Bermuda Itinerary

Newstead Belmont Hills Resort Pool

Bermuda

Sometimes you’ve got to get away and recharge without your kiddos.  You come back refreshed, unstressed, and ready to be the best parent possible.  Bermuda was the perfect location for us because it is only a 2-hour flight from Boston. With its pink sand beaches, turquoise waters, and charming colonial towns, is the ideal destination for a mix of relaxation and adventure. This 5-day Bermuda itinerary will guide you through the island’s best activities, attractions, and local cuisine.  My good friend and I spent four fabulous nights there.  Here was our Bermuda itinerary:

Where do you fly in?

The best place to fly in is L. F. Wade International Airport

CLICK HERE TO FIND AN AMAZING FLIGHT

DAY 1

Took our flight from Boston to Bermuda.  (2-hour flight!)

Checked into our hotel, The Fourways Inn. (Read our full review of the hotel HERE)

The Fourways Inn, Bermuda

We went to the local market to buy cheese and cocktails.  We had planned on spending the rest of the afternoon by the pool, but it rained.  That was fine since we enjoyed rosé and cheese near the terrace. 

We had an amazing dinner at the restaurant.

 Dining room of The Fourways Inn

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Itinerary for a Perfect Week in St. Martin/St. Maarten

girls in the pool in St. Maarten

St. Martin/ St. Maarten Itinerary

 We rarely go to the same destination twice, so when we return somewhere it speaks highly of that destination.  St. Martin/St. Maarten is an island where we felt safe exploring, comfortable driving, and loved the variety of activities.  The people are so welcoming and love to share their culture with visitors.  Since the island is half Dutch and half French, you feel like you’ve traveled to two islands in one trip. Looking for a perfect week in St. Martin/St. Maarten

Get ready to fall in love with the Caribbean charm, crystal-clear waters, and vibrant culture of St. Martin. From relaxing on breathtaking beaches to savoring mouthwatering local cuisine, this 5-day itinerary has everything you need to make the most of your trip.

Where do you fly in to St. Martin/ St. Maarten 

The best place to fly in is Princess Juliana International Airport

CLICK HERE TO FIND AN AMAZING FLIGHT

Itinerary for a perfect week in St. Martin: 

DAY 1

I always spend the first full day enjoying my hotel/rental and spending time in the sun and sand with my family.  Enjoy the pool or the closest beach and soak up all the sunshine!

girl jumping into the pool in St. Martin

Lunch: Kali’s Beach Bar.  This is a toes-in-the-sand restaurant, located on the serene Friar’s Bay Beach. This laid-back beachfront spot serves fresh, flavorful Caribbean dishes like grilled fish, spicy ribs, and fried plantains.  Kids can play in the sand while you enjoy a cocktail and wait for your food. With its reggae vibes and ocean views, it’s the perfect introduction to the easygoing island lifestyle. 

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Itinerary for a Perfect Week in Grand Cayman

 

Sunset in Grand Cayman

When we traveled to Grand Cayman we had one thing in mind…get away from the depressing lovely piles of New Hampshire snow.  We wanted to soak in the sunshine and play in the sand.  Stunning beaches, crystal-clear waters, and incredible food come together for the ultimate Caribbean getaway. Whether you’re lounging on 7 Mile Beach, swimming with stingrays, or savoring fresh seafood, this island has something for everyone. Follow this 5-day Grand Cayman itinerary to experience the best of the island, including must-visit attractions, top-notch restaurants, and local favorites you won’t want to miss!  Here is our Itinerary for a Perfect Week in Grand Cayman:

Where do you fly in?

The best place to fly in is Owen Roberts International Airport 

CLICK HERE TO FIND AN AMAZING FLIGHT

Where did we stay?

We rented an amazing condo at the Regal Beach Club. There were 2 pools and right on the stunning Seven Mile Beach.  The beaches were never crowded and the sand was powder white.

CLICK HERE TO FIND THE PERFECT RENTAL

DAY 1

We always spend the first full day enjoying our hotel and spending time in the sun and sand with our family.  Splash in the pool or head to the closest beach and soak up all the sunshine!

After playing in the sun we had to do a few errands. Since we stayed at a condo, we went to the market to load up on local food to make for breakfasts and lunches. We found a farmer’s market and bought delicious local fruit and vegetables.

After lunch, we rented jet skis on 7 Mile Beach, one of the most beautiful beaches in the Caribbean. With its soft white sand, turquoise water, and calm waves, it’s perfect for sunbathing, swimming, or paddleboarding. Take a leisurely stroll along the shoreline, and don’t forget to snap some photos of the stunning ocean views.

Girls walking on sand in Grand Cayman

Dinner:  Deckers Caribbean Grill   This is a fun beach bar where you can sit with your feet right in the sand. This local favorite known for its relaxed vibe and delicious dishes. Their fresh seafood, jerk chicken, and tender steaks are crowd-pleasers, but the star of the show is their signature all-you-can-eat lobster night. Pair your meal with a tropical cocktail for the perfect end to your first day in paradise.

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