The Ultimate 5-Day Summer Itinerary for Your Cape Cod Getaway

With dune-lined beaches and quaint New England towns, there’s no place quite like Cape Cod, especially during the summer season. There are many adventures to be had, sun rays to be soaked in, restaurants to dine in, and a rich history to learn.

If you’re thinking about a summer getaway to Cape Cod but you’d rather not spend hours planning your vacation, no worries! We’ve already completed that step for you.

Here is our ultimate 5-day summer itinerary that details nearly every aspect of your getaway from accommodations to activities. That way, you can spend less time planning and more actually enjoying your visit.

Interested in a weekend getaway? You may also want to check out our 3-day summer itinerary!

Also, don’t forget to request your FREE copy of our Cape Cod Vacation Guide and you’ll instantly receive a full list of our area’s top activities, attractions, restaurants, and more.

Get Your Free Guide to Cape Cod, MA Now!

Your Perfect 5-Day Summer Itinerary

Day One

1. Check Into the Chatham Gables Inn

Exterior ViewAn unforgettable getaway to Cape Cod calls for a very special place to stay! You’re invited to join us at our historic and inviting Chatham bed and breakfast, consistently rated as one of the best and most romantic places to stay in Cape Cod.

Our 170-year-old inn was once the home of a famous sea captain during the 1800s. Today, Chatham Gables Inn provides a classic bed and breakfast experience with beautifully decorated guest rooms, luxurious amenities, and an award-winning gourmet breakfast served each morning.

When you arrive in Cape Cod, check into your chosen guest room and unwind a bit before heading out to explore the area!

2. Take a Stroll Through Downtown Chatham

Described as a paradise of sand, surf, and quaint New England charm, the town of Chatham is the perfect place to enjoy a romantic stroll with your loved one. It’s also a great way to start your summer getaway with us and discover why so many visitors come back to Chatham again and again.

Downtown Chatham consists of blocks and blocks of unique shops, restaurants, and opportunities for sightseeing. As you and your sweetheart explore, be sure to stop by Kate Gould Park to enjoy live music performances (only available during the summer) or visit the wide variety of boutique stores, bookshops, and art galleries.

Feeling hungry? Delight your taste buds at one of downtown’s most popular restaurants such as Del Mar Bistro or the Lazy Lobster.

No matter how you decide to spend your evening in Downtown Chatham, it’s sure to become one of the highlights of your Cape Cod vacation.

Day Two

1. Visit the Local Beaches

south beach chatham gables

After a full night’s rest and a delicious breakfast at the Chatham Gables Inn, the best way to start your first full day in Cape Cod is to advantage of our famous beaches!

Each Cape Cod beach is unique in its own way and provides plenty of opportunities for fun-in-the-sun. Some of the most popular beaches near our bed and breakfast include the Cape Cod National Seashore and Chatham Lighthouse Beach.

Interested in a private island experience? Our Castaway Add-On Package is only available to our summer guests and includes a $50 gift certificate for a grab and go lunch from the Fish Pier Market and transportation to and from your own private escape on North Beach.

2. Discover Local History and Art at the Museums

With a slew of historic sites and museums, Cape Cod is practically a living history museum in and of itself! We encourage you to find your favorites and spend a relaxing afternoon learning more about our fascinating region. Here are just a few that you may be interested in!

  • Cape Cod Lighthouses: Cape Cod, MA is known for its impressive number of historic lighthouses, so visiting one or two for yourselves is an absolute must! The Chatham Lighthouse is the closest to our bed and breakfast and also one of the most photographed in Cape Cod! The Three Sisters Lighthouses are also very well-known local icons and boast a very interesting past that your tour guide will be more than happy to share with you.
  • Chatham Shark Center: Dedicated to honoring one of the area’s most beloved native inhabitants, the magnificent Great White Shark, the Chatham Shark Center is a great place to spend your time in Cape Cod.
  • Cape Cod Museum of Art:  This museum’s mission is to preserve, study, interpret, treasure, and exhibit works by phenomenal artists associated with Cape Cod, the islands of Martha’s Vineyard and Nantucket. Including works drawn from the broader context of human, art, and art history, the Cape Cod Museum of Art provides visitors with a context for the region’s artistic heritage.

3. Dine at One of Our Favorite Lobster Shacks

A visit to Cape Cod is hardly complete with tasting fresh lobster, which is considered to be a local delicacy. That’s why you’ll find several incredible lobster shacks throughout the Cape!

If you’re craving delicious seafood and the flavorful shellfish, your options are nearly limitless. Just to help you get started, here is a look at just a couple of our personal favorites.

  • The Lobster Pot: Noted as a Provincetown gem, the Lobster Pot offers memorable seafood dishes and lovely views of the harbor. You’ll also find lobster served in many different forms on their menu including ravioli, tacos, cakes, and many more.
  • The Cape Sea Grille: Located in a renovated sea captain’s home, this setting is ideal for couples who want to relax and enjoy a sumptuous meal. They have a great selection of lobster dishes, but the one that is highly preferred is their pan seared whole lobster.

Day 3

1. Bike Down the Cape Cod Rail Trail

Formerly a bustling railroad track, the Cape Cod Rail Trail is one of our area’s most popular outdoor attractions. The 22-mile trail winds alongside the coast and through several notable Cape Cod towns including Dennis, Harwich, Brewster, Orleans, Eastham, and Wellfleet. There are also many great spots to take a detour or stop for a break such as Nickerson State Park and the Cape Cod National Seashore.

You can decide whether you want to bike the entirety of the trail or just specific sections. If you make it to the end of the trail in Wellfleet, however, we highly recommend continuing to Maguire Beach Landing for fantastic shelling and to take a refreshing dip in the Atlantic.  

For your convenience, here is the online Cape Cod Rail Trail map and our closest bike rental shop!

2. Catch a Movie at the Wellfleet Drive-In or Orpheum Theater

This classic date night idea is a must for your 5-day summer itinerary in Cape Cod! The Wellfleet Drive-In Theater allows you to watch the season’s newest and hottest films on a 100-by-44 foot screen from the comfort of your own vehicle.

The complex is also home to the Wellfleet Dairy Bar and Grill (which sells movie concessions), a mini-golf course, restaurant, a flea market, and an indoor theater in case of rain.

The Orpheum Theater is a historic venue located just minutes from the Chatham Gables Inn and features first-run major motion pictures, art house films, provocative documentaries, and movies created by local filmmakers.

For a romantic night out with your sweetheart, our Date Night and Romance Package includes two movie tickets to the Orpheum Theater, popcorn and a drink, and a $50 gift certificate to the local restaurant of your choice. It’s the perfect way to reignite the sparks and relive the magic of your first date!

Day Four

1. Enjoy a Day Trip to Martha’s Vineyard or Nantucket

Now that you’ve experienced some of the best things to do in Cape Cod, it’s time to take your adventure to the next level!

Martha’s Vineyard and Nantucket are two beautiful islands located south of Cape Cod and very popular destinations for people visiting the Cape. Ferries are available to deliver you to your favorite island, so be sure to catch one of the earliest departures so you can plenty of time to enjoy all of the incredible activities and attractions.

Here is a quick look at each island to help you decide which one to see, or if you’re feeling adventurous, you may want to visit both!

Martha’s Vineyard

After taking the ferry from Woods Hole to Martha’s Vineyard, you’ll soon discover why this quaint island is recognized as one of Cape Cod’s top destinations! Not only is the island stunningly beautiful, but it also boasts a wide variety of activities that any visitor can enjoy!

You may want to discover the island’s five lighthouses or bask in the sunshine on Lobsterville Beach, which is also a popular spot for local fishermen.

Delight your inner child with a visit to the Flying Horses Carousel, the nation’s oldest platform carousel! This incredible work of art was constructed by Charles Dare of New York Carousel Manufacturing in 1876 and originally operated on Coney Island until it was acquired by the Vineyard Trust in 1986.

For lunch, you’ll find a plethora of fine restaurants to grab a bite. One of our favorite casual lunch spots in Martha’s Vineyard is Martha’s Chowder Company, which is known for its award-winning seafood and mouth watering burgers.


Nantucket is found 30-miles south of Cape Cod and can be accessed after an approximate 80-minute ferry ride.

Once you’ve arrived in Downtown Nantucket, you’ll be free to explore the island and experience for yourself why many of our guests make the excursion.

The Coskata-Coatue Wildlife Refuge is the ideal spot for any nature lover and boasts 16-miles of hiking trails that will lead you through various salt marshes and sand dunes. Three iconic lighthouses, including the highly-photographed Great Point Light, provide breathtaking, panoramic views from their summits!  

Many people visit Nantucket view the island’s historic homes which date back to the 1800s and beautifully illustrate Nantucket’s intriguing past. If this sounds like an activity that you’ll enjoy, head over to Main and Orange Streets to see the magnificent homes that once housed wealthy sea captains, merchants, and ship owners.

When your adventures have worked up an appetite, stop by American Seasons for a delicious meal prepared using only the freshest local ingredients.

Day Five

1. Take a Whale Watching or Great White Skyhawk Tour

Whale Surfacing - Whale Watching PackageThe last day of your Cape Cod vacation calls for an unforgettable excursion that you’ll be talking about for years to come. Here are our top suggestions for Cape Cod tours that you’ll love.

Whale Watching

Whale watching is an extraordinary experience, and Cape Cod is one of the top spots in the nation to spot the majestic beasts. Plus, whale watching season runs from April-October, meaning your summer vacation will fall right in the prime time for this unforgettable adventure.

Whale Watching Dolphin Fleet is known as “New England’s First and Finest Whale Watch” and guarantees both your satisfaction and comfort when embarking on one of their excursions.  See these creatures from the air-conditioned cabin or from the sunny observation deck!

Don’t forget to bring your cameras for this trip, because you’ll definitely want to capture the moment a humpback or finback whale break the surface of the water.

The Great White Skyhawk Tour

This incredible sightseeing tour could be a once-in-a-lifetime opportunity, and we offer this experience to our guests at the Chatham Gables Inn.

The Great White Skyhawk Tour includes a flight over the Lower Cape Cod region where you’ll see the lighthouses, beaches, and Monomoy Island from a completely new angle. After your flight, visit Chatham Fish Pier and enjoy a lunch fresh from the sea.

2. Tour the Local Wineries

After an exciting bike ride, there is nothing quite unwinding with your loved ones at Cape Cod’s exquisite wineries and vineyards.

One of our favorites to visit during the summer is Truro Vineyards of Cape Cod, a popular local winery known for its bold and intense flavors. Tours and tastings are offered during the summer with outdoor live music entertainment as an added bonus.

If you and your sweetheart prefer craft beers over wine, spend your afternoon exploring these fantastic local breweries instead!

3. Watch the Sunset in Chatham

The perfect way to end your 5-day summer itinerary in Cape Cod is by watching the sunset! It’s a perfectly simple yet romantic activity that beautifully wraps up your summer vacation experience.

There are many wonderful places to watch the sunset in Chatham, but some of the best include the aforementioned Chatham Lighthouse Beach, Monomoy Island, and Harding Beach.

After watching the sun dip below the horizon, return to the Chatham Gables Inn for a full evening of well-deserved relaxation.

Book Your Summer Escape to Cape Cod Today

The Nantucket Guest RoomIf you love our 5-day summer itinerary, then you’re ready to book your next beach getaway with us at the Chatham Gables Inn!

Treat you and your sweetheart to a comfortable and romantic stay in our Nantucket Suite! This popular guest room boasts a private terrace, a queen-sized bed with luxury linens, a spa bathroom, and a peaceful sitting area.

Also, don’t forget to browse our tempting specials and packages and in-room delights to discover how you can add even more to your Cape Cod getaway!  

Check our availability today and book your next getaway with us. We can’t wait to see you this summer!