

Traveler tip: When rebooking, always make sure you're able to view the new boarding passes or confirmed flights online or via app. I was able to see my parents' rebooked flight, but not the rebooked flight for me and my brother. While waiting in the airport for them to uncover the issue was likely better than trying to call the airline directly, this is something we know now going forward.


Crazy travel stories aside, we truly enjoyed this year's family vacation to Bermuda. As a family who has done national parks for the last several years, it was so nice to be in a tropical location with sandy beaches and snorkeling. Our Airbnb was the perfect escape from the overcrowded pools and beaches, and we'd highly recommend our location or something similar. Bermuda is perfect for 4-6 day stay for a couple or family who wants some warm weather, beautiful tropical water, and a short flight to paradise!


bottom of page