Step into a world of elegance, history, and coastal beauty. Our Southern Charms & Beach Vacation is a premier senior-friendly touring trip designed for those who appreciate a slower pace without missing a single iconic sight. Spanning seven days, this journey balances the sophisticated urban history of Savannah, GA, and Charleston, SC, with the sun-drenched relaxation of Hilton Head, SC. Whether you are tracing the footsteps of early settlers or enjoying a breeze on a private beach, this program provides the perfect trip with a balance of guided tours and self-exploration time.

As we approach the America 250 celebrations, there is no better time to explore the roots of our nation. This fully escorted tour takes the stress out of travel, providing seamless transportation, luxury accommodations, and expert storytelling. You’ll stay at the world-class Omni Hilton Head Oceanfront Resort, enjoy private carriage rides through historic districts, and explore the very sites where American history was forged. Curated specifically for senior group travel, we ensure every detail—from luggage handling to pace—is optimized for your comfort and enjoyment.

Our Tour Highlights:

• Savannah’s Storied Squares: A comprehensive trolley tour through the nation’s largest National Historic Landmark District.

• Charleston by Carriage: Experience the “Holy City” the traditional way with a horse-drawn carriage ride through antebellum neighborhoods.

• Fort Sumter & Liberty: Stand where the first shots of the Civil War were fired and explore the America 250 heritage.

• Lowcountry Luxury: Three nights at the Omni Hilton Head Oceanfront Resort, offering private beach access and breathtaking Atlantic views.

• Boone Hall Plantation: Tour one of America’s oldest working plantations, famous for its breathtaking Avenue of Oaks.

• Nautical Wonders: A relaxing dolphin watch boat tour in Hilton Head and a visit to the legendary USS Yorktown aircraft carrier.

• Roundtrip Airfare: Departures from Boston Logan Airport.

• Hometown Pick Up Guarantee: Stress-free roundtrip transfers to/from Logan Airport.

• Premium Accommodations: 1 Night in Savannah, 3 Nights at the Omni Hilton Head Oceanfront Resort, and 2 Nights in Charleston.

• Culinary Delights: 15 Meals (6 Breakfasts, 3 Lunches, and 6 Dinners) featuring authentic Southern cuisine.

• Professional Oversight: A dedicated Best of Times Travel Tour Manager throughout the trip, with all gratuities included.

• Exclusive Experiences: All trolley tours, carriage rides, harbor cruises, and museum admissions are fully curated and pre-arranged.

• Optional Travelers Insurance by Chubb is offered - Click Here for Details on Chubb Travel Insurance Program

 * Single Group Pick-Up.  Non-Group Bookings will be provided a hometown pick-up if within 25 Miles of Boston Logan Airport or will be required to travel to the nearest Best of Times or Group Set Pick-Up Location. Best of Times Travel will notify you of the closest departure point to where you live approximately 3 weeks prior to the trip departure date.  

Savannah, GA - For history lovers, Savannah is a living museum. Founded in 1733, this city serves as a vital chapter of the America 250 story. You’ll wander through cobblestone streets and lush green squares that look much as they did before the Revolution.

Hilton Head Island, SC - Nature takes center stage here. Voted the #1 island in the U.S., Hilton Head offers a serene landscape of maritime forests and sandy shores. Our stay at the Omni Hilton Head Resort ensures you have the time to enjoy world-class golf, lagoon trails, or simply a cocktail by the ocean.

Bluffton, SC - A “well-kept secret” of the South, Bluffton is a charming riverside town brimming with eclectic art, unique culture, and incredible Southern hospitality. It’s the perfect spot to experience the “state of mind” that makes the Lowcountry so beloved.

Charleston, SC - Consistently named the friendliest city in America, Charleston is a window into colonial history. From the bustling City Market to the jasmine-scented alleyways, the “Best City for History” will captivate you with its preserved architecture and deep patriotic roots.

Omni Hilton Head Oceanfront Hotel - An idyllic oceanfront resort on Hilton Head Island. Omni Hilton Head Oceanfront Resort embodies the essence of its location, overlooking the Atlantic Ocean, a beautiful beach and three championship golf courses. As part of the prestigious Palmetto Dunes Oceanfront Resort Community, it’s a standout destination among Hilton Head resorts. Omni Hotels & Resort was just awarded by JD Powers #1 in Guest Satisfaction among Upper Upscale Hotel brands and Conde Nast Traveler’s Readers also voted the Omni Hilton Head Oceanfront Resort as #2 Resort in the South. With access to 11 miles of lagoon trails, tennis courts, private beach access, sparkling swimming pools and wellness areas, guests can fill their days with enriching experiences. Charming guest accommodations are decorated with a neutral palette augmented by ocean views and splashes of color, creating a unique setting among hotels and resorts in Hilton Head. Dining venues are a blend of fine and casual, with creative chefs serving everything from prime steaks and seafood to Stance coffee and snacks. Located on the #1 ranked US island by Conde Nast Traveler, Omni Hilton Head Oceanfront Resort is the premier Hilton Head beach resort, making it the ultimate destination for island getaways and celebratory events.

Are you ready to experience the trip of a lifetime?

Rates and itineraries shown here were in effect at the time of printing and no changes are anticipated; however, Best of Times Travel reserves the right to withdraw any tour or to make any rate changes, as necessary. Prices are subject to change. A deposit is always required to confirm a reservation. A Deposit of $1000pp, plus insurance premium (if selected) is due upon registration to confirm your reservation. Travel Insurance: We recommend your purchase of optional travel insurance. This optional travel insurance is per person and the premium is based on the overall trip cost. Travelers MUST purchase the plan at the time of initial deposit. Coverage will not be in place unless your full Deposit is received. Cancellation schedule and fees are in place regardless of cancellation reason (including, but not limited to, force majeure, health pandemics or government restrictions). Travel Insurance Premium is also Non-Refundable regardless of cancellation reason. Payment in full must be received by August 1st, 2026 or this may result in an automatic cancellation. Please note: All cancellations must be made in writing and sent to Best of Times Travel via email to cancellations@bestoftimestravel.com or via traditional mail. The date of cancellation is deemed to be the date received by Best of Times Travel. Cancellation Charges for this programs are as follows: Cancellations from date of booking until 8/1/2026 have no cancellation fee. Cancellations from 8/2/2026 until 9/1/2026 will be assessed a cancellation fee of 75% of the total fare. Cancellations after 9/1/2026 will receive no refund, 100% of the total fare. Best of Times Travel is not responsible for any refunds over and above said amount. Best of Times Travel reserves the right to issue any refunds, in whole or in part, in the form of future travel credit.

*Pre-Existing Medical Condition Exclusion Waiver has the following stipulations: plan must be purchased within 15 days of initial trip payment, insured must be medically able to travel at time of purchasing the plan, all pre-paid, non-refundable trip costs need to be insured.  This information is a brief description of the features of this insurance program. Coverage & pricing may vary by state. The provision of this document is for informational purposes only and is not an insurance contract. Coverage is being marketed by Chubb Insurance Solutions Agency, Inc. located at 202 Halls Mills Road, Whitehouse Station, New Jersey 08889. Insurance benefits are underwritten by ACE Property & Casualty Insurance Company located at 436 Walnut Street, Philadelphia, Pennsylvania 19106.