Looking to escape for a long weekend? Bermuda is the perfect destination for a quick getaway. With its pink sand beaches, stunning turquoise waters and incredible cuisine, this island paradise is just a short flight away. This Bermuda itinerary shows you exactly how to spend 4 days on the island, including where to stay, what to eat, and the best things to do.
Bermuda is a stunning British island territory located in the North Atlantic Ocean, roughly 650 miles east of North Carolina. Known for its distinctive pink sand beaches, crystal-clear turquoise waters and charming pastel-colored buildings, this 21-square-mile island paradise offers the perfect blend of British sophistication and Caribbean relaxation. Despite its small size, Bermuda packs an incredible punch with world-class golf courses, fascinating historical sites dating back to the early 1600s, spectacular snorkeling and diving opportunities including numerous shipwreck sites and a warm, welcoming culture that keeps visitors coming back year after year.
The island enjoys a subtropical climate that makes it an ideal destination nearly year-round, with warm summers perfect for beach activities and mild winters that still allow for outdoor exploration. Whether you’re seeking adventure through water sports and cave exploration, relaxation on some of the world’s most beautiful beaches, or cultural enrichment through museums and historic towns like St. George’s (a UNESCO World Heritage Site), Bermuda delivers an unforgettable experience that feels worlds away from the everyday hustle and bustle.
4-Day Bermuda Itinerary for the Perfect Long Weekend
Day 1 of Your Bermuda Itinerary: Thursday – Arrival
Fly into Bermuda on a Thursday evening flight. If you’re lucky enough to live somewhere that BermudAir flies, like Westchester County, NY, jump at the chance to fly Bermuda’s official airline. We flew in on one of their Thursday evening direct flights and landed at 9pm Atlantic Time. (Don’t forget there is a time difference from the East Coast of the US to Bermuda, they are one hour ahead there).
Customs at the airport at that time of night is usually very fast, so no need to worry about long lines. Simply take a taxi to your hotel and get settled in for the weekend.
Where to Stay in Bermuda
We stayed at the Rosedon Hotel, an amazing boutique, adults-only hotel right in the city of Hamilton, next door to the Fairmont Hamilton Princess. I can’t recommend it enough. The hotel was quiet, our room was gorgeous and the food was phenomenal. The entire property exudes Bermudian charm and sophistication, making it the perfect home base for a romantic getaway or a girls’ trip.
If you’re looking for a bigger hotel or something kid-friendly or family-friendly, I’ve rounded up more of my favorite luxury resorts at the bottom of this post.
Day 2: Friday – Cave Adventures & Hamilton
Morning: Breakfast & Cave Tour
On the first full day of your Bermuda long weekend itinerary, start the morning with breakfast at your hotel. If you’re staying at the Rosedon, the breakfast is absolutely amazing, so don’t miss it. They start serving breakfast at 7am during the week and 7:30am on the weekends.
Head out early for a cave tour. Bermuda’s natural caves are truly spectacular and shouldn’t be missed during your visit.
Adventure Option: Hidden Gems Tour
If you’re adventurous, I recommend doing the 7-hour Hidden Gems Tour. This tour has a good amount of walking, including some hiking on inclines and in wooded areas with wet surfaces, so be prepared. But if I could handle it, anyone can!
You’ll visit 3 dry caves and 1 wet cave that you have the opportunity to go swimming in. Then you’ll head to a cliff jumping spot with the clearest water you’ve ever seen. Lastly, you’ll go to a private beach in Cooper’s Island Nature Reserve where you can either relax, swim or snorkel.
You’ll finish this tour with lunch at Eliana’s, and I guarantee you’ll have one of the best meals in Bermuda. Definitely order the fish with a side of tartar sauce and ginger beer. It’s truly phenomenal.
Relaxed Option: Crystal Caves
If hiking isn’t your thing, I suggest going to Crystal Caves. You still get to experience Bermuda’s amazing natural wonders but Crystal Cave and Fantasy Cave are much easier to access. They have man-made stairs that provide easy access to bring you down into the caves and a floating platform to allow you to explore them.
Eat lunch at Cafe Ole. They have one of the best fish sandwiches on the island. One of our taxi drivers from the weekend said it was his favorite fish sandwich in Bermuda, and I feel like that’s saying a lot coming from a local.
I’m covering more about my Bermuda itinerary, specifically the Bermuda caves on my Substack if you’re interested in more information about this activity and which one I’d personally recommend.
Afternoon: Pool Time
After your tour, head back to your hotel for a little bit of time at the pool or beach relaxing. We grabbed an iced latte at the Bagels & Brews Cart at the Rosedon before heading down to the pool for a couple of hours.
Evening: Explore Hamilton & Dinner
After getting ready for dinner, explore Bermuda’s capital, Hamilton, before heading to the Princess for Marina Nights, a fun weekly event on Friday night with drinks, food, live music and entertainment. Make sure to grab a Goslings Dark ‘n Stormy (Bermuda’s National Cocktail) or a Rum Swizzle.
Make a late reservation for dinner at Huckleberry Brasserie at the Rosedon. I highly recommend the tuna appetizer, steak frites and seared tuna with mustard sauce and asparagus on the side. Finish with the black cherry cake, it’s absolutely delicious.
If you’re feeling up to it, go for an after-dinner drink at the Intrepid Bar at The Princess Hotel.
Day 3 of Your Bermuda Itinerary: Beach Day & St. George’s
Morning: Breakfast & Beach
Start with breakfast at the hotel and then pack your stuff to spend the morning at the beach. Bermuda is home some of the world’s greatest beaches and you need to add at least one to your Bermuda itinerary. Every single one of them is more beautiful than the last with clear water and spectacular views. Tobacco Bay, Elbow Beach and Horseshoe Bay Beach are just a few favorites and among some of the most beautiful beaches in the Caribbean.
Tobacco Bay is the best option if you’re planning on exploring St. George’s after since it’s so close. It is an absolutely picturesque cove with sparkling turquoise ocean water and unique rock formations. They have a variety of amenities including bathrooms, food, drinks, along with lounge chair and umbrella rentals, but you can also just drop your towel on the sand and enjoy the day.
Afternoon: Explore St. George’s
Head to the historic town of St. George’s after the beach to do some exploring and a little bit of shopping. This UNESCO World Heritage Site is full of history and charm. Make sure to stop by the Unfinished Church, St. Peter’s Church, Fort St. Catherine and more historic sites in town.
One of my favorite stores to shop in is Lili Bermuda Perfumery. If you’re looking for a unique Bermuda gift for someone else or yourself, this is one of the best places. They also offer a perfume workshop where you create your own signature fragrance to take home with you with their consultant perfumers.
If you happen to be there on a Saturday or a Wednesday, book Afternoon Tea with Sweet P in Lili Bermuda’s garden. The tea, finger sandwiches, petit fours and scones were such a treat and so incredibly delicious.
Evening: Dinner at Aurora
Head back to the hotel to get ready for dinner at Aurora, a beautiful seafood restaurant with outdoor seating on the water overlooking the Hamilton harbour. It’s located in the Newstead Belmont Hills Golf Resort. If you can grab a dinner reservation around sunset, I highly recommend it. We loved the sushi rolls, stuffed tiger shrimp and spaghetti vongole.
Day 4: Sunday – Royal Naval Dockyard & Departure
Enjoy breakfast at the hotel one last time, followed by a morning exploring the Royal Naval Dockyard. From Hamilton the best way to get there is by hopping on the public transportation ferry on Front Street, the blue route takes you right there. Not only is it convenient, but the ride offers some of the best views.
Even if you’re not interested in maritime history the Dockyard is a great place to visit. Make sure to stop by the Clocktower Mall to shop local boutiques, the National Museum of Bermuda and enjoy lunch at the Frog & Onion Pub and Restaurant.
Head to the airport for your flight home. If you’re flying with BermudAir back to Westchester County, there’s a late afternoon 3pm flight.
Also worth noting: you go through customs in Bermuda, which makes landing back in the United States super quick. No need to go to the international terminal in the US or go through customs when you land. You simply walk off the plane and go straight home.
Where to Stay in Bermuda
Rosedon Hotel (My Choice)
This boutique, adults-only hotel in Hamilton is absolutely stunning. The rooms are gorgeous, the property is quiet and peaceful, and the food at Huckleberry Brasserie is phenomenal. Perfect for couples looking for a romantic getaway or for a girls’ trip.
Other Great hotel Options for a Bermuda long weekend:
The Loren at Pink Beach: A luxury boutique hotel on the south shore with stunning ocean views and private beach access.
Rosewood Bermuda: A 5-star, upscale resort perfect for families with multiple pools, a spa, various dining options and world-class golf.
The Reefs Resort & Club: A cliff-top, family owned resort with direct beach access and incredible sunset views on the south shore in the Southampton Parish.
Cambridge Beaches Resort & Spa: An oceanfront resort on Bermuda’s west end with a private beach and cottage-style accommodations. it has multiple waterview restaurants and bars and is home to four private beaches and two private coves
Grotto Bay Beach Resort & Spa: A family-friendly resort with cave pools and beach access. This is also the only hotel in Bermuda with an all-inclusive option that includes not only all of your meals and beverages (alcohol included) along with public transportation passes for the bus and ferry.
Hamilton Princess & Beach Club: A refined hotel located on Hamilton Harbour with a full service marina and a private beach club. It’s the OG Millennial Pink Hotel, the iconic “Pink Palace”.
Best Restaurants for Your Bermuda Itinerary
Based on our long weekend in Bermuda, here are my top restaurant recommendations:
- Huckleberry Brasserie at the Rosedon Hotel: Amazing tuna appetizer, steak frites, and black cherry cake.
- Eliana’s: Part of the Hidden Gems Tour. The fish with tartar sauce is unforgettable.
- Aurora: Beautiful waterfront dining with excellent sushi rolls and seafood.
- Cafe Ole: Home to one of the best fish sandwiches on the island and a local favorite.
- Swizzle Inn Pub & Restaurant: The Original Swizzle Inn is Bermuda’s oldest pub and the birthplace to it’s namesake Rum Swizzle cocktail!
- Sweet P Afternoon Tea: Perfect for a special treat in St. George’s.
- Sunken Harbor Club: A one-of-a-kind dining experience highlighted by highlighted by authentic Bermudian fare and local ingredients. Don’t skip enjoying a drink at the cocktail bar!
Final Tips for Your Bermuda Long Weekend
- Fly BermudAir if possible. The service is excellent, your vacation truly starts the moment you step on board. Also clearing customs in Bermuda before your return flight saves so much time.
- Use public transportation like the bus or ferry or take taxis. Bermuda doesn’t allow rental cars, but taxis are readily available. Plus the bus and ferry are a fun way to explore.
- Book dinner reservations in advance, especially for popular spots like Aurora and Huckleberry.
- Don’t skip the caves. They’re truly one of Bermuda’s most unique natural attractions.
- Every beach is stunning. You can’t go wrong with any beach you choose.
- Pack reef-safe sunscreen. Bermuda is serious about protecting its coral reefs.
Bermuda is the perfect destination for a long weekend escape. With beautiful beaches, incredible food, fascinating caves, and charming towns to explore, you can pack so much into just four days. Whether you’re looking for adventure or relaxation, this Bermuda itinerary has something for everyone.
PIN my Long Weekend in Bermuda Itinerary for LATER:
Leave a Reply